Things To Do In Woodstock CT: Top 15 Most Unique Spots | Stanton House Inn
Roseland Cottage, one of the best things to do in Woodstock, CT

Things to Do in Woodstock CT: Top 15 Most Unique Spots

A view of Woodstock Valley in northeastern Connecticut

Welcome to the heart of New England, the charming town of Woodstock, Connecticut. This town is rich in history and graced with picturesque landscapes. It offers a unique blend of attractions, activities, and dining experiences. Are you a history buff? Or perhaps an outdoor adventurer? Maybe you’re seeking a cozy weekend escape? You’re sure to enjoy exploring the top picks of things to do in Woodstock, CT. Let’s get started!

Quick hits

  • Explore the town of Woodstock for historic sites, recreational activities & wineries.
  • Visit Roseland Cottage & Bowen House to explore the town’s rich history or Taylor Brooke Winery for handcrafted wines.
  • Putnam and Pomfret nearby offer arts scene, antique shops & restaurants!

things to do in woodstock ct map 1 Things to Do in Woodstock CT: Top 15 Most Unique Spots
Map design by Stanton House Inn with elements from Flaticon

A Brief History of Woodstock, Connecticut

Old photo of Roseland Cottage

Woodstock, founded in 1686, is nestled in the beautiful Woodstock Valley and is the second biggest town in Connecticut. That’s by size, spanning over 62 square miles, and just behind Greenwich, Connecticut. It’s still a very small town, with its 8,221 people. Woodstock is also home to the prestigious Woodstock Academy.

Colonial Era

Puritan missionary John Eliot established “praying towns” in the mid-17th century. In these villages, Native Americans were expected to abandon their traditional customs. Material assistance, free education, and closer ties to the colonists was the trade-off. Wabaquasset, in present-day Woodstock, was the largest of three praying towns in northeastern Connecticut. King Philip’s War of 1675 divided the community. Locals fled the town. The final end came in 1676, when the English marched through town and burned it down. In 1682, Massachusetts purchased a tract of land from the Mohegans, which included Woodstock. In 1686, a group of 13 Roxbury residents named the town New Roxbury. The town renamed itself Woodstock after a town in England in 1690. Connecticut absorbed Woodstock in 1749.

Until the 18th century, Woodstock was primarily a farming community. Following the War of 1812, it developed into an industrial center. Active industries in town by 1820 included:

  • distilleries
  • wheel wrights
  • oil mills
  • fulling mills
  • carding machines
  • grist mills
  • saw mills
  • goldsmiths
  • and shoe factories

However, by the mid-nineteenth century, industry had nearly died out, and Woodstock reverted back to a rural state. The town instead became one of the most popular summer destinations in New England for wealthy East Coast city dwellers.

Henry C Bowen

Henry Chandler Bowen

Henry C. Bowen, a Woodstock native, was instrumental in this development. Bowen, who founded The Independent, helped found the Republican Party, and led the lay managers of Plymouth Church, made significant investments in his hometown’s development. He drew many other wealthy members of society to spend the summers with him, and many of them settled there as well.

Bowen, dubbed “Mr. Fourth of July,” hosted the best 4th of July celebrations in all Connecticut in Woodstock in the late 1800s. Speeches, fireworks, and pink lemonade drew 10,000 people to the festivities. Bowen eventually gave the community Roseland Park, which included a man-made lake.

Bowen’s summer home on Woodstock Hill was visited by three US Presidents:

  • Despite Bowen’s prohibition on drinking and smoking, Ulysses S. Grant spent the night there. He even bowled his first strike in the bowling alley at Roseland Cottage.
  • In 1883, Rutherford B Hayes came to speak in support of national education aid.
  • Benjamin Harrison planted a liberty tree during a Fourth of July celebration.

Roseland Cottage

Henry C Bowen and his wife Lucy Bowen built the Roseland Cottage in 1846 as a summer home. Other names include the Pink House or Bowen House. Joseph C. Wells designed it, using inspiration from Andrew Jackson Downing’s design books. Fine Homebuilding magazine named Roseland one of the 25 most important houses in America in 2006.

