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!

I currently just stayed at trailside inn for and overnight and it was very clean! The beds and sheets were comfortable as well. The drive to the mountain is only 8-10min depending on traffic. I would stay here in the future! Thank you!

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!

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.

Wonderful hosts, excellent location. Peaceful get-away with with plenty of things to do near by. Like covered bridges? Check. Like waterfalls? Check. Food? Hiking? Shopping? Check!!! A dream wedding location and again, the hosts, Josh and Ann, tend to every detail. Thank you for all you did to make my son and daughter-in-law's beautiful wedding weekend special.

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.

One of the best weekends of my life. Had a wedding here, and the owners went above and beyond to make sure everything was perfect.

If you're considering an event here, you should immeadiately choose Trailside for it. I could not possibly be happier with how everything turned out, and will make a point to return during ski season for more of the same environment.

When we were pulling in it was somewhat reminiscent of a scary movie or possibly a Stephen King novel, but then when we met the owners all of that somewhat went away. They were super welcoming and helpful. The scenery was amazing! I work too much so when I found no TV in the rooms it was refreshing. You can truly disconnect if you want! There were plenty of wifi connections so accessing anything was good. Pro tip, change the wifi connection to get the best service when moving through the Inn and grounds(not sure if that makes sense, but if you go and your internet isn’t working well use another one of their connections, these people rock and have 4-5 different wifi connections). Phone service on the other hand, not good, which brings me back to being able to truly disconnect. The owners recommended checking out the game room and I’m glad we did. There was a tv down there and you could watch tv, or better yet, play music through the cable music stations! They also have jumbo jenga, cornhole, jumbo connect 4, 2 foozball tables, a pool table, and a professional beer pong table(along with a few more things). I would stay here a thousand times over! They have some cool merch too!! My wife and I got two hoodie long sleeve tshirts. The decor is awesome, it’s very “elegant log cabinesque”. The floors are awesome, the tables are beautiful(made of humongous logs), and the shower was amazing(sad to say their water pressure and shower head I 10 times better than my own!). Thank you Josh and Ann!!! Hope to meet again!

I recently stayed at The Trailside Inn when I went up to Killington to Ski for the weekend, and I could not have been happier with my decision. Ann and Josh were so friendly and accommodating the entire trip, whether it was maintaining the breakfast bar every morning, or keeping the fire place going at night, their care and attention to details was not unnoticed. You really feel like you are staying at someone's house, but with the conveniences of a standard hotel. The Inn was spotless, and featured nice amenities like boot/ski warmers after skiing, a full breakfast, a game room with a pool table/ tons of board games, and a coffee/tea bar that was always available (and much welcomed) after a day of being in the cold. The rooms were clean and and cozy and were exactly what any skier needed after a day on the mountain. Overall, I loved staying at the Trailside Inn and will definitely be back in the future!

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 pushing you to do things 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, and active weekend.

Very enjoyable stay. The hosts are knowledgeable and happy to share recommendations for skiing, food, and other activities. Extremely family friendly. The rooms are tastefully done, quirky. There's always coffee brewed, and the common area is comfortable.

Absolutely wonderful Inn featuring very accommodating owners, helpful staff and comfortable surroundings. Toasty fireplace and a great breakfast too. We will definitely be going back!

The Trailside Inn was the perfect fit for our annual company ski trip. They have plenty of private rooms and beds. The common area with the massive fireplace is a perfect gathering area and the basement game room was great for late night fun which did not disturb anyone sleeping.

The Trailside Inn was great. The atmosphere had all the little touches we wanted in a Vermont experience. The innkeepers were very friendly and relaxed. When we left they had great suggestions for places to stop on the way home. The rooms did not have tv's, which was perfectly fine with us. The sitting area had a beautiful working fireplace. Very charming stay.

A great inn for a weekend getaway to Killington. Very homey feeling, the owners are friendly and the rooms feel clean and freshly renovated. The wood cabin type interiors are different from other hotels in a nice way. Common area is comfy for a seat by the fire at the end of the day. Would definitely return.

Fantastic, wonderful, magnificent place! Trailside Inn will always be our special place that fills our heart with love every time we visit. In July 2019 we had the perfect wedding and it is all thanks to Ann and Josh the fantastic owners. All of our family members have been raving about how unique and wondful our wedding was! ( Last two photos by Clove Hitch Photography)

Amenities galore. This place is the ideal location for a ski trip with your friends or family. When you pull up there is an overhang for unloading incase of heavy snow (or rain). (10) Complementary BOOT DRYERS. The great room is huge and is where the delicious free breakfast is served. Fire was roaring as soon as we arrived was going every day. The GAME ROOM in the basement was a huge bonus. I've never stayed somewhere that had this big of a game room with almost NO electronics. Great to see. Extra bathrooms throughout the Inn came in handy since I was sharing a room with 4 friends. Service with a smile, very clean and well thought-out decor made this trip an awesome visit to Vermont.

Went here for a wedding. The place itself was wonderful and cozy. The drive through Vermont to get to the place was wonderful. I would definitely recommend it, especially in the winter. Great place for a ski trip.

My go to recommendation for lodging in the greater Killington area! Freshly renovated rooms with a modern mountain feel and nod to their rustic past. The fireplace in the main lobby is amazing and the downstairs features a great common space with fun games for all ages. I've referred guests here for weddings, corporate retreats, ski and summer vacations. A family owned business with excellent inn keepers and attitude. They're always updating something so you'll feel confident your vacation will be great!

Location is a short drive from Killington & Pico Ski Resorts, walking distance from the Green Mountain National Golf Course (Top 3 course in the state of Vermont), and biking distance to the new Sherburne Trails which are ideal for family friendly cross country mountain biking. They're also a short drive from some of the best hiking trails in the state (Deer Leap, Green Mountain Trails and Appalachian & Long Trails) and small lakes in the area for kayaking and paddle boarding.

They have partnerships with local area shops for Rentals and Rental Delivery if your group wants to get outfitted for snow sports, cycling, or paddling equipment.

5-stars!