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Weddings

The Trailside Inn

Killington, VT View map Visit website
2022 Couples' Choice Awards Winner
Rating 5.0 out of 5
28 reviews
Up to 150 guests

About

2022 Couples' Choice Awards Winner
Up to 150 guests

A Few 2020 Dates are still available - Contact us today!

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.

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?

$3,750

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

$3,750

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

No

Which of the following are included in starting site fee?

Clean Up
Event Planning
Parking
Set Up

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

Cake Cutting

What is the maximum capacity of your venue?

150

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
Set Up
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

28 Reviews

Write a review
Rated
5.0
out of 5.0
Recommended by 100% of couples
  • Quality of service
    Rating 5 out of 5
  • Average response time
    Rating 5 out of 5
  • Professionalism
    Rating 5 out of 5
  • Value
    Rating 5 out of 5
  • Flexibility
    Rating 5 out of 5

53 User photos

  • Dominique
    Dominique P. Married on 10/09/2021
    Rating 5 out of 5
    • Quality of service
      Rating 5.0 out of 5
    • Responsiveness
      Rating 5.0 out of 5
    • Professionalism
      Rating 5.0 out of 5
    • Value
      Rating 5.0 out of 5
    • Flexibility
      Rating 5.0 out of 5

    Awesome people, beautiful venue

    I really can't think of anything the folks at The Trailside Inn could do to improve the wedding experience here. Ann and Josh were flexible, helpful, and great at communicating with us through a pandemic. We started planning our wedding in 2019 and like many others were not able to hold our wedding in 2020 but did have our party in 2021. Ann and Josh made the initial planning low stress and easy to navigate and managed to keep that vibe through to our wedding day itself. In short, they're incredibly easy to work with and very helpful. The venue is beautiful and awesome! The recent renovations to guest rooms and the game room turned out really well. The whole place has a rustic/hip (still modern and super clean) vibe. Our wedding took place at the beginning of October and the outdoor area where the ceremony was set up could not have worked out better. It's a really cool spot! Our families aren't from VT so an additional advantage to having our wedding at Trailside for the weekend was that our guests had the chance to explore the area. So, they all made the trip up for our wedding of course, but most guests turned the trip into even more of a weekend getaway than we planned it to be (which we all definitely needed after being locked down for so long). In short, the people are knowledgeable and helpful and the place is beautiful and fun!

    The Trailside Inn's reply:

    As much as working through a pandemic is just not ideal, we are truly grateful that it allowed us to work with our postponement couples for so long! This wedding was no exception. Thank you both for sticking through it with us, despite the surreal obstacles.

    The unique elements that you brought to this weekend made it so fun and funky and enjoyable! Your individual styles were woven in perfectly & we loved to see that come to life
  • Kristina
    Kristina C. Married on 08/28/2021
    Rating 5 out of 5
    • Quality of service
      Rating 5.0 out of 5
    • Responsiveness
      Rating 5.0 out of 5
    • Professionalism
      Rating 5.0 out of 5
    • Value
      Rating 5.0 out of 5
    • Flexibility
      Rating 5.0 out of 5

    Trailside Inn is the BEST!

    Wow! Trailside Inn offered everything we could have ever imagined in our wedding weekend and more! Josh and Ann, the owners of the Inn and the day-of wedding coordinators are total rock stars at what they do. As you plan your wedding, they will be by your side the whole way recommending vendors and fitting all of the details together. Then during the weekend, they make sure EVERYTHING happens without a hitch. They are so welcoming to all of the guests and make sure to be on a first name basis with all parents, aunts, uncles, and grandparents. Our guests raved about them and how well they complement their cozy, ski-themed inn! Unique wedding features that come with Trailside (most of which we didn’t even know we wanted until we saw them) include the Friday night welcome gathering for all guests to catch up and get to know new people, the Barn and Loft apartments for the wedding parties to stay in, the beautiful wooden altar for the ceremony, the tent on site for dinner and the party (!), and the game room in the basement for the after party! Trailside truly far exceeded our expectations and made our special weekend as perfect as we ever could have imagined. We cannot thank Josh and Ann enough! We 1,000% recommend Trailside for your wedding and can’t wait to get back this winter to ski Killington/Pico and relive our incredible memories! -Jeff and Kristina 8/28/21

    The Trailside Inn's reply:

    It was so fantastic working with you both! The love and organization that you put into planning your weekend really showed :) We are THRILLED that everything was just as you had hoped and that your guests felt welcomed

Awards

  • 28
  • WeddingWire Couples' Choice Awards 2022 Winner
  • WeddingWire Couples' Choice Awards 2020 Winner
  • WeddingWire Couples' Choice Awards 2019 Winner
  • WeddingWire Couples' Choice Awards 2018 Winner

Pricing

Team

Ann & Josh
Ann & Josh
Owners

With a passion for what we do and the utmost attention to detail, we are here to make you and your guests feel right at home throughout your event. We want to ensure that your wedding is all that you've envisioned and more!

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!

Map

115 Coffeehouse Road Killington, VT, 05751
8024228800
Location of (The Trailside Inn)

The Trailside Inn frequently asked questions

What items and services are included in the starting site fee at The Trailside Inn?

The Trailside Inn includes the following items and services for wedding events in its starting site fee:
  • Clean Up
  • Event Planning
  • Parking
  • Set Up

At The Trailside Inn, what items and services related to wedding catering are included in the cost?

The Trailside Inn includes the following items and services in its wedding catering costs:
  • Cake Cutting

What are the most important characteristics of The Trailside Inn in terms of venue type, style and location?

The space offered by The Trailside Inn for wedding events is known for:
  • Inn/B&B

What kind of indoor/outdoor options are available at The Trailside Inn for wedding events?

The Trailside Inn offers the following indoor/outdoor options for weddings:
  • Indoor
  • Covered Outdoor
  • Uncovered Outdoor

What kind of wedding events does The Trailside Inn offer?

The Trailside Inn offers the following types of wedding events:
  • Ceremony
  • Reception
  • Bridal Shower
  • Engagement Party
  • Rehearsal Dinner

What services does The Trailside Inn offer for wedding events?

The Trailside Inn offers the following services for wedding events:
  • Accommodations
  • Clean Up
  • Event Planner
  • Set Up
  • Wifi

What furniture and decorations does The Trailside Inn have available for wedding events?

The Trailside Inn offers the following furniture and decor items for weddings:
  • Audio Equipment
  • Dance Floor
  • Decor
  • Tents
  • Tent Accessories

What percentage of users recommend The Trailside Inn and which are the most valued aspects of their wedding services?

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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