10 Best Things to Do in Woodstock, Connecticut

By VI Staff on July 25, 2021 - Updated

Roseland Cottage

The second biggest town in Connecticut, Woodstock spans 62 miles, and while it has a relatively small population, the town is home to a variety of attractions and outdoor recreational activities to enjoy. Notable historic and cultural things to see include Roseland Cottage, the lovely Palmer Arboretum, the working dairy farm of Fairvue, and Palmer Hall. Head head to the Town Beach for some canoeing, kayaking and fishing. Certain attractions may be temporarily closed or require advance reservations. Some restaurants are currently offering pickup only. Hours/availability may have changed.

1.Roseland Cottage

Roseland Cottage, also known as Henry C. Bowen House or as Bowen Cottage, is a historic house that is one of the best and most beautifully preserved Gothic summer houses in the nation. Listed on the National Register of Historic Places and a National Historic Landmark, the house was built in the Gothic Revival style in 1846 as the summer home of Henry and Lucy Bowen and their young family, and today is a museum that features spectacular interiors with original Gothic furniture. The house is surrounded by a pristine boxwood parterre garden, a garden house, a carriage barn, an icehouse, and the nation's oldest surviving indoor bowling alley. The house is renowned for hosting to the largest Fourth of July celebrations in the United States during the 1870s along with prominent guests such as Ulysses S. Grant, Benjamin Harrison, and John C. Fremont.

556 CT-169, Woodstock, Connecticut 06281, Phone: 617-227-3956

2.Taylor Brooke Winery

Taylor Brooke Winery is a family-owned and operated winery that began as a hobby and quickly grew into one of the region’s finest wineries. Established in 1999 by Richard and Linda Auger with just 300 vines, today the winery has 7,200 vines that produce a range of 17 small batch wines. Located on what was once one of the oldest and largest farms in town, the winery produces dry, estate grown whites and reds, fruit-infused Rieslings, and a trio of dessert wines, all of which can be sampled in the tasting room with locally produced cheeses. Visitors can also enjoy self-guided tours of the vineyard, picnic lunches on the grounds, sipping wines by the glass or the bottle on the patio overlooking the vineyards.

848 CT-171, Woodstock, CT 06281, Phone: 860-974-1263

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3.Things to Do in Woodstock, Connecticut: Scranton's Shops

Scranton’s Shops is the place to go for the finest antiques, beautiful furniture, pottery, country items, collectables, and gifts. Housed in an early New England Blacksmith shop in South Woodstock, the charming store spans over 3,800 square feet across two floors and hosts 85 vendors selling a wide range of arts, crafts, antiques, décor, pieces of furniture, handmade pottery, and other one-of-a-kind items. Scranton’s Shops is open Monday, Wednesday, Thursday, Friday, Saturday and Sunday from 11:00 am to 5:00 pm.

300 CT-169, South Woodstock, CT 06267, Phone: 860-928-3738

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4.Devon Point Farm, Woodstock, Connecticut

Devon Point Farm is an organic, working farm that raises rare, heritage breed American Milking Devon cattle, grass-fed beef and heritage pork, along with organic vegetables, and raw apple cider. The farm, which is open to the public at various times, also offers a Pick-Your-Own Pumpkin Patch, a vintage 1898 Apple Cider Press where visitors can make their own fresh cold-pressed Raw Apple Cider, a summer farm camp for children, and a cozy barn where guests can tuck into hot cider donuts, hot mulled cider, and refreshing apple slushies in summer.

54 Joy Rd, Woodstock, CT 06281, Phone: 860-942-6292

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5.Things to Do in Woodstock, Connecticut: Woodstock Orchard

Nestled in the beautiful rolling hills of Woodstock, Woodstock Orchards is a family-owned and operated fruit and vegetable retail stand that sells sell a large variety of farm-fresh vegetables in the summer, along with pick-your-own apples and blueberries on a seasonal basis. Woodstock Orchards has a retail store that sells an abundance of farm-fresh, locally-grown items, including over 20 varieties of apples, pumpkins, squash, decorative gourds, hot peppers, and homemade apple cider and an award-winning Dragon’s Blood Elixir Hot Sauce. Visitors can pick their apples and blueberries, and gift baskets and certificates are available for special occasions.

494 CT-169, Woodstock, CT 06281, Phone: 860-928-2225

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6.Things to Do in Woodstock, Connecticut: Pomfret Wine and Spirits

Pomfret Wine and Spirits is a wine shop in northeastern Connecticut that offers a wide selection of wines, craft beers and spirits. Located near two wineries in Woodstock, the store boasts over 400 varieties of wine from national brands to exclusive and rare labels, along with an extensive collection of domestic and craft beer, spirits, liqueurs and aperitifs. Pomfret Wine and Spirits host a variety of functions and events throughout the year and support several community charities and organizations.

640 Pomfret St, Pomfret, CT 06258, Phone: 860-928-2946

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7.The Mansion at Bald Hill, Woodstock, CT

The Mansion at Bald Hill is an elegant bed and breakfast and historic landmark restaurant on Plaine Hill Road in Woodstock. Built in the 1890s as the summer home of the industrialist Clarence W. Bowen, the slightly formal, Victorian-style restaurant and B&B exudes elegance and charm with tasteful décor, working fireplaces and comfortable en-suite guest rooms. Surrounded by 90 acres of magnificent gardens and grounds, the restaurant serves a menu of American cuisine with Italian and Japanese influences with signature dishes such as Maryland crab cakes, cheddar-lobster macaroni and cheese, osso buco with potatoes and asparagus, and New Zealand lamb chops. The restaurant is open for dinner Tuesday through Sunday and for Sunday brunch.

29 Plaine Hill Rd, Woodstock, CT 06281, Phone: 860-974-3456

8.Sherwood's Restaurant & Bar, Woodstock, CT

Sherwood's Restaurant & Bar is a locally-owned and operated eatery that serves delicious homemade fare in a casual and relaxed setting. Established in 2009, the family-friendly restaurant is open for lunch and dinner, seven days a week and offers a range of delicious appetizers, entrées, fresh salads, and desserts. Signature dishes include prime steak, fresh seafood, chicken dishes, and pasta plates, along with a range of casual wines, craft beers and other beverages.

35 CT-171, Woodstock, CT 06281, Phone: 860-963-2080

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9.The Vanilla Bean Cafe, Woodstock, CT

The Vanilla Bean Café is a charming café that serves a casual menu of American staples in a relaxed setting and hosts live music and open-mike nights throughout the week. Located in a restored, early 19th-century barn in scenic Pomfret, the family-owned and operated café has been serving a menu of freshly prepared, from-scratch fare made with locally sourced ingredients since 1989 and has a loyal following of customers. The menu features house-made soups, gourmet sandwiches, and light entrées of fresh meat, prime meats and organic vegetables, along with freshly baked goods such as bagels, croissants, muffins, and cookies every morning. Blackboard lunch and dinner specials are available on a daily basis.

450 Deerfield Rd, Pomfret Center, CT 06259, Phone: 860-928-1562