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The Trailside Inn
The Trailside Inn
Couple photoshoot
Couple photoshoot
Toast
Toast
Ceremony
Ceremony
First dance
First dance
Outdoor wedding setup
Outdoor wedding setup
Outdoor photoshoot
Outdoor photoshoot
Celebration
Celebration
Couple photoshoot
Couple photoshoot
Venue
Venue
Main course
Main course
Bonfire
Bonfire
First dance
First dance
Salad
Salad
Just married
Just married
Couple's portrait
Couple's portrait
Wedding vows
Wedding vows
Venue
Venue
Exterior
Exterior
The view
The view
Wedding
Wedding
The Trailside Inn
The Trailside Inn
The Trailside Inn
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The Trailside Inn

About

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.

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
  • Coordination
  • Event rentals
  • Catering
  • Set up
  • Clean up

Venue and day of coordination services are included in the venue fee.


Accommodations

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.

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Frequently asked questions

Do you have a site fee for wedding receptions at your venue?

Yes

What is the starting site fee for wedding receptions during peak season?

5,800

What is the starting site fee for wedding receptions during off-peak season?

5,800

Do you have a site fee for wedding ceremonies at your venue?

No

Which of the following are included in the starting site fee?

Clean Up
Event Planning
Parking
Set Up

Which of the following are included in the cost of wedding catering?

Cake Cutting

How many event spaces or rooms does your venue offer?

4

Describe your venue:

Inn/B&B

What kind of settings are available?

Indoor
Covered Outdoor
Uncovered Outdoor

Which of the following wedding events does your venue service?

Ceremony
Reception
Bridal Shower
Engagement Party
Rehearsal Dinner

What event services do you offer?

Accommodations
Clean Up
Event Planner
Wifi

What event items are available?

Audio Equipment
Dance Floor
Decor
Tents
Tent Accessories

What food and beverage items are available?

Barware
China
Chocolate Fountain
Flatware
Glassware
Linens

What transportation and access is available?

Parking
Wheelchair Access

What months are included in your peak season?

June
July
August
September
October

What months are included in your off-peak season?

June
July
August
September
October

Reviews of The Trailside Inn

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This AI-generated summary gives you a snapshot of the overall ratings and feedback from the reviews this vendor has received.

Review summary

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The Trailside Inn in Vermont is highly praised by multiple reviewers for being the perfect venue for a wedding weekend. Josh and Ann, the owners and wedding coordinators, are described as exceptional and go above and beyond in every aspect of wedding planning. Reviewers highlight the stress-free and fun planning process, the cozy ski lodge vibe, seamless execution of the event, and the beautiful photos taken on the stunning property. Guests appreciate the convenience of having everything in one location and the helpfulness of the staff throughout the weekend, making it a highly recommended choice for couples looking for an intimate and special wedding experience in Vermont.

Review summary

Powered by AI
This AI-generated summary gives you a snapshot of the overall ratings and feedback from the reviews this vendor has received.

The Trailside Inn in Vermont is highly praised by multiple reviewers for being the perfect venue for a wedding weekend. Josh and Ann, the owners and wedding coordinators, are described as exceptional and go above and beyond in every aspect of wedding planning. Reviewers highlight the stress-free and fun planning process, the cozy ski lodge vibe, seamless execution of the event, and the beautiful photos taken on the stunning property. Guests appreciate the convenience of having everything in one location and the helpfulness of the staff throughout the weekend, making it a highly recommended choice for couples looking for an intimate and special wedding experience in Vermont.

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Lauren
Lauren Sent on 10/04/2025
5 out of 5 rating

The Perfect Place

I had my wedding August 2, 2025 at The Trailside Inn and I could not have imagined a more perfect venue for our big day! From day one, working with Ann and Josh was so easy. They are quick with communication, kind people, and helpful through EVERY SINGLE part of the planning process. I really wanted a location where all of our guests could stay at one place, and Trailside was just that - hanging out all day, no driving anywhere, it was perfect. Parking, common spaces, outdoor patio, comfy beds.. it just felt like one big happy reunion of all our favorite people together. Josh was great with set up and patient with a few of my guests who ask way too many questions. Ann was so calm and wonderful doing so many behind the scenes tasks so I did not have to think about anything (that is in addition to all the coordination she did with vendors before the big day). Lastly, the PICTURES OMG. We got the hillside blue skies shots, we got forest woods shots, our wedding photos are just so amazing and we never had to leave Trailside’s property. If you want that perfect, outdoor, Vermont wedding without the hassle of being at a resort, and with the benefit of working directly with the owners who care so much about you and your memories THIS IS IT BOOK NOW!
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Lily Sent on 12/07/2025
5 out of 5 rating

