Top 15 Must-Do Activities in Windham, Connecticut

Summary of Attractions in Willimantic

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

Windham in Northeastern Connecticut contains the city of Willimantic, which developed around a textile industry in the late 19th century.

There is an excellent small museum dedicated to the cotton mill that was once crucial to the city’s economy.

The numerous charming 19th-century properties on Prospect Hill signify the wealth generated by the textile trade for Willimantic. Additionally, the downtown area, lined by Main Street, bursts with music and activity during the summer.

Indeed, the city exhibits a genuine sense of community. This is particularly evident during the Third Thursday Street Fest, where artists and artisans from Willimantic and surrounding areas showcase their crafts, accompanied by live music and delectable food options.

1. Windham Textile & History Museum

From the 1800s well into the latter decades of the 20th century, Willimantic’s economy was primarily influenced by the textile industry.

To illustrate its significance, the Willimantic Linen Company’s Mill No. 4 was the world’s largest cotton mill upon its inauguration in 1880. During my visit, I discovered that it was the first mill designed for electric lighting.

This mill was acquired by the American Thread Company in 1898, which expanded its production until its closure in 1985. Although Mill #4 was destroyed by fire in 1995, a significant portion of the complex remains intact.

Visitors can explore recreations of the factory’s boarding houses and the manager’s office, while another building houses replica sewing machines from the factory.

The museum’s knowledgeable staff share captivating insights into life in the mills, along with a broader perspective on Windham’s history.

If your visit coincides with Halloween or Christmas, you can expect engaging events such as spooky tours or visits from Santa.

2. Prospect Hill Historic District

Anyone appreciating Victorian architecture will be captivated by this elegant neighborhood of Willimantic, which developed between 1865 and 1930.

The abundance of ornate 19th-century architecture is truly impressive. Notably, Prospect Hill boasts one of the highest concentrations of buildings from this era in the state.

There are 993 contributing buildings, 600 of which are residences, with more than half constructed prior to the turn of the century.

Exploring Prospect Hill is best done on foot, allowing visitors to admire favorites in Italianate, Second Empire, Queen Anne, Stick, and Shingle architectural styles.

3. Connecticut Eastern Railroad Museum

This charming museum is located on the site of the former Columbia Junction Freight Yard. It features an intriguing collection of original and replica railroad structures along with vintage rolling stock.

The main building is the Columbia Junction Roundhouse, which was renovated in the 1990s using the original late 19th-century foundations, completing the project in 2001.

Also on-site is Chaplin Station, established in 1872 and moved to the museum site in 1995, later joined by the restored Groton Freight House.

Visitors can view impressive locomotives, such as an EMD SW8 used for switching, and a New Haven EMD FL9, both from the 1950s.

One aspect that stands out about the museum is the ongoing restoration work, which creates a vibrant atmosphere during visits.

A highlight of the museum’s calendar is Railroad Day at the end of August, featuring train rides, live music, and numerous family-friendly activities.

4. Main Street Historic District

The historical core of Willimantic stretches back over 300 years, commencing with a series of mills established at the confluence of the Natchaug and Willimantic Rivers.

It was not until the 1870s that Main Street evolved into a commercial corridor. Fast forward 150 years, and downtown Willimantic now represents a vibrant central business district, extending approximately four blocks along Main Street.

Live performances can be found at the Windham Theatre Guild, as well as a diverse assortment of dining and drinking establishments. Options range from craft beer to gourmet coffee, Mexican cuisine, pizza, boba tea, and more.

At the southwest end, visitors can embark on a hike along the Air Line State Park Trail. Back in town, Jillson Square hosts numerous local events, including the Willimantic Carnival in May. Additional downtown events will be discussed later in this guide.

5. Philip Lauter Park

A cherished public park, Philip Lauter Park is ideally situated alongside the Natchaug River and is equipped with numerous facilities for families.

During the summer months, visit the Splash Park and Waterfront, which operate from mid-June through August, allowing children to swim in the gentle river or enjoy the interactive fountains.

The park also includes standard playgrounds for kids, a well-equipped skate park, basketball courts, pavilions, open lawns, and picnic areas. Essentially, it offers everything needed for a perfect family outing in summer.

Philip Lauter Park is additionally popular for fishing and features a thriving community garden.

6. Mansfield Hollow Lake

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

Mansfield Hollow Lake was established in the early 1950s, and its dam site has been listed on the National Register of Historic Places since 2003. The State Park located on the western shore features trails for hiking, mountain biking, and cross-country skiing.

For a more extensive adventure, consider the Nipmuck Trail, which traverses Mansfield’s wilderness for approximately 35 miles.

The dam itself also holds allure for hikers, with picnic areas available both by the lake and downstream.

7. Allanach-Wolf Woodlands

Located in Mansfield, Joshua’s Tract Conservation and Historic Trust was founded in 1966 to preserve areas of natural or historical significance.

One such property is Allanach-Wolf Woodlands in Windham, which covers over 120 acres of predominantly forested land, donated to the trust by Ada Wolf in 2007.

This woodland features streams that flow into Lake Marie, a 22-acre shallow pond. For those seeking an easy walk to appreciate fall foliage, this path is ideal.

