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Things to Do in Windsor Connecticut

Discover the best activities and attractions in Windsor, Connecticut, from historical landmarks and scenic parks to local dining and cultural events. Dive into our guide to plan your perfect visit!

Windsor, Connecticut has many attractions that can be showcased in one image. Picture a serenely beautiful New England landscape in the heart of summer. In the foreground, there is the lush green foliage of Northwest Park, with its well-maintained trails. The Lakefield reservoir is on the right, casting shimmering, sunlight-spangled reflections onto the water. A little further back, we see the iconic architecture of the Windsor Historical Society, softened by distance and atmospheric perspective. Then, on the horizon, a gentle roll of the Talcott Mountain Ridge crowns the pastoral scene. The sky is a radiant azure, dotted with soft-edged cumulus clouds. All of this frames together a picturesque tableau of Windsor's charm, devoid of people, text, and brands.

Explore the Windsor Historical Society

One of the first stops you might enjoy in Windsor is the Windsor Historical Society. It’s a treasure trove of local history and provides fascinating insights into the town’s past.

The museum has exhibits that showcase the lives of early settlers, Native American artifacts, and Windsor’s role in the American Revolution.

They often hold events and educational programs that are great for families and history enthusiasts.

If you’re interested in genealogy, their research library is a fantastic resource to trace your family roots.

Visit the Vintage Radio and Communications Museum of Connecticut

This unique museum is perfect for tech aficionados and history buffs alike. The Vintage Radio and Communications Museum covers the evolution of communication technology over the decades.

From old radios and telegraphs to early televisions and computers, there’s a wide variety of vintage gadgets to fascinate any visitor.

It’s said that visitors love the hands-on exhibits, where you can actually tinker with some of the old equipment.

The knowledgeable staff and volunteers are always eager to share stories and answer questions.

Stroll Through Northwest Park

If you’re looking to enjoy nature, Northwest Park in Windsor is a must-visit. This expansive park offers 473 acres of beautiful scenery, hiking trails, and picnic areas.

The park features a nature center that frequently hosts educational programs for both kids and adults.

For birdwatchers, it’s a haven to spot various native bird species throughout the year.

In the winter, the park even has trails for cross-country skiing and snowshoeing, making it a year-round outdoor attraction.

Explore the Suffield Farmers Market

Just a short drive from Windsor, the Suffield Farmers Market is a delightful spot to explore on a Saturday morning. It’s a great way to support local farmers and artisans.

You can find everything from fresh produce and baked goods to handmade crafts and flowers.

The market has a warm, community feel and often features live music and food trucks, adding to the festive atmosphere.

It’s a perfect way to spend a leisurely morning and stock up on some local goodies.

Spend a Day at the Connecticut Trolley Museum

This museum is another gem for those fascinated by historical technology. The Connecticut Trolley Museum offers an interactive experience with its extensive collection of vintage trolleys.

You can even take a ride on one of the antique trolleys, which is quite a nostalgic experience.

The museum also has an impressive collection of railway memorabilia and displays that detail the history of trolley systems in the region.

It’s a wonderful outing for families, and kids particularly enjoy the trolley rides.

Go Wine Tasting at Sharpe Hill Vineyard

If you enjoy a good glass of wine, a visit to Sharpe Hill Vineyard is highly recommended. Located about an hour from Windsor, this vineyard offers a serene countryside setting to enjoy delicious wines.

The vineyard features a beautiful tasting room where you can sample a variety of their award-winning wines.

The staff is incredibly knowledgeable and can guide you through the different tasting notes and vineyard history.

Many people say that the wines are exceptional, and the vineyard often hosts events like wine dinners and concerts.

Discover Local Art at Windsor Art Center

For art lovers, the Windsor Art Center is a fantastic spot to explore local and regional artistic talent. The gallery features rotating exhibits showcasing various forms of visual art.

There are frequent art shows, workshops, and talks where you might have the opportunity to meet the artists.