Look no further

My husband and I got married at the Trailside Inn in August 2025 & it was the BEST decision we could've made - I cannot imagine having gotten married anywhere else. The Inn itself is the epitome of Vermont. Its cozy, inviting ski lodge vibe creates the most special & intimate place for you and your family & friends to enjoy for the entire weekend. The other real prize is Josh & Ann, the inn owners and wedding coordinators. They are truly the absolute best of the best in every way... down to earth, genuinely great people but also absolute masters at everything wedding. They will directly connect you with some of VT's most fantastic vendors, and are SO helpful throughout the entire planning process. You hear a lot about how stressful wedding planning can be, but with Josh and Ann's help it actually felt 0% stressful and 100% fun and exciting, as it should be. We feel so so lucky that we came across this very special Inn and had the pleasure of meeting and working with Josh and Ann. Our guests have had so many positive things to say about the weekend afterward... some may have even said it was the best wedding they've attended yet. We cannot recommend getting married here enough, so please look no further!!!!
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Anna Sent on 10/18/2025
5 out of 5 rating

Trailside is the best!

Where do we even start with praising Trailside and Josh and Ann? From our first visit, we knew that we were in good (and very seasoned) hands. They were there every step of the way, from answering all of my questions, to asking us questions we hadn’t even thought of, to communicating directly with so many vendors. Every vendor we chose only had incredible things to say about them, and it is clear why. Not only are they organized and professional, but they care about you and making your wedding perfect.

All of our guests are still talking about how incredible the weekend was and how much they loved Trailside. As a bride who had trouble delegating, my stress and anxiety melted away the minute we got to Trailside for the weekend. Josh and Ann made everything so simple and easy for us and handled every issue and detail and the weekend was perfect because of that.

It is clear how much Josh and Ann care about what they do and the people they work with. They go above and beyond and exceeded all expectations. We are so grateful to them for everything they did throughout the process but especially for our wedding weekend. Trailside will always have a special place in our hearts!
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Alyssa Sent on 09/17/2025
5 out of 5 rating

Amazing venue!

Josh and Ann and the Trailside Crew are truly incredible! All of our guests told us how much they adored the property. Josh, Ann and the crew all worked tirelessly all weekend to make sure everything was set up exactly as we envisioned and ensured everything went smoothly for our wedding. We truly couldn’t have asked for better people to support us through our wedding weekend! Josh and Ann were there with us through the entire planning process, offering their professional advice and making sure all the necessary details were given the attention needed. 
Kathryn
Kathryn Sent on 07/23/2025
5 out of 5 rating

Trailside Inn

We are so glad to have chosen Trailside for our wedding venue. It was lovely to have everyone in one location for the whole weekend and many of our guests commented on how nice it was to not have to worry about transportation between events. The owners, Josh and Ann, were incredibly helpful with managing vendors and implementing our vision for the weekend. They have been doing weddings for many years at this point (we were their 100th wedding!) and it shows. They have personal relationships with the local vendors and know all the potential hiccups that we never would have thought of on our own. We would 100% choose them again!
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Liz Sent on 07/20/2025
5 out of 5 rating

Best weekend ever

We can't say enough great things about Ann and Josh and the Trailside Inn. The venue was fantastic. We received so many compliments (and still are) about how wonderful the entire weekend was. Having everyone on site was a dream, especially considering most of our guests travelled a distance. The communal spaces were large and welcoming, allowing for plenty of space to socialize with our guests the entire weekend. The rooms were comfortable and clean. The surrounding area is beautiful and makes for amazing photo opportunities.

We received glowing feedback from every vendor we interacted with about how amazing Josh and Ann are, and after the weekend, we certainly know why. They were extremely professional and communicative, often responding within minutes of our many questions. They had a planning meeting with us several months in advance which was super helpful in terms of making decisions and feeling confident that things would run smoothly. We didn't hire a wedding planner and unsurprisingly have never planned a wedding before- this was no issue thanks to their tremendous help- they think of absolutely everything! It is clear they are passionate about this place, and we are so very grateful to them. Trailside and Killington will always be a special place to us.

