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The Trailside Inn Reviews

The Trailside Inn View more information

Reviews

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WeddingWire Couples' Choice Awards 2024 Winner
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55 reviews
100% recommend it
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Awards

55
WeddingWire Couples' Choice Awards 2024 Winner
WeddingWire Couples' Choice Awards 2023 Winner
WeddingWire Couples' Choice Awards 2022 Winner
WeddingWire Couples' Choice Awards 2020 Winner
WeddingWire Couples' Choice Awards 2019 Winner
WeddingWire Couples' Choice Awards 2018 Winner
Weddingwire
5.0/5 55 reviews
Google
4.7/5 104 reviews
  • Skylar
    Skylar H. Sent on 09/24/2024
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    Best 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.
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    Kara M. Sent on 09/14/2024
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    Amazing and unforgettable wedding venue!

    The Trailside Inn made our wedding day truly unforgettable. From the years of planning to the moment we arrived, Josh and Ann were so supportive and made the experience seamless. They helped to ensure our vision came to life, and we couldn't be more thankful! All of our guests raved about the inn, the florals, the food, and about the overall weekend experience. We felt so well taken care of, and it truly made the day and weekend stress-free and enjoyable for us. Would absolutely recommend The Trailside Inn to anyone looking for a magical weekend experience!

    The Trailside Inn's reply:

    Magical, it was! Your wedding had such an amazing Old Hollywood vibe to it...so chic & classy! It was wonderful working with you both; we really enjoyed being able to help with your weekend
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    Are you interested?

  • Zac
    Zac V. Sent on 09/13/2024
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    If 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!

    The Trailside Inn's reply:

    Thank you for the 10 stars!!
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    Sarah M. Sent on 12/27/2023
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    Exactly the spot we wanted

    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!

    The Trailside Inn's reply:

    What an incredible event it was! It has been a pleasure getting to know you both and watching your event come together. Thank you so much for the wonderful review
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    Hannah F. Sent on 08/18/2024
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    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.

    The Trailside Inn's reply:

    We are so fortunate to be able to share this slice of Vermont heaven! It was a pleasure to get to know you both and to help your special weekend dreams come true. Thank you for trusting us to do so! We hope that you are able to visit in the future and reminisce on those wonderful times
  • Lindsay
    Lindsay Sent on 09/28/2024
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    The 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
  • Mary
    Mary C. Sent on 06/27/2024
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    Perfect 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!!

    The Trailside Inn's reply:

    We are so grateful that you chose Trailside for your venue!! It was wonderful getting to know you both
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    Molly D. Sent on 10/23/2023
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    Book your wedding here!!!

    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!

    The Trailside Inn's reply:

    It was so great working with both of you! And Molly, the fact that you are in events added something extra! It was a joy to plan with the two of you -- the details of your weekend were really unique & made it all so fun! We look forward to seeing you in the future :)
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    Alexandra S. Sent on 10/02/2023
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    The Best Decision Ever!

    Ann and Josh are the most amazing people to work with. They are so kind, responsive, and helpful during the entire wedding planning process. It can feel overwhelming when you start to plan a wedding and not know where to begin. Ann and Josh had a ton of recommended vendors and wedding weekend timelines that were the perfect starting place and guided us through the entire process. Not to mention they were always available to answer questions (and there were a lot!). The inn itself is so beautiful. The grounds are amazing and we were so happy to have the inn full with our friends and family all weekend long. Having the inn reserved for all our guests made it so much easier to spend time with each person throughout the weekend. It was heartwarming to see everyone in the great room mingling and chatting. The fact that the welcome party, ceremony, reception, and after party took place at the same location also made it super easy for everyone and gave people time to explore the beautiful town of Killington throughout the weekend. All of our guests felt relaxed and happy to not need to rush around from place to place for the various wedding activities. Having our wedding at the Trailside Inn was the best decision we made. We are so grateful to Ann and Josh for all of their help and we will be returning there for years to come. We would recommend this venue to anyone!