The center also hosts classes and workshops if you’re interested in honing your own artistic skills.

It’s a cultural hub in Windsor and a great way to support local art and creativity.

Relax at Windsor Meadows State Park

Windsor Meadows State Park is a lovely place to relax and enjoy the outdoors. Located along the Connecticut River, it’s an excellent park for picnics, fishing, and kayaking.

The park has several miles of scenic trails that are perfect for walking or biking.

Many locals find it a quiet retreat from the bustle of daily life, making it a great spot to unwind.

If you’re interested in fishing, the river is well-stocked, and you might find it a great way to spend a leisurely afternoon.

Take a Tour of the Oliver Ellsworth Homestead

The Oliver Ellsworth Homestead is another historical site in Windsor that’s well worth a visit. The homestead was the home of Oliver Ellsworth, one of the Founding Fathers and the third Chief Justice of the United States.

The house is beautifully preserved and offers a glimpse into 18th-century life.

Guided tours are available, which provide detailed insights into Ellsworth’s life and contributions to American history.

The grounds are also lovely to explore, with beautiful gardens and scenic views.

Dine at Union Street Tavern

Union Street Tavern is a popular dining spot in Windsor, known for its welcoming atmosphere and delicious American fare.

The restaurant offers a varied menu, including burgers, steaks, and seafood, so there’s something for every taste.

The tavern also boasts a great selection of craft beers and cocktails, making it a perfect spot for a relaxed meal or a drink with friends.

Many patrons rave about the friendly service and the cozy, pub-like ambiance.

Savor Ice Cream at Bart’s Drive-In

If you have a sweet tooth, you won’t want to miss a visit to Bart’s Drive-In. This local favorite serves up some of the best ice cream in the area, along with classic diner fare.

Bart’s is charmingly retro, with a nostalgic vibe that adds to the experience.

They offer a wide range of ice cream flavors, sundaes, and milkshakes, perfect for a treat on a warm day.

In addition to ice cream, they serve burgers, hot dogs, and fries, making it a great spot for a casual meal.

Participate in the Annual Windsor Freedom Trail Run

The Windsor Freedom Trail Run is a meaningful and active way to engage with the community. This annual event commemorates Windsor’s role in the Underground Railroad and celebrates the town’s rich African American history.

The run features a 5K and a family walk, making it accessible for participants of all ages and fitness levels.

Not only is it a great way to get some exercise, but it also supports a significant cause and fosters community spirit.

Participants often appreciate the educational aspect of the event, which includes stops at historical landmarks related to the Underground Railroad.

Enjoy a Show at the Connecticut Science Center

Located not far from Windsor in Hartford, the Connecticut Science Center is a fantastic destination for a day of interactive learning and fun. The center features over 165 hands-on exhibits covering various scientific topics.

It’s an excellent spot for families, as it offers something for visitors of all ages, from young kids to adults.

The center also has a state-of-the-art 3D theater and frequently hosts live science demonstrations and workshops.

Visitors often highlight the engaging exhibits and the enthusiastic staff, making it a highly recommended outing.

Enjoy the Scenery at Riverfront Recapture

Riverfront Recapture is a beautiful area along the Connecticut River that offers various recreational activities. The area includes parks, trails, and boat launches, providing plenty of opportunities for outdoor fun.

You can enjoy a leisurely walk or bike ride along the scenic trails, have a picnic, or even rent a kayak to explore the river.

The area frequently hosts community events, concerts, and festivals, adding to its vibrant atmosphere.

It’s a wonderful way to enjoy the natural beauty of the Connecticut River and spend time outdoors.

Shop at the Shoppes at Buckland Hills

If you’re in the mood for some retail therapy, the Shoppes at Buckland Hills is just a short drive from Windsor. This large shopping mall features a wide range of stores, from popular brands to local boutiques.

The mall also offers several dining options, from fast food to sit-down restaurants, making it easy to spend an entire day shopping and dining.

