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Vermont Road Trip Ideas – Things to Do Around Woodstock, VT

Woodstock, Vermont is a popular destination for tourists to visit, year-round. The downtown’s quaint charm and historic buildings are what you’d envision for a New England town with lots of local shops and restaurants.

The surrounding area offers plenty of options for outdoor recreation along with other interesting and fun places.

I’m sharing more about the top things to do in Woodstock, Vermont during your next road trip in Vermont.

Woodstock is home to Marsh-Billings-Rockefeller National Historical Park, the only national park in Vermont. Woodstock also has three historic covered bridges. 

Farmhouse Pottery in Vermont

Find a One-of-a-Kind Piece at Farmhouse Pottery

1837 W Woodstock Rd, Woodstock, VT 

You can shop for one-of-a-kind handcrafted pottery, apparel, and decor at Farmhouse Pottery.

Farmhouse Pottery in Vermont

If you’re flying back home there is also an online store if you’re concerned about traveling with your purchases.

Farmhouse Pottery in Vermont

Look for their “Seconds and Sale collection” for additional savings on handcrafted products that are last-chance offers or apprentice-made pots.

Farmhouse Pottery in Vermont

Inside the store, shoppers can watch the Master Potters at work from a large viewing window.

Farmhouse Pottery in Vermont

Farmhouse Pottery offers pottery workshops where beginners and seasoned artists can learn more about the craft through hands-on instruction to create a one-of-a-kind piece of pottery.

Billings Farm and Museum in Vermont

Visit Billings Farm & Museum

69 Old River Rd, Woodstock, VT

(Check their website for hours of operation)

Billings Farm & Museum is an outdoor history museum where guests can learn more about what farming was like during the 1890s.

Animal lovers will enjoy visiting the farm animals in the historic barns.

Highlights of the property include:

  • Heifer and Cow Barn
  • Draft Animal Barn
  • Cow Barn
  • Chicken Barn
  • Education Barn
  • Small Animal Barn
  • Farm Life Exhibits
  • “A Place in the Land” is a 32-minute film about Billings Farm & Museum and the adjoining Marsh-Billings-Rockefeller National Historical Park.
  • Icehouse
  • Farmhouse Cafe
  • Walking Trail
  • Farm Manager’s House
  • Garden Shed
  • Sunflower House
  • Production Gardens

Public Wagon Rides are included with admission and available seasonally on select dates.

Marsh-Billings-Rockefeller National Historical Park

Explore Marsh-Billings-Rockefeller National Historical Park

69 Old River Rd, Woodstock, VT (Park at Billings Farm & Museum)

The Marsh-Billings-Rockefeller National Historical Park walking entrance is across the street from the Billings Farm & Museum.

The historical park has the boyhood home of one of America’s first conservationists, George Perkins Marsh.

The home was later owned by Frederick Billings, a successful lawyer and businessman, who was also passionate about conservation.

Mary F. Rockefeller (Billing’s granddaughter) and her husband Laurance S. Rockefeller gave the property to be used as a National Historic Park on August 26, 1992.

The National Historic Park has 20 miles of trails and carriage roads open from dawn until dusk for hiking and equestrian use.

Mount Tom in Woodstock Vermont

Hike Mount Tom and The Pogue

69 Old River Rd, Woodstock, VT (Park at Billings Farm & Museum)

Mount Tom is part of 550 acres of the oldest professionally managed forest in the United States.

The peak at Mount Tom stands at 1357 feet.

map of Mount Tom in Woodstock Vermont

I recommend taking a picture of the map to use as a reference for the trails.

There aren’t many signs on the trails that provide an overview of the area to help you identify where you’re at within the park.

It can be a bit challenging to figure out your bearings without a map.

hikers at Mount Tom in Woodstock Vermont

The carriage trails are wide and have a gradual incline.

Mount Tom in Woodstock Vermont

Once you’re at the top of the carriage trail, you’ll be rewarded with scenic views of Pogue Lake, which has hiking trails around the perimeter.

