The Trailside Inn Reviews
Reviews
We're all about trust. Our community relies on honest reviews to help you make those big decisions with ease.
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Featured
![Lauren]()
Lauren Sent on 10/04/2025The Perfect Place
I had my wedding August 2, 2025 at The Trailside Inn and I could not have imagined a more perfect venue for our big day! From day one, working with Ann and Josh was so easy. They are quick with communication, kind people, and helpful through EVERY SINGLE part of the planning process. I really wanted a location where all of our guests could stay at one place, and Trailside was just that - hanging out all day, no driving anywhere, it was perfect. Parking, common spaces, outdoor patio, comfy beds.. it just felt like one big happy reunion of all our favorite people together. Josh was great with set up and patient with a few of my guests who ask way too many questions. Ann was so calm and wonderful doing so many behind the scenes tasks so I did not have to think about anything (that is in addition to all the coordination she did with vendors before the big day). Lastly, the PICTURES OMG. We got the hillside blue skies shots, we got forest woods shots, our wedding photos are just so amazing and we never had to leave Trailside’s property. If you want that perfect, outdoor, Vermont wedding without the hassle of being at a resort, and with the benefit of working directly with the owners who care so much about you and your memories THIS IS IT BOOK NOW! -
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Lily Sent on 12/07/2025
Look no further
My husband and I got married at the Trailside Inn in August 2025 & it was the BEST decision we could've made - I cannot imagine having gotten married anywhere else. The Inn itself is the epitome of Vermont. Its cozy, inviting ski lodge vibe creates the most special & intimate place for you and your family & friends to enjoy for the entire weekend. The other real prize is Josh & Ann, the inn owners and wedding coordinators. They are truly the absolute best of the best in every way... down to earth, genuinely great people but also absolute masters at everything wedding. They will directly connect you with some of VT's most fantastic vendors, and are SO helpful throughout the entire planning process. You hear a lot about how stressful wedding planning can be, but with Josh and Ann's help it actually felt 0% stressful and 100% fun and exciting, as it should be. We feel so so lucky that we came across this very special Inn and had the pleasure of meeting and working with Josh and Ann. Our guests have had so many positive things to say about the weekend afterward... some may have even said it was the best wedding they've attended yet. We cannot recommend getting married here enough, so please look no further!!!! -
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![Kathryn]()
Kathryn Sent on 07/23/2025Trailside Inn
We are so glad to have chosen Trailside for our wedding venue. It was lovely to have everyone in one location for the whole weekend and many of our guests commented on how nice it was to not have to worry about transportation between events. The owners, Josh and Ann, were incredibly helpful with managing vendors and implementing our vision for the weekend. They have been doing weddings for many years at this point (we were their 100th wedding!) and it shows. They have personal relationships with the local vendors and know all the potential hiccups that we never would have thought of on our own. We would 100% choose them again! -
Liz Sent on 07/20/2025
Best weekend ever
We can't say enough great things about Ann and Josh and the Trailside Inn. The venue was fantastic. We received so many compliments (and still are) about how wonderful the entire weekend was. Having everyone on site was a dream, especially considering most of our guests travelled a distance. The communal spaces were large and welcoming, allowing for plenty of space to socialize with our guests the entire weekend. The rooms were comfortable and clean. The surrounding area is beautiful and makes for amazing photo opportunities.
We received glowing feedback from every vendor we interacted with about how amazing Josh and Ann are, and after the weekend, we certainly know why. They were extremely professional and communicative, often responding within minutes of our many questions. They had a planning meeting with us several months in advance which was super helpful in terms of making decisions and feeling confident that things would run smoothly. We didn't hire a wedding planner and unsurprisingly have never planned a wedding before- this was no issue thanks to their tremendous help- they think of absolutely everything! It is clear they are passionate about this place, and we are so very grateful to them. Trailside and Killington will always be a special place to us.
P.S. for other wedding couples: we had rain nearly the entire wedding day, except a short 20-30 minute break. We were able to sneak out during the brief pause of rain and there were beautiful photo opportunities, just steps from the Inn. We ended up having the ceremony under the tent, and as you can see, we were situated in front of the opening, with the greenery and rain behind us, and it was beautiful! Not what we planned, but beautiful. Ann and Josh made a rainy day wedding go forward without a hitch. -
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![Lindsay]()
Lindsay Sent on 09/28/2024The best!!