Visitors often find it a convenient and enjoyable shopping destination with plenty of variety.

The mall frequently has sales and special promotions, so keep an eye out for discounts and deals during your visit.

Experience the Charm of Windsor Town Green

The Windsor Town Green is the heart of the community, offering a charming and historic setting to explore. The green is surrounded by historic buildings, shops, and restaurants, making it a lovely spot for a leisurely stroll.

Throughout the year, the town green hosts various events, including concerts, farmers markets, and festivals, adding to its vibrant atmosphere.

It’s a perfect place to relax, people-watch, and enjoy the town’s community spirit.

Many locals and visitors alike find it a quintessential part of the Windsor experience.

Unwind at Enders Island

Although a bit of a drive from Windsor, Enders Island is a beautiful and serene retreat that’s well worth the visit. The island is home to a stunning garden, a chapel, and breathtaking views of the Long Island Sound.

It’s an ideal spot for quiet reflection, a picnic, or simply enjoying the natural beauty of the area.

The island also hosts retreats and workshops focused on spirituality and creativity, offering opportunities for personal growth and relaxation.

Visitors often remark on the peaceful and rejuvenating atmosphere, making it a perfect getaway from the hustle and bustle of everyday life.

Explore Windsor Center River Trail

The Windsor Center River Trail is a scenic pathway perfect for walkers, joggers, and nature enthusiasts. Running along the Farmington River, it offers fantastic views and a serene environment.

The trail is ideal for a relaxing stroll or a more vigorous run, depending on your pace preference.

People love the well-maintained path and the peaceful setting, making it a wonderful escape from the hustle and bustle of daily life.

The trail is family-friendly, and you might even see locals walking their dogs or children riding bikes.

Discover Treasures at Bart’s Garden Center and Greenhouse

If you have a green thumb or simply enjoy plants, Bart’s Garden Center and Greenhouse is a fantastic place to visit. This local gem offers a wide variety of plants, flowers, and gardening supplies.

Whether you’re looking for seasonal blooms, houseplants, or outdoor gardening essentials, Bart’s has a great selection.

The staff is knowledgeable and always willing to offer advice on plant care and gardening tips.

People often mention the fantastic selection and the friendly, helpful service they receive when visiting Bart’s.

Join the Fun at the Windsor Monarch Festival

The Windsor Monarch Festival is a beloved annual event celebrating the migration of monarch butterflies. It’s a family-friendly festival with plenty of activities for kids and adults alike.

Visitors can learn about the life cycle of monarch butterflies and what can be done to help preserve their habitats.

The festival often features crafts, face painting, live music, and educational booths.

It’s a wonderful community event that brings people together to enjoy nature and support environmental conservation efforts.

Savor Delicious Treats at Get Baked Bakery

For those with a sweet tooth, a visit to Get Baked Bakery is a must. This local bakery offers a wide range of delicious pastries, cookies, cakes, and other treats.

They are known for their creative and delectable baked goods, with many people raving about their fresh, made-from-scratch offerings.

Whether you’re stopping in for a quick bite or ordering a custom cake for a special occasion, the quality and flavor are always top-notch.

The cozy atmosphere and friendly service add to the charm of this delightful bakery.

Have a Relaxing Evening at Great Pond State Forest

Great Pond State Forest is a great spot for those who enjoy outdoor activities and nature. The forest offers a variety of trails for hiking, bird watching, and even some peaceful lakes for fishing.

It’s said that visitors love the tranquil setting and the beautiful, natural scenery.

The forest is also home to several species of wildlife, providing an excellent opportunity for nature photography or simply enjoying the peaceful environment.

Whether you’re looking for a short walk or an extended hike, Great Pond State Forest offers a perfect getaway to unwind and connect with nature.

Linger Over a Coffee at BeanZ & Co.

BeanZ & Co. is a unique coffee shop in Windsor known for its inclusive employment practices and delicious coffee. The café serves a variety of coffee drinks, teas, and light bites in a welcoming environment.

