Top 15 Attractions and Activities in Windsor, CT

Summary

Northwest Park
Vintage Radio and Communications Museum of Connecticut
Windsor Historical Society
Windsor Green
Oliver Ellsworth Homestead
Windsor Center River Trail
Back East Brewery
Windsor Art Center
Connecticut Valley Tobacco Museum
Northwest Park Country Fair
New England Air Museum (NEAM)
Hartford
Thomas Hooker Brewery
The Wood Memorial Library and Museum
Keney Park Golf Course

Established in 1633, the first English settlement in the state of Connecticut is the town of Windsor, located a few miles up the Connecticut River from Hartford.

In Windsor, visitors can explore this rich history at the local historical society and the Oliver Ellsworth Homestead, which was once the residence of one of the contributors to the drafting of the United States Constitution.

During the early 20th century, Windsor served as the center of Connecticut’s shade tobacco industry. While tobacco farming has largely waned, I found the seasonal exhibition at Northwest Park to be particularly engaging.

Windsor is especially picturesque around the town green, which is surrounded by impressive civic buildings, charming older homes, and a selection of local eateries.

Let’s discover the top attractions in Windsor:

1. Northwest Park

As indicated by its name, this extensive municipal park is situated in the far northwest of Windsor, on land once dedicated to tobacco cultivation.

Over recent decades, nature has reclaimed the area. Within the park’s boundaries, there exists a variety of forests, open fields, wetlands, and the southern bank of the Farmington River, all accessible via over a dozen miles of walking trails.

In more formal areas, visitors can stroll through a butterfly garden and an organic garden. At the Nature Center, one can learn about the wildlife and natural history of the Connecticut Valley. Moreover, children are particularly enchanted by the Heritage Breed farm animals present outside.

Numerous Coffee House Concerts are held throughout the year, so it is advisable to keep up with the schedule. Lastly, if you visit post-snowfall, cross-country skis or snowshoes can be rented to explore the park in a unique manner.

2. Vintage Radio and Communications Museum of Connecticut

This local museum exceeded my expectations. The extensive collection features radios, accessories, cameras, home computers, and broadcast equipment, organized chronologically from the 1800s to the 1980s.

Among the unique exhibits is a 1930s Crosley fridge/radio, and I enjoyed the opportunity to operate an authentic television studio camera from the 1970s.

Other remarkable displays include a radio repair bench from the 1940s, a complete timeline of home computers, and a functioning 1940s Wurlitzer jukebox.

The museum features its own amateur radio station, along with a recreated broadcasting studio, allowing visitors to delve into the Golden Age of Radio.

3. Windsor Historical Society

The “First in Connecticut” town has extensive history to reveal, which can be explored at the local historical society, open each week from Wednesday to Saturday.

The society boasts a rich collection of more than 11,000 pieces, encompassing Native American artifacts, decorative arts, fine arts, household items, personal belongings, tools, machinery, and equipment dating back to the town’s establishment in 1633.

In addition to the exhibit galleries located at 96 Palisado Avenue, the society features a Hands-on-History Learning Center for children and offers tours of two historic properties on-site.

These include the clapboard Strong-Howard House (1758) and the Dr. Hezekiah Chaffee House, a prominent brick mansion built in 1767.

4. Windsor Green

The town green presents a picturesque view, characterized by a long stretch of grass interspersed with trees.

This area serves as the town’s heart, flanked by the library and town hall, and hosts a diverse array of international cuisines, including Puerto Rican, pho, steaks, and pizza.

On Thursday evenings throughout the summer, the green comes alive with performances by various bands and solo artists, coinciding with the farmers’ market, where local produce, including fruits, vegetables, eggs, cheeses, herbs, and baked goods, can be purchased directly from the growers. This time of year truly highlights the vibrancy of Windsor.

A notable monument on the green is the Windsor War Memorial, created by distinguished sculptor and Windsor resident Evelyn Beatrice Longman in 1929. It features a bronze eagle set atop a stone cairn.

5. Oliver Ellsworth Homestead

A significant figure in early American history resided in this grand Georgian property located at 788 Palisado Avenue.

Oliver Ellsworth (1745-1807), an attorney, was instrumental in drafting the United States Constitution and served as a senator for Connecticut, as well as the nation’s third Chief Justice.

This two-and-a-half-story home, constructed in 1781, originally featured five bays with a later recessed addition supported by Tuscan columns.

The interior of the residence has been preserved to reflect its 19th-century character, linking visitors to Ellsworth and his lineage.

The building has been under the stewardship of the Connecticut Daughters of the American Revolution since 1903, with the property open for public viewing on Saturdays.

6. Windsor Center River Trail

One of the advantages of this 1.3-mile trail along the Farmington River is its accessibility by foot from the town center, with trailheads located near the train station and Palisado Avenue.

The paved loop offers a gentle walk, winding through wetlands, a pond, and alongside the riverbank.

Due to the presence of standing water, it is advisable to carry insect repellent. Nevertheless, it provides a tranquil retreat into a bird-rich natural setting on terrain suitable for strollers and wheelchairs.

7. Back East Brewery

Connecticut has fully embraced the craft beer movement, and in Windsor, visitors will find themselves close to two boutique breweries.

Back East Brewery, located a short taxi ride west in Bloomfield, features a convivial taproom that operates from Wednesday to Sunday, offering a wide variety of beer styles, from traditional to experimental.

One standout beer I encountered here was Boom! Roasted, a Coffee Stout produced in collaboration with local Perkatory Coffee Roasters.

Typically, there are 15 or more choices on tap. For those indecisive about what to choose, a flight of four can be ordered. On pleasant days, the outdoor patio is a lovely spot to relax, often accompanied by live music and food trucks.

