15 Best Things to Do in Windsor (CT)

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

In Windsor you can investigate this storied past at the local historical society and the Oliver Ellsworth Homestead. This was once the residence of one of the men who helped draft the United States Constitution.

In the first decades of the 20th century Windsor was the capital of Connecticut’s shade tobacco industry. Tobacco growing has all but disappeared, but I was engrossed by the seasonal exhibition at Northwest Park.

Windsor is especially pretty around the town green, hemmed by grand civic buildings, handsome old residences, and a clutch of local restaurants.

Let’s explore the best things to do in Windsor:

1. Northwest Park

As the name suggests, this sprawling municipal park is in the very northwest of Windsor on land that was once given over to tobacco farming.

Over the last few decades nature has taken over once more. Within the park’s boundaries there’s a diversity of woodland, open fields, wetlands and the south bank of the Farmington River. It’s all served by more than a dozen miles of walking trails.

In more formal spaces you can wander a butterfly garden and organic garden, and at the Nature Center you can find about the wildlife and natural history of the Connecticut Valley. Meanwhile kids will be besotted with the Heritage Breed farm animals outside.

There’s a series of Coffee House Concerts throughout the year, so I’d stay up to date with the calendar. Lastly, if you come after snowfall you can rent cross-country skis or snowshoes to explore the park in a new way.

2. Vintage Radio and Communications Museum of Connecticut

This is just the sort of local museum I hoped to find in a town like Windsor, but with dimensions that caught me off guard.

The collection of radios, radio accessories, cameras, home computers and broadcast equipment is extensive. It’s all organized in chronological order starting in the 1800s and leading up to the 1980s.

One of the quirkier exhibits is a Crosley fridge/radio from the 1930s, and I loved getting to maneuver a genuine television studio camera from the 1970s.

Some other noteworthy exhibits include a radio repair bench from the 1940s, a complete timeline of the home computer and a working 1940s Wurlitzer jukebox.

The museum has its own amateur radio station, as well as a recreated broadcasting studio. So you can really travel back to the Golden Age of Radio.

3. Windsor Historical Society

I’m sure you can tell that the “First in Connecticut” has a lot of history to uncover. This can be done at the local historical society, open four days a week from Wednesday to Saturday.

The society’s collection is deep and rich, counting more than 11,000 pieces. Among them are Native American objects, decorative arts, fine art, household objects, personal items, tools, machinery and equipment going back as far as the town’s foundation in 1633.

Along with the exhibit galleries at 96 Palisado Avenue, the society has a Hands-on-History Learning Center for wee ones, and arranges tours of two historic properties on the site.

These are the clapboard Strong-Howard House (1758), and the Dr. Hezekiah Chaffee House, an imposing brick mansion from 1767.

4. Windsor Green

Windsor looks positively idyllic from this long strip of grass sprinkled with trees.

The green is the center of town in every sense, bordered by the library and town hall. There’s a small but international array of restaurants for Puerto Rican, pho, steaks, and pizza.

On Thursday evenings all through the summer the green comes alive with concerts by a genre-hopping variety of bands and solo artists.

These all coincide with the farmers’ market, where you can buy local fruits, vegetables, eggs, cheeses, herbs, baked goods and more, direct from the producers. To my mind, it’s the best time to be in town.

A monument that warrants a close-up look on the green is the Windsor War Memorial. This was created by eminent sculptor and Windsor resident Evelyn Beatrice Longman in 1929 and comprises a bronze eagle atop a stone cairn.

5. Oliver Ellsworth Homestead

A monumental figure in the early history of the United States lived at this grand Georgian property at 788 Palisado Avenue.

The lawyer Oliver Ellsworth (1745-1807) helped draft the United States Constitution. He served as the senator for Connecticut and was the nation’s third Chief Justice.

His two and a half-storey homestead was built in 1781, originally composed of five bays, but with a later recessed extension supported by Tuscan columns.

The house’s interior has been preserved as it was in the 19th century. I got chills knowing that the decor and furnishings were related to Ellsworth and his descendants.

The building has been in the hands of the Connecticut Daughters of the American Revolution since 1903. On my visit, the property was open on Saturdays.

6. Windsor Center River Trail

One of a few things to love about this 1.3-mile trail along the Farmington River is that you can get onto it on foot from the center of town. There are trailheads by the train station or from Palisado Avenue.

The looping paved route is an easy stroll, threading through a patch of wetland, as well as a pond and of course the riverbank.

Because of the standing water I’d advise you to bring bug spray. The upside is a peaceful escape to bird-rich nature on wheelchair and stroller-friendly terrain.

7. Back East Brewery

I don’t think anywhere has embraced the craft beer phenomenon quite like Connecticut. In Windsor you’ll be within striking distance of two small-scale breweries.

Back East Brewery is a brief cab ride west in Bloomfield and has a sociable little taproom open Wednesday to Sunday, serving a range of brews, from traditional to out-there.

The beer that blew me away here was Boom! Roasted. This is a Coffee Stout, and a collaboration with the local Perkatory Coffee Roasters.

There are 15 or more on tap at any time. If you can’t make up your mind you can order a flight of four. On sunny days you can find a seat at the outdoor patio, and there’s often live music as well as a food truck.

8. Windsor Art Center

In a converted freight house next to the Amtrak line downtown, the Windsor Art Center is dedicated to visual and performing arts.

