15 Best Things to Do in Windsor (CT)

Imagine a place where colonial charm meets vibrant modern life, nestled along the picturesque Connecticut River. Welcome to Windsor, Connecticut, a town steeped in history as the first English settlement in the state, yet buzzing with contemporary attractions. From tranquil natural parks and fascinating museums to bustling craft breweries and a thriving arts scene, Windsor offers a surprisingly diverse array of experiences that cater to every kind of traveler.

Whether you’re a history buff eager to walk in the footsteps of pioneers, a nature lover seeking serene trails, or a family looking for engaging activities, Windsor promises an unforgettable escape. The best time to visit is during the spring or fall, when the weather is mild and the natural beauty of New England truly shines, though summer brings lively outdoor events. Plan to spend at least two to three days to fully immerse yourself in its unique blend of past and present.

Northwest Park

Northwest Park is a true gem, offering a sprawling 473 acres of natural beauty and recreational opportunities that make it a favorite among locals and visitors alike. What makes this park unique is its incredible diversity, featuring miles of hiking and biking trails winding through forests, meadows, and wetlands. You can spend hours exploring its varied landscapes, encountering local wildlife, or simply enjoying a peaceful picnic amidst nature.

Beyond the trails, the park boasts an animal barn with farm animals that delight children, a nature center with educational exhibits, and even an accessible playground. In colder months, parts of the park transform into a cross-country skiing haven. It’s a perfect escape for anyone looking to reconnect with the outdoors, offering something for all ages and activity levels. Families with young children will particularly appreciate the animal encounters and open spaces for play, while solo travelers and couples can find tranquility on the quieter trails.

Vintage Radio and Communications Museum of Connecticut

Step back in time at the Vintage Radio and Communications Museum of Connecticut, a truly unique attraction that unveils the fascinating history of communication technology. This isn’t just a collection of old radios; it’s a journey through the evolution of how we connect, from early telegraphs and crystal radios to the golden age of broadcasting and beyond. What makes this museum special is its hands-on approach and the sheer volume of meticulously preserved artifacts.

You’ll see antique radios, early televisions, phonographs, and even military communication equipment, many of which are in working order. Knowledgeable volunteers, often enthusiasts themselves, are on hand to share stories and demonstrate how these vintage machines brought the world into people’s homes. It’s a nostalgic trip for older generations and an eye-opening experience for younger visitors to see how far technology has come. This museum is ideal for history buffs, technology enthusiasts, and anyone curious about the roots of our digital world.

Windsor Historical Society

The Windsor Historical Society serves as the vibrant heart of the town’s rich past, preserving and sharing the stories of Connecticut’s first English settlement. Housed in a beautifully maintained historic building, the society offers engaging exhibits that delve into Windsor’s significant role in American history, from its indigenous roots to its colonial founding in 1633 and its development through the centuries. You can explore fascinating artifacts, period rooms, and rotating displays that illuminate daily life, industry, and notable figures from Windsor’s past. Beyond the main museum, the society also maintains several historic homes, including the Dr.

Hezekiah Chaffee House (c. 1765) and the Strong-Howard House (c. 1812), offering guided tours that transport you directly into different eras. This attraction is a must-visit for anyone interested in American colonial history, local heritage, or genealogy. It’s perfect for history enthusiasts and curious minds of all ages, providing a deep dive into the foundational stories of Connecticut.

Windsor Green

The Windsor Green is not just a patch of grass; it’s the historic and cultural heart of Windsor, a living testament to the town’s enduring legacy as Connecticut’s first English settlement. This picturesque common, surrounded by historic homes, churches, and civic buildings, has been the focal point of community life for nearly four centuries. What makes it special is its tangible sense of history mixed with its present-day vibrancy.

You can stroll along its tree-lined paths, relax on a bench, and admire the classic New England architecture that frames it. The Green often hosts community events, farmers’ markets, concerts, and festivals, especially during warmer months, bringing people together in a quintessential small-town setting. It’s a perfect spot for a leisurely walk, a picnic, or simply soaking in the charming atmosphere. The Windsor Green is ideal for anyone looking for a relaxed experience, offering a glimpse into classic New England town life, and it’s completely free to enjoy.

Oliver Ellsworth Homestead

Step into the 18th century at the Oliver Ellsworth Homestead, the impeccably preserved home of one of America’s Founding Fathers and the third Chief Justice of the United States. This magnificent colonial mansion, built in 1781, offers a rare glimpse into the life and times of a pivotal figure in early American history. What makes the homestead unique is its authentic preservation, complete with original furnishings and personal artifacts that belonged to Ellsworth and his family.