I don’t even know if there are words to describe how incredible Josh and Ann and the Trailside inn are. We held our wedding at Trailside and cannot imagine doing it elsewhere. Our vision was to have everyone on the same property for the whole weekend, and watching families and friends intermingle, knowing they didn’t have to drive or travel, was amazing. Josh and Ann are extremely detail oriented, and truly know how to do weddings. They are super involved in the planning, as they help coordinate and personally know all of their preferred vendors, create timelines and spreadsheets for us, and give their two cents, which cut our stress and workload in half. They are so on the ball and have plans for every kind of scenario which made us feel so at ease. It was forecast to rain on/off on our wedding day (it didn’t), and they were fully prepared for whatever we wanted/what weather permitted. We ended up getting a beautiful day, which Josh fully predicted. Our guests absolutely loved being in one spot for the whole weekend and loved the feel of their rooms, which were clean and cozy, as well as everything the property had to offer. We are so grateful for their expertise, their extremely chill vibes, and their beautiful property. Endless thank you’s to Josh and Ann. They helped make it the best day of our lives.
photo creds @goldwingphotography -
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![Skylar]()
Skylar Sent on 09/24/2024Best Venue
I cannot say enough positive things about my experience at trailside, and with Josh and Ann. They were calming, knowledgeable, and kind throughout the entire process. Their preferred vendor list was amazing, and we had many guests telling us that the food both nights was the best they had ever had at a wedding. We will be encouraging all of our friends to get married at Trailside. It was truly the best weekend of our lives and better then anything we could have imagined. -
![Zac]()
Zac V. Sent on 09/13/2024If you want a perfect wedding weekend book with Trailside
The only reason I’m giving The Trailside Inn 5 stars is because I can’t give them 10. Josh and Ann are absolute pros and wonderful people. As soon as we met them we felt like we had been friends forever. Our wedding was the most perfect weekend we could have ever imagined. If you are looking for a gorgeous location for your friends and family to spend a wedding weekend there can’t be many places better than Trailside. Can’t recommend them enough, 10/10! -
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Hannah Sent on 08/18/2024
Just Book Already - beautiful, welcoming, magical experience
We’re still on cloud nine after having our wedding at The Trailside Inn. It’s hard to put into words just how incredible the whole experience was. Tucked away in the stunning Vermont countryside, this place is pure magic. The views—mountains, lush woods, and a charming babbling brook—were the perfect backdrop for our ceremony and photos. So many of our guests said they couldn’t get over how peaceful and beautiful everything felt.
But what really makes The Trailside Inn stand out are the people running it. They aren’t just great at what they do—they’re genuinely kind and down-to-earth. From day one, they made us feel like family. They helped us with every little detail, offered great advice when we needed it, and were always there with a smile and a sense of calm. It was clear that they really cared about making our day special, not just as a job but because they wanted to see us happy.
The whole weekend felt like a getaway for everyone. Having the inn to ourselves made it all the more special. The rooms are cozy and comfortable, and we loved gathering around the fire pit at night with our closest friends and family. It was exactly the laid-back, intimate vibe we were hoping for.
If you’re looking for a wedding venue that’s beautiful, welcoming, and feels like a hidden gem, The Trailside Inn is it. We couldn’t have asked for a better place or better people to share our wedding day with. We’ll be treasuring these memories for a long, long time. -
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![Mary]()
Mary Sent on 06/27/2024Perfect wedding venue!!
We had the absolute BEST wedding weekend at the Trailside Inn. I cannot describe enough how wonderful it was to work with Josh and Ann -- they are so thorough, calm, kind, creative, etc. and made all of our wedding dreams come true. The vibe I wanted for the wedding was summer camp party meets elegant cocktail party, and Trailside Inn accomplished both of those flawlessly. I would not change a single thing about this venue; we absolutely loved it. I wish we could have a million more weddings to go back every weekend, and our friends and family keep saying this too!! -
Cassidy Sent on 09/04/2023
The Trailside Inn Excellent!!!