Mount Tom in Woodstock Vermont

Dress in layers for the hike. Especially if you’re visiting in the fall.

hikers at Mount Tom in Woodstock Vermont

We carried our coats on our way up the carriage trail because we warmed up quickly.

hikers at Mount Tom in Woodstock Vermont

On the way back down we were grateful for our raincoats.

Woodstock Vermont

Explore Woodstock Village

Woodstock Village has a variety of local shops to check out.

store in Woodstock Vermont

You’ll find boutiques that sell apparel, art, decor, sporting goods, jewelry, gifts, and more.

Vermont Flannel Co. in Woodstock Vermont

The Vermont Flannel Company, an American company established in 1991, is a popular option if you’re looking for a new handcrafted flannel.

 Woodstock Vermont

Downtown also has interesting architecture and scenic spots for photo ops.

Woodstock Vermont

Many buildings in town date back to the late 1800s.

 Woodstock Town Smiler in Woodstock Vermont

Admire the Art on the Woodstock Town Smiler

 6 Elm St, Woodstock, VT

Be on the lookout for the Woodstock Town Smiler chalkboard featuring beautiful art.

 Woodstock Vermont

Parking in Historic Downtown Woodstock

Depending on when you visit, parking could be more limited.

Six-hour metered and kiosk parking is available in Woodstock Village Monday through Saturday, 10 AM –4 PM.

The parking meters accept coins, credit cards, and the ParkMobile App.

There is free parking at Woodstock Village on Sundays, and most holidays, north of the Green on Elm Street and off Pleasant Street, west of Town Hall, or at the elementary school on weekends only.

Covered bridge in Woodstock Vermont

View the Covered Bridges in Woodstock, VT

There are 100+ covered bridges in Vermont.

Woodstock has four covered bridges that go over the Ottauquechee River.

  • Lincoln Covered Bridge – 530 US-4, Woodstock, VT 
  • Middle Covered Bridge – Mountain Ave, Woodstock, VT
  • Taftsville Covered Bridge – Covered Bridge Road, Woodstock VT ( off Route 4)
  • Quechee Covered Bridge – 4, Waterman Hill Rd, Quechee, VT
Sugarbush Farms Woodstock Vermont

Sample Vermont-Made Products at Sugarbush Farms

591 Sugarbush Farm Rd, Woodstock, VT

Sugarbush Farm is a 550-acre hillside farm in central Vermont that’s home to the second, third, and fourth generations of the Luce family.

Sugarbush Farms in Vermont

The farm was bought by Jack and Marion Ayres in 1945, and today, it’s run by their daughter and her family.

This was the first farm in Vermont to start packaging cheese in waxed bars. The waxed bars made it easier to transport the cheese without refrigeration.

cheese sample at Sugarbush Farms Woodstock Vermont

You’ll want to try both the cheese and maple syrup samples. Their original Natural Smoked Cheese is very popular.

The cheese is smoked with Hickory and Maple wood chips in their farm smokehouse for three days, with no artificial smoke flavor added.

Sugarbush Farms Woodstock Vermont

Inside the Sugarhouse you can learn more about the maple syrup-making process.

Sugarbush Farms Woodstock Vermont

Did you know that it takes four maple trees all season to make one gallon of pure maple syrup?!!

With that knowledge, it’s easier to understand why the price of 100% pure maple syrup is higher than other low-quality syrup products you find at the grocery.

syrup sample at Sugarbush Farms Woodstock Vermont

Their Amber maple syrup flavor was my favorite during our maple syrup sampling.

maple syrup from Sugarbush Farm

They also have a nice sampler kit that makes a great gift or souvenir from your visit.

Sugarbush Farms in Vermont

During the warmer months, a few farm animals are at the farm, and a playground is near the parking area and a hiking trailhead.