The venue opened in 2007 and has a calendar of temporary exhibitions for well-known and breakout talent from the Connecticut area. I caught an intriguing show, pairing photography and poetry, all inspired by light.

Live music, talks and poetry readings are also on the schedule. If you’re based locally you can check out classes and workshops for anything from watercolors to yoga.

Every now and again the center arranges “Open Studios” when you can meet the resident artists, explore their studios and purchase a unique creation.

9. Connecticut Valley Tobacco Museum

During its peak in the Prohibition years, the shade tobacco industry laid claim to more than 20,000 acres in the Connecticut Valley.

The main crop was a hybrid created in the early 20th century using over 30 samples from Sumatra and Cuba. These were grown in humid conditions on grids in cotton tents.

At this seasonal museum in Northwest Park you can take a look at the valley’s 2,500 years of tobacco growing heritage. In the Archive Building the timeline exhibition walks you through this chronology.

You’ll discover what makes the soils on the riverbanks so suited to this crop, and delve into the Native American origins of the tobacco plant in New England. I was captivated most of all by the audio accounts by tobacco workers.

10. Northwest Park Country Fair

A much anticipated date on the town’s calendar, the Northwest Park Country Fair falls around the end of September. For a few hours this event brings a world of old-fashioned fun.

There are competitions for arts and crafts, cooking, gardening and flower arrangement, as well as hayrides, pony rides and all kinds of games for children.

From my experience, the live music is fantastic, and does not stop all day. You can also bid for a bargain at the silent auction and see a variety of performances and demonstrations by local organizations, students and scouts.

The park’s Maple Sugar House opens its doors during the event, as does the Tobacco Museum.

11. New England Air Museum (NEAM)

I’d make the short drive up to Bradley International Airport for this high-quality aviation museum. Set in three immense climate-controlled hangars, the New England Air Museum goes into depth on the aviation industry in Connecticut and the region.

A name that looms large is Igor Sikorsky, who founded his famous aircraft company in Stratford, Connecticut.

Nine Sikorskys await you at the museum, including a Sikorsky S-39 (the oldest surviving Sikorsky), and the last remaining Sikorsky VS-44 flying boat.

Also riveting is what is arguably the oldest surviving aircraft in the United States. This is a balloon basket flown over Hartford around 1870 by the pioneer balloonist Silas M. Brooks (1824-1906).

Along with more than 55 aircraft on show, the museum maintains a changing display of engines, as well as engrossing exhibitions. These cover the local aerospace company Pratt & Whitney, and figures like the Connecticut aviation pioneer Percival H. Spencer (1897-1995).

12. Hartford

Windsor has much to recommend it, but the state capital is a mere six minutes to the south by train. There’s much more than a weekend’s worth of things to get up to in Hartford.

You could pass your time savoring Baroque masterpieces by the likes of Caravaggio at the Wadsworth Atheneum or visiting the marvelous Gothic home of Mark Twain. This is considered one of the world’s great writers’ house museums.

The Bushnell Center for Performing Arts receives big name musicians and comedians, while I can’t forget the 18th-century Old State House, the very source of democracy in Connecticut.

Children will be in awe of the high-tech interactive fun at the Connecticut Science Center. You can watch the Colorado Rockies’ big prospects in action for the Hartford Yard Goats at the excellent Dunkin’ Park.

13. Thomas Hooker Brewery

The taproom and visitor center for this local small batch brewery, just over the town line in Bloomfield, is now deep into its second decade.

Thomas Hooker has six main beers, complemented by a huge selection of seasonal and limited release brews.

Beer always tastes better when you go to the source, and, fortunately, Thomas Hooker’s taproom is open seven days a week. They pour a big choice of beers, while filling growlers and selling cans to go.

There’s an outdoor patio, a gift shop, and free Wi-Fi here.

Among the 20 beers on draught when I wrote this article were mainstays like #NOFILTER, Hop Meadow IPA and Blonde Ale.

There’s also a selection of citrusy IPAs, a Chocolate Truffle Stout, an Irish Red and a Pulp’d, a Berliner Weisse brewed with raspberries.

14. The Wood Memorial Library and Museum

Make your way across the Connecticut River where you’ll find yourself in the East Windsor Hill Historic District.

Main Street in South Windsor is edged by folk vernacular architecture from 1700 to 1860, with some examples on a truly palatial scale.

You can set foot inside one of these buildings at the Wood Memorial Library and Museum, open all day Monday and Thursday.

This attraction, dating from 1927, stages temporary exhibitions for local history, art and nature. Those shows are complemented by large permanent collections for ornithology, Native American history, local decorative arts, and the history of the state.

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

When I was here there was a compelling showcase for indigenous artifacts unearthed locally along the Connecticut River.

15. Keney Park Golf Course

On both sides of the town line between Windsor and Hartford there’s a highly-regarded public golf course.

The first nine holes at Keney Park were laid out by the renowned architect Devereux Emmet in 1927. Until the 2010s the course was under the management of a for-profit firm and had lost its high reputation. Now it’s come under the wing of the City of Hartford once more.

The course has bounced back with a thorough refurbishment of its tee boxes, fairways, bunkers, greens, and clubhouse. You can now find it on lists of the best public courses in the country.

Even for non-residents the rates are economical. When I compiled this list, you could play 18 holes for under $50 on weekdays. Before your round you can sharpen up at the range, green and short game area.