Recommended by 100%
28 User photos
Kristen Haldeman · Married on 06/22/2019
Absolutely perfect and affordable venue
Trailside has two main benefits, the owners and the inn itself.
Sent on 06/30/2019
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 :)
The Trailside Inn's reply:
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!Elizabeth · Married on 09/07/2019
Best wedding and weekend of our lives!!!
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.
Sent on 09/10/2019
We gave Trish a very low budget and I couldn't believe how she transformed every inch of our reception, she must have hand picked every flower. We had the best food I've ever had at a wedding and Vermont Farms even catered our after party. The after party was held right on site on the lower floor of Trailside. No shuttles needed, no hotel employees trying to quite down the party, just you and all your family continuing the dancing, singing, and great times! Homer, our photographer, understood everything we were asking for and made it happen. We have the most beautiful, natural, real photos from the wedding. No fake or cheesy forced pictures and he was still able to capture every moment.
I want to jump back to Josh and Ann and make sure this review is clear. Josh and Ann are AMAZING! They made sure every detail was handled and we never worried for a moment. They truly care about the people they invite into their home and make you feel like family. If you are still reading this review and want to have the most relaxed, fun, perfect wedding, then you found what your looking for at Trailside Inn.
Jacqueline Fries · Married on 08/17/2019
Quintessential Vermont Wedding Venue
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!
Sent on 08/22/2019
The Trailside Inn's reply:
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!Alison J Parker · Married on 07/13/2019
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.
Sent on 07/31/2019
The Trailside Inn's reply:
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 · Married on 07/06/2019
Our 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!
Sent on 07/15/2019
The Trailside Inn's reply:
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 :)Cheryl Potter · Married on 10/13/2018
#happilyeverhuber was a success!
it was a wonderful long weekend -followed up by my sister getting married - it was just a fairytale and wonderful!
Sent on 10/16/2018
The Trailside Inn's reply:
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 · Married on 08/18/2018
Perfect place for a wedding
Josh and Ann work with you to make sure it is a perfect day. They think of everything!
Sent on 10/16/2018
The Trailside Inn's reply:
It was such a special time :-) Thank you for allowing us to share in it! We wish you happiness always!
Coetta Eckler · Married on 08/18/2018
A 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.
Sent on 10/17/2018
The Trailside Inn's reply:
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 · Married on 08/11/2018
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.
Sent on 09/19/2018
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 and family there. Plus, everything was on site - ceremony, cocktail hour, and reception - so our guests didn't need to go anywhere.
The Trailside Inn is the whole package with the best wedding planners you could ever ask for. We HIGHLY recommend the Trailside Inn as a wedding venue!!
The Trailside Inn's reply:
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 · Married on 08/04/2018
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 very flexible with my requests when it came to decor, layout, timing, etc., and had a lot of great suggestions. One of the vendors mentioned to us that Ann and Josh are some of the most organized/on-top-of-thing people they've encountered in the wedding industry. We always felt that we were in good hands, and never felt stressed. Our wedding was everything we hoped it would be, and I don't think it would have been anywhere near as good if we had gone someplace else. Thanks Josh and Ann! We'll be back for skiing!
Sent on 08/13/2018
The Trailside Inn's reply:
"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 · Married on 07/28/2018
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 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!!
Sent on 08/11/2018
The Trailside Inn's reply:
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!Stella · Married on 07/07/2018
Wouldn't it be nice if the innkeepers were logisitical masterminds but also super tasteful and friendly hosts? Josh and Ann at the Trailside Inn were such a pleasure to work with. From the initial planning to the sort of gametime adaptations on the day of, Josh and Ann offered so much resourcefulness and so much of this happy guidance to us. Our experience with the Trailside family and the venue in general was beyond what we would have dared to hope for our wedding.
Sent on 07/20/2018
We are realizing how many skillful touches that there were now that we are talking about it. They literally customized our weekend at the Inn. We think because they are logistical masterminds, they enjoy facilitating the process. Communicating about details was clear and easy from the beginning. Then on the day of, Josh and Ann coordinated the caterers, the band, the table and linen rentals, skillfully freeing us up to share a moment with a friend here, a moment with a family member there, and so on. It was such a happy day. They welcomed our crazy lawn games and added theirs to the mix.
Our friends and family kept telling us how great Josh and Ann were about hiking suggestions, biking routes, and golf courses. They have a magic way of taking care of things invisibly or checking with us about how we would like something to be. But they also just sometimes chatted and hung out with people when they had a minute. The tasteful, open-minded way that Josh and Ann welcomed people really invited our families to come together and created an environment where so many special moments between so many people could take place.
