February 15, 2021

Woodstock Inn Wedding Venue: Planner’s Ultimate Guide

If you’re planning a Vermont wedding, there is no better venue to bring your friends and family than the Woodstock Inn & Resort. Nestled in the heart of the Green Mountains in the cozy town of Woodstock, the resort is the perfect spot for your family and friends to celebrate together in one place. We love the area so much that we plan weddings in Woodstock 2-3 times per year. Here’s why it is such a magical New England destination.

Why are weddings at the Woodstock Inn & Resort so special, and why do you love working there?

Woodstock Inn weddings are special to us for so many reasons, but what we love most is that the Inn offers guests all of the charm and recreation of a small Vermont town, but with the amenities and hospitality of a classic luxury resort. And, since Woodstock is a small town, it feels as if your wedding celebration takes over the whole town for the weekend— in the absolute best way!

woodstock inn wedding invitations

The Woodstock Inn property is cozy, and convenient, and offers a chance for your guests to experience the best of Vermont with ease. You will instantly feel welcomed when you are greeted atop the sprawling outdoor stairs by the concierge who tends to your luggage with a smile. Upon entering the foyer, you are instantly warmed by a large fireplace and lounge. Grab a coffee and read, or belly up to the bar at the Red Rooster to plan your next adventure. The Inn’s concierge team is amazingly attentive and offers vast knowledge of the town’s must-see spots.

The Inn itself is located directly on bustling Main Street in Woodstock, which is filled with shops, restaurants, and cafes to explore including F.H. Gillingham & Sons General Store—a Woodstock favorite.


Plus the Inn boasts a variety of stunning guest rooms and suites, several different indoor and outdoor ceremony locations, a beautiful front garden for cocktails, the expansive South Garden for tented events up to 300, an outdoor fire pit, the light-filled Rockefeller Room for brunch, a lower level game room, a spa with outdoor saltwater pool and hot tub, and two restaurants onsite.

Guests have access to the Golf Club and are within close proximity to ski resorts including the resort’s own Suicide Six. Plus, the neighboring town of Quechee boasts attractions including the beautiful Quechee Gorge and Simon Pearce Restaurant & Mill.  Does a trip to Vermont get any better than this?

For what type of couple do you recommend a wedding at the Woodstock Inn?

The Woodstock Inn is ideal for the couple who wants their wedding to feel like an elevated family reunion in the mountains—a rejuvenating weekend for their friends and family to come together, explore and connect with each other, even outside of the planned wedding events. We truly love it when family members and friends meet for the first time at the couple’s rehearsal dinner, then bump into each other at the spa or on the golf course later in the weekend. By the end of the trip, it is as if they have known each other forever.

Woodstock Inn wedding party

The Woodstock Inn is an ideal spot for the nature-loving couple that does not want to bring guests to a place that feels too remote or isolated. Most couples who love the Woodstock Inn actually live in bigger cities, but enjoy getting outdoors as much as possible. Just two hours away from Boston, and 4-5 hours from NY and Philly, it is an easy destination without having to hop on a plane.

Vermont destination wedding welcome bag

Most of our couples who get married here also like to plan fun activities for their guests throughout the weekend, including fly-fishing, morning golf for the groomsmen, a trip to Farmhouse pottery, hiking, skiing or mountain biking, spa treatments or time at the pool. Plus, the surrounding downtown area is walkable for guests to grab a coffee, some local produce and Vermont-made cheese.

How can we utilize the entire property for a wedding at the Woodstock Inn?

The options are endless here, but they vary based on season and guest count. So, we will start with the option we utilize in the summer/early fall months.

In the summer/early fall, most of our clients opt to get married on property atop Kelly Way Garden for mountain views, or at nearby Billings Farm surrounded by expansive farmland.

Another option on property is in front of the classic white Paul Barn, a quintessential Vermont background. These spaces host anywhere from 150-250 guests. Note: if you are bringing guests to Kelly Way or Billings, we always provide shuttle transportation as this is not walkable.

the Paul Barn at the Woodstock Inn
the Paul Barn at the Woodstock Inn

Following the ceremony, we host a cocktail hour in the front lawn of the inn, allowing us to keep the tent in the South Garden a dramatic surprise.

grand entrance on front steps of Woodstock Inn

wedding cocktail hour on Woodstock Inn front lawn

For the reception, the South Garden allows for a tent of up to 300 people, and it’s a magical space for dinner and dancing.