The Best Things to do in Woodstock CT

Roseland Cottage

Get ready to fall under the spell of Woodstock’s diverse attractions and activities. Most come for Roseland Cottage or the annual Woodstock Fair. But there are plenty of outdoor activities to take advantage of the bucolic scenerey here.

Roseland Cottage

Travel back through the annals of history by visiting the iconic Roseland Cottage, also known as the Pink House. This National Historic Landmark, showcasing stunning Gothic Revival style architecture, is nestled amid beautiful gardens.

The pink home has tall, angular gables, gingerbread trim, and 21 formal flower gardens bordered by dwarf boxwood hedges. Roseland Cottage is a prime example of Victorian Gothic Revival architecture. Tell-tale signs are its:

  • Pointed gables
  • Scrolled bargeboards
  • Multiple tall chimneys
  • Diamond-shaped leaded glass windows

Entryway to Roseland Cottage

Over the past 150 years, its exterior walls of board and batten wood siding have been painted in 13 different shades of pink. You can still find the original furniture and knickknacks of the owners in the house.

Historic New England purchased it in 1970 and now offers public tours. Some of the other buildings to be on the lookout for are the carriage barn and an ice house.

The Cottage boasts the first indoor bowling alley in the country. Don’t forget to stop by the Roseland Cottage Gift Shop to pick up Connecticut souvenirs, crafts, and books related to the site’s fascinating history.

Roseland Park

Roseland Park

If you’re in pursuit of outdoor adventures, Roseland Park is just the place. This 500-acre park features:

  • A beautiful lake
  • Playgrounds
  • Picnic sites
  • Fishing
  • Basketball courts
  • A driving range
  • A nine-hole golf course

Woodstock Historical Society

Immerse yourself in the town’s charmed past with a visit to the Woodstock Historical Society. This organization preserves and shares the history and culture of Woodstock. A majority of its work is through its extensive collection of artifacts, documents, and photographs.

Taylor Brooke Winery

Experience the flavors of Woodstock at Taylor Brooke Winery. This family-owned Connecticut vineyard produces handcrafted wines using estate-grown grapes. You can:

  • Sample their exquisite wines in the tasting room
  • Take a self-guided tour of the vineyard
  • Enjoy a picnic lunch with a glass of wine on the patio overlooking the stunning vineyards.

A visit to Taylor Brooke Winery is a must for wine lovers exploring Woodstock, Connecticut.

Taylor Brooke Brewery

Delight in top-tier craft beer at Taylor Brooke Brewery, the first Connecticut brewery in Woodstock. The brewery opened its doors in July 2019, providing a unique selection of brews. You can try them through flight samples, growler fills, and full pours!.

Savor your preferred beer in the indoor taproom. Alternatively, you can relax on the outdoor patio and lawn. The ambiance creates an ideal setting for a relaxed afternoon, enjoying the company of friends and fellow beer enthusiasts.

Fairvue Farms

Dairy cow at Fairvue Farms

Experience Woodstock’s rustic charm at Fairvue Farms, an organic working dairy farm. Here, they raise rare American Milking cattle and produce grass-fed beef and heritage pork. In addition, the farm grows organic vegetables and produces raw apple cider. Head here to enjoy various activities such as pumpkin picking and making fresh cold-pressed raw apple cider using the vintage 1898 Apple Cider Press. There’s also a cozy barn to indulge in delicious apple cider donuts from this top pick of CT cider mills.

With picturesque views and a taste of farm life, Fairvue Farms is a must-visit site in Woodstock, Connecticut.

Woodstock Orchards

A picture of the beautiful Woodstock Orchards in CT, where visitors can enjoy things to do in Woodstock CT such as apple picking and hayrides.

Experience the charm of Woodstock Orchards, a family-owned farm and retail stand. They offer a delightful selection of fresh produce:

  • Over 20 varieties of apples in their CT apple orchards
  • Pumpkins
  • Squash
  • Decorative gourds
  • Hot peppers
  • Their award-winning Dragon’s Blood Elixir Hot Sauce.

