15 Most Beautiful Places In Woodstock, Vermont

Woodstock, Vermont, is a quintessential Northeast town. The 1880s pink sandstone Norman Williams Public Library is one of the historic buildings around the central area, known as the Green. Billings Farm & Museum, just north of town, is a working dairy farm with an 1890 home and exhibits depicting 19th-century farm life. Trails crisscross the Marsh-Billings-Rockefeller National Historical Park, which includes a Queen Anne–style mansion from the 1800s.

These are just a few of the many amazing places to see in Woodstock, Vermont. This blog post highlights 15 of the top sites to see and photograph in Woodstock, Vermont – the blog does include a few locations in Pomfret, Vermont, which is adjacent to Woodstock. Don’t miss out on seeing these places:

Billings Farm & Museum

  • Address: 69 Old River Rd, Woodstock, VT
  • Directions: Here

Billings Farm & Museum is located only a half-mile stroll from Woodstock’s village center and is considered one of the best outdoor history museums in the country. Billings Farm & Museum is dedicated to bringing education and entertainment to visitors of all ages by combining a fully operational Jersey dairy farm with educational exhibits, interactive programs, and events.

Cloudland Farm

  • Address: 1101 Cloudland Rd, Woodstock, VT
  • Directions: Here

Cloudland Farm is a diverse working farm that has been in the Emmons family since 1908. It is located in the pastoral hills of Pomfret, Vermont (just west of Woodstock). The four-mile trip up the picturesque Cloudland Road offers stunning views as part of the Cloudland experience. Black Angus cattle, laying hens, Cornish-cross meat chickens, turkeys, pastured Berkshire pigs, and a variety of vegetables are all raised/grown on the farm. The farm’s market sells items made on-site and in the surrounding area.

FH Gillingham & Sons

  • Address: 16 Elm St, Woodstock, VT
  • Directions: Here

F.H. Gillingham & Sons has been located at 16 Elm Street, Woodstock, Vermont for over 130 years. A visit to the store is a step back in time, where you will find traditional and latest products all in one place. There are also many historic archives throughout the store for visitors to learn more about the store, the town, and Vermont. The store is renowned throughout Woodstock and New England as it is a true Vermont general store experience.

First Congregational Church of Woodstock

  • Address: 36 Elm St, Woodstock, VT
  • Directions: Here

The First Congregational Church of Woodstock, Vermont is an active Congregational church in Woodstock, Vermont. The original building was constructed in 1807. Interestingly enough, the church acquired a bell produced by Paul Revere. The building was rebuilt in 1890 and it truly is a beautiful structure. Check it out right in Downtown Woodstock!

Five Elm Arches

  • Address: 304 Prosper Rd, Woodstock, VT
  • Directions: Here

Dan Ladd is the creator of the Five Elm Arhces on Prosper Road in Woodstock. Ladd is an artist who uses plants as his medium. He redirects nature in unique ways to create art and the Five Alm Arches are one of his most famous pieces.

Golden Cow Barn

  • Address: 738 Old River Rd, Woodstock, VT
  • Directions: Here

The Golden Cow Barn is a great barn to photograph when traveling outside downtown. The barn is well-maintained and is private. The plaque near the door states the barn was built in 1840.

Kelly Way Gardens

  • Address: 109 Kelly Way, Woodstock, VT
  • Directions: Here

Kelly Way Gardens is a farm-to-table program that was developed from the ground up to provide the Woodstock Inn & Resort with an on-site holistic food source. They focus on rare and heritage varieties. With with over 200 varieties of vegetables, 50 varieties of herbs and edible flowers, 75 varieties of berries and orchard plantings, and, a mushroom glen, the chefs at the Woodstock Inn always have fresh foods to use and be inspired by. In addition, the farm grows 200 different types of cut flowers which are put on display in the inn. Master gardener Benjamin Pauly tends to the 3-acre garden, which is harvested daily and given to the culinary staff while still warm from the sun.

Visitors of the farm are also able to sign up for Red Barn Dinners which are located right on the farm and feature Master Gardener Benjamin Pauly and Resort Executive Chef Rhys Lewis. Learn more at https://www.woodstockinn.com/do/things-to-do/red-barn-dinners

Marsh-Billings-Rockefeller National Historical Park

  • Address: 54 Elm St, Woodstock, VT
  • Directions: Here

The only national park in the United States dedicated to conservation history and the changing character of land stewardship is Marsh-Billings-Rockefeller National Historical Park in Woodstock.

The historic Marsh-Billings-Rockefeller property opened to the public in June 1998 as Vermont’s first national park. The park is named for George Perkins Marsh, one of the country’s first global environmental thinkers, who grew up on the property, and Frederick Billings, an early conservationist who established a progressive dairy farm and professionally managed forest on the former Marsh farm.

