15 Best Things to Do in Windsor (CT)

Written by Veronique Raes
Updated on
Our travel recommendations are based on our personal experiences and research, written by locals and travel experts with deep familiarity with the destination. When you book a hotel or tour that we link to, we may earn a commission.

The first English settlement in the state of Connecticut is the town of Windsor a few miles up the Connecticut River from Hartford and founded in 1633. In Windsor you can investigate this storied past at the local historical society and the Oliver Ellsworth Homestead, 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 tobacco industry, which has all but disappeared, save for a few farms and an interesting exhibition at Northwest Park.

Windsor will feel especially genteel on 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

Northwest ParkSource: Jennifer Yakey-Ault / shutterstock
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, and within the park’s boundaries there’s a diversity of woodland, open fields, wetlands and the south bank of the Farmington River, all served by more than 12 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, while kids will be besotted with the Heritage Breed farm animals outside.

There’s a series of Coffeehouse Concerts throughout the year, and if you come after a 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

Vintage Radio And Communications Museum Of ConnecticutSource: Vintage Radio & Communications Museum of Connecticut / facebook
Vintage Radio And Communications Museum Of Connecticut

This is just the sort of local museum you hope to find in a town like Windsor, but with dimensions that may catch you off guard.

The collection of radios, radio accessories, cameras, home computers and broadcast equipment is extensive and is organised 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, while you can manoeuvre 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 juke box.

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

3. Windsor Historical Society

Windsor Historical SocietySource: LEE SNIDER PHOTO IMAGES / shutterstock
Windsor Historical Society

You can be sure that the “First in Connecticut” has a lot of history to uncover, and 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, including 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

town hallSource: Jennifer Yakey-Ault / shutterstock
Town Hall

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

The green is the centre of town in every sense, bordered by the library and town hall, and a small but international array of restaurants for Indian, pho 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, all coinciding with the farmers’ market, where you can buy local fruits, vegetables, eggs, cheeses, herbs, baked goods and more, direct from the producers.

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

5. Oliver Ellsworth Homestead

Oliver Ellsworth HomesteadSource: Oliver Ellsworth Homestead EMA / facebook
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, 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.

As you see it, the house’s interior has been preserved in the 19th century, and has decor and furnishings related to Ellsworth and his descendants.

The building has been in the hands of the Connecticut Daughters of the American Revolution since 1903, and is open to the public on weekends.

6. Windsor Center River Trail

Windsor Center River TrailSource: Jennifer Yakey-Ault / shutterstock
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 centre of town, either 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 you may need to bring bug spray, but the upside is a peaceful escape to bird-rich nature on wheelchair and stroller friendly terrain.

7. Back East Brewery

Back East BrewerySource: Back East Brewing Company / facebook
Back East Brewery

Nowhere has embraced the craft beer phenomenon quite like Connecticut, and 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 Thursday to Sunday and serving a range of ales, porters and seasonal brews.

In 2019 one of the beers making waves was the Ice Cream Man IPA, brewed with citra hops for a flavour not far off a sophisticated orange creamsicle.

There are 15 or more on tap at any one time, and if you can’t make up your mind you can order a flight of four for $7. 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

Windsor Art CenterSource: Windsor Art Center / facebook
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 programme of temporary exhibitions for well-known and breakout talent from the Connecticut area.

Live music, talks and poetry readings are also on the schedule, as well as classes and workshops for anything from watercolors to yoga.

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

9. Connecticut Valley Tobacco Museum

Connecticut Valley Tobacco MuseumSource: Connecticut Valley Tobacco Museum / facebook
Connecticut Valley Tobacco Museum

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

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

At this newly renovated 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 new timeline exhibition walks you through this chronology.

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

10. Northwest Park Country Fair

Northwest Park Country FairSource: www.northwestpark.org
Northwest Park Country Fair

A much anticipated date on the town’s calendar, the Northwest Park Country Fair falls around the end of September and for a few hours 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.

You can catch some live music, bid for a bargain at the silent auction and see a variety of performances and demonstrations by local organisations, 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)

New England Air MuseumSource: New England Air Museum / facebook
New England Air Museum

Make the short drive up to Bradley International Airport for this museum set in three immense climate-controlled hangars and going into depth on the aviation industry in Connecticut and the wider 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, 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 absorbing exhibitions on the local aerospace company Pratt & Whitney, and figures like the Connecticut aviation pioneer Percival H. Spencer (1897-1995).

12. Hartford

HartfordSource: Sean Pavone / shutterstock

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

You could pass your time savouring Baroque masterpieces by the likes of Caravaggio at the Wadsworth Athenium or visiting the marvellous Gothic home of Mark Twain, considered one of the world’s great writers’ house museums.

The Bushnell Center for Performing Arts receives big name musicians and comedians, while the 18th-century Old State House is the very source of democracy in Connecticut.

Children will be awe of the high-tech interactive fun at the Connecticut Science Center, and you can watch the Colorado Rockies’ big prospects in action for the Hartford Yard Goats at the brand new Dunkin’ Donuts Park.

13. Thomas Hooker Brewery

Thomas Hooker BrewerySource: Thomas Hooker Brewery / facebook
Thomas Hooker Brewery

The taproom and visitor centre for this local small batch brewery, just over the town line in Bloomfield, is now in 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 pouring a big choice of beers, 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 we wrote this article in 2019 were mainstays like #NOFILTER, Hop Meadow IPA and Blonde Ale, as well as a selections of citrusy IPAs, a Chocolate Truffle Stout, an Irish Red and a Pulp’d, a Berliner Weisse brewed with blackberries.

14. The Wood Memorial Library and Museum

The Wood Memorial Library And MuseumSource: Wood Memorial Library & Museum / facebook
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, 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.

In summer 2019 there was an endearing exhibition of bird photography to mark the 110th anniversary of the Hartford Audubon Society, matched with the museum’s impressive collection of mounted birds.

15. Keney Park Golf Course

Keney Park Golf CourseSource: Keney Park Golf Course / facebook
Keney Park Golf Course

On both sides of the town line between Windsor and Hartford there’s a well-regarded public golf course, the first nine holes of which were laid out by the renowned architect Devereux Emmet in 1927. Until recently Keney Park Golf Course was under the management of a for-profit firm and had lost its high reputation, but has since 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, and now features on lists of the best public courses on the country.

Even for non-residents the rates are affordable, costing $42 and $44 for 18 holes on weekdays and weekends.

Before your round you can sharpen up at the range, green and short game area.

15 Best Things to Do in Windsor (CT):

  • 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