Downtown Woodstock Vermont destination wedding

With its green mountains, picturesque barns, quaint small towns, apple trees, maple syrup, cheese and craft beer, Vermont is everything you want a New England state to be. While most people consider a destination wedding in California or Mexico, there are plenty of other options. Why not opt for something a bit more off the beaten path like a small town all-American destination wedding in Vermont?

Late summer and early fall are the ideal times for a Vermont destination wedding. Woodstock, Vermont is the quintessential small town. It offers everything you need for a fun-filled destination wedding. Located just 2.5 hours from Boston's Logan Airport and New York's Albany Airport, Woodstock is a great destination for anyone living in the New England or New York areas.

Taftsville covered bridge woodstock vermont

Woodstock is full of shops, general stores and cafes. It is close to some great breweries, cheese farms and dozens of picturesque sightseeing spots, including those stunning barns and covered bridges that make Vermont so unique.

We have sampled the restaurants and explored the town and have put together what we think is the perfect destination wedding weekend itinerary in Woodstock, Vermont.

Here it is: 

Day 1: Arrival

A wedding weekend should last for no less than three days. With this length of time, your guests will have plenty of chances to see the town, try local restaurants, and explore in addition to taking part in the wedding activities. Out-of-town guests will arrive in Albany or Boston and then make the 2.5 hour journey to Woodstock, Vermont by car.

Vermont destination wedding views bridges

You can welcome your guests with a basket filled with local goodies like Vermont beers, apples, fruit spreads and snacks. Then, your guests can begin checking into the town's best accommodations, the Woodstock Inn.

Welcome baskcet Vermont destination wedding

The Inn's front lawn is the perfect place to host a welcome reception once everyone is settled in. The stunning space is ideal for mixing and mingling. Guests who arrive late can take part in the party before they check in. For refreshments, you can serve local craft beer and cider and offer tapas-like snacks such as a cheese and charcuterie spread.

Woodstock Inn Vermont wedding and event venue front lawn

Woodstock has plenty of great restaurants. You can suggest a few or just let your guests explore for the evening on their own.

Day 2: Explore, Taste and See

On the first full day, you can organize a tour in and around Woodstock so that your guests have a chance to see why you love Vermont.

Start off the morning with a visit to Billings Farm and Museum. Here you can tour the farm, hang out with the resident goats and take a stroll through the museum. After Billings, your group can make a stop at Sugarbush Farm for a cheese and maple syrup tasting. There are several historic barns and covered bridges between these two farms. 

Billings Farm and Museum Vermont Horses

billings farm woodstock vermont 3

Billings farm woodstock vermont 2

After the farm tours, it's time to head to Long Trail Brewery for lunch and beer tasting. You can plan to dine on the picnic tables overlooking the river. This is the perfect opportunity to let your guests fill up on pub fare and amazing local beer. After eating, they can explore the river. After the picnic, it will be time to head back to Woodstock for the afternoon. 

Long Trail Brewery Woodstock Vermont

Long trail brewery woodstock vermont wedding and event venue

The late afternoon is a good time to have the wedding rehearsal. Once the practice is finished, you can head over to enjoy a rehearsal dinner at Simon Pearce. You can take over the patio area for the meal. It is a good ideal to plan for an early dinner. If you can do this, your guests can take advantage of the views and explore the shop and glass blowing studio before it gets dark. Simon Pearce can accommodate large and small groups, making it a great option for a rehearsal dinner.

Simon Pearce Woodstock Vermont wedding event venue

Simon pearce woodstock vermont restaurant

After dinner, your party can head back to the Woodstock Inn. If your guests are not ready for bed, send them to the basement for an evening of video games, scrabble, checkers, skee-ball, and every other childhood game you can think of. The best part of the game room is that all the games are super sized!

Day 3: The Wedding Day at the Hewitt Hill Farm

Hewitt Hill Farm Woodstock Vermont Wedding Venue Barn 1

Begin the day by letting your wedding guests have a little free time.

Arrange for your bridal party to head over early to spend the morning on the Hewitt Hill Farm while they prepare for the big day. You can hire a shuttle to take your guests between Woodstock and the farm. The drive only takes about 15 minutes.

Hewitt Hill Farm Woodstock Vermont Wedding Venue Barn 2

Hewitt Hill Farm Woodstock Vermont Wedding Venue Barn

Plan for a ceremony under the apple tree with views of the lake. When the "I dos" have been said, you can host a cocktail hour on the estate's patio. This can be followed by a dinner and reception in Hewett Hill's barn.

