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x5 Couples' Choice Awards

Won the Couples' Choice Awards thanks to recommendations from couples on Weddingwire.com.
  • 2023
  • 2022
  • 2020
  • 2019
  • 2018

The Trailside Inn

Up to 150 guests
Availability
Responds within 24 hours

Highly recommended

Pricing Information

These prices are available for the months of June through October. These prices are available for the months of June through October.
Reception
$3,750 starting price
Reception
$3,750 starting price

Do you want more pricing details?

About

On WeddingWire since 2016

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

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
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40 Reviews

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

66 User photos

  • Emily
    Emily H. Married on 10/08/2022
    5 out of 5 rating
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    Amazing Vermont Wedding Venue

    Trailside Inn was the perfect place for us to have our wedding and our wedding was beyond anything that we could have imagined. Josh and Ann sell the idea of a wedding weekend, and we got just that. Three full days spent alongside our family and friends and it was truly a magical experience.

    Our dream wedding was to get married in Vermont, and spend the weekend alongside our family and most of our guest list. Around 85% of the guests ended up staying at Trailside with us. It gave us significantly more time with all of our guests and also allowed the guests to meet and get to know each other, which made our wedding weekend even that much more special. Trailside also allows guests to check in on Thursday night, which close to half of our guests chose to do, allowing us even more time to spend with our family and friends, while also allowing our guests the opportunity to explore Vermont and sightsee without having to feel rushed to get back for wedding events.

    According to the guests, the overwhelming sentiment about the room accommodations were great. The rooms were the perfect mix of Vermont rustic charm, all while having the necessities to make a cozy weekend away. We didn’t have any issues with our lodging whatsoever, in large part due to the owners of Trailside, Josh & Ann. They were on top of everything.

    We booked Trailside about 14 months before our wedding date. From the initial meeting before we booked Trailside for our wedding, all the way through the end of our wedding weekend, Josh & Ann were extremely helpful and easy to work with. They know all the right questions to ask to make sure your day is what you want, and were also able to help us work through some nontraditional components to make sure everything ran smoothly. They know what they are doing and have their operation extremely dialed.

    We chose from a list of vendors they had previously worked with, and all of them were phenomenal. They have good working relationships with some truly great vendors, who just like Trailside have an extremely dialed operation. If they are available, we highly recommended sticking to the "Recommended Vendors" list as much as possible, because their prior experience at Trailside made our weekend run seamless.

    We highly recommend booking Trailside Inn for a wedding venue. Our weekend was perfect and we attribute most of that to Josh and Ann and Trailside Inn.

    The Trailside Inn's reply:

    The weekend wedding experience really is the best! It is such a great way to spend time with loved ones & not feel rushed. We are so glad that you got to experience that and enjoy yourselves! And yes - we are so fortunate to have an absolutely stellar bunch of vendors that we work with....truly the best. Congratulations and best wishes always to you both!!
  • K
    Kaitlyn S. Married on 10/01/2022
    5 out of 5 rating
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      5.0 out of 5 rating
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      5.0 out of 5 rating
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      5.0 out of 5 rating
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      5.0 out of 5 rating
    • Flexibility
      5.0 out of 5 rating

    Absolutely Amazing

    We just had our wedding at the Trailside Inn, and Ann and Josh were absolutely amazing. They’re LGBT friendly and made us feel welcome from the very first conversation. They were prepared for everything and anything, and helped us through every step of preparing for our big day! Their inn was located between both of our families and we loved the idea of having everyone in one location for the weekend. They have a list of vendors who they have vetted and know will do a great job. (Go with the taco truck!) The vibe at The Trailside Inn is amazing. Ann and Josh make you feel like a friend and they are there all weekend to ensure you are enjoying yourself and not stressing. Even our friends and family couldn’t stop saying how great the location, Josh & Ann, and the weekend were. If you’re looking for a place where you can relax and spend time with those you love most, then this is the place for you!

    The Trailside Inn's reply:

    We couldn't agree more - our vendors are amazing! Thank you for all of the beautiful words about them and us. We are so glad that everyone had an amazing time, especially the brides! It was our pleasure to have everyone for the weekend & we hope to see you again :)
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Awards

40
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

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

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

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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