Can not say enough great things about this venue! Josh & Ann are wonderful and help you with every step of the process from start to finish. They keep in contact with you through the planning process and assist you the weekend of with anything you may need! Highly recommend for anyone wanting an adorable Vermont Inn and a weekend of fun!! -
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Heather Sent on 08/28/2023
Magical Weekend Wedding
Planning a wedding or a destination wedding, Trailside Inn is the spot! The grounds; with the relaxing stream running around the property, the woods and wildflowers really giving you all the VT vibes. The surrounding destinations to visit while your there are fabulous! Josh and Ann couldn't have been more helpful, professional, caring, and fun. They really take you step by step in planning your special day. Even answering ALL the questions, and I had a lot! If you are looking for a wedding destination that people are still raving about weeks and months later, please check them out!! Josh and Ann helped us created the most magical, enchanted forrest style wedding weekend of our dreams! -
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![Devin]()
Devin Sent on 08/24/2023Perfect Vermont Venue
The Trailside was the perfect wedding venue for us and our guests. It was amazing to have the entire place for our friends and family for the weekend and allowed people to really get to know each other. Josh and Ann were incredibly organized and helpful throughout the entire planning process and the day of the wedding, which allowed myself and my *husband* to focus on each other and the day. -
![Sadie]()
Sadie Sent on 07/12/2023Hosts with the mosts
Josh and Ann are the most amazing hosts. Everything about trailside is incredible. The entire wedding was smooth and amazing because Josh and Ann (owners) are there every step of the way. They communicate, they help, and their amazing space was the talk of the wedding. We got so so many compliments on how things looked, the rooms, the feel, and the accommodations. I cannot recommend them enough. I was a needy & picky bride and they took it all in stride and made my weekend dreams come true. -
Alexis Sent on 01/16/2023
Best Decision Ever!
From the first day we met Josh for a wedding venue tour, we knew something felt special about this place. To be honest, it was the only venue we toured and there was no question that we wanted to have our special day at Trailside. Josh and Ann are beyond exceptional. They know what they’re doing and they do it well, as if it was one of their own friends or family getting married! Everything about our wedding weekend was beautiful, we had so many guests tell us it was the best wedding they’d ever been to. And it certainly felt that way to us as well. I’m so grateful that Josh and Ann helped coordinate the wedding of a lifetime! We have zero regrets in choosing Trailside and are so fortunate we’ll have the sweetest memories to last a lifetime! Book them now!! -
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Katie Sent on 10/29/2022
Wedding weekend perfection
We recently hosted our wedding at The Trailside Inn on 8/27 and I will recommend this venue to everyone and anyone I can. It's everything you could ask for when booking a destination wedding. Trailside is located close to so many hiking trails and quiet little Vermont towns. It has the amazing convenience of on-site lodging and you get the whole venue for a weekend making for such a special experience. From start to finish, the innkeepers Ann and Josh went above and beyond. They come with recommendations for every part of the weekend and are always available and responsive to questions. They helped communicate with vendors leading up to the wedding and made sure the whole wedding day went smoothly. Our guests raved about how fun the weekend was (and even how comfy the beds are). Ann and Josh help take so much stress out of the planning process. I can confidently say choosing The Trailside Inn was the easiest decision in our whole wedding planning process. I'm really hoping one of our guests will decide to host their wedding there so we can experience another Trailside event! -
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![Lauryn]()
Lauryn Sent on 10/10/2022Our Dream Wedding!
If you are in doubt at all, book now! You will not regret it! Ann and Josh are incredible hosts and absolute wizards at helping you organize vendors and plan wedding details. The site is beautiful and all the guests are still raving about how much fun they had over the wedding weekend. The game room was a big hit and Josh and Ann helped us with all our personalized touches, like photos over the fireplace and homemade décor for the ceremony. The Trailside Inn was the perfect spot for our dream wedding and we could not have asked for a better weekend! -
Livvy Sent on 09/14/2022
Best wedding weekend
If you are considering booking The Trailside Inn for your wedding - DO IT. Josh and Ann, and their family, are truly wonderful people who went above and beyond to help us have the wedding day of our dreams. The Inn has gotten some major updates in the past few years (AC in rooms, new bathrooms, solar power) and was a comfortable spot to host almost all of our wedding guests for the weekend. We loved being able to spend as much time as possible with our guests and not need to worry about transportation or any other logistics like that.
As for the planning process, Josh and Ann were immensely helpful - quick to respond to emails or even jump on the phone when needed. They know the industry and most area vendors well so it was really invaluable to be able to lean on them when we had questions or concerns.
Our wedding at Trailside was beyond anything we could have imagined and we are so grateful! -
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Alexa Sent on 08/25/2022
Amazing Weekend
What a magical weekend made even better by the Innkeepers Ann and Josh. Our guests were absolutely thrilled to have the whole inn to ourselves to reconnect with those we haven’t seen in a while. Ann and Josh took care of everything and enabled me to sit back, relax, and truly enjoy the weekend with family and friends. The best wedding weekend I could’ve ever imagined. -
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![Liz]()
Liz W. Sent on 07/21/2022Excellent Venue for Vermont Wedding
We are so, so happy we found Trailside Inn. We hosted a cross-border wedding (half Canadian/ half American from all over) and having the weekend, along with use of the entire Inn for our guests, was a great way to break the ice and have people get together in a relaxing atmosphere. So many people said it was the best wedding they had been to and really enjoyed the venue. There are activities for everyone to enjoy in Killington (great shopping, food, hiking, golf, swimming, etc.) and all of the recommended vendors are top notch and run like a well-oiled machine. We used VT Farms Catering (a must!), Celebration rentals, Linen Shop, and Caja Madera. Josh and Ann were super helpful and supportive throughout the whole process and kept us sane! We had to postpone our original 2021 date because of COVID and they were very accommodating. If I could do it all over again I wouldn’t change a single thing about our wedding here. -
Courtney Sent on 07/07/2022
Beautiful weekend with the best planning duo a bride could ask for!
