Windham is a charming town in Windham County, Connecticut. The city had a population of 23,833 as of 2023. It is often called “Thread City” due to its rich history in the textile industry. Windham is known for its close-knit community and scenic surroundings. It includes several distinctive areas, such as Willimantic, Windham Center, North Windham, and South Windham.
Windham spans 27.9 square miles, with a mix of land and water. The area’s landscape showcases New England’s rural beauty with its rolling hills, open spaces, and historic architecture. One of the town’s notable features is the Willimantic River, which historically powered local mills and factories, sparking the region’s industrial growth in the 19th century.
The town is home to Eastern Connecticut State University, contributing to a vibrant local culture and diverse population. Among its unique sites, Windham boasts landmarks on the National Register of Historic Places, such as the Main Street Historic District and Windham Center Historic District.
With its blend of history, educational institutions, and picturesque landscapes, Windham remains a key part of Connecticut’s heritage and appeal.
Are you planning an exploration of Windham? Check out the best things to do in Windham, CT.
Things To Do in Windham, CT
1. Visit the Windham Textile & History Museum
Windham Textile & History Museum
Step back in time and explore Connecticut’s rich industrial past at the Windham Textile & History Museum. Known as the “Thread City Museum,” this location delves into Windham’s textile heritage, tracing its development from the 19th century to the present.
Visitors can view historic textile machinery, factory tools, and old photographs that bring the bygone era of mill work alive. Exhibits include displays of machinery that once filled the mill floors, recreating the atmosphere of the bustling textile industry.
The museum provides a fascinating look at the lives of textile workers, many of whom were immigrants. You can visit the worker’s dormitory exhibit, set up to replicate the living conditions of those who worked the mills. The museum offers guided tours that give deeper insights into the local industry’s impact on Windham and the surrounding area.
In addition to permanent exhibits, the museum frequently hosts special events, workshops, and lectures, making it an engaging spot for both locals and tourists. It’s an ideal destination for history buffs and anyone interested in learning more about the roots of this unique town.
Address: 411 Main St, Willimantic, CT 06226
2. Attend Events at the Windham Town Green
The Windham Town Green is the heart of the community and a gathering place for many of the town’s best events. This scenic, open space offers a welcoming atmosphere for locals and visitors alike. Throughout the year, the town green hosts a variety of events, including seasonal markets, holiday celebrations, and outdoor concerts.
One of the highlights is the annual Farmers’ Market, where vendors gather to sell fresh produce, artisanal goods, and homemade treats. During the holiday season, the green transforms into a winter wonderland with festive decorations, a tree-lighting ceremony, and live entertainment. Music lovers will enjoy the summer concert series, which brings local bands and performers to the green for free shows under the stars.
The Windham Town Green is also a great place for a casual picnic or a leisurely stroll when there are no events taking place. Its well-kept lawns, shady trees, and central location make it a perfect spot to relax and soak up the community’s friendly vibe.
Address: 283 Prospect St, Willimantic, CT 06226
3. Explore Eastern Connecticut State University’s Campus
Eastern Connecticut State University (ECSU) is more than just an educational institution; it’s a vital part of Windham’s culture and history. Established in 1889, ECSU’s campus spans 182 acres and offers a blend of classic architecture and modern facilities. Walking through its grounds, you’ll encounter a range of beautifully landscaped areas, including gardens, tree-lined paths, and inviting green spaces.
The university’s buildings reflect a mixture of historical and contemporary styles. Shafer Hall, for instance, is a beautiful example of classic academic architecture. Meanwhile, the Fine Arts Instructional Center, a modern facility, hosts art exhibits, theater performances, and music events that are open to the public.
A visit to ECSU also offers access to the J. Eugene Smith Library, which often displays local historical documents and art collections, giving visitors a glimpse into Windham’s cultural roots. For nature lovers, the Arboretum on campus has a variety of native plant species, perfect for a scenic stroll. ECSU truly feels like a community gathering spot, with events, activities, and open areas inviting everyone to enjoy.
Address: 83 Windham St, Willimantic, CT 06226
4. Spend Time at Jillson Square Park
Jillson Square Park offers a slice of nature right in the heart of Windham. Known for its open green spaces and community feel, this park is the perfect place to relax or enjoy a small outdoor gathering. Jillson Square frequently hosts local events, especially during warmer months, making it a lively spot to visit year-round.
At the center of the park is a historic bandstand, where you can often find live music performances and cultural events. It’s a popular place for community concerts, adding a lively vibe to the park’s atmosphere. The park also features benches and shaded areas where you can unwind with a book or simply watch the world go by.
Jillson Square Park’s open layout makes it ideal for family outings, casual picnics, or even just a quiet walk. Seasonal festivals, like the annual Fourth of July celebration, bring the community together with fireworks, food trucks, and activities for all ages. The park’s spacious design means there’s always room for everyone to enjoy the outdoor setting.
Address: 533 Main St, Willimantic, CT 06226
5. Visit the Garden on the Bridge
The Garden on the Bridge is a unique attraction that combines natural beauty with local history. This elevated garden is set on an old bridge that spans the Willimantic River, creating a peaceful green space right over the water. The garden includes colorful flower beds, benches, and a scenic view of the river, making it a picturesque spot for visitors to take in the scenery.