Guided tours lead you through the elegant rooms, sharing stories of Ellsworth’s contributions to the drafting of the Constitution, his diplomatic missions, and the daily routines of a prominent 18th-century family. The beautiful grounds also feature historic gardens. This attraction is a must-visit for American history enthusiasts, especially those interested in the post-Revolutionary War period and the lives of the nation’s founders. It provides a tangible connection to the past and a deeper understanding of the forces that shaped the United States.

Windsor Center River Trail

The Windsor Center River Trail offers a refreshing escape into nature right from the heart of town, providing a scenic pathway along the majestic Connecticut River. What makes this trail special is its accessibility and the stunning views it provides of the river and its natural surroundings. Perfect for walking, jogging, or biking, the paved trail is well-maintained and offers a peaceful environment to enjoy the outdoors.

You’ll discover interpretive signs along the way, sharing information about the river’s ecology and the history of the area. It’s a fantastic spot to watch boats glide by, observe local birdlife, or simply enjoy a quiet moment by the water. The trail connects to other local paths and parks, offering opportunities for longer excursions if you desire. This trail is ideal for active individuals, families looking for a leisurely stroll, or anyone seeking a beautiful natural setting without venturing too far from town amenities.

Back East Brewery

For craft beer aficionados, Back East Brewery is a must-visit destination, offering a taste of Connecticut’s thriving brewing scene. What makes Back East unique is its dedication to quality and variety, producing a wide range of beers from crisp lagers to hoppy IPAs and rich stouts, all crafted with passion. Located in a modern industrial space, the brewery boasts a spacious and inviting taproom where you can sample their latest creations on draft or grab cans to go.

You can often take a peek into the brewing process through large windows, and friendly staff are always ready to discuss their beers and recommendations. The atmosphere is casual and lively, often featuring local food trucks on weekends and special events. This brewery is perfect for adults looking to enjoy expertly crafted beverages in a relaxed setting. Whether you’re a seasoned beer connoisseur or just curious about craft brewing, you’ll find something to savor here.

Windsor Art Center

The Windsor Art Center is a vibrant hub for local and regional artistic expression, showcasing a diverse range of contemporary and traditional art forms. What makes this center special is its commitment to fostering creativity within the community, offering a rotating calendar of exhibitions that feature established and emerging artists. You’ll discover everything from paintings and sculptures to photography and mixed media, ensuring there’s always something new and inspiring to see.

Beyond exhibitions, the Art Center hosts workshops, classes, and cultural events, making it a dynamic space for both viewing and creating art. The intimate gallery setting allows for a personal connection with the artwork, and you often have the chance to meet the artists themselves during opening receptions. This center is ideal for art lovers, creative individuals, and anyone seeking cultural enrichment. It’s a wonderful way to support local talent and experience the artistic pulse of Windsor.

Connecticut Valley Tobacco Museum

Delve into a unique piece of Connecticut’s agricultural heritage at the Connecticut Valley Tobacco Museum. This niche museum offers a fascinating look into the history and cultivation of broadleaf tobacco, a crop that profoundly shaped the economy and landscape of the Connecticut River Valley for centuries. What makes this museum unique is its focus on this specific, often overlooked, aspect of local history.

You’ll learn about the entire process of tobacco farming, from planting and harvesting to drying in traditional tobacco barns, and its impact on the region’s people and culture. The exhibits feature vintage tools, photographs, and artifacts that tell the story of the farmers, the laborers, and the industry itself. It’s a compelling educational experience that sheds light on a significant part of New England’s past. This museum is perfect for history buffs, those interested in agricultural heritage, or anyone seeking a truly off-the-beaten-path cultural insight.

Northwest Park Country Fair

The Northwest Park Country Fair is an annual highlight in Windsor, transforming the expansive Northwest Park into a vibrant celebration of local heritage, agriculture, and community spirit. What makes this fair special is its authentic, small-town charm mixed with a wide array of family-friendly activities. You can expect live music, craft vendors showcasing local artisans, delicious food trucks offering everything from classic fair fare to gourmet bites, and engaging demonstrations of traditional skills.

Children will love the animal exhibits, pony rides, and various games, while adults can enjoy browsing unique crafts and soaking in the festive atmosphere. It’s a wonderful opportunity to experience a quintessential New England country fair, connecting with local traditions and enjoying a day of wholesome fun. This event is perfect for families, couples, and solo travelers looking for a lively and authentic local experience. Be sure to check the dates, as it’s a seasonal event, typically held in the fall.

New England Air Museum (NEAM)

Just a short drive from Windsor, the New England Air Museum (NEAM) is a spectacular destination for aviation enthusiasts and curious minds of all ages. What makes NEAM truly special is its immense collection of aircraft, ranging from early biplanes and World War II fighters to modern jets and helicopters, housed in multiple vast hangars. You can get up close to these magnificent machines, marveling at their engineering and historical significance.