Pick your own apples and blueberries, and savor the flavors of Woodstock’s bountiful harvest at this charming farm.

Harrisville Golf Course

Golf course in northeastern Connecticut

Harrisville Golf Course is a 9-hole public course in Woodstock, Connecticut, that welcomes golfers of all skill levels. The course is designed with varying difficulty levels to challenge seasoned golfers while remaining accessible to beginners. The course features beautiful fairways and greens, strategically placed hazards, and magnificent views of the Connecticut countryside. Golfers can practice their swing on the driving range, and a pro shop sells all golfing necessities. The Harrisville Golf Course provides a welcoming and enjoyable environment for all, whether you’re looking to improve your game or simply enjoy a leisurely round.

Crystal Pond Park

Retreat to the peaceful haven of Crystal Pond Park, a scenic park featuring a pond, walking trails, and picnic areas. Perfect for a relaxing day with family or friends, the park offers opportunities for fishing, boating, hiking, and picnicking.

All amidst the tranquil beauty of Woodstock Valley, visitors can enjoy the peaceful atmosphere of the park and take in the stunning views of the surrounding

The Woodstock Fair

Ferris wheel at the Woodstock Fair

Feel the thrill of the annual Woodstock Fair, held every Labor Day weekend and drawing visitors from all over the region. This popular event features:

  • Agricultural exhibits
  • Live entertainment
  • Carnival rides
  • Food vendors

Providing a fun-filled experience for the whole family.

No visit to Woodstock, CT would be complete without attending this beloved local tradition.

Shopping in Woodstock, CT

Make your way to South Woodstock and discover a multi-vendor marketplace that sits on the list of best antique stores in Connecticut.

Scranton’s Shops

Items for sale at one of the shops in Woodstock, Connecticut

Scranton’s Shops is a haven for antiques enthusiasts and shoppers looking for unique items. Scranton’s Shops offers a wide selection of unique items on two floors. From clothing and jewelry to home decor, this multi-vendor store is a trove. It’s an essential stop during your visit to South Woodstock, CT.

Restaurants in Woodstock, CT

Rustic dining in Woodstock, CT

Considering its size, your dining options are rather limited here. But in the vein of the rural nature, you’ll still find local inns that also serve meals beyond breakfast. Check-out the Mansion at Bald Hill and the Inn at Woodstock Hill if that intrigues you.

The Vanilla Bean Cafe

A view of The Vanilla Bean Cafe in Woodstock, Connecticut

Satisfy your foodie desires with a meal at The Vanilla Bean Cafe. This popular restaurant serves American cuisine in a restored 19th-century barn. The cozy atmosphere at the Vanilla Bean Cafe and menu of house-made soups, gourmet sandwiches, and light entrées make it a must-visit.

The Vanilla Bean Cafe is more than just a restaurant; it’s an experience to remember. Every morning, delight in a variety of mouth-watering dishes prepared with fresh, organic vegetables and prime meats. Also, enjoy freshly baked pastries such as bagels, croissants, muffins, and cookies. The cafe’s relaxed atmosphere, live music, and open-mic nights make it a favorite among both locals and visitors.

Hotels, Inns, and Places to Stay in Woodstock, CT

The fare at a local bed and breakfast

Following a day spent discovering the delights of Woodstock, rest your head at one of the town’s comfortable accommodations. It is almost a two-hour drive from our CT bed and breakfast in Greenwich, Connecticut, after all. As far as the best Connecticut bed and breakfasts here, you’ve got two great options in town: Both are elegant, charming, and offer exceptional service and a taste of New England’s rich history.

The Mansion at Bald Hill

Relish the opulence and sophistication at The Mansion at Bald Hill, a stunning historic inn and restaurant known for its exquisite dining and breathtaking grounds. Dating back to the early 19th century, The Mansion at Bald Hill offers a beautiful and luxurious setting for:

Indulge in their American cuisine with Italian and Japanese influences, or relax with a spa treatment, fitness center session, or a dip in the outdoor pool.

The Inn at Woodstock Hill

For a dash of historic allure, book a stay at The Inn at Woodstock Hill, a historic bed and breakfast offering a range of accommodations, including rooms with private bathrooms, suites, and cottages.