People often mention the positive atmosphere and the great-tasting coffee as major highlights.

The café also frequently hosts community events and live music, making it a lively spot to hang out.

It’s a wonderful place to support a local business while enjoying a tasty beverage.

Experience a Performance at the Windsor Art Center Train Station

The historic train station, now part of the Windsor Art Center, is a unique venue for various performances and events. From theater productions and concerts to art shows and community workshops, there’s always something interesting happening here.

The intimate setting provides a great experience for seeing local talent and engaging with the Windsor arts community.

It’s said that the performances are always high quality, and the diverse range of events means there’s something for everyone to enjoy.

Check their schedule to see what exciting events are coming up during your visit.

Explore Lucas Farm

Lucas Farm is a charming local farm offering a variety of fresh produce, seasonal activities, and educational tours. It’s a wonderful destination for families, especially during the harvest season when you can pick your own fruits and vegetables.

People love the farm’s friendly atmosphere and the opportunity to experience rural life close to the town.

The farm also hosts seasonal events like pumpkin picking in the fall and berry picking in the summer.

It’s a fantastic way to spend a day outdoors while also supporting a local business.

Shop for Vintage Finds at The Windsor Thrift Shop

The Windsor Thrift Shop is a hidden treasure for those who love vintage items and unique finds. The shop offers a wide range of goods, including clothing, furniture, home décor, and much more.

People say they love the thrill of discovering one-of-a-kind items at affordable prices.

The store is well-organized, and the staff are helpful, making it a pleasant shopping experience.

It’s a great place to find a special piece for your home or add something unique to your wardrobe.

Marvel at the Architecture of First Church in Windsor

The First Church in Windsor is not only a stunning architectural landmark but also a significant part of the town’s history. Founded in 1630, it’s one of the oldest congregations in Connecticut.

The beautiful building and its serene surroundings make it worth a visit, even if you’re not attending a service.

The historic church often hosts concerts, lectures, and community events, so check their schedule to see if there’s something interesting happening during your visit.

Many people find it a peaceful place to reflect and appreciate the town’s rich history.

Visit Wintonbury Hills Golf Course

If you’re a golf enthusiast, Wintonbury Hills Golf Course in nearby Bloomfield is a must-visit. This public course is known for its challenging layout and beautiful scenery.

The course features 18 holes set against a picturesque backdrop, making it a great spot for a relaxing round of golf.

People often praise the well-maintained greens and fairways, as well as the friendly and professional staff.

The course also has a practice area, pro shop, and a lovely clubhouse where you can enjoy a meal or a drink after your game.

Enjoy a Performance at the Bushnell Center for the Performing Arts

While not in Windsor itself, the Bushnell Center for the Performing Arts in Hartford is worth the short drive. This historic theater hosts a wide range of performances, from Broadway shows and concerts to comedy and dance.

Many visitors enjoy the elegant architecture and the high-quality productions that are showcased here.

The venue frequently offers discounted tickets and special promotions, so keep an eye out for deals when planning your visit.

It’s a fantastic way to experience some culture and entertainment during your stay in the Windsor area.

Uncover History at the New England Air Museum

A short drive from Windsor, the New England Air Museum in Windsor Locks is a haven for aviation enthusiasts. The museum boasts a vast collection of aircraft, from vintage bi-planes to modern jets.

The interactive exhibits and historic displays provide a fascinating look at aviation history and technology.

Visitors often highlight the knowledgeable staff and the opportunity to explore the inside of some aircraft.

It’s a great educational outing for families and anyone interested in the history of flight.

Spend a Day at Northwest Park Nature Center

For those who love nature, the Northwest Park Nature Center in Windsor offers a variety of programs and activities. The center features educational exhibits on local wildlife, agriculture, and natural history.

The park frequently hosts events such as guided nature walks, birdwatching tours, and seasonal celebrations.

