8 Reviews
Guest Capacity
Venue Setting

About The Trailside Inn

Perfect for Vermont Weekend Weddings, Vacations, Reunions, Retreats and More

From casual to elegant, they can help build your dream wedding and host your family and friends! Our 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 our babbling brook. Our 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 can include a Friday night welcome party, Saturday ceremony & reception, and a Sunday morning brunch. 

Facilities and Capacity
The venue can accommodate 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 with our venue fee.

Services Offered
The Trailside Inn provides event planning services to ensure that each couple's wedding day is covered from start to finish. Services offered include:

  • Accommodations
  • Event rentals
  • Catering
  • Set up
  • Clean up


The Trailside Inn also features a variety of room accommodations for couples and guests.  The comfort of our spaces and the exclusive use of our property make for an unique and memorable experience for the groups that we host. Their lodging includes standard queen rooms, efficiency apartments, self-contained apartments, and bunk rooms.

Categories: Wedding Venue

Regions serviced: Burlington

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8 Reviews for The Trailside Inn

out of 5.0
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Decor (2)
Photobooth (2)
Tent Accessories (2)
Tents (2)
Parking (2)
Indoor (1)
Covered Outdoor (1)
Liability Insurance (1)
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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 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!

View Vendor Response
Profile Picture Olivia, 8/4/18, 1 Review
Category: Ceremony & Reception Venue, Lighting & Decor, Party Supplies, Rehearsal Dinner Location, Wedding Planning

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!!

Photo of The Trailside Inn in Killington, VT
Photo of The Trailside Inn in Killington, VT
Photo of The Trailside Inn in Killington, VT
Photo of The Trailside Inn in Killington, VT
Photo of The Trailside Inn in Killington, VT
Photo of The Trailside Inn in Killington, VT
Photo of The Trailside Inn in Killington, VT
Photo of The Trailside Inn in Killington, VT
View Vendor Response
Profile Picture Melissa, 7/28/18, 1 Review
Category: Ceremony & Reception Venue, Event Rentals & Photobooths, Flowers, Rehearsal Dinner Location, Wedding Planning

The Trailside Inn Pricing

The Trailside Inn Price Rates

Reception Site Fee
Site Fees Include:
Clean Up
Event Planning
Set Up
Wedding Catering Avg. Price Per Person
Catering Prices Include:
Cake Cutting
Wedding Cake

The Trailside Inn FAQ

Venue Highlights
Maximum Capacity
Guest Minimum
Event Spaces
Destination, Private, Rustic/Country
Covered Outdoor, Indoor, Uncovered Outdoor
Peak Season Months:
Bridal Shower
Engagement Party
Rehearsal Dinner
Clean Up
Event Planning
Event Rentals
Liability Insurance
Set Up
All Inclusive Packages
Bridal Suite
In-House Bar
In-House Catering
Outside Vendors
Pet Friendly
Preferred Vendors Only
Wireless Internet
Aisle Markers
Aisle Runners
Audio Equipment
Chair Covers
Dance Floor
Tent Accessories
Chocolate Fountain
Wheelchair Access


72 Photos

My Photo Album

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Trailside - Property

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Professional Network & Endorsements

I recommend The Trailside Inn for any event

We love ann Ann and Josh, they always make our stay special! Trailside Inn is so cozy and relaxing, so much to do in the area, you'll never be disappointed!


115 Coffeehouse Road, Killington, VT 05751   See On Map
802-422-8800 (phone)