BOOK THIS VENUE! My husband and I got married at The Trailside Inn this past weekend and could not be happier with how everything went.
The inn itself is the perfect setting for a weekend destination getaway. The surrounding area is gorgeous, with waterfalls and scenic hiking right down the street. The rooms are all beautifully updated with new bathrooms and hardwood. The lodge, downstairs game room and backyard with fire pit are fantastic spots to congregate with guests. The atmosphere is relaxed and inviting, and we received SO many compliments about everything from our guests.
In addition to the beautiful setting, the owners, Josh and Ann, were amazing throughout the entire process. They were incredibly organized and professional. They had google sheets and questionnaires and would remind us about deadlines and timelines in a way that made everything a breeze as far as planning goes. We went with all their recommended vendors and were not disappointed. They clearly love what they do and it shows.
In choosing The Trailside Inn, you will not only get the best wedding planning duo ever, but you will feel like you've gained some true friends. Josh joined in on some lawn games with our guests and Ann seamlessly walked us through all of the finer details of the weekend while easing our nerves. My husband was deployed for much of the pre-wedding planning and I can personally say I am forever grateful to both Josh and Ann for not only making everything easier but fun at the same time. I cannot imagine having our wedding anywhere else. If you are fortunate enough to find them free, book without delay! -
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![Nick]()
Nick Sent on 06/09/2022Perfect Wedding Weekend
Trailside was everything we could have wanted in a venue, and more! Our guests were so impressed with the location and how friendly the staff was. I highly recommend Trailside if you are looking for a great place to host friends and family for a stress-free wedding weekend. -
![Dominique]()
Dominique Sent on 01/18/2022Awesome people, beautiful venue
I really can't think of anything the folks at The Trailside Inn could do to improve the wedding experience here. Ann and Josh were flexible, helpful, and great at communicating with us through a pandemic. We started planning our wedding in 2019 and like many others were not able to hold our wedding in 2020 but did have our party in 2021. Ann and Josh made the initial planning low stress and easy to navigate and managed to keep that vibe through to our wedding day itself. In short, they're incredibly easy to work with and very helpful. The venue is beautiful and awesome! The recent renovations to guest rooms and the game room turned out really well. The whole place has a rustic/hip (still modern and super clean) vibe. Our wedding took place at the beginning of October and the outdoor area where the ceremony was set up could not have worked out better. It's a really cool spot! Our families aren't from VT so an additional advantage to having our wedding at Trailside for the weekend was that our guests had the chance to explore the area. So, they all made the trip up for our wedding of course, but most guests turned the trip into even more of a weekend getaway than we planned it to be (which we all definitely needed after being locked down for so long). In short, the people are knowledgeable and helpful and the place is beautiful and fun! -
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Kristina Sent on 10/14/2021
Trailside Inn is the BEST!
Wow! Trailside Inn offered everything we could have ever imagined in our wedding weekend and more! Josh and Ann, the owners of the Inn and the day-of wedding coordinators are total rock stars at what they do. As you plan your wedding, they will be by your side the whole way recommending vendors and fitting all of the details together. Then during the weekend, they make sure EVERYTHING happens without a hitch. They are so welcoming to all of the guests and make sure to be on a first name basis with all parents, aunts, uncles, and grandparents. Our guests raved about them and how well they complement their cozy, ski-themed inn! Unique wedding features that come with Trailside (most of which we didn’t even know we wanted until we saw them) include the Friday night welcome gathering for all guests to catch up and get to know new people, the Barn and Loft apartments for the wedding parties to stay in, the beautiful wooden altar for the ceremony, the tent on site for dinner and the party (!), and the game room in the basement for the after party! Trailside truly far exceeded our expectations and made our special weekend as perfect as we ever could have imagined. We cannot thank Josh and Ann enough! We 1,000% recommend Trailside for your wedding and can’t wait to get back this winter to ski Killington/Pico and relive our incredible memories! -Jeff and Kristina 8/28/21
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![Jeff]()
Jeff Sent on 08/28/2021PERFECT New England Wedding Venue
From the very first steps of walking onto the property at the Trailside Inn, we KNEW this would be our wedding venue.