Marked trails weave through the woods, and a delightful butterfly garden blossoms with color during spring and summer. Members of the 860 Rocks facebook group often hide painted stones for others to discover here.

8. Mansfield Drive-In Theatre

For a glimpse into mid-century Americana, the largest of the remaining drive-in theaters in Connecticut is situated just outside Willimantic in Mansfield. At the time of writing, it was one of only three still operating in the state.

Established in 1954, the theater accommodates 950 vehicles and features three screens that showcase double features simultaneously.

The starting time for the first screening varies according to sunset, and guests can enjoy a recently refurbished snack bar, offering both sweet and savory treats.

On Sunday mornings, the site transforms into Eastern Connecticut’s largest flea market, hosting numerous vendors indoors and outdoors.

9. Lebanon Green Vineyards

A notable stop on the Connecticut Wine Trail, this vineyard set in rolling hills cultivates Vinifera and French Hybrid grapevines selected for their resilience to the challenging cold winters of Northeastern Connecticut.

The white varieties at Lebanon Green include Chardonnay, Cayuga, and Riesling, while the reds comprise Cabernet Franc and St. Croix.

Producing nine distinct wines, the winery specializes in blends such as Liberty White, made from Cayuga and Chardonnay, or War Office Red, which includes Cabernet Franc and St. Croix.

The vineyard welcomes guests for tastings in a relaxed setting from Friday to Sunday throughout the summer. Additionally, a sophisticated program of live music is featured on Saturdays during the season.

10. Prudence Crandall Museum

A simple drive east along Connecticut Route 14 will take you to the residence of abolitionist Prudence Crandall (1803-1890), who is recognized as Connecticut’s official state heroine.

Between 1832 and 1834, she established the “Prudence Crandall School for Negro Girls” at this location, which was ultimately closed due to mob violence.

Crandall faced three court trials for her resolve to provide private education for young African American women.

The property features four period rooms that allow visitors to retrace the steps of Crandall and her students. The galleries offer deeper insights into Crandall’s experiences and the historical context of America during that time, incorporating three rotating exhibitions.

There is also a research library and a gift shop. It is advisable to take some time to explore the tranquil landscaped grounds surrounding the house.

11. Raspberry Knoll Farm

This farm in North Windham is renowned as Northeastern Connecticut’s primary destination for picking fruit, vegetables, herbs, and flowers.

While it would be impossible to enumerate all of Raspberry Knoll’s crops, it is clear that raspberries dominate.

Here, a full dozen varieties of raspberries are cultivated, thriving during summer and autumn, alongside blueberries, strawberries, and blackberries.

For vegetables, the range includes everything from asparagus to zucchini, while among the herbs, you can find basil, cilantro, peppermint, thyme, lavender, and parsley.

The flower field boasts over thirty varieties available for cutting, sold by the pound. Raspberry Knoll Farm also operates a farm stand, offering all of these products, as well as honey and homemade jams.

12. Willimantic Footbridge

For those interested in the historical development of towns in Connecticut, the Willimantic Footbridge provides a fascinating insight. Linking the south bank of the Willimantic River to downtown, this footbridge dates back to 1906.

This 590-foot steel truss structure remains one of the last surviving footbridges in the state from the early 20th century.

The Willimantic Footbridge is unique as it is the only bridge in Connecticut that crosses both a river and railroad tracks.

It was added to the National Register of Historic Places in 1979 and features informational plaques detailing its history.

13. Beaver Brook State Park

For an immersive natural experience, the undeveloped Beaver Brook State Park is an ideal choice, straddling the Windham and Chaplin town lines.

The park spans over 400 acres, encompassing Bibbins Pond, which is stocked with trout for fishing and features a mowed area with decking and a State Park kiosk at its shore.

Boating is permitted on this 20-acre pond during the summer months, and there is a geocache available on three different trails.

The state acquired the park in the 1950s, utilizing funds donated to the state by attorney George Dudley Seymour (1859-1945).

Seymour is particularly notable for being a leading advocate for Revolutionary War martyr Nathan Hale to be recognized as a national hero.

14. Third Thursday Street Fest

Between May and September, Main Street transforms into a vibrant gathering place every third Thursday evening of the month, an event that has been flourishing since 2002.

As you stroll through the Third Thursday Street Fest, you will encounter live music, street performances, and more than 100 vendors from Willimantic and beyond.

Participants can experience the diversity of arts and crafts produced in Connecticut. Naturally, there are craft beers, local wines, and an array of international cuisines highlighting Willimantic’s rich culture.

Main Street is categorized into color-coded sections during the event, and in the Uptown Area, there is a dedicated children’s zone with plenty of activities to keep the young ones entertained.

15. Boom Box Parade

One of my favorite events in Connecticut, Willimantic’s annual Boom Box Parade has been celebrated every Fourth of July since 1986. The tradition began when a marching band could not be found for Windham’s Memorial Day parade.

In response, five weeks later, for Independence Day, the local radio station WILI-AM broadcast marching band music. Residents were invited to tune in and play the music from their boom boxes while they marched.

Participation is open to all, with the only requirement being the wearing of red, white, and blue, and carrying a radio tuned to WILI (1400-AM).

No pre-registration is necessary, and the crowd assembles at Jillson Square by Main Street at 09:00 on July 4.

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