15 Best Things to Do in Windham (CT)

Written by Veronique Raes
Updated on
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Windham in North-eastern Connecticut contains the city of Willimantic, which developed around a textile industry in the late 19th century.

There’s a fantastic little museum dedicated to the cotton mill was once so central to the city’s fortunes.

The hundreds of dainty 19th-century properties on Prospect Hill indicate the sort of wealth that the textile trade generated for Willimantic.

The city now has a real sense of togetherness and community, shown by the Third Thursday Street Fest in summer when artists and crafters from Willimantic and the wider area display their wares, paired with live music and great food.

1. Willimantic Textile & History Museum

Willimantic Textile &; History MuseumSource: Hadassah Eastern Connecticut / facebook
Willimantic Textile & History Museum

From the 1800s well into the last decades of the 20th century Willimantic’s economy was driven by the textile industry.

To give a sense of its size, the Willimantic Linen Company’s Mill No. 4 was the world’s largest cotton mill when it opened in 1880, and the first designed for electric lighting.

That mill was purchased by the American Thread Company in 1898 and expanded production, eventually closing in 1985. Mill #4 burnt down in 1995 but a big portion of the complex remains.

You can enter recreations of the factory’s boarding houses and the manager’s office, while a second building holds replica sewing machines from the factory.

The museum’s knowledgeable staff will have lots of captivating snippets about life in the mills, and Willimantic’s past in general.

If you come at Halloween or Christmas there’s normally something fun happening, like a spooky tour or a visit from Santa.

2. Prospect Hill Historic District

Prospect Hill Historic DistrictSource: en.wikipedia.org
Prospect Hill Historic District

Anyone with an eye for Victorian architecture will be besotted with this genteel corner of Willimantic that grew up between 1865 and 1930. The quantity of ornate 19th-century architecture is almost overwhelming; Prospect Hill has one of the largest single concentrations of buildings from this era in the state.

There are 993 contributing buildings, 600 of which are houses, more than half of which were completed before the turn of the century.

Prospect Hill is best discovered on foot, as you pick out your favorites in the Italianate, Second Empire, Queen Anne and Stick and Shingle styles.

3. Connecticut Eastern Railroad Museum

Connecticut Eastern Railroad MuseumSource: Connecticut Eastern Railroad Museum / facebook
Connecticut Eastern Railroad Museum

This lovable museum is found on the site of the old Columbia Junction Freight Yard, and preserves an exciting collection of original and replica railroad structures and vintage rolling stock.

The main building here is the Columbia Junction Roundhouse, reborn in the 1990s using the late-19th-century foundations of the original, and completed in 2001. Also here is Chaplin Station, constructed in 1872 and relocated to the museum site in 1995, and joined by the restored Groton Freight House a little later.

There are some impressive locomotives to size up too, like an EMD SW8, used from shunting/switching and a New Haven EMD FL9, both from the 1950s.

A great thing about the museum is that restoration works constantly taking place, so there’s always a lot of life when you visit.

The highlight of the calendar at the museum is Railroad Day at the end of August, bringing train rides, live music and all kinds of family fun.

4. Philip Lauter Park

Philip Lauter ParkSource: Ashmita Mukherjee / facebook
Philip Lauter Park

A treasured public space, Philip Lauter Park has an idyllic location next to the Natchaug River, and is crammed with amenities for all the family.

In summer the headline is the Splash Park and Waterfront, open from mid-June to the end of August for swimming in the gentle river and running wild among the fountains and spouts.

There are also conventional playgrounds for children, as well as a well-equipped skate park, basketball court, pavilions, open lawns and picnic tables.

Philip Lauter Park is also a popular fishing spot and has a community garden in great health.

5. Mansfield Hollow Lake

Mansfield Hollow LakeSource: Jeff Holcombe / shutterstock
Mansfield Hollow Lake

This reservoir on Windham’s northern boundary provides drinking water for Willimantic and controls flooding in the Thames River watershed.