The Trailside Inn has "rustic Vermont" all over it. From the driveway, to the wooden covered interior, to the fire pits, babbling creek, beautiful views, and unbelievable guest rooms. If you are looking for that perfect Vermont experience/getaway wedding, this is the place.
The property is surrounded by ample green space for activities and lounging throughout a weekend event. The interior of the venue is tons of exposed wooden beams, wooden tables, and has such a cozy VT vibe. This is what we were looking for.
The owners, Josh and Ann, don't consider themselves Wedding Planners, but rather Wedding Guides. They are both there to walk you through every step of the way, but only to ensure you are getting the wedding you deserve, and to ask the questions you may not have even thought about. Their openness to our ideas, and their suggestions (local vendors, caterers, and tips on where to swim, golf, bike, hike, all the fun!) were all discussed enthusiastically, and in a timely manner. We thoroughly appreciated the constant communication with the venue, even if it was the smallest of questions. Even throughout the weekend, Josh and Ann were as hands on or hands off as we wanted, and were both always nearby if we needed anything at all. Josh and Ann are pros at making sure your wedding weekend is what you're looking for. They absolutely know their stuff!
Beyond being so knowledgeable on wedding weekend events, Josh and Anna are just some of the nicest people you will ever meet or work with. Our guests loved the feel of a privately, locally owned venue like this, and Josh and Ann are a testament to that. They made sure our guests were taken care of, and we never stopped hearing how much everyone loved both of them.
There are also two dedicated spaces, separate from the main venue (but only 10 yards away) which housed our wedding party, the spaces have private bedrooms, full kitchens, a billiard table, and allowed our wedding party to have that “VIP” experience they all deserved. This was AMAZING to have throughout the weekend if anyone just needed to step away from it all for a few minutes, or relax in a private space with close friends.
The venue itself is perfect for a relaxing weekend. From the absolutely gorgeous guest rooms (seriously, everyone was SO thrilled with the spaces, beds, and amenities), to the game room (billiards, jenga, music, lounge furniture, private restrooms, beer pong, etc.) which is open for late-night fun. The back deck of the venue was also a treat as our guests were able to enjoy a beverage and food off the grill while being immersed in the surrounding VT wilderness, any time they wanted!.
Being able to have your own little getaway for the weekend where all guests stay on site, and the only people on site are your guests, was really such a unique wedding experience. We were really able to make it our own.
We were looking for a perfect, and private New England location that housed our guests for an entire weekend, and the Trailside Inn could not have been more perfect. If we had the opportunity to ever get married again, this would be the place. Maybe a 5 year reunion celebration? We're SO in!
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![Courtney]()
Courtney Sent on 08/09/2021Best. Weekend. Ever.
We recently got married at the Trailside and we have not stopped smiling since. It has taken us several attempts to find the right words to describe how perfect our wedding weekend at the Trailside was. The environment and atmosphere that innkeepers Ann and Josh have cultivated is one of a kind. If you are even considering the Trailside as a possible venue, legitimately forget all the others and cha cha slide over to the Trailside.
The idea of holding a 3-day long celebration with all your loved ones as the only guests in their stunning property is brilliant. From arrival to checkout, Ann and Josh made everything simple, streamlined and actually fun. They have experience in both hospitality and wedding industries, which made us feel like we were treated as human beings rather than just another client. They are so caring and really make you feel like a long time friend.
We originally planned our date in 2020 and due to COVID we had to postpone. Josh and Ann always kept us updated on the new state regulations as they came out and they were quick to respond to any questions or requests. When we ultimately had to postpone, they offered a new date in 2021 without hesitation. It was amazing to have such support and to feel like a priority during such a stressful time.
They also have a lot of professional connections with amazing vendors. They coordinate the needs of the wedding couple and timing behind the scenes, so we wouldn’t have the stress of planning all the details. Throughout the weekend, we never had to worry about anything because Josh and Ann were on top of it. No detail, no matter how small, was forgotten. From helping us organize decorations, putting our gifts/cards into a box that we could easily put into our car, and resupplying food or wedding favors, they’re like awesome wedding ninjas and we were so busy having fun we didn't even notice it happening.
Josh and Ann are also very communicative and easy to talk with via phone, email or video. Since the very first meeting with them, the entire process of pre-wedding planning, day of the wedding coordination, and even after the wedding details, they answered all questions quickly and professionally, and quelled our nerves when we got the jitters.