The Trailside Inn's reply:
We feel so fortunate that you chose Trailside Inn as your venue. We are the lucky ones to have worked with you - getting to know you both, having the opportunity to meet your family & friends, watching your weekend come together. We have never hosted a wedding where so many elements were truly inclusive of all guests...from painting fun signage; collecting wildflowers to create bouquets and table pieces; constructing a beautiful chuppah; to an intense, riveting game of whiffleball. It is clear that you both have an amazing relationship with each other and all of those around you. What an incredible chance for us to witness this. Thank you. Thank you for letting us be a part of your wedding weekend!Benjamin · Married on 09/03/2017
Best venue and innkeepers/hosts EVER!!! The innkeepers Josh and Ann are amazing - were attentive to all of our and our guests needs and made everything flow with ease. In addition they are so friendly and kind; I feel like they are now part of the family. The venue is gorgeous, inviting, cozy, unpretentious, and everything we wanted for our weekend. The ability to have the entire property for just our wedding guests was such a special thing. It helped make everyone feel at home so that we could just all have that much more fun. I can't say enough good things about this place and the innkeepers. Our decision to use this as our venue was easily the best decision we could have made. They suggested other amazing vendors and from there our whole affair came together perfectly. Five stars is not nearly enough!! If you are looking for a venue for 50-100 people look no further. I promise you will be thrilled with your choice.
Sent on 09/13/2017
The Trailside Inn's reply:
Thank you so much for the AMAZING review! It was such an honor to host your wedding and to be a part of your celebration. We appreciate all of the kind words about us and our property. Please come for a visit in the future!Francis · Married on 08/26/2017
Amazing! 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!
Sent on 11/04/2017
The Trailside Inn's reply:
It is almost your first anniversary and we are reminiscing fondly on your 2017 wedding weekend! It was so fantastic to have your event here at Trailside - it was a weekend we will never forget. We look forward to each and every one of your visits!Kristen · Married on 08/25/2017
The 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!
Sent on 10/26/2017
The Trailside Inn's reply:
It was SUCH a wonderful weekend!! It was a true pleasure to be able to host you both, along with family and friends. We are so grateful that you chose Trailside for your wedding venue. Thank you for allowing us to be a part of your celebration! We truly appreciate the review and thoughtful words. We hope that the end of summer treats you well & we look forward to seeing you again soon!Emma · Married on 07/29/2017
We had our wedding at the Trailside last weekend, and it was incredible! We live in Amsterdam but have family all over the world. Because we live far away from our friends and family, we really wanted a wedding that felt more like a family reunion, where the priority was spending time together with the people we love. The Trailside Inn was the perfect venue for us since everyone we invited (approx 75) could stay on-site in their beautiful inn. We had a BBQ welcome party on the deck/lawn on Friday night (including lawn games and bonfire), the ceremony by the brook and reception in the beautiful tent on Saturday, and a group brunch in the great room of the lodge on Sunday - everything on-site, meaning no shuffling people or having to deal with transportation logistics. On Saturday morning guests did activities in the area, such as hiking, biking, walking to a nearby waterfall, brewery tour, etc. Josh and Ann were the best sources of information when it came to things to do and took the time to chat with guests who needed suggestions. They were very responsive and helped us think through all the details, and are very well connected with the vendors in their area. During the weekend they were very hands-on, and went above and beyond our expectations in terms of making the setting look amazing, facilitating logistics, and making sure everyone had a wonderful time. All of the little things made such a difference - you forget how many details are involved in throwing a party, and without Josh and Ann we would have had to figure all of these out ourselves. There presence really made the difference between us running around stressed out and us enjoying every moment of the weekend. We were so impressed by their flexibility and willingness to help us create the wedding we were envisioning. I cannot speak highly enough of the two of them or of the venue, and hope that other couples are lucky enough to have their perfect wedding here as well!
Sent on 08/05/2017
The Trailside Inn's reply:
Words cannot express the gratitude that we feel towards both of you for choosing Trailside as your wedding venue and allowing us to be such a part of your celebration. It has been an amazing ride, getting to know you both, getting to know your families and being there for your weekend. Thank you for taking the time to write such a thoughtful review and to share your kind words. We are still celebrating with a few of our gifts - Stroop waffle and Hagelslag!Beth · Married on 07/29/2017
I don't even know where to begin. From start to finish everything about The Trailside Inn was perfect. Not only was the location breathtaking, but Josh and Ann's attention to every single detail allowed us, the parents, to enjoy every moment. This gift cannot be understated. Our guests had only rave reviews for both Trailside and for Josh and Ann. We couldnt' have been more pleased and grateful Thank you!
Sent on 10/24/2017
The Trailside Inn's reply:
It was such a pleasure to help you through our portion of the process, getting to know your family along the way. Everyone involved - the bride & groom, parents, other family, friends, vendors - worked so very hard toward a wonderful event...we are so happy that it all allowed you to enjoy yourselves!By clicking "Request pricing" I agree to sign up and accept WeddingWire's Terms of Use.
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