Mansfield Hollow Lake was created at the turn of the 1950s and the dam site has been listed on the National Register of Historic Places since 2003. Mansfield Hollow State Park is on the western shore, and has trails for hiking, mountain biking and cross-country skiing.

You can pick up the Nipmuck Trail here, which courses through Mansfield’s wilderness for 35 miles.

The dam itself is also a much loved spot for hiking, with picnic areas both by the lake and downstream from the dam.

6. Allanach-Wolf Woodlands

Allanach-Wolf WoodlandsSource: joshuastrust.org
Allanach-Wolf Woodlands

Based in Mansfield, Joshua’s Tract Conservation and Historic Trust was incorporated in 1966 to help conserve areas of natural or historic interest.

One such property can be found in Windham at the Allanach-Wolf Woodlands, more than 120 acres of mostly forested land, donated to the trust by Ada Wolf in 2007. The woods are laced with streams, which flow into the 22-acre shallow pond called Lake Marie.

Marked trails weave off into the woods and there’s a lovely little butterfly garden that bursts into color in spring and summer.

People from the 860 Rocks facebook group hide painted stones for others to discover here.

7. Mansfield Drive-In Theatre

Mansfield Drive-In TheatreSource: Mansfield Drive-in Theatre & Marketplace / facebook
Mansfield Drive-In Theatre

For a slice of mid-century Americana, the largest of the remaining drive-in theatres in Connecticut is just outside Willimantic in Mansfield.

Dating back to 1954 the theatre has space for 950 cars, with three screens showing double bills simultaneously.

Naturally the time of the first screening changes according to sunset, and there’s a newly refurbished snack bar for sweet or savoury theatre treats.

On Sunday mornings the site becomes Eastern Connecticut’s largest flea market, with dozens of vendors trading indoors and outside.

8. Lebanon Green Vineyards

Lebanon Green VineyardsSource: Lebanon Green Vineyards / facebook
Lebanon Green Vineyards

A stop on the Connecticut Wine Trail, this vineyard in rolling countryside grows Vinifera and French Hybrid vines selected to withstand the harsh North-eastern Connecticut winters.

The white grapes at Lebanon Green include Chardonnay, Cayuga and Riesling, while among the reds are Cabernet Franc and St. Croix.

Producing eight different wines, the winery specialises in blends like Liberty White, from Cayuga and Chardonnay, or War Office Red, with Cabernet Franc and St. Croix.

The vineyard is open for tastings in a relaxed atmosphere from Friday to Sunday in summer, and there’s a classy program of live music on Saturdays.

9. Kerri Art Studio and Gallery

Kerri Art Studio And GallerySource: Kerri Art Studio and Gallery / facebook
Kerri Art Studio And Gallery

This late-19th-century store on 861 Main Street is the base for artist Kerri Quirk, who is something of an outsider, having earned a great deal of praise deviating from the conventions of the art world.

Both deaf and with autism, Kerri’s work is fresh, bright, fun and confrontational.

She paints here five days a week, while the gallery hangs exhibitions of her work, as well as revolving shows by local and not so local artists.

Along with originals, Kerri’s art is printed on mugs, clothing and more.

There’s regular live music, group paint nights and the gallery participates in the Third Thursday Street Fest which we’ll talk about below.

10. Prudence Crandall Museum

Prudence Crandall MuseumSource: Prudence Crandall Museum / facebook
Prudence Crandall Museum

A simple drive east on Connecticut Route 14 will bring you to the home of the abolitionist Prudence Crandall (1803-1890), Connecticut’s official state heroine.

Between 1832 and 1834 she ran the “Prudence Crandall School for Negro Girls” here, which was shut down because of mob violence.

Crandall endured three court trials for her determination to provide private education for young African American women.

At the property there are four period rooms where you can walk in the footsteps of Crandall and her students, while the galleries go into more depth on Crandall’s story and the landscape in America at the time, with three changing exhibitions.

There’s also a research library and a gift shop, and it’s worth giving yourself some time to wander the house’s landscaped grounds.