    The Trailside Inn's reply:

    Thank you SO much for all of the compliments! We had an absolutely wonderful time planning with you & getting to know you through this process! Your kindness & sweet energy just made all of it so easy and fun. We are so happy that your weekend was filled with quality time with family & friends. We look forward to seeing you in the future!
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    Cassidy W. Sent on 09/04/2023
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    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!!

    The Trailside Inn's reply:

    Thank you so much for the lovely review :) We are thrilled that you had a wonderful wedding weekend (and planning experience leading up to it!). It was our pleasure to be a part of it all.
  • Devin
    Devin D. Sent on 08/24/2023
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    Perfect 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.

    The Trailside Inn's reply:

    We can never say it enough, but you summed it up perfectly: "...the entire place for our friends & family for the weekend...allowed people to really get to know each other..." This is the BEST part of a weekend event at Trailside. So glad that you enjoyed your wedding weekend and were able to focus on you as a couple! It was a pleasure to host you & your guests and to work with you & get to know you!
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    Analis F. Sent on 07/17/2023
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    Absolutely amazing !!

    The Trailside Inn is absolutely beautiful. We loved the laid back atmosphere. We specifically chose this venue so all of our friends and family could enjoy the views & be all together under one roof. Josh & Ann are absolutely wonderful. They helped with everything & we couldn’t be more grateful. They responded to emails quickly & kept in touch the entire time we were planning our wedding. I highly recommend having your wedding at The Trailside Inn. It was completely stress free & they did an amazing job with absolutely everything. Thank you again!

    The Trailside Inn's reply:

    We are so glad that you found us when looking for a place that everyone could be together for the weekend! That is what we, too, love about our property. We really loved seeing all of the traditional elements of your weekend meld with the modern pieces! It was absolutely lovely to host you both & your families. Hope to see you soon :)
  • Sadie
    Sadie R. Sent on 07/12/2023
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    Hosts 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.

    The Trailside Inn's reply:

    Let's just get this out of the way...we would never consider you a needy or picky bride! Not at all! We received so many comments from vendors on how excited they were for this wedding and how fun & different it was! We were all so thrilled to see it all come together...the colors, the fun elements, all of the fantastic details!
    Thank you so much for being so great through the entire process - it was a joy!
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    Taylor J. Sent on 07/16/2023
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    perfect venue

    First off, Josh and Ann are amazing; professional and just experts at what they do. It rained buckets on my wedding day and they made it so I didn't even care. The Inn itself is so charming, the work they have put into it is high quality and beautiful. This space creates a fun but intimate setting for your special day. Get married here! You won't regret it!

    The Trailside Inn's reply:

    The beauty of Vermont still remains even when raining! It was such an incredible weekend and we are so thankful to have met you both & to have worked with you through this process. Thank you for all the kind words. We hope to see you again!
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    Emily H. Sent on 10/27/2022
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    Amazing Vermont Wedding Venue

    Trailside Inn was the perfect place for us to have our wedding and our wedding was beyond anything that we could have imagined. Josh and Ann sell the idea of a wedding weekend, and we got just that. Three full days spent alongside our family and friends and it was truly a magical experience.

    Our dream wedding was to get married in Vermont, and spend the weekend alongside our family and most of our guest list. Around 85% of the guests ended up staying at Trailside with us. It gave us significantly more time with all of our guests and also allowed the guests to meet and get to know each other, which made our wedding weekend even that much more special. Trailside also allows guests to check in on Thursday night, which close to half of our guests chose to do, allowing us even more time to spend with our family and friends, while also allowing our guests the opportunity to explore Vermont and sightsee without having to feel rushed to get back for wedding events.

    According to the guests, the overwhelming sentiment about the room accommodations were great. The rooms were the perfect mix of Vermont rustic charm, all while having the necessities to make a cozy weekend away. We didn’t have any issues with our lodging whatsoever, in large part due to the owners of Trailside, Josh & Ann. They were on top of everything.