Visitors of the site can wander through one of Vermont’s most stunning settings, beneath the shadow of sugar maples and 400-year-old hemlocks, across covered bridges, and alongside rambling stone walls, in one of the state’s most picturesque environments. It is a landscape of extinction, rebirth, and preservation. The park is a tale of stewardship, of people caring for their surroundings, of people who share a deep connection to the land and a sense of optimism for the future.

Mount Tom

  • Address: Mount Tom Rd, Woodstock, VT
  • Directions: Here

Mount Tom is a modest peak in Woodstock that stands at 1357 feet. It is a part of the Marsh-Billings-Rockefeller National Historical Park. The peak has a multitude of hiking, running, and Nordic skiing trails, and has many sites dedicated to the national park. From Mount Tom, hikers will enjoy incredible panoramic views of Woodstock and beyond!

Norman Williams Public Library

  • Address: 10 The Green, Woodstock, VT 05091
  • Directions: Here

The Norman Williams Public Library in Woodstock, Vermont, is housed in a historic 1883 building that welcomes everyone through its doors. The library has a knowledgeable staff to help you explore their 55,000+ sources.

Sleepy Hollow Farm

  • Address: 3429 Cloudland Rd, Woodstock, VT
  • Directions: Here

Sleepy Hollow Farm has been in existence since the original Cape farmhouse was built in the late 1700’s. The 115-acre Sleepy Hollow Farm sits off Cloudland Road, a winding, narrow dirt road lined by thickets of maple trees and old farmhouses. It has become one of the most popular photo spots in Vermont and really shines when the leaves change. Head to the farm early if you visit in the fall because photographers and sightseers from all over seek out the farm.

Sugarbush Farm

  • Address: 591 Sugarbush Farm Rd, Woodstock, VT
  • Directions: Here

Sugarbush Farm is one of the most beautiful farms I have visited in Vermont. The farm is family-owned by the Luce Family and they have run the farm for 3 generations. Sugarbush Farm is notroious for its cheeses and pure maple syrups which are both made right at the farm.

In total, the farm spans about 500 acres and consists of many great sights. There is a small red covered bridge, farms animals, a small chapel, an operational sugar house, and a store.  Free admission and open year-round daily from 9-5. You can also purchase their products at https://sugarbushfarm.com/.

Taftsville Covered Bridge

  • Address: Covered Bridge Rd, Woodstock, VT
  • Directions: Here

Taftsville Covered Bridge is a must-see covered bridge in Vermont near downtown Woodstock, VT. The bridge is 189 feet long and cars are able to cross the bridge along with people. Taftsville covered bridge was built in 1836 to carry traffic over the Ottauquechee River. The bridge design features a two-span multiple kingpost truss with an arch.

Woodstock Inn

  • Address: 14 The Green, Woodstock, VT
  • Directions: Here

The Historic Woodstock Inn & Resort, located in the heart of Woodstock, Vermont, is a year-round resort that honors Laurance and Mary Rockefeller’s vision. The Inn is loved for its preservation of New England history, heritage, and elegance, and it has a long history in the Woodstock community.

The inn’s history dates back to 1793 when the original tavern was built on the site to host visitors. The tavern evolved since the 1700s into a full-service inn that has hosted countless visitors.

Woodstock Middle Covered Bridge

  • Address: Mountain Ave, Woodstock, VT
  • Directions: Here

After the existing iron bridge proved unsafe, the Middle Covered Bridge was completed in 1969. The contemporary 139-foot bridge pays respect to the historic craftsmanship of 19th-century wooden covered bridges. It is distinguished by its open trusses that overlook the Ottauquechee River and is accessible to both pedestrians and vehicular traffic.

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  1. Several of these spots are NOT in Woodstock, but are in the town of Pomfret, Woodstock’s neighbor to the north. Also, the photo of Mt Tom is the WRONG one, there is a Mt Tom in Mass which is I believe what that photo is of.

  2. Several of these spots are NOT in Woodstock, but are in the town of Pomfret, Woodstock’s neighbor to the north. Also, the photo of Mt Tom is the WRONG one, there is a Mt Tom in Mass which is I believe what that photo is of.

  3. I grew up in Woodstock and most of these places are well known to me. Although I haven’t lived in Woodstock since my teen years, I do try to get back Alumni time..
    Woodstock will always be home to me.

    1. I love hearing that! Woodstock truly is such a gem. So much to offer during all seasons. Hope you get back again soon!

  4. I grew up in Woodstock and most of these places are well known to me. Although I haven’t lived in Woodstock since my teen years, I do try to get back Alumni time..
    Woodstock will always be home to me.

    1. I love hearing that! Woodstock truly is such a gem. So much to offer during all seasons. Hope you get back again soon!