Families will appreciate the children’s programs, which often include hands-on activities and crafts related to nature.

It’s an excellent resource for learning about the local ecosystem while enjoying the beauty of the park.

Sample Local Brews at Back East Brewing Company

If you’re a fan of craft beer, a visit to Back East Brewing Company in Bloomfield is highly recommended. The brewery offers a range of delicious beers, from hoppy IPAs to smooth stouts.

The taproom has a relaxed and welcoming atmosphere, making it a great place to sample different brews and chat with friends.

Visitors often mention the knowledgeable staff and the variety of seasonal and limited-edition beers available.

The brewery also hosts events like trivia nights and live music, adding to its lively ambiance.

Explore the Oliver Ellsworth Homestead

The Oliver Ellsworth Homestead is a historical gem in Windsor, offering a glimpse into colonial life and the legacy of Oliver Ellsworth, one of the Founding Fathers.

Guided tours provide detailed insights into Ellsworth’s contributions and the era in which he lived.

Visitors appreciate the well-preserved artifacts and the knowledgeable guides who bring history to life.

The beautiful grounds are perfect for a leisurely stroll, making it a great destination for history buffs and casual visitors alike.

Relax and Unwind at Windsor Meadows State Park

For a day of relaxation, Windsor Meadows State Park along the Connecticut River is an ideal spot. The park offers scenic views, picnic areas, and trails for walking or biking.

Fishing enthusiasts will find well-stocked waters, making it a popular spot for casting a line.

Visitors often mention the tranquility of the park and the opportunity to unwind in a natural setting.

Whether you’re looking for a quiet spot to read a book or an active outing with family, Windsor Meadows State Park is a great choice.

Embark on a Windsor Freedom Trail Run

Participating in the Windsor Freedom Trail Run is a meaningful way to engage with the local community and learn about the town’s role in the Underground Railroad.

The event includes a 5K run and a family walk, making it accessible for all ages and fitness levels.

Participants often appreciate the historical landmarks along the trail, which provide educational stops and a deeper understanding of the town’s heritage.

It’s a wonderful way to combine fitness, history, and community spirit in one event.

Indulge at Great Pond State Forest

Great Pond State Forest offers a serene escape for nature lovers. The forest features a variety of trails for hiking, bird watching, and exploring.

The tranquil setting and diverse wildlife make it a perfect spot for nature photography.

Visitors frequently mention the well-maintained trails and the peaceful ambiance of the forest.

It’s an excellent destination for a day of outdoor adventure or a quiet retreat into nature.

Dine at Union Street Tavern

Union Street Tavern in Windsor is a beloved spot for a delicious meal and a cozy atmosphere. The restaurant offers a diverse menu with options ranging from juicy burgers to fresh seafood.

People often rave about the friendly service and the wide selection of craft beers and cocktails.

The tavern’s welcoming vibe makes it a perfect place to unwind with friends or enjoy a meal with family.

Specials and events are frequently available, so be sure to check out what’s on offer during your visit.

Windsor Center River Trail

A walk along the Windsor Center River Trail offers scenic views and a peaceful environment perfect for walking or jogging.

The trail runs along the Farmington River, providing a serene backdrop for your stroll.

Visitors love the well-maintained pathway and the opportunity to see local wildlife.

It’s a family-friendly spot where you might find locals walking their dogs or children riding bikes.

Shop at the Windsor Thrift Shop

The Windsor Thrift Shop is a treasure trove of unique finds, offering vintage items, clothing, furniture, and more.

Shoppers enjoy the thrill of finding one-of-a-kind pieces at great prices.

The well-organized store and friendly staff make it a pleasant shopping experience.

If you’re on the hunt for something special, this thrift shop is worth a visit.

Experience Wine Tasting at Sharpe Hill Vineyard

A visit to Sharpe Hill Vineyard offers a delightful wine tasting experience in a beautiful countryside setting.