    We booked Trailside about 14 months before our wedding date. From the initial meeting before we booked Trailside for our wedding, all the way through the end of our wedding weekend, Josh & Ann were extremely helpful and easy to work with. They know all the right questions to ask to make sure your day is what you want, and were also able to help us work through some nontraditional components to make sure everything ran smoothly. They know what they are doing and have their operation extremely dialed.

    We chose from a list of vendors they had previously worked with, and all of them were phenomenal. They have good working relationships with some truly great vendors, who just like Trailside have an extremely dialed operation. If they are available, we highly recommended sticking to the "Recommended Vendors" list as much as possible, because their prior experience at Trailside made our weekend run seamless.

    We highly recommend booking Trailside Inn for a wedding venue. Our weekend was perfect and we attribute most of that to Josh and Ann and Trailside Inn.

    The Trailside Inn's reply:

    The weekend wedding experience really is the best! It is such a great way to spend time with loved ones & not feel rushed. We are so glad that you got to experience that and enjoy yourselves! And yes - we are so fortunate to have an absolutely stellar bunch of vendors that we work with....truly the best. Congratulations and best wishes always to you both!!
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    Kaitlyn S. Sent on 10/05/2022
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    Absolutely Amazing

    We just had our wedding at the Trailside Inn, and Ann and Josh were absolutely amazing. They’re LGBT friendly and made us feel welcome from the very first conversation. They were prepared for everything and anything, and helped us through every step of preparing for our big day! Their inn was located between both of our families and we loved the idea of having everyone in one location for the weekend. They have a list of vendors who they have vetted and know will do a great job. (Go with the taco truck!) The vibe at The Trailside Inn is amazing. Ann and Josh make you feel like a friend and they are there all weekend to ensure you are enjoying yourself and not stressing. Even our friends and family couldn’t stop saying how great the location, Josh & Ann, and the weekend were. If you’re looking for a place where you can relax and spend time with those you love most, then this is the place for you!

    The Trailside Inn's reply:

    We couldn't agree more - our vendors are amazing! Thank you for all of the beautiful words about them and us. We are so glad that everyone had an amazing time, especially the brides! It was our pleasure to have everyone for the weekend & we hope to see you again :)
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    Alexis M. Sent on 01/16/2023
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    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!!

    The Trailside Inn's reply:

    We are so happy that you felt something special...we did too! You are both such lovely, kind people and we were happy to host your wedding weekend
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    Katie K. Sent on 10/29/2022
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    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!

    The Trailside Inn's reply:

    Your review + chatting up Trailside are the best thanks we could ever ask for! Word of mouth recommendations are everything for a small business :) We are so thrilled that you had such an amazing experience for your wedding weekend. It really was so beautiful and we were happy to be there to help along the way. Here's hoping that you get your wish to return as a wedding guest next time!
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    Alexa L. Sent on 08/25/2022
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    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.

    The Trailside Inn's reply:

    We are always hopeful that relaxation will set in early on with the weekend's start...so very glad that you felt that way! It was an incredible weekend with lots of time with friends & family...and gorgeous weather! Thank you for allowing us to help and for the connection to a new vendor. Best always to you both! Hope we see you again very soon :)
  • Liz
    Liz W. Sent on 07/21/2022
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    Excellent 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.

    The Trailside Inn's reply:

    We, too, are so happy that you found Trailside Inn! It was a pleasure to help you both (finally) get to the weekend wedding you wanted :) And we couldn't agree more - we are so fortunate to have a fantastic group of vendors to work with!! They are top notch. We wish you the best always and hope to see you in the near future!
  • Lauryn
    Lauryn C. Sent on 10/10/2022
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    Our 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!