11. Raspberry Knoll Farm

Raspberry Knoll FarmSource: Raspberry Knoll Farm / facebook
Raspberry Knoll Farm

This farm in North Windham is billed as North-eastern Connecticut’s premier destination for pick-your-own fruit, vegetables, herbs and flowers.

We would never be able to list all of Raspberry Knoll’s crops, but it’s fair to say that raspberries are front and centre.

There are 12 raspberry varieties, ready in summer and autumn, along with blueberries, strawberries and blackberries.

For veggies, there’s everything from asparagus to zucchini, and among the herbs there’s basil, cilantro, peppermint, thyme, lavender and parsley.

The flower field has more than thirty varieties for cutting, and are sold by the pound.

Raspberry Knoll Farm also runs a farm stand, selling all of this produce, as well as honey and homemade jams.

12. Willimantic Footbridge

Willimantic FootbridgeSource: Pi.1415926535 / Wikimedia
Willimantic Footbridge

If you’re interested in how town’s in Connecticut have developed over the last century, there’s a fascinating piece of infrastructure linking the south bank of the Willimantic River with downtown.

Built in 1906, this 180-metre steel truss crossing is one of the last remaining footbridges in the state from the early 20th century.

The Willimantic Footbridge is a curiosity for another reason, as it’s the only bridge in Connecticut to cross both a river and railroad tracks.

The bridge was added to the National Register of Historic Places in 1979 and has information plaques detailing its history.

13. Beaver Brook State Park

Beaver Brook State ParkSource: Codymcarlson / Wikimedia
Beaver Brook State Park

If you need to get out into nature, the undeveloped Beaver Brook State Park is a good pick, straddling the Windham and Chaplin town lines.

In more than 400 acres, the park encompasses Bibbins Pond, which is stocked with trout for fishing and has a mowed area with decking and a State Park kiosk on its shore.

Boating is permitted on this 20-acre pond in the summer months, while there’s a geocache that you can track down on three different trails.

The park came into state hands in the 1950s, using funds donated to the state by the attorney George Dudley Seymour.

14. Third Thursday Street Fest

Third Thursday Street FestSource: 3rd Thursday Street Festival / facebook
Third Thursday Street Fest

Between May and September Main Street is flooded with people every third Thursday evening of the month for an event that has been going strong since 2002. Ambling through the Third Thursday Street Fest you’ll be greeted by live music, street theatre and more than 100 vendors from Willimantic and the wider region.

You’ll get to see the full breadth of arts and crafts produced in Connecticut, and of course there’s craft beer, local wine and delicious international cuisine to make clear just how diverse Willimantic is.

Main Street is divided into color-coded sections during the event and in the Uptown Area there’s a children’s space with lots of things to keep wee ones engaged.

15. Boom Box Parade

Boom Box ParadeSource: WLI Boom Box Parade / facebook
Boom Box Parade

Willimantic’s annual Boom Box Parade has taken place every 4th of July since 1986. The tradition was born when no marching band could be found for Windham’s Memorial Day parade, and five weeks later for Independence Day the local radio station WILI-AM played the marching band music on the air for people to tune in and play from boom boxes as they marched.

Anybody can take part, and the only prerequisite is to be wearing some red, white and blue and carry a radio tuned to WILI (1400-AM). No pre-registration is needed, and the crowd gathers at Jillson Square by Main Street at 09:00 on July 4.

15 Best Things to Do in Windham (CT):

  • Willimantic Textile & History Museum
  • Prospect Hill Historic District
  • Connecticut Eastern Railroad Museum
  • Philip Lauter Park
  • Mansfield Hollow Lake
  • Allanach-Wolf Woodlands
  • Mansfield Drive-In Theatre
  • Lebanon Green Vineyards
  • Kerri Art Studio and Gallery
  • Prudence Crandall Museum
  • Raspberry Knoll Farm
  • Willimantic Footbridge
  • Beaver Brook State Park
  • Third Thursday Street Fest
  • Boom Box Parade