The inn’s restaurant serves breakfast, lunch, and dinner. And their event spaces provide an enchanting backdrop for bed and breakfast weddings, corporate events, and other special occasions, if you’re duly enchanted.

Directions to Woodstock, CT

Route 169 through Woodstock, Connecticut

Reaching Woodstock, CT is straightforward, whether you’re coming from the north, south, east, or west. If traveling from the north, follow these directions:

  1. Take I-84 East to Exit 73 for CT-190 toward Union/Stafford Springs.
  2. Turn left onto CT-190 West and continue for about 7 miles.
  3. Turn right onto CT-171 North.
  4. Woodstock, Connecticut will be on your left after approximately 6 miles.


Coming from the south, take I-84 West to Exit 73 for CT-190 toward Union/Stafford Springs, turn right onto CT-190 West, and follow the same route as mentioned above.

From the east, take I-395 North to Exit 97 for CT-171 North and continue for about 6 miles. From the west, take I-84 East to Exit 73 for CT-190 and follow the same directions as the northern route.

Or take Route 169, a scenic byway and one of the best fall foliage driving routes in Connecticut.

More Towns and Cities to Explore Near Woodstock, CT

Lake in Putnam

Though Woodstock, CT is undeniably enchanting, consider exploring nearby towns and cities for even more New England charm and attractions. Putnam, CT is famous for its vibrant arts scene, antique shops, and restaurants. Pomfret, CT, meanwhile, boasts beautiful countryside, wineries, and historic sites.

Discover this and more unique attractions throughout Connecticut with our free travel guide.

Putnam, CT

Unearth the lively town of Putnam, CT, with its thriving arts scene, antique shops, and restaurants.

  • Stroll through the historic downtown area
  • Explore the Putnam River Trail
  • Visit the Putnam History Museum
  • Check out the Putnam Arts Council

All of these attractions offer a glimpse into the town’s rich culture and history.

Putnam is the perfect complement to your Woodstock, CT adventure, showcasing the best of New England charm.

Pomfret, CT

Explore the charming town of Pomfret, CT, where you can:

Pomfret is an ideal destination for a peaceful retreat amidst the picturesque rolling hills of New England, not far from the town beach.


Woodstock, CT, with its rich history and charming attractions, is a captivating New England destination. You can explore the town’s historic sites, indulge in local cuisine, or enjoy the great outdoors.

Frequently Asked Questions

What is Woodstock Connecticut known for?

Woodstock, Connecticut is known for its tranquil atmosphere, historical significance and beautiful pastoral scenes. It’s the second largest town in Connecticut in terms of area, but has a relatively small population.

Is Woodstock CT rural?

Woodstock, the biggest town in northeastern Connecticut in terms of acreage, is rural and full of historic charm. It boasts more operating dairy farms than any other town in Connecticut, and strong support for open space conservation and the farming community. These factors together paint a picture of a quintessential New England community.

Is Woodstock CT a good place to live?

Woodstock CT is an ideal place to settle down for those looking for a tranquil and safe place to live. With an agricultural background, numerous dairy farms, excellent schools and family-friendly environment, it offers peace and relaxation, although the average commute to work is longer than the national average.

What are some must-see attractions in Woodstock, CT?

Top attractions in Woodstock, CT are historic places like Roseland Cottage, Roseland Park, the Woodstock Historical Society. Taylor Brooke Winery and the annual Woodstock Fair are also must-see attractions. Visiting Roseland Cottage is a great way to experience the history of the area. The house was built in 1846 and is a National Historic Landmark. It is open for tours and special events throughout the year. Roseland Park is a great place to spend the day. It has a playground

Are there any wineries in the area?

Yes, there are wineries in the area – Taylor Brooke Winery and Taylor Brooke Brewery both located in Woodstock, CT.

When is a good time to visit Woodstock, Connecticut?

Labor day weekend is a famous time to visit for the annual celebration. October is also ideal, as Woodstock is on a famous CT fall foliage driving route, Route 169.


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