Woodstock, Connecticut
A Brief About Woodstock, Connecticut

Have you ever been to Woodstock, CT?

Nestled in the scenic countryside of Connecticut is the charming town of Woodstock. As the second-largest town in the state, Woodstock stretches out over 62 square miles of picturesque American landscape.

This welcoming town is home to a vibrant population of residents who embody the community spirit that has thrived here since the town’s founding. Settled in the early 1700s, Woodstock’s rich history can still be seen today through its treasured landmarks and beautiful architecture. With a total area that is home to lush forests and sprawling farms, it’s easy to understand why Woodstock is considered one of the most beautiful places in the world. Whether you’re a visitor or a local, there’s always something new to discover in this captivating town.

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Mark Tetreault II
RE/MAX Bell Park Realty

610 Hartford Pike
Killingly, CT 06241

(860) 377-2595

The History Of Woodstock, Connecticut

Nestled in the northeastern corner of Connecticut, Woodstock is a small town known for its natural beauty and peaceful vibe. But did you know that this charming community has a fascinating history dating back to the colonial era? From Native American settlements to Revolutionary War heroes, Woodstock has a rich legacy that reflects the cultural and social changes of the past centuries.

Early History

Before European settlers arrived in the area, Woodstock was inhabited by the Nipmuc and Mohegan tribes. These indigenous people thrived in the forests and rivers of what is now known as Woodstock, using the land for hunting, fishing, and agriculture. In the early 18th century, European colonizers began to establish settlements in the area, leading to conflicts with the Native American tribes. The town of Woodstock was officially founded in 1686 and named after Woodstock, England.

The Revolutionary War

During the Revolutionary War, Woodstock played a key role in the fight for independence. The town was a strategic location for supplying troops and was home to several notable Revolutionary War figures, such as General Israel Putnam, who was known for his daring exploits during the war. The Putnam Memorial State Park is now located in Woodstock, dedicated to honoring General Putnam’s legacy.


After the war, Woodstock underwent a period of industrialization, with mills and factories popping up throughout the town. The woolen industry was particularly successful in Woodstock, as the town had ample water resources to power the machinery. Many of the historic buildings from this era are still standing today, giving visitors a glimpse of Woodstock’s industrial past.

Modern Developments

In the 20th century, Woodstock took on new developments and transformations. The town became a popular vacation spot for city-dwellers from nearby Boston and New York, drawing crowds to its pristine lakes and forests. The town began to embrace a more eco-friendly, sustainable lifestyle, with a focus on organic farming and green initiatives.


Today, Woodstock is a vibrant community with a strong sense of history and environmental consciousness. Visitors can explore the town’s historic sites, hike through its beautiful parks and trails, and sample farm-fresh produce from local markets. Woodstock’s character is a testament to its evolution over time, reflecting the values and aspirations of its residents.

Amazing Restaurants Around Woodstock, Connecticut
The Woodstock Tavern
35 Route 171 Woodstock, CT 06281
The Mansion at Bald Hill
29 Plaine Hill Rd. Woodstock CT, 06281
Thai Basil
18 Route 171, Woodstock, CT 06281
Woodstock Trading Post
688 CT-169, Woodstock, CT 06281
The Hare and The Hound
58 Main Street, Putnam, CT 06260
Things To Do Around Woodstock, Connecticut

Woodstock, CT is a charming town located in the northeastern part of the state. It is a place rich in history with its quaint New England architecture and beautiful landscapes. If you are planning a trip to the area, here are some of the best things to do in Woodstock, Connecticut.

Rosewood Cottage

Visit Roseland Cottage

Roseland Cottage is a historic house museum that is a must-visit attraction in Woodstock. Built in the 1840s, this pink house is a beautiful example of Gothic Revival architecture. The stunning gardens and grounds are also worth exploring, with their beautiful flower beds and unique rock formations. What’s even cooler about the Roseland Cottage is that it was the summer home to Henry Bowen, the found of the anti slavery newspaper, The Independent.

Go hiking at Mashamoquet Brook State Park

If you are looking for some outdoor adventure, Mashamoquet Brook State Park is the perfect place to visit. The park features several hiking trails that are suitable for all skill levels. You can also enjoy swimming, fishing or picnicking in the park.

Tour Taylor Brooke Brewery

If you are a beer lover, a visit to Taylor Brooke Brewery is a must. The brewery is family-owned and has been brewing beer in Woodstock since 2010. You can take a tour of the brewery and learn about the beer-making process, in addition to enjoying a tasting of their delicious brews.