We wish we could leave more than five stars, because the Trailside and its lovely innkeepers deserve so much more than that (like, at least 100 stars). We love you Ann and Josh! Thanks for our dream weekend!
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![Amanda]()
Amanda Sent on 07/19/2021Better than we could have dreamed up
I cannot say enough about our entire wedding weekend with Trailside. Ann and Josh go above and beyond in everything they do, and are so seamless about their work you never even notice what’s happening until this beautiful wedding comes alive in front of you. From sending an email to see if the venue was open and getting a call from Josh twenty minutes later, to debriefing and laughing with josh and Ann after the wedding, they were the most supportive and fun coordinators you could ask for. This wedding was better than anything I could’ve ever asked for. From the beautiful scenic environment, to the low key vibe that allowed everyone to mix and mingle, to the AMAZING vendors like Caja Madera taco truck for the welcome party, to The Linen Shop VT and Raine or Shine Rentals. The highlight was VT Farms Catering and Vermont DJ. We had rain during our wedding day and Ann and Josh pulled together a beautiful ceremony under the tent last minute. It was perfect and everything happened with no stress. Our guests continue to rave about the wedding, saying it was one of the best they’ve ever been to. You plan a wedding for so long, that when it comes together this beautifully you can’t feel anything but grateful, and SO much of that is due to Trailside Inn and Ann and Josh and the stellar team they put together. If you are looking for a beautiful Vermont vibe, wedding coordinators and inn owners who feel like family, and killer food and dancing, you have your spot. My fiancé and I joke that we will be back to Trailside Inn next weekend because it was so perfecT there! -
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![Lauren]()
Lauren Sent on 06/30/2021Perfect Wedding Venue
It’s hard to even know where to begin when talking about Trailside and the lovely Inn owners, Josh and Ann. Let me start by saying if you are considering having your wedding at Trailside, just do it! We had our wedding there in June of 2021 and it was perfect. We loved the idea of having a weekend long event and it was so wonderful and unique to be able to find a place to do that where our guests would be the only ones on the (absolutely stunning) property. My husband and I had the best weekend - even better than we could have hoped for - and our guests have already started to request that we plan a 5 year anniversary party at Trailside. Josh and Ann are so organized, detail oriented and easy to communicate with - in addition to just being wonderful people! They made every part of the planning process so easy and seamless, even as we dealt with changes due to COVID. Due to the pandemic, we ended up making some pretty significant changes to our plans just a few months out and they could not have been more helpful or supportive during that process. All of the vendors they recommended were equally as great. We had tacos from Caja Madera on Friday night and our reception dinner was done by Black Diamond BBQ with dessert from Dream Makers Bakers. All were recommended to us by Trailside and our guests continue to tell us how amazing the food was all weekend (best wedding food they’ve ever had!) :) As we went through the planning process and interacted with different vendors, all of them told us that we were in excellent hands with Josh and Ann and that they absolutely loved working with Trailside. As someone who knew nothing about planning or coordinating a wedding, but who is also very type A and anxious, I can honestly say that I had no anxiety during the wedding weekend because Josh and Ann were on top of anything that came up. From pre-wedding planning to day of coordination, they were truly there for anything and everything we could have wanted or needed. We can not recommend them highly enough! -
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Jess Sent on 11/06/2019Best decision ever
My husband, Colin and I had our wedding at Trailside over the long weekend in October and we could not be happier with our decision! Trailside was the first venue we went to look at after getting engaged and after seeing the Inn and meeting with Josh and Ann, we knew instantly that Trailside was the place for us. We went to a few more places, just to be sure, but by the end of the weekend we had committed to our wedding date.
Throughout the entire planning process, Ann and Josh were nothing but amazing! They're recommendations and guidance were spot on and they really supported us in planning a weekend that was truly unique to our vision and style. Going into the process, we were both pretty nervous as neither of us were too keen on large parties or being the center of attention, but Josh told us from the beginning to think about it as a fun weekend with our friends and family and at some point we were just going to get married. It really made us feel at ease and that's exactly what we were able to do.
By the time our wedding weekend came around, we felt fully prepared and knew we were in good hands. Both Ann and Josh made sure both us and our guest had everything we needed and ensured that everyone had a truly amazing time. They checked in on us and our families regularly and we got some many compliments from our guest about their experience at Trailside. The vendors they recommended were wonderful and really allowed us to tailor the weekend to our needs. The relationships they've formed with these vendors over the years made for a stress-free experience as everyone was clear on expectations, timelines, and all the (many) details that go into a wedding.