8. Windsor Art Center

Housed in a repurposed freight building adjacent to the Amtrak line downtown, the Windsor Art Center is devoted to both visual and performing arts.

Opened in 2007, the venue rotates exhibitions featuring established and emerging artists from the Connecticut area. I attended a fascinating exhibition that combined photography and poetry, all revolving around the theme of light.

Additionally, live music, lectures, and poetry readings form part of the center’s programming. For local patrons, classes and workshops cover topics from watercolor painting to yoga.

Occasionally, the center hosts “Open Studios,” allowing visitors to engage with resident artists, tour their studios, and purchase original artwork.

9. Connecticut Valley Tobacco Museum

At its apex during the Prohibition era, the shade tobacco industry covered over 20,000 acres in the Connecticut Valley.

The primary crop was a hybrid developed in the early 20th century, combining over 30 varieties from Sumatra and Cuba, cultivated under humid conditions on grids within cotton tents.

This seasonal museum in Northwest Park provides insight into the valley’s 2,500-year history of tobacco cultivation. In the Archive Building, the timeline exhibition chronicles this narrative.

Visitors will discover the unique characteristics of the riverbank soils that facilitate this crop’s growth, as well as the Native American origins of the tobacco plant in New England. I found the audio narratives shared by tobacco workers to be particularly captivating.

10. Northwest Park Country Fair

A highly anticipated event on the town’s calendar, the Northwest Park Country Fair occurs around late September, bringing old-fashioned fun for a limited time.

Competitions for arts and crafts, cooking, gardening, and flower arranging abound, along with hayrides, pony rides, and various games for children.

In my experience, the live music offered is exceptional, providing entertainment throughout the day. Attendees can also take part in a silent auction and witness a variety of performances and demonstrations presented by local organizations, students, and scouts.

During the event, the park’s Maple Sugar House and Tobacco Museum open their doors to the public.

11. New England Air Museum (NEAM)

A short drive to Bradley International Airport leads you to this exceptional aviation museum. Encompassing three vast climate-controlled hangars, the New England Air Museum provides an immersive experience into the aviation industry of Connecticut and the surrounding region.

Igor Sikorsky, renowned for his contributions to aviation, established his famous aircraft company in Stratford, Connecticut.

Visitors can view nine Sikorsky aircraft, including the Sikorsky S-39, the oldest surviving Sikorsky, and the last operating Sikorsky VS-44 flying boat.

Noteworthy is what might be the oldest surviving aircraft in the United States: a balloon basket utilized over Hartford around 1870 by pioneering balloonist Silas M. Brooks (1824-1906).

In addition to showcasing over 55 aircraft, the museum features a rotating display of engines and captivating exhibits focusing on local aerospace manufacturer Pratt & Whitney, as well as notable figures like Connecticut aviation pioneer Percival H. Spencer (1897-1995).

12. Hartford

While Windsor has numerous attractions, the state capital is merely a six-minute train ride to the south, offering plenty of activities to engage in over a weekend.

Visitors might enjoy exploring Baroque masterpieces by renowned artists like Caravaggio at the Wadsworth Atheneum or visiting the exquisite Gothic residence of Mark Twain, one of the world’s premier writers’ house museums.

The Bushnell Center for Performing Arts showcases notable musicians and comedians, and one cannot overlook the historic Old State House, a symbol of democracy in Connecticut since the 18th century.

Families can enjoy high-tech interactive exhibits at the Connecticut Science Center, and catch the Hartford Yard Goats, playing at the excellent Dunkin’ Park, featuring prospects from the Colorado Rockies.

13. Thomas Hooker Brewery

This local brewery’s taproom and visitor center, located just beyond the town boundary in Bloomfield, has been operational for over a decade.

Thomas Hooker Brewery offers six core beers, complemented by a large selection of seasonal and limited-edition brews.

Having the opportunity to experience beer directly from the source adds to its appeal. Fortunately, the brewery’s taproom is open seven days a week, featuring a diverse range of beers while also offering growlers and cans for purchase.

The venue includes an outdoor patio, gift shop, and complimentary Wi-Fi.

Among the 20 beers available during my visit were classics like #NOFILTER, Hop Meadow IPA, and Blonde Ale, alongside citrusy IPAs, a Chocolate Truffle Stout, an Irish Red, and a Berliner Weisse brewed with raspberries called Pulp’d.

14. The Wood Memorial Library and Museum

Crossing the Connecticut River leads to the East Windsor Hill Historic District.

Main Street in South Windsor is lined with folk vernacular architecture dating from 1700 to 1860, showcasing some truly grand examples.

Visitors have the opportunity to step into one of these historic buildings at the Wood Memorial Library and Museum, which is open daily on Mondays and Thursdays.

This establishment, dating back to 1927, hosts temporary exhibitions focusing on local history, art, and nature, complemented by significant permanent collections in ornithology, Native American history, local decorative arts, and state history.

The Wood Memorial Library also features a collection of new adult fiction and serves children and young adults.

During my visit, an engaging exhibition showcased indigenous artifacts discovered locally along the Connecticut River.

15. Keney Park Golf Course

On both sides of the town line between Windsor and Hartford lies a well-regarded public golf course.

The initial nine holes at Keney Park were designed by celebrated architect Devereux Emmet in 1927. Until the 2010s, the course was managed by a for-profit entity, resulting in a decline in its reputation. However, it has since returned under the jurisdiction of the City of Hartford.

With a comprehensive renovation of its tee boxes, fairways, bunkers, greens, and clubhouse, the course has regained its status as one of the best public courses in the nation.

Even for non-residents, the rates remain reasonable, with weekday 18-hole rounds under $50. Prior to your game, you can practice at the driving range, green, and short game area.

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