    The Trailside Inn's reply:

    We like our new title of "wizards"! :) There was so much enjoyment in helping plan your weekend and getting to know the two of you! You are both such special people and your weekend will never be forgotten
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    Courtney P. Sent on 07/07/2022
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    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!

    The Trailside Inn's reply:

    What an amazing weekend! Thank you for all of the compliments...we appreciate each & every one! It was fantastic working with you & helping to put the weekend together. And even better to know that you were so pleased with it all! Please come by whenever you're anywhere near Killington! Best always
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    Krystal N. Sent on 07/24/2022
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    A perfect, green wedding get away!

    Ann and Josh at the Trailside Inn are fantastic. We wanted a smaller wedding where all of our guests were able to stay on site for our weekend to all be together. Our wedding at the Trailside Inn captured our vision and more! Ann and Josh worked closely with us throughout our entire planning phase. They were unbelievably helpful by recommending and continuing contact with other vendors. Ever since we signed our contract to the day after our wedding, I truly felt that Ann and Josh had our wedding vision at heart.

    The Trailside Inn's reply:

    Thank you so much for the kind review
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    Kelsey K. Sent on 07/01/2022
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    Go Trailside or don't go at all

    We booked The Trailside Inn in early 2021 amidst high market demand for wedding venues on popular dates. Josh, one of the innkeepers, was very flexible in offering us a video tour of the lodge via FaceTime, and answered all our questions with complete honesty and transparency. We made two planning visits between booking and our wedding, during which Josh and Ann (Josh's wife, co-innkeeper, and lead event coordinator), helped us turn our concepts and ideas into concrete plans. They provided vendor recommendations, guidance on ceremony and reception processes, and valuable insight based on their years of experience. Overall, the booking and planning process could not have been easier with the help of Josh and Ann.

    On wedding weekend, things were even better. The Trailside is a family owned and operated business, and the nature of the venue means it will be just your friends and family on the property throughout your event. As a result, Josh and Ann are able to provide unbeatable personal attention and detailed service. Ann is also an outstanding event coordinator--once you work out your contract details with individual vendors, Ann handles all further correspondence and operational planning for setup, execution, and takedown. The ultimate consequence of this level of attention and service is that once you show up, you can enjoy your time with your friends and family rather than worrying about putting on a big party.

    Importantly, Josh and Ann are also very familiar with all the other vendors you'll need. Because the Trailside's main business is the provision the party space and lodging (and because tourism/hospitality are some of Vermont's top industries), things like food, flowers, music, and tables/chairs/place settings all come from separate vendors. Although this can be a lot to manage in the beginning, Josh and Ann have great working and personal relationships with nearly every vendor in the area, and can provide a direct line to whoever you need, even if you're having trouble getting in touch. This is an invaluable asset that reduces the stress of managing several contacts at once. Further, the nature of this arrangement means you have 100% complete customizability in how things look, sound, feel, and go throughout the weekend. Want to ride bicycles down the aisle? They've done it, and know a photographer that will make it look like the cover of a Nicholas Sparks novel. Want a Celtic harpist to play Lord of the Rings melodies as you marry in the woods? Not a problem. At the Trailside, you're not limited to the standardized "packages" that a lot of all-inclusive venues offer, and although it's more work, it's very much worth it.

    One of the most unique parts of the Trailside experience is having the entire property to yourself for an entire weekend. Josh and Ann help you organize and execute a "welcome party" on the day before your wedding so guests can get in, get fed, and get to know each other more casually before reconvening the next day for the big event. This pays off immensely in creating familiarity between guests so that when dancing time comes, nobody is bashful. I'm fairly certain every single guest we had on our weekend commented not only on how beautiful the property was, but how great it was that the whole weekend was just our group.

    Ultimately, if you decide you want to (or are told by your families that you have to) engage with the wedding industrial complex, there is no better way to do it than the Trailside way.

    The Trailside Inn's reply:

    Wow - 'thank you' just doesn't do it!! It was such a pleasure to work with you toward your vision of your most special weekend
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