Many exhibits are interactive, allowing you to try flight simulators, learn about aviation principles, and even sit in the cockpit of some planes. The museum also hosts restoration projects, where you can watch skilled technicians bring historic aircraft back to life. It’s an inspiring and educational experience that celebrates human ingenuity and the thrill of flight. NEAM is ideal for families, history buffs, aspiring pilots, and anyone fascinated by the marvels of aviation.

Hartford

While not in Windsor itself, a visit to Hartford, Connecticut’s vibrant capital city, is an essential day trip given its close proximity and wealth of attractions. What makes Hartford special is its rich history intertwined with a modern urban pulse. You can explore the stunning Connecticut State Capitol Building, a gilded architectural marvel, and the historic Old State House.

Literary enthusiasts will be drawn to the Mark Twain House & Museum and the Harriet Beecher Stowe Center, offering intimate glimpses into the lives of these iconic authors. The Wadsworth Atheneum Museum of Art, one of the oldest public art museums in the U.S., boasts an impressive collection spanning centuries. Beyond history and culture, Hartford offers diverse dining, lively entertainment venues, and beautiful parks like Bushnell Park. It’s an ideal destination for those seeking a more urban experience, offering a broad spectrum of activities for history buffs, art lovers, and foodies.

Thomas Hooker Brewery

Thomas Hooker Brewery, named after the influential founder of Connecticut, is another cornerstone of the state’s craft beer scene, offering a distinct experience from its counterparts. What sets Thomas Hooker apart is its established reputation for brewing a diverse portfolio of award-winning beers, from classic ales to innovative seasonal brews. Located in an expansive facility, the brewery provides a welcoming and often bustling taproom where you can enjoy fresh pints, sample tasting flights, and purchase cans or growlers to take home.

They often host live music, trivia nights, and food trucks, creating a lively community atmosphere. Guided tours of the brewing facility are sometimes available, offering insights into their process and history. This brewery is perfect for beer enthusiasts looking to explore well-crafted local beers and enjoy a social, relaxed environment. It’s a great spot to unwind after a day of sightseeing.

The Wood Memorial Library and Museum

The Wood Memorial Library and Museum is a charming and often overlooked cultural gem that serves as both a community library and a repository of local history and art. What makes this institution unique is its beautiful architecture, originally built as a private residence, and its dual role in serving the intellectual and cultural needs of the community. You can explore the library’s collection of books, attend author talks, or discover rotating art exhibits in its gallery spaces, which often feature local artists.

The museum section offers insights into local history, showcasing artifacts and documents related to the area’s past. It’s a peaceful place to spend an hour, whether you’re looking for a quiet reading spot, an engaging art display, or a snippet of local heritage. The Wood Memorial Library and Museum is ideal for book lovers, art enthusiasts, and those seeking a quiet, culturally enriching experience in a beautiful setting.

Keney Park Golf Course

For golf enthusiasts, the Keney Park Golf Course offers an exceptional experience on a historic and beautifully maintained public course. While primarily located in Hartford, its close proximity makes it a fantastic option for visitors staying in Windsor. What makes Keney Park Golf Course special is its rich history, having been designed by the renowned golf course architect Devereux Emmet in 1927, and its recent multi-million dollar restoration that brought it back to its original grandeur.

You’ll navigate challenging holes set amidst rolling terrain, mature trees, and scenic vistas, providing both a test of skill and a picturesque backdrop. The course offers a full 18-hole championship layout, a pro shop, and often a casual grill for post-game refreshments. It’s an ideal destination for avid golfers looking for a high-quality public course experience. Whether you’re a seasoned player or looking for a memorable round, Keney Park delivers.

Plan Your Visit

Windsor, Connecticut, truly surprises and delights with its compelling blend of historical depth, natural beauty, and vibrant modern attractions. As you’ve explored, this charming town offers everything from peaceful river trails and engaging museums to lively craft breweries and annual community celebrations. Whether you’re a solo adventurer tracing the footsteps of history, a couple seeking a romantic getaway, or a family looking for diverse activities, Windsor promises a memorable experience.

Its compact size makes it easy to navigate, and its welcoming atmosphere invites you to linger and discover hidden gems. Remember to leverage the detailed cost information to tailor your trip to your budget, allowing you to maximize your enjoyment without overspending. So, pack your bags, embrace your curiosity, and get ready to uncover the unique charm of Windsor – a destination that beautifully encapsulates the spirit of New England and eagerly awaits your visit!