Simon Pearce

Artisan Glassmaking at Simon Pearce

1760 Quechee Main St, Quechee, VT (14 minutes from Woodstock, VT)

Simon Pearce glassware

Simon began apprenticing in his father’s pottery studio in Ireland at age 16 and later learned from glassmakers all over Europe.

He founded a studio in Ireland in 1971 and moved his studio to the historic woolen mill in Vermont in 1981.

Simon Pearce in Vermont

The showroom displays beautiful pieces that are functional works of art.

There are now twelve Simon Pearce stores across the United States and their products can also be found in 400+ retailers.

Simon Pearce Restaurant in Vermont

Dine Near a Waterfall at Simon Pearce Restaurant

1760 Quechee Main Street, Quechee, Vermont

(Open for reservations Wednesday- Sunday)

Simon Pearce Restaurant serves local American cuisine made with local ingredients. The restaurant has been voted one of “America’s Most Romantic Restaurants.”

Patrons at the restaurant can enjoy views of the Ottauquechee River waterfall and covered bridge. 

This is a popular restaurant and you need an advanced reservation for your desired date/ time.

glassblower at Simon Pearce

Watch Artisans in Action at Simon Pearce

You can observe glassblowing artisans in action on the lower level of Simon Pearce.

glassblower at Simon Pearce

After watching the glass that’s transformed into a beautiful piece, you’ll have an even greater appreciation of their craftsmanship.

Quechee Covered Bridge in Vermont

Admire Quechee Covered Bridge

4, Waterman Hill Rd, Quechee, VT (14 minutes from Woodstock, VT)

scenic view from Simon Pearce

The lower level of Simon Pearce also has an outside observation area that provides another perspective of the Quechee Covered Bridge and Ottauquechee River waterfall.

scenic view by the Quechee Covered Bridge in Vermont

There is parking near the opposite side of the covered bridge for another vantage point.

110 Grill New Hampshire

Cross State Lines to Dine at 110 Grill West Lebanon

250 N Plainfield Rd, West Lebanon, NH

110 Grill offers “Modern American Cuisine, in a Trendy Casual Atmosphere” and has several locations throughout New England.

We learned the hard way that most restaurants in Vermont need advanced reservations.

An employee at Sugarbush Farms told me that many locals drive to New Hampshire for more dining options.

sandwich at 110 Grill New Hampshire

Here are a few recommendations from our visit.

Hot Honey Chicken Sandwich: chicken breast brined in pickle juice, deep fried in cajun-seasoned flour, shredded lettuce, and pickle chips on a griddled bun, topped with hot honey.

fish and chips at 110 Grill New Hampshire

Fish & Chips: North Atlantic cod, fried in seasoned flour and served with French Fries, tartar sauce, and coleslaw.

Reuben sandwich at 110 Grill New Hampshire

110 Reuben: Certified Angus Corned Beef® with Swiss and sauerkraut, topped with their special dressing on griddled marble rye.

Harpoon Brewery Taproom and Beer Garden in Vermont

Local Brews at Harpoon Brewery Taproom and Beer Garden

336 Ruth Carney Drive, Windsor, VT (24 minutes from Woodstock, VT)

Harpoon Brewery Taproom and Beer Garden is a great place to go for craft beer and American fare.

I tried one of their local ciders and everyone else at our table ordered their preferred craft beer.

If you happen to order the UFO beer, it’s fun to watch the blueberries as they float up and down the glass.

Harpoon Brewery Taproom and Beer Garden in Vermont

There is indoor dining and an outdoor patio and I’d recommend making a reservation ahead of time if possible.

burger at Harpoon Brewery Taproom and Beer Garden in Vermont

The Vermont Wagyu burger was the favorite menu item at our table.

It’s made with 100% pure wagyu beef cooked to order and served on Martin’s potato roll, iceberg lettuce, tomato, and their signature fry sauce.

sandwich at Harpoon Brewery Taproom and Beer Garden in Vermont

I tried the “Locals Only! Turkey Sandwich” with sweet potato waffle fries.