Take a Scenic Drive on Route 169

Route 169 is a scenic byway that runs through Woodstock. The drive will take you through rolling hills, farmland, and beautiful forests. Along the way, you can stop at some of the small towns that dot the route, such as Brooklyn and Pomfret, which also have some interesting historical sites.

Explore the Woodstock Academy Museum

The Woodstock Academy Museum is a fascinating museum that showcases the history of one of the oldest schools in the United States. The museum features exhibits on different aspects of the school’s history, including its founding in the 19th century, the evolution of its curriculum, and the lives of some of its most famous alumni.

Check Out Woodstock Hill Historic District

If you’re a history buff and enjoy taking a stroll through time, then you simply must check out the Woodstock Hill Historic District. Tucked away in the northeastern corner of Connecticut, this charming little district is home to some of the most beautiful and well-preserved historic homes and buildings in the entire state. You’ll marvel at the colonial era architecture, and delight in the quaint charm that surrounds you at every turn. Take a leisurely walk through the streets, and soak up the rich history and beauty that has been preserved for generations to come.

Education Around Woodstock, Connecticut

Education is the foundation of successful communities. Woodstock, Connecticut, is a picturesque town with a rich history and a commitment to education. This town has a reputation as a great place to live, work, and learn. The community’s dedication to education is evident in the quality of its schools and programs.

Woodstock, Connecticut, has a small town feel with plenty of educational opportunities. The town has three schools that serve students from kindergarten through grade 12. Woodstock Elementary School provides educational programs for students in kindergarten through grade three. Woodstock Middle School enrolls students in grades four through eight, and Woodstock Academy provides academic programs for students in grades nine through 12.

The Woodstock Academy

The Woodstock Academy is the pride of the town’s educational system. It is a public school that offers a variety of academic programs, including Advanced Placement courses, vocational programs, and the International Baccalaureate Program. The school also has an impressive athletics program, which has produced numerous state champions.

In addition to its public schools, Woodstock, Connecticut, has many private schools. The Rectory School is a boarding school located in the town that offers an educational program for grades K-9. The school has an excellent faculty and has provided a great education to students for over 100 years. Other private schools in the area include Marianapolis Prep, Putnam Science Academy, and The Hyde School.

Woodstock, Connecticut, is committed to providing students with a well-rounded education. The town has a variety of extracurricular activities that cater to students’ interests. These activities include sports, music, theater, debate, robotics, and more. There is something for every student, regardless of their interests.

Community Happenings Around Woodstock, Connecticut

Connecticut is a state full of charming historic towns, and Woodstock is no exception. Located in Windham County, Woodstock’s picturesque scenery, rich history, and vibrant community make it a go-to destination for those who appreciate small-town living. Whether you’re looking to move to the area or just planning a weekend getaway, here’s everything you need to know about this charming community.

woodstock castle

A Rich History

Woodstock’s rich history spans over three centuries. The town was incorporated in 1686 and boasts many historic buildings and sites that are great to explore. Visit the “Quiet Corner” of Connecticut and check out the Roseland Cottage, which is famous for its Victorian-era architecture and rose gardens. Or stop by Taylor Brooke Winery, where you can sip on a glass of wine while you tour the restored 1806 round barn.

Natural Beauty

The natural beauty of Woodstock is breathtaking, especially during the fall season. The town is surrounded by forests and has many parks, such as the James L. Goodwin State Forest and Mashamoquet Brook State Park. These parks offer an array of recreational activities, including hiking, camping, and fishing.

Vibrant Community

The tight-knit community of Woodstock is very welcoming and friendly. You’ll find plenty of events and activities scheduled throughout the year, from the Woodstock Fair to the community’s annual tree lighting ceremony. Historically, the town’s most significant gathering has been the annual Woodstock Academy Thanksgiving Day football game–a tradition that has been going on for over 100 years.

New Roxbury Land Trust

The New Roxbury Land Trust has been created to protect every square mile of the natural beauty of Roxbury, Connecticut and the surrounding areas including Woodstock. With the support of the Conservation Commission and Woodstock Board, the trust aims to preserve America’s environment for future generations.

This non-profit organization holds a vital role in preventing harmful construction projects and promoting sustainable development. The trust’s focus is on maintaining the ecological balance of Roxbury, including its forests, wetlands, and other critical natural habitats. By collaborating with local residents and businesses, the Roxbury Land Trust hopes to create a more sustainable future for the community.

food, dishes, restaurant

Culinary Delights

Despite the small size of the town, Woodstock has a great culinary scene. From fine dining at the Inn at Woodstock Hill to the very casual Lunch Box Deli, there are plenty of options for foodies in Woodstock. If you’re looking for a great cup of coffee, stop by Uncommon Grounds or check for local roasted coffee makers at the Farmers’ Market.