P.S. for other wedding couples: we had rain nearly the entire wedding day, except a short 20-30 minute break. We were able to sneak out during the brief pause of rain and there were beautiful photo opportunities, just steps from the Inn. We ended up having the ceremony under the tent, and as you can see, we were situated in front of the opening, with the greenery and rain behind us, and it was beautiful! Not what we planned, but beautiful. Ann and Josh made a rainy day wedding go forward without a hitch.
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Kelsey Sent on 07/07/2025
5 out of 5 rating

Exactly what we envisioned

Ann and Josh and their family and staff were wonderful throughout the entire process. We wanted a place where we could spend the entire weekend celebrating with our family and friends and with close family member being in a wheelchair, finding the perfect place was a challenge and trailside inn checked all the boxes. From the first planning call knowing nothing about planning a wedding, we felt in good hands. They helped ensure our vendors were meeting requirements and the weekend of the wedding things could not have gone more smoothly because of them. We had so many family members remark it wad the best wedding they had been to. The backdrop of the Trailside Inn made it the most magical weekend and surpassed all of our expectations. Thank you Ann and Josh! If you are looking for a place where you can spend 3 days celebrating with your guests and enjoying the beauty of Vermont, choose the Trailside Inn.
Lindsay
Lindsay Sent on 09/28/2024
5 out of 5 rating

The best!!

I don’t even know if there are words to describe how incredible Josh and Ann and the Trailside inn are. We held our wedding at Trailside and cannot imagine doing it elsewhere. Our vision was to have everyone on the same property for the whole weekend, and watching families and friends intermingle, knowing they didn’t have to drive or travel, was amazing. Josh and Ann are extremely detail oriented, and truly know how to do weddings. They are super involved in the planning, as they help coordinate and personally know all of their preferred vendors, create timelines and spreadsheets for us, and give their two cents, which cut our stress and workload in half. They are so on the ball and have plans for every kind of scenario which made us feel so at ease. It was forecast to rain on/off on our wedding day (it didn’t), and they were fully prepared for whatever we wanted/what weather permitted. We ended up getting a beautiful day, which Josh fully predicted. Our guests absolutely loved being in one spot for the whole weekend and loved the feel of their rooms, which were clean and cozy, as well as everything the property had to offer. We are so grateful for their expertise, their extremely chill vibes, and their beautiful property. Endless thank you’s to Josh and Ann. They helped make it the best day of our lives.
photo creds @goldwingphotography
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Skylar
Skylar Sent on 09/24/2024
5 out of 5 rating

Best Venue

I cannot say enough positive things about my experience at trailside, and with Josh and Ann. They were calming, knowledgeable, and kind throughout the entire process. Their preferred vendor list was amazing, and we had many guests telling us that the food both nights was the best they had ever had at a wedding. We will be encouraging all of our friends to get married at Trailside. It was truly the best weekend of our lives and better then anything we could have imagined.
K
Kara Sent on 09/14/2024
5 out of 5 rating

Amazing and unforgettable wedding venue!

The Trailside Inn made our wedding day truly unforgettable. From the years of planning to the moment we arrived, Josh and Ann were so supportive and made the experience seamless. They helped to ensure our vision came to life, and we couldn't be more thankful! All of our guests raved about the inn, the florals, the food, and about the overall weekend experience. We felt so well taken care of, and it truly made the day and weekend stress-free and enjoyable for us. Would absolutely recommend The Trailside Inn to anyone looking for a magical weekend experience!
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Awards

62
WeddingWire Couples' Choice Awards 2026 Winner
WeddingWire Couples' Choice Awards 2024 Winner
WeddingWire Couples' Choice Awards 2023 Winner
WeddingWire Couples' Choice Awards 2022 Winner
WeddingWire Couples' Choice Awards 2020 Winner
WeddingWire Couples' Choice Awards 2019 Winner
WeddingWire Couples' Choice Awards 2018 Winner

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Professional Network & Endorsements

2 Endorsements
Barrie Fisher Photo Barrie Fisher Photo Wedding Photographers

I recommend The Trailside Inn for any event

Cronin Hill Photography Cronin Hill Photography Wedding Photographers

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!

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The Trailside Inn frequently asked questions

The Trailside Inn includes the following items and services for wedding events in its starting site fee:
  • Clean Up
  • Event Planning
  • Parking
  • Set Up
The Trailside Inn includes the following items and services in its wedding catering costs:
  • Cake Cutting
The space offered by The Trailside Inn for wedding events is known for:
  • Inn/B&B
The Trailside Inn offers the following indoor/outdoor options for weddings:
  • Indoor
  • Covered Outdoor
  • Uncovered Outdoor
The Trailside Inn offers the following types of wedding events:
  • Ceremony
  • Reception
  • Bridal Shower
  • Engagement Party
  • Rehearsal Dinner
The Trailside Inn offers the following services for wedding events:
  • Accommodations
  • Clean Up
  • Event Planner
  • Wifi
The Trailside Inn offers the following furniture and decor items for weddings:
  • Audio Equipment
  • Dance Floor
  • Decor
  • Tents
  • Tent Accessories
The Trailside Inn is recommended by 100% of couples who have used their services. Their overall rating is 5.0, with the same score awarded for quality of service, flexibility, value, professionalism and average response time.
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