A Few 2020 Dates are still available - Contact us today!
Weekend Wedding Package - From casual to elegant, they can help build your dream wedding and host your family and friends! Their wedding packages offer exclusive use of the property for your event. For the weekend, the entire property is yours and yours only.
Imagine a beautiful, outdoor ceremony held by their babbling brook. Their charming & cozy Great Room can be used for your rehearsal dinner, cocktail hour and reception. For larger events, they have an outdoor space with a reception tent. They also have backup rain locations in the main inn. Each wedding package is built per event, based on your vision and preferences. Your perfect Vermont wedding weekend includes a Friday night welcome party, Saturday ceremony & reception, and a Sunday morning brunch.
Facilities and Capacity
The venue can accommodate an event up to 120 guests and offers four event spaces for wedding ceremonies, receptions, bridal showers, rehearsal dinners, and engagement parties. The Great Room is ideal for rehearsal dinners, cocktail hours, and receptions. They provide a reception tent with lighting, barn wood bar and dance floor included in the venue fee.
The Trailside Inn provides event planning services to ensure that each couple's wedding day is covered from start to finish. Services offered include:
Venue and day of coordination services are included in the venue fee.
The Trailside Inn features a variety of room accommodations, sleeping up to 100 of your guests exclusively onsite. The comfort of their spaces and the private use of the property make for a unique and memorable experience for the groups that they host. Their lodging includes standard queen rooms, efficiency apartments, self-contained apartments, and bunk rooms.
The 2019 season is sold out. We are booking 2020 dates.
21 Reviews for The Trailside Inn
Recommended by 100% of couples
37 User photos
Jess Banks · Married on 12/10/2019
Best decision ever
My husband, Colin and I had our wedding at Trailside over the long weekend in October and we could not be happier with our decision! Trailside was the first venue we went to look at after getting engaged and after seeing the Inn and meeting with Josh and Ann, we knew instantly that Trailside was the place for us. We went to a few more places, just to be sure, but by the end of the weekend we had committed to our wedding date.Sent on 11/06/2019
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.
The Trailside Inn's reply: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 · Married on 09/21/2019
The best wedding weekend
Josh and Ann the owners of the Inn are amazing. They make sure your wedding is the most memorable day of your life, as it should be! They take care of everything the second you step through the door. They coordinate very well with all of their preferred vendors to make sure everything goes smoothly. Highly recommend Trailside! Our family and friends loved it as well!! Their social media page gives you great insight into their wedding weekends and vendors too!Sent on 10/08/2019
The Trailside Inn's reply: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 · 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.
The Trailside Inn's reply: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...
The Trailside Inn Price Rates