Despite our initial reservations when it came to planning a wedding, we had the absolute best time and that had so much to do with Ann and Josh and the beautiful Vermont backdrop that Trailside provides. We can not more highly recommend Trailside and it will always have a special place in our hearts. If a date opens up and you have the chance to hold your own wedding at Trailside TAKE IT IMMEDIATELY. I promise you that you will not regret it. -
![Tara]()
Tara Sent on 10/08/2019The best wedding weekend
Josh and Ann the owners of the Inn are amazing. They make sure your wedding is the most memorable day of your life, as it should be! They take care of everything the second you step through the door. They coordinate very well with all of their preferred vendors to make sure everything goes smoothly. Highly recommend Trailside! Our family and friends loved it as well!! Their social media page gives you great insight into their wedding weekends and vendors too! -
Daniel Sent on 10/07/2019
Why settle for a Wedding Day when you can have a Vermont Wedding Weekend?
Everyone says that their wedding was the best day of their lives. That's certainly true, but imagine if all of your guests tell you that your wedding was the best one they had ever BEEN TO! We heard that a lot after our wedding. The Trailside Inn has a lot of special going for it.
First, Josh and Ann, the Innkeepers are magnificent people. It didn't matter that we didn't the foggiest idea about how to plan a wedding. With a little bit of vision, anyone can do it with their help! The one thing that my wife and I said along the way was that they make it feel as if your wedding is the only one that they have to plan for the year. They are prompt, thorough, and really care. Even through some freak-out moments on our end of the planning process, Josh reminded us that as part of the contract, we had a "No freaking out clause" and that everything was going to be fine. Aside from all of that, we feel as if we made friends for life. They're just that cool.
Second, the "Wedding Weekend" format is particularly heart warming. Your best friends and family arrive for an outdoor get-together on the eve of your wedding, then spend the wedding day exploring the beautiful Killington area before the ceremony. This really breaks the ice for the whole weekend. By the time the ceremony and reception come around, there is enough comfort and familiarity to dance your tails off and not care who is watching! When the weekend is over (it still goes by fast, believe me) you've reacquainted old friends and family and fostered new friendships.
Third, the recommended vendor list that Josh and Ann have is top-notch. We took their advice on catering, photography, rentals, flowers, favors and makeup. The Killington and surrounding area has a small family feel and everyone is remarkable.
Last, but certainly not least, The Trailside Inn is the perfect place for your wedding. Its combination of rustic elegance meets modern farmhouse make for a cozy feeling for all who attend. The best part about this venue over others is that it's all yours for the weekend. -
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![Jackie]()
Jackie Sent on 09/27/2019Absolutely Amazing!
Having our wedding at the Trailside Inn was the best choice we ever made for our wedding day. The quality of service from the InnKeepers/Wedding Coordinators, Ann and Josh, made our special day flow and they executed everything seamlessly. Ann and Josh communicated with us throughout the entire year to assist in the planning process, the level of detail they put into the pre-wedding set-up was fantastic and made us feel less stressed for our big weekend. As for the Inn, what an amazing place, the feeling/decor is what captured our attention when we chose the place, and the amount of feedback from our guests reassured us that we choose the right place. We choose the venue based on its location, the decor and the fact you get the entire Inn for the weekend. If you are looking for a great venue that will allow everyone to have a laid back/stress free weekend, then this is place to have the wedding of your dreams. We have recommend this venue to several of our friends and hope to go back to take part in our friends wedding. Thank you Josh and Ann for all the help with vendors, sharing past ideas and making our wedding weekend one to remember forever. -
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Alison Sent on 07/31/2019
Best Wedding Ever
They say your wedding day is supposed to be the best day of your life, and for my husband and I it truly was. That was in large part to the team at Trailside. Josh and Ann are wonderful people who honestly care about the couples they work with and will do anything in their power to make the wedding planning process (and the wedding weekend itself) stress free. I’m a perfectionist and had exactly in my head how I wanted the weekend designed, the look and feel, etc. – and they, along with a rockstar group of local vendors, created an experience that was beyond perfect (seriously go with their list of preferred vendors, you can’t go wrong). Nearly all of my guests said it was the best wedding they’ve ever been to. If you are hoping for a picture-perfect Vermont wedding, look no further. Trailside is AMAZING and someplace we plan on visiting again and again. -
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![Sandy]()
Sandy Sent on 07/15/2019Our wedding
Where do we even begin?! From the moment we decided to have our wedding at Trailside Inn, Ann and Josh have been the most organized, helpful and detailed coordinators. They made planning a wedding from out of state so simple and seamless from the very first meeting up until the weekend of. All of their suggestions from our amazing catering to florals to welcome party details - s’mores and beer were spot on!! On the actual wedding weekend, Ann and Josh were there every moment for us and our guests, but not intrusive at all, helping us put on such a great party! A thunderstorm passed through on our wedding day and we had to change our ceremony and cocktail hour plans but it didn’t matter in the slightest. Ann and Josh took attention to every detail and even moved the beautiful arbor under the tent so we could still get married under it! All our friends and family have been telling us that this was one of the best weddings they have been to and much of that is because of our wonderful hosts at Trailside Inn. If you envision having your wedding in the mountains where the majority of your guests can all stay under the same roof, have a whole weekend of amazing food and drink, games, lovely breakfast, and with the most relaxed vibe you could have on your wedding day, look no further and book at Trailside! You will be in wonderful hands like we were. We can’t thank you enough for helping us plan such an amazing event and we hope that we have made friends for years to come! -
![Kristen]()
Kristen Sent on 06/30/2019Absolutely perfect and affordable venue
Trailside has two main benefits, the owners and the inn itself.
