The Trailside Inn Reviews

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

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.

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!

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!!

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.

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.

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!

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.

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.

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!

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!

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!

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!

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!

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.

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!

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.

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!

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 :)

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.

Ann and Josh and their family and staff were wonderful throughout the entire process. We wanted a place where we could spend the entire weekend celebrating with our family and friends and with close family member being in a wheelchair, finding the perfect place was a challenge and trailside inn checked all the boxes. From the first planning call knowing nothing about planning a wedding, we felt in good hands. They helped ensure our vendors were meeting requirements and the weekend of the wedding things could not have gone more smoothly because of them. We had so many family members remark it wad the best wedding they had been to. The backdrop of the Trailside Inn made it the most magical weekend and surpassed all of our expectations. Thank you Ann and Josh! If you are looking for a place where you can spend 3 days celebrating with your guests and enjoying the beauty of Vermont, choose the Trailside Inn.

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.

We had our wedding here in August and could not have had a more wonderful experience. From the second we visited the Trailside Inn to see if it was a good fit for our wedding, we knew we were in good hands. Josh and Ann were superb to work with: responsive, organized, informative, compassionate, and so helpful. They're both wonderful hosts and wonderful people. The venue itself is also a gem. The photos on their website and blog speak for themselves and we appreciated how we maintained the whole property was. If you're considering the Trailside Inn, DO IT!

Working with Josh and Ann was such a pleasure, my husband and I could not recommend to me enough. As someone who works in events I could not have asked for better planning, organization, coordination and accommodations from both Josh and Ann! Not to mention Trailside inn and the entire property is breathtaking - our wedding was everything we hoped for and more! We plan to visit Trailside Inn as a tradition and hope one of our friends or family member’s gets married there one day as well!