15 Best Things to Do in Windham (CT)

Written by Veronique Raes
Updated on
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Windham in Northeastern 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 that 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. I’m also fond of the downtown area, threaded by Main Street and full of music and fun in summer. 

In fact, the city has a real sense of togetherness and community. This is obvious during the Third Thursday Street Fest. On these evenings artists and crafters from Willimantic and the wider area display their wares, paired with live music and great food.

1. Windham Textile & History Museum

Willimantic Textile &; History MuseumSource: Hadassah Eastern Connecticut / facebook
Windham 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. On my visit I found out that it was the very first to be designed for electric lighting.

That mill was purchased by the American Thread Company in 1898 and expanded production, eventually closing in 1985. Mill #4 burned 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 share lots of captivating snippets about life in the mills, and Windham’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 knocked me sideways. In fact, 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 these 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. It preserves an exciting collection of original and replica railroad structures and vintage rolling stock.

The main building 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. This was 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.

Something that gets me about the museum is that restoration works are 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. On the agenda are train rides, live music, and all kinds of other family fun.

4. Main Street Historic District

The old heart of Willimantic goes back more than 300 years to a set of mills erected at the junction of the Natchaug and Willimantic Rivers. 

It wasn’t until much later, in the 1870s that Main Street became a commercial thoroughfare. Fast forward 150 years and downtown Willimantic is a happening central business district, across about four blocks of Main Street.

There’s live entertainment at the Windham Theatre Guild, as well as a good selection of places to eat and drink. I found craft beer, gourmet coffee, Mexican, pizza, boba tea and more.

At the southwest end you can head off on a hike along the Air Line State Park Trail. Back in town, Jillson Square is the location for a lot of local events, including the Willimantic Carnival in May. I’ll talk about a few more events around downtown later in my list.

5. 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, head here for the Splash Park and Waterfront. They’re open mid-June through August for kids to swim in the gentle river or run 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. In short, I think you’ve got all you need for a family day out in summer. 

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

6. 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. The State Park is on the western shore, and has trails for hiking, mountain biking and cross-country skiing.

My recommendation for a longer adventure is the Nipmuck Trail, 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.

7. 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. If you’re searching for an easy walk to enjoy the fall foliage, this would be my pick. 

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.

8. 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 theaters in Connecticut is just outside Willimantic in Mansfield. When I wrote this list it was one of just three still in business in the state. 

Dating back to 1954 the theater 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 recently refurbished snack bar for sweet or savory theater treats.

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

9. 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 Northeastern Connecticut winters.

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

Producing nine different wines, the winery specializes 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. There’s a classy program of live music on Saturdays during the season.

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 are four period rooms where you can walk in the footsteps of Crandall and her students. Here 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. I think it’s worth taking some time to wander the house’s peaceful landscaped grounds.

11. Raspberry Knoll Farm

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

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

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

There are a full dozen raspberry varieties growing here. These are 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 farmstand, 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 towns 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, the Willimantic Footbridge dates back to 1906. .

This 590-foot steel truss crossing is one of the last remaining footbridges in the state from the early 20th century.

The Willimantic Footbridge intrigues me 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. This 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 (1859-1945). 

What makes Seymour so interesting to me is that he was the foremost champion of Revolutionary war martyr Nathan Hale as a national hero.

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 theater 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. 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. In the Uptown Area there’s a children’s space with lots of things to keep little ones happy.

15. Boom Box Parade

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

One of my favorite events in CT, Willimantic’s annual Boom Box Parade has taken place every Fourth of July since 1986. The tradition was born when no marching band could be found for Windham’s Memorial Day parade.

So, five weeks later for Independence Day the local radio station WILI-AM played the marching band music on the air. People were invited 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):

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