In the colder months, we often use the Rockefeller Room for the ceremony, which is full of bright light and overlooks the South Garden. We then continue into cocktail hour in the Garden Terrace. And for the reception, guests can either move back to the Rockefeller Room (120 guests), or into the Woodstock Ballroom for a “chalet chic” vibe of up to 200 guests.

What is your rain plan at the Woodstock Inn?

When we’ve planned an outdoor ceremony, and the rain plan must take effect, we typically embrace the use of the Rockefeller Room for the ceremony and the Garden Terrace & Woodstock Ballroom for cocktail hour. We will remain in the tent for the reception, with heating and clear siding pulled down.

tent reception at Woodstock Inn

Luckily, the tent on the South Garden is just a few steps from the Garden Terrace, and our team and the concierge team will have umbrellas at the ready when it is time to move there for dinner and dancing!

Have you worked with the Woodstock Inn’s preferred vendors?

While the Woodstock Inn does not require couples to work with certain vendors, we are happy to share our experience with those we love to work with when we are planning a celebration here.

Woodstock Inn's front lawn during an event

A huge benefit of a wedding at the Inn is their in-house culinary team. All food and beverage is provided by the Inn, and the experience does not disappoint. Their menus are individually tailored to your liking and boast organic and locally grown produce —with sophisticated and elegant presentation.

The Inn provides classic linen, tables, chairs and place settings, which can be upgraded should you wish to do so.  Tenting is a breeze in the South Garden, and we always work with Rain or Shine for tenting, upgraded wood tables and chairs. There is no need for a restroom rental or generator rental here, as this is provided at the Inn.

What do you recommend for guest accommodations?

As for lodging, guests can stay onsite at the Inn (we typically contract a room block or full buy-out of the inn), or stay nearby. We often secure additional room blocks at The Shire Woodstock and 506 on the River. We suggest providing transportation to and from all hotels, or if your ceremony is at Billings Farm or Kelly Way. We use Vermont VIP concierge for this.

What are some Insider tips when planning an event at the Woodstock Inn?

A few little tidbits:

There are two lovely churches within walking distance to the Woodstock Inn. If you prefer to get married in a church, followed by a reception at the Inn, check out Our Lady of the Snows and St. James Episcopal Church, both just a stone’s throw away.

While you may want to stay on property for your wedding celebration, we suggest doing first look photos at the iconic covered bridge in Woodstock. Then, shuttle your wedding party over to Billings Farm or walk to Paul Barn for lovely wedding party pictures.

The in-house Pastry Chef at the Woodstock Inn is out of this world. Be sure to try their house-made rolls (we literally dream about them) and wedding cake, which are just as beautiful as tasty.

rustic luxury wedding in Vermont

Because events must end at 10 PM, most of our clients choose to host an afterparty. You can do so onsite in the Ballroom, or look off site at places including Tonic, a new restaurant downtown.


What is something you have not done at the Woodstock Inn but would love to?

With microweddings and small celebrations at the forefront, we would love to utilize the front lawn for a small, alfresco outdoor dinner.  We imagine bistro lights in the trees and a long table directly in the center of the lawn, with the beautiful facade of the inn as your background. Or, we could do this secluded near Paul Barn or high atop Kelly Way Gardens for a Napa feeling!

We also have not yet worked in the modern but rustic Red Barn at Kelly Way gardens, and would love to. It is ideal for a farm-to-table meal of 30-40 guests. We’d love to explore these intimate options with a couple looking for something small but remarkable.


Want to see a real wedding at the Woodstock Inn?  Click to see more photos and full video from Kirby & Patrick’s wedding at the Woodstock Inn.

Considering a New England destination wedding or a wedding at the Woodstock Inn?  Our team at Whim Events is ready to put our experience to work for you.  Find out more about our full service wedding planning and floral design.

Photos by Fat Orange Cat Studio

Woodstock Inn Wedding Venue at a Glance

Venue: Woodstock Inn & Resort
Address: 14 The Green, Woodstock, VT 05091
Phone: +18023326853
Website: https://www.woodstockinn.com/
Capacity: Up to 300 guests
Events: Ceremony, cocktail hour, reception, dinner and dancing