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Venues in Killington, VT,
(802) 422-8800
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5.0 out of 5
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  • 21 Reviews


    Jess Banks

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    5 out of 5
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  • 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... Read more

    responded with the following comments.

    We are so incredibly grateful that you decided to book Trailside for your wedding venue! It was wonderful getting to know you both, planning with you, then seeing the weekend come together (and ending our 2019 wedding season with you!). Thank you SO very much for all of the compliments & kind words

    Tara Walsh

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    5 out of 5
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  • 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!

    responded with the following comments.

    Thank you, thank you! We are so grateful that you had such a memorable weekend and enjoyed our preferred vendors as much as we do! (We do have quite a bit of fun with our photo social media!) Please visit when you're on the east coast :)

    Elizabeth

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    5 out of 5
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  • Best weekend of our lives! I cant say enough about how amazing the entire weekend went at Trailside Inn. When you book your wedding at Trailside the entire facility is rented out just to your party for the whole weekend. Everyone says how fast the wedding goes by so having the whole weekend made all the difference and made us feel we could really enjoy every minute with our family. Josh and Ann, the owners of Trailside, are the two most wonderful people. They made us feel at home the second we walked in and they made sure everything ran smoothly with all our vendors, we never worried about a single detail. Every vendor we selected was also based on Trailside's recommendations and we couldn't be happier with our choices. Homer Horowitz-Clove Hitch Photography, Vermont Farms Catering, and Trish at Pittsfield Garden Center, you would be CRAZY not to use these vendors. We gave Trish a very low budget and I couldn't believe how she transformed every inch of our reception, she must have... Read more

    responded with the following comments.

    The love and humor surrounding your weekend is still lingering within the walls of Trailside :-) We very much appreciate the takeaways - the extended time that a weekend event affords you & that you cannot go wrong with our suggested vendors! (We cannot ever say enough how fortunate we are to be able to work with such amazing people!) Thank you both for the incredibly kind review, the laughs, the memories and hopefully future visits!! 'Til then...

    Jackie bendick

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    5 out of 5
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  • 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 t... Read more

    responded with the following comments.

    Thank you so very much for the wonderful review. It makes us so very happy that Trailside was everything that you were looking for in your wedding venue! It was a pleasure to be able to help coordinate your weekend of events. It would be wonderful to have you back again!

    Jacqueline Fries

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    5 out of 5
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  • Trailside Inn is not only a gorgeous venue, but the Inn keepers, Josh and Ann, helped us a create a wedding weekend we will never forget. They put so much time and effort in to coordinating with our vendors, preparing a timeline of events for us, and ensuring that we had every last detailed covered!

    responded with the following comments.

    Thank you so much for trusting us and booking Trailside as your wedding venue :) It was a pleasure to get to know you both and we are grateful to have been a part of your wedding weekend!

    Daniel

    reviews
    5 out of 5
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  • 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... Read more

    responded with the following comments.

    We are so appreciative of your review!!! And cannot tell you how thankful we are that you chose Trailside for your wedding venue. We may not have otherwise crossed paths, but are so grateful that we have! Thank you for all the kind words and compliments. It was such a pleasure to work with you both

    Alison J Parker

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    5 out of 5
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  • 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.

    responded with the following comments.

    It was such an incredible weekend! We are so thankful for all of the time spent with you both, getting to know you (and your vision for the weekend as well!). We are grateful for all of the wonderful vendors that we work with and are so glad that you got to experience this firsthand! Thank you for all of your kind words about our beautiful state, property and the inn. We absolutely look forward to many future visits!

    Sandy

    reviews
    5 out of 5
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  • 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... Read more

    responded with the following comments.

    We are so incredibly happy to be a piece of your lifelong connection to the area! Thank you for choosing Trailside as your wedding venue and entrusting us with working with you to make your weekend everything you hoped it'd be. What an amazing weekend it was! We, too, hope that we have made friends for years to come! We can't wait to see you this winter :)

    Kristen Haldeman

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    5 out of 5
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  • 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 lov... Read more

    responded with the following comments.

    We are SO thrilled that it was the wedding that you'd hoped for! Thank you so very much for all your kind comments about us and the property. We are so fortunate to live in this beautiful setting and are grateful that we could share a slice of it with you & your guests!

    Cheryl Potter

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    5 out of 5
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  • it was a wonderful long weekend -followed up by my sister getting married - it was just a fairytale and wonderful!

    responded with the following comments.

    A wonderful weekend, indeed!! You were a big part of making the fairytale :) It was so nice to see the sister bond at work! Thank you, Cheryl, for the lovely review. We hope to see you again someday!

    Robert Eckler

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    5 out of 5
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  • Josh and Ann work with you to make sure it is a perfect day. They think of everything!

    responded with the following comments.

    It was such a special time :-) Thank you for allowing us to share in it! We wish you happiness always!

    Coetta Eckler

    reviews
    5 out of 5
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  • 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.

    responded with the following comments.

    It was such a pleasure to have everyone here for your weekend :) We will never forget it! Thank you from the bottom of our hearts for having your special day at Trailside.

    MicheleandJoshua

    reviews
    5 out of 5
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  • If we could give Josh and Ann (the owners of The Trailside Inn) TEN stars, we would. We could not have asked for more reliable, diligent, professional, and personable people to help plan and run our wedding. They went above and beyond to make our experience before, during, and after our wedding virtually stress-free. They have so many connections with wonderful local vendors, and did most of the communication with the vendors for us. They were always fast to respond to questions/concerns, and they always had an answer. We did not have to worry about anything on our wedding day. We were able to enjoy EVERY moment of our special day, knowing that Josh and Ann had every last detail under control. They were "on," making sure everything was perfect, from the time our first guests arrived on Friday, to when our last guest left on Sunday. The inn itself is so cozy and comfortable. It was absolutely amazing to be able to take over the entire inn for the weekend, having only our friends... Read more

    responded with the following comments.

    It was so wonderful to see this event come together! From our very first meeting until your incredible weekend was complete...we enjoyed every moment of the process! It was a pleasure to get to know you both, your families, your friends. Watching you both so truly full of joy on your wedding day...that was everything! We look forward to your future trips to Killington :)

    Olivia

    reviews
    5 out of 5
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  • Our friends and family have told us this was the best wedding they've ever been to. We were looking for a venue where we could not only get married but also hang out all weekend, spending time with the people we love rather than fussing over details. The Trailside checked all the boxes and then some! We loved that it was cozy, inviting, and friendly, and really set the tone for the weekend. It was an amazing place for our group of 100 to gather, from the Friday night welcome party to the Sunday farewell brunch. We visited a few times for planning meetings before the event, and Ann and Josh were very welcoming and on top of the details. It was such a relief to work with two people who not only had the experience and knew what questions to ask, but also really cared about us and our wedding. They also had some great suggestions for vendors, including Woodbelly Pizza (Friday dinner), Vermont Farms Catering (Saturday dinner), and Woodstock Farmers Market (Sunday brunch). Josh and Ann were ... Read more

    responded with the following comments.

    "Best wedding they've ever been to"...that's hard to beat! What a fantastic compliment, along with all of the others. Thank you so very much for the incredibly kind review. It was a wonderful weekend and we are so happy that you had the wedding you'd been hoping for! Many thanks for showing us a new way to transform our space!

    Melissa

    reviews
    5 out of 5
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  • I 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 fel... Read more

    responded with the following comments.

    What a pleasure to host this family!! And we love that it was all about family. Thank you so much for letting us share in your weekend! We love the photos :-) Please come back any time!

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