You can keep the Vermont theme going by serving fresh pressed apples, bourbon in copper mugs, local craft beer and cider. Another only-in-Vermont option is an open-fire barbecue with cooked-to-order meats and vegetables. You can even serve apple pie that has been baked over an open flame.

Vermont Wedding and Event Venue Catering

After dinner, you can dance the night away under the stars!

Hewitt Hill Farm Woodstock Vermont Wedding event Venue Barn

The Details

Where to stay

Woodstock Inn- 150 rooms

Woodstock inn Vermont Wedding and Event Venue 2

The Woodstock Inn is a boutique inn with all the amenities of a five star resort. It offers a state of the art athletic center, a golf course, indoor and outdoor event facilities and a full service day spa. Despite all these features, it somehow manages to feel small and quaint. The Inn also has two restaurants, Richard's Tavern and Red Rooster. In addition, there is the Fairway Grill, which opens seasonally.

Hewitt Hill Farm- 11 Rooms, accommodates 28 guests

Hewitt Hill Farm estate Woodstock Vermont

Hewitt Hill Farm is located just 15 minutes from Downtown Woodstock in North Pomfret. Hewitt Hill is an exclusive-use farmhouse estate that has 11 bedrooms. In all, the property can host up to 28 guests. Hewitt Hill sits on over 100 acres of farmland. It features open lawn space, apple orchards, a lake and three barns.

Additional accommodations in Woodstock

506 on the River Inn

Jackson House Inn

Farmhouse at Robinson Farm

Where to eat

Simon Pearce

Simon Pearce Restaurant and bar vermont

For lunch, a visit to the Simon Pearce factory is a must. Sit out on the enclosed patio overlooking the covered bridge and dam. Enjoy a sampling of local cheese and a signature cocktail. After lunch, stroll the shop, where you can buy everything from glassware to farmhouse pottery.

Worthy Kitchen

Worthy Kitchen Woodstock Vermont

For beer lovers and farm-to-fork enthusiasts, Worthy Kitchen is THE place right now in Woodstock. Ask any local where to eat and the response will almost always be “Worthy Kitchen.” This restaurant has over 20 local craft beers on tap. The menu changes based on what is fresh. The options are posted daily on a chalkboard. 

Richard's Tavern

image provided by Woodstock Inn

image provided by Woodstock Inn

For a real tavern-style meal head to Richard's Tavern at the Woodstock Inn. The dark wood beams, low ceilings, large leather chairs, cozy wood bar, and dim lighting makes for a perfect casual-yet-intimate setting. While the hotel may advertise Richard's Tavern as "casual pub fare," you might find that "casual" is an understatement. We noshed on a delicious seafood stew, lobster Cobb salad and a swordfish appetizer. All these dishes were worthy of a five star restaurant.

What to do

Cheese Tasting

Vermont Cheese Woodstock Destination Wedding Weekend

Everywhere you turn in Vermont, you will see signs for cheese tasting. Here are a few of our favorite cheese farms near Woodstock, Vermont.

Plymouth Cheese

Sugar Bush Farm

Vermont Farmstead Cheese

Cabot Cheese

Brewery and distillery tours and tastings

Long trail brewery beer tasting wedding and event venue

While most of the breweries are about an hour north of Woodstock, the trip is well worth it. 

Long Trail Brewery

Harpoon Brewery

Worthy Kitchen (restaurant with over 20 local beers on tap)

Vermont Spirits Distilling Co.

Silo Vodka Distillery

Billings Farm & Museum

Billings Farm Woodstock Vermont

Billings Farm is a historic dairy farm and museum that will transport you back into time. Tour and explore the farm and spend time with the sheep, horses and other livestock.

Where to shop

Simon Pearce quechee vermont shopping

General stores

General stores seem to be on every corner in Vermont. They are the best places to snag local goods like maple syrup, beer, moonshine, mustard, pickles, cheese and anything else made and packaged in Vermont. 

Woodstock Farmers Market

A local market that has a great selection of local favorites.

Farmhouse Pottery

If you have a love for beautiful things, especially pottery, then a stop at Farmhouse Pottery is a must.

Simon Pearce

Simon Pearce is the place to go for all things glass. Everything sold here is hand blown onsite.

Simon Pearce Glass Vermont

Woodstock and the surrounding areas are perfect for a destination wedding weekend. 

Have any local insight on Woodstock, Vermont or another similar wedding weekend destination? We want to hear about it!!