Events

The Trailside Inn is perfect for Vermont weddings, groups, reunions, and corporate retreats. The intimacy of our spaces and the exclusivity of our property make for a unique, memorable experience for the group that we host. We would love to work with you to make the very most of your time in Killington! 

Interested in learning more?  Visit our WEDDINGS and GROUPS pages!

Brianna

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 I planned a summer offsite for our company, but we wanted spouse and kids to be able to come out for the weekend prior to doing work stuff during the following week. We had a big group and a variety of ages and interests. Josh did a great job helping us plan a fun weekend of activities for the kids, teenagers and adults; a hike up the Green Mountain Trail, a Wilderness Survival Class for the Kids, day at Okemo Adventure Resort, pizza at Ramunto's, tour of the Plymouth Cheese Company, paddle-boarding and kayaking on the lake. Everyone had a great time! Josh also helped us plan the corporate activities which included an evening trip to the Long Trail Brewing Company along with a great dinner at a local restaurant one night, a day of caving and repelling for our team-building event. He connected us to a caterer who delivered lunch and dinner every night, the food was great even though we were high-maintenance with regard to the food; vegetarians, egg and shellfish allergies and gluten-free being part of the requirements for every meal. The hotel was clean and very nice, rustic with a modern cabin feel - it's a really great place. Beautiful surroundings, peaceful and lots of fun stuff to do. Josh and Ann were always available and took great care of us. They are awesome people - it was the best offsite we've had yet. Would definitely go back but when it's snowing so we can hit the slopes!

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​This was a PERFECT venue for a wedding! The inn is beautiful, located in a gorgeous setting surrounded by forests and mountains. The ceremony was held along a babbling brook - couldn't have asked for a more picturesque spot! In addition to the venue itself, Josh an Ann, the Innkeepers were incredibly accommodating, kind and caring. They went above and beyond to make every detail of the weekend perfect. It was immediately apparent that they care deeply about their guests, and understand how a personalized touch can make an entire wedding experience feel even more special and intimate. Kudos to Josh, Ann and the Trailside Inn! I couldn't recommend a wedding venue more highly.

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David

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Awesome corporate retreat! ​Thanks to Josh and Ann, they did everything they could to welcome our group and ensure that our three day event event was a success. The Trailside Inn rooms were great, and the meeting facilities and common areas were clean and comfortable. This is a great place to stay and perfect to host large groups, we will definitely be coming back again.

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​​My friends and I have been staying here a few years now and Josh is always extremely helpful when booking our group. He's responsive on email and always works hard to find the best of everything, food, activities and more. Ann is super nice too and is always there to help. I love this place and the beard that goes with it!

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Great place and even better service! If you want to deal with owners who truly care about their guests, then this is the place to stay. Only stayed one night while setting up a large group outing in a month and Josh was great in helping us plan our itinerary as well as meeting all of our needs. Cant wait to go back in October and experience what Vermont is all about!

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​What a very special place to lay your head down and convenient location to go out and enjoy the fabulous surroundings. The owners Ann and Josh are very special people and devoted innkeepers along with their lovely children. Our stay at Trailside Inn was with 30-40 of our dearest family, friends and co-workers for our sons wedding. We stayed at the Inn for three nights and it's a great place for all of us to get together and be in one place the days before the wedding. The rooms are clean, private and very comfortable as well as the large, friendly and comfortable common area where we all gathered each day. On a scale of 1-10 I would rate the Inn and our stay a 20. I can't say enough about Ann and Josh and their warm hospitality.

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I've stayed at Trailside Inn before and was excited to hear that they were able to accommodate our group. Once again, I wasn't disappointed. The best part of the stay was being able to use the communal lounge, living room and fireplace. Not needing to search for a place for our large group to meet and hang out simplified the whole vacation and allowed me to relax rather then play travel coordinator. Thanks again!

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Amazing stay! I stayed at the Trailside Inn while in Vermont for a snowshoe race. It was a great experience! The hospitality from the innkeepers was incredible and the atmosphere is so friendly and inviting. The great room has a fire going for all the guests to congregate around after a long day out enjoying the Vermont snow. The place was very clean and the room was comfortable. I would highly recommend this to anyone looking to stay in the Killington area!

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The Trailside Inn is fantastic! We are having our wedding guests stay here when I get married in October. I stayed there this past weekend and it is very quiet and comfortable. The owners really encourage you to do activities outside and have great tips for hiking, biking, and skiing trails! They are amazing people and I would recommend it to anyone looking for a quiet, scenic, secluded, fun and active weekend.

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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, and our 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 couldn't have been more pleased and grateful, thank you!

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