The vineyard’s tasting room allows you to sample a variety of award-winning wines while learning about the winemaking process.

People often mention the knowledgeable staff and the exceptional quality of the wines.

Events like wine dinners and concerts add to the appeal, making it a perfect destination for wine enthusiasts.

Enjoy a Show at the Connecticut Science Center

The Connecticut Science Center in Hartford offers a day of interactive learning with over 165 hands-on exhibits.

Perfect for families, the center caters to visitors of all ages, from young kids to adults.

The 3D theater and live science demonstrations are highlights for many guests.

It’s a fantastic destination for an educational yet fun-filled day.

Visit Bart’s Drive-In

Bart’s Drive-In is a retro gem serving up some of the best ice cream and classic diner fare in the area.

The nostalgic atmosphere adds to the charm, and the wide range of ice cream flavors, sundaes, and milkshakes are perfect for a sweet treat.

Visitors also enjoy the burgers, hot dogs, and fries, making Bart’s a great spot for a casual meal.

It’s a beloved local spot for those craving delicious comfort food.

Windsor Art Center Train Station

The Windsor Art Center Train Station is a unique venue hosting various performances and events, from theater productions to art shows.

The historic setting provides an intimate environment to enjoy local talent and community workshops.

The diverse range of events means there’s always something interesting happening.

Check their schedule to see what’s on during your visit for a cultural experience in Windsor.

Get Baked Bakery

Get Baked Bakery in Windsor offers a delectable range of pastries, cookies, and cakes that are made from scratch.

People rave about the creative and fresh baked goods, making it a must-visit for those with a sweet tooth.

The bakery also provides custom cakes for special occasions, ensuring top-notch quality and flavor.

The cozy atmosphere and friendly service make every visit enjoyable.

Explore Lucas Farm

Lucas Farm is a charming destination offering fresh produce, seasonal activities, and educational tours.

The farm’s friendly atmosphere makes it perfect for family visits, with events like pumpkin picking in the fall and berry picking in the summer.

Visitors appreciate the opportunity to experience rural life and support a local business.

It’s a great way to spend a day outdoors, enjoying the beauty of the farm.

Admire the Windsor Historical Society

One of the first stops you might enjoy in Windsor is the Windsor Historical Society. It’s a treasure trove of local history and provides fascinating insights into the town’s past.

The museum showcases the lives of early settlers, Native American artifacts, and Windsor’s role in the American Revolution.

They often hold events and educational programs great for families and history enthusiasts.

If you’re interested in genealogy, their research library is an excellent resource to trace your family roots.

Enrich Your Experience at the Vintage Radio and Communications Museum

This unique museum is perfect for tech aficionados and history buffs alike. The Vintage Radio and Communications Museum covers the evolution of communication technology over the decades.

From old radios and telegraphs to early televisions and computers, there’s a wide variety of vintage gadgets to fascinate any visitor.

It’s said that visitors love the hands-on exhibits, where you can actually tinker with some of the old equipment.

The knowledgeable staff and volunteers are always eager to share stories and answer questions.

Explore Northwest Park

If you’re looking to enjoy nature, Northwest Park in Windsor is a must-visit. This expansive park offers 473 acres of beautiful scenery, hiking trails, and picnic areas.

The park features a nature center frequently hosting educational programs for both kids and adults.

For birdwatchers, it’s a haven to spot various native bird species throughout the year.

In the winter, the park even has trails for cross-country skiing and snowshoeing, making it a year-round outdoor attraction.

Discover Local Art at Windsor Art Center

For art lovers, the Windsor Art Center is a fantastic spot to explore local and regional artistic talent. The gallery features rotating exhibits showcasing various forms of visual art.

There are frequent art shows, workshops, and talks where you might have the opportunity to meet the artists.

The center also hosts classes and workshops if you’re interested in honing your artistic skills.

It’s a cultural hub in Windsor and a great way to support local art and creativity.

Avery Ingram

Avery Ingram

Contributor

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