The Trailside Inn

"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!"

"Trailside Inn is a gem! We at Catering By Dale have truly enjoyed working with the owners, Ann & Josh as they are very serious about their business. They are the most professional, easy to work with, accommodating & kind venue owners and their attention to detail is that of a top notch wedding coordinator! They know their business and the devotion to it is always demonstrated by the seamless flow of each event. Team CBD returned last weekend glowing about the wedding they had just worked and how they LOVED the owners! We have more weddings there and can't wait! If you are looking to book an adorable venue, this is it!"

"What makes this venue stand out in my mind is the kindness and inclusivity of the staff and owners. The guests of the wedding I photographed were having the time of their life! I loved the game room for the guests to use while getting ready. The owners are super nice and accommodating as well. I can't wait to photograph another wedding there!"

"My experience with Trailside Inn was so delightful, I'm not even sure how to start describing it. In the summer of 2021 my (then) fiancé and I were somewhat frantically searching for a wedding venue. We wanted a place where we would be able to host most if not all of our family and friends because the most important thing was that we were able to relax and connect with our guests. It was on a rainy July day when we drove RT 100 to the Trailside Inn to meet with Josh and Ann. Even in with the dreary weather, the Inn stood out. Nestled in the woods, just down the road from Killington it had the perfect mix of Vermont beauty and solitude. The interior of the inn has been lovingly cared for by Josh and Ann and manages to be effortlessly cool. And then there was Josh and Ann themselves. They are so down to earth but obviously very capable and organized. We knew they would be a huge asset when it came to planning. And honestly, it lived up to our wildest dreams. Josh and Ann are super stars. They were so helpful every step of the way. Whether it was contacting a vendor or answering a question about "how is X typically done" I felt so confident that we had things under control because of them. The weekend itself was, if possible, even more relaxing. When we arrived on Thursday we unloaded food and decor and they just took it all and I didn't have to worry about it again. It left us so much more time to relax and be present. The inn itself was so perfectly charming. We were very fortunate with the weather and got to explore some of the local area but we also enjoyed hanging out in the common rooms for breakfast, after dinner games, and general socializing. We wanted together time, and we got it. If I were to do it over, I would get married at Trailside every time."

"Really beautiful place! The wood features in the room and throughout the venue is from an architectural dream! The staff was very friendly and were sure to help with any questions about the town and the scenic hikes! Definitely recommend to have an event here! Very accommodating and absolutely one of the wonders of the world! It was really great to sit outside and enjoy the nature during your morning coffee or laying under the stars in the crisp fall weather."