Owners: Josh and Ann (and their family) were unbelievably amazing. From the first meeting we we felt like we'd known them forever and were hooked. They are built in wedding planners as well and they had an extensive list of vendors to use. It was helpful in picking out the perfect vendors and knowing which ones to avoid. Made the whole process insanely easy for my wife and I. They then helped communicate with them and organize orders (I had no idea what we'd need to get from a rental company for example and they knew exactly what worked in their tent and site). They were professional and warm and just made us feel at home. With out their help there is no way this whole process would have gone so smoothly.
The Venue: Oh my god this place. It was gorgeous. Perfect summer Vermont location. Green and lush around the hotel with a beautiful spot for the ceremony and their own tent. Everyone we invited was in love with it. I can't say enough how the ability to be at the venue with only our people (no randos) for the entire weekend made the event. It would not have had the same vibe or fun at any other location. It gave us the ability to see everyone for multiple days instead of cramming it into the ceremony time. Beautiful picture locations onsite and very close by. Also, insanely affordable, we saw places elsewhere that were double for a sunday afternoon.
In general, they did so many little touches that helped to make it special. I would not change a thing about our wedding and half want to get married again to get to go back :) -
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![Coetta]()
Coetta Sent on 10/17/2018A wonderful experience for our special day.
Josh and Ann were very attentive to us and our guests. They answered all of our questions that we had about any details and gave us advice when needed while we were planning our day. I loved the idea of having the Inn to ourselves with our family and friends for the entire weekend. -
Melissa Sent on 08/11/2018I could not be happier!! The Trailside Inn exceeded our expectations in every way - the grounds are gorgeous with a relaxed vibe, the Inn was cozy and welcoming and the Inn Keepers and family were the best hosts and hostesses you could ever ask for. From the moment I arrived I was able to relax and enjoy Vermont and my family, with full confidence that Josh and Ann had everything under control. All our guests have been raving about the entire weekend and say that it was one of the best weddings ever!! We had a ton of kids staying at the Inn and attending the wedding and they had a blast! The yard games and game room provided them entertainment and space to just be kids! You would never have guessed that a third of the guests were children! I wanted my wedding weekend to be all about family; a pause in the every day craziness of life; a time for everyone to be able to appreciate the ones they love. After it was all over and we headed home, I reflected back on our days at the Inn and felt very grateful for the entire weekend and I would do every moment exactly the same. A very heartfelt thank you to the Josh, Ann, Brex, Quinn and the Trailside Inn. You are truly the best!!
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Francis Sent on 11/04/2017Amazing! Ann and Josh at Trailside Inn are amazing. They are so professional and friendly. We never had to worry about anything and could just enjoy our wedding weekend. This is a great place to get away, get your family and friends together and really enjoy life and each other!
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Kristen Sent on 10/26/2017The Trailside Inn was the perfect venue for our dream wedding on 8/26/17! As a destination wedding it allowed for all of our guests to stay on site and thus created a reunion type feel for the entire weekend. We are two months out from our big day and family and friends are still giving us compliments on how great it was. Josh and Ann, the innkeepers, are incredible! They didn't let us miss any details and it allowed for a perfectly smooth weekend. They also helped us find vendors to fill our needs and budget which was a huge help since I was planning this from out of town. The natural surroundings created absolutely stunning photos. I just recently got my pictures back and was able to relive it, once again being reminded of how amazing it truly was. I give this venue nothing but the highest recommendations. You won't be disappointed!
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