The sandwich is made with roasted turkey, a spread of Blake Hill Preserves Rhubarb with Dandelion and honey jam swirled with VT creamery goat cheese, mixed greens, red onion, bacon, roasted tomato aioli, and sliced apple served on King Arthur Baking Co bread.

I requested Alexe’s chili oil aioli to dip my fries in and couldn’t get enough of it! If you’re a fry dipper I recommend ordering this sauce for your fries.

playground near Harpoon Brewery in Vermont

If you’re visiting with kids there is a playground nearby where they can burn off extra energy.

Blake Hill Speciality Preserves Shop

Sample Jam at Blake Hill Preserves Speciality Shop

60 Artisans Way, Windsor, VT ( 24 minutes from Woodstock, VT)

Speaking of Blake Hill Preserves, you can sample and purchase an assortment of jam flavors from their store conveniently across the parking lot from the brewery.

Blake Hill Speciality Preserves Shop

The hardest part may be narrowing down your favorite sweet, savory, and spicy jams. The jams are always gluten-free and natural too.

SILO Distillery in Vermont

Sample Craft Spirits at SILO Distillery

3 Artisans Way, Windsor, VT (24 minutes from Woodstock, VT)

SILO Distillery takes pride in producing a local product that goes from farm to barn to bottle.

SILO Distillery in Vermont

The grain comes from Grembowicz Farm in North Clarendon, Vermont and everything is done at their barn distillery from start to finish.

The artisanal craft spirits are made with local and natural ingredients.

SILO Distillery in Vermont

Their cucumber vodka and maple-flavored whiskey were our favorites.

Great River Outfitters in Vermont

Get on the Water With Great River Outfitters

36 Park Rd; Windsor, Vermont

(Their season is from Memorial Day to Indigenous Peoples Day [Columbus Day])

If you want to connect with nature on the Connecticut River, Great River Outfitters offers rentals for canoes, kayaks, SUP boards, rafts & river tube float trips, and camping.

This outfitter is located within walking distance of the brewery and the distillery.

trail to Thundering Brook Falls in Vermont

A Short Scenic Hike to Thundering Falls

2295 River Rd Fork, Killington, VT (28 minutes from Woodstock, VT)

map for Thundering Brook Falls in Vermont

The Thundering Brook Falls hiking trail is a .5 mile out and back that takes an average of 11 minutes to complete according to AllTrails.

view from trail to Thundering Brook Falls in Vermont

This is an easy waterfall to hike to, even in the rain.

view from trail to Thundering Brook Falls in Vermont

Most of the hiking trail to the waterfall is on the scenic boardwalk followed by a short dirt trail that weaves over to the waterfall viewing area.

 trail to Thundering Brook Falls in Vermont

The best times to visit the waterfall are through the months of March-October.

 Thundering Brook Falls in Vermont

The observation platform allows you to safely view the waterfall as you glance above and below.

 Thundering Brook Falls in Vermont

Thundering Brook Falls is the sixth largest waterfall in Vermont at 140 feet tall.

The hiking trail also connects to the Appalachian Trail if you want to continue your hiking journey.

Killington Ski Resort in Vermont

Visit Killington Ski Resort

3861 Killington Road, Killington, VT (21 minutes from Woodstock, VT)

Killington Ski Resort has bragging rights as the largest ski resort in the eastern United States with nearly 2000 skiable acres and is home to the largest vertical drop in New England at 3,050 feet.

The ski resort also offers snow tubing and scenic winter gondola rides to experience scenic mountain views for non-skiers and snowboarders.

During the off-season, there is a Summer Adventure Center, golf course, and bike park.

view from top of the Okemo Fire Tower Ludlow VT

Additional Adventures in Vermont

creek by vacation rental at The Mill Ludlow VT

Where We Stayed in Vermont

We stayed in a 3-bedroom vacation rental in a condo in a historic building in downtown Ludlow. Our vacation rental was a great base for mini road trips while exploring Vermont.

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