Walking along the bridge, you’ll find interpretive signs that tell the story of the area’s industrial past. The bridge, originally built in the early 20th century, was transformed into a garden to honor Willimantic’s history and culture. It’s now a serene retreat where visitors can enjoy beautiful plants and learn about the town’s heritage.
With its river views and blooming flowers, the Garden on the Bridge is a photographer’s delight. It’s an ideal spot for a peaceful stroll, a reflective moment, or a quick photo session. Whether you’re visiting in spring when the flowers are in full bloom or during the autumn for the foliage, the bridge offers a scenic experience in any season.
Address: 322 Main St, Willimantic, CT 06226
6. Discover Local Art at ArtSpace Gallery
ArtSpace Gallery is a gem for art enthusiasts visiting Windham. This gallery offers an intimate look into the creative spirit of local artists, displaying a diverse range of work from paintings and photography to sculpture and mixed media. Located in downtown Willimantic, ArtSpace is part of a community-driven effort to support and showcase regional talent.
The gallery frequently updates its exhibitions, ensuring there’s always something new and interesting on display. Local artists, both emerging and established, use the space to explore themes that resonate with the community, making each visit feel personal and engaging.
ArtSpace also hosts occasional events, workshops, and meet-the-artist nights, giving visitors the chance to connect with the artists behind the works. Beyond just viewing art, visitors can purchase pieces directly from the gallery, supporting local talent and taking home a bit of Windham’s creative energy.
Address: 480 Main St, Willimantic, CT 06226
7. Check Out the Willimantic Brewing Company
Willimantic Brewing Company
The Willimantic Brewing Company is a beloved local spot and a must-visit for anyone exploring Windham. Housed in a former post office building from 1909, this brewery brings historic charm and modern flavors together. Inside, the high ceilings and vintage decor create a cozy yet lively atmosphere that appeals to locals and tourists alike.
The brewery is known for its handcrafted beers, each brewed on-site. Their rotating selection often includes unique brews with creative names, drawing inspiration from the local area. For beer lovers, the “Hop River IPA” or the “Postmaster Pale Ale” are standout choices, and the brewery also offers a range of seasonal and specialty options.
Beyond the beer, Willimantic Brewing Company serves up a menu filled with delicious pub fare. Whether you’re in the mood for a burger, wings, or something a bit more unique, their dishes pair perfectly with their drinks. The brewery hosts events and specials throughout the week, making it a lively destination to meet friends or unwind after a day of exploring Windham.
Address: 967 Main St, Willimantic, CT 06226
8. Attend a Show at the Windham Theatre Guild
For lovers of the performing arts, the Windham Theatre Guild is a must-visit. This local theater company has a reputation for delivering high-quality productions in an intimate, friendly setting. Established in 1985, the guild puts on a variety of performances each season, ranging from classic plays and musicals to contemporary works and original productions.
The theater’s cozy atmosphere enhances the experience, making you feel connected to the performers. Productions often include local talent, which adds a unique, community-oriented vibe to each show. Audiences can expect popular titles as well as family-friendly shows, ensuring there’s something for everyone.
In addition to regular shows, the guild offers events like improv nights, acting workshops, and open mic sessions. These events allow visitors to get involved and experience the local arts scene firsthand. If you’re in town during one of their shows, an evening at the Windham Theatre Guild is a fun way to experience local talent and enjoy live entertainment.
Address: 779 Main St, Willimantic, CT 06226
9. Explore Frog Bridge, a Unique Landmark
Frog Bridge is an iconic landmark that captures the quirky spirit of Windham. Officially named the “Thread City Crossing,” this bridge is famous for its four large bronze frog sculptures perched atop giant spools of thread. Built in 2001, the bridge symbolizes Windham’s historic connection to the textile industry, while the frogs add a playful twist that locals and visitors love.
The idea of frog sculptures on a bridge may sound unusual, but it ties into a local legend. As the story goes, in 1754, townspeople mistook the sounds of bullfrogs for an enemy attack, leading to the “Battle of the Frogs” tale. Today, the sculptures honor this amusing piece of local folklore and are a favorite photo spot for visitors.
Walking across Frog Bridge offers not only a chance to see these unique statues up close but also a scenic view of the Willimantic River below. It’s a quick stop but a memorable one, and it’s easy to include in your Windham itinerary. The bridge’s mix of history, humor, and art makes it a must-see in town.
Address: South St & Main St, Willimantic, CT 06226
10. Relax in Lauter Park along the Willimantic River
Lauter Park is a hidden gem in Windham, offering a peaceful retreat along the scenic Willimantic River. This riverside park is a favorite among locals for its laid-back atmosphere and natural beauty. It’s the perfect spot to unwind, whether you’re looking to have a quiet picnic, enjoy a leisurely stroll, or simply relax by the water.
The park offers ample space for outdoor activities, including a playground for kids, open fields, and a designated area for swimming. There’s also a walking path along the river, allowing visitors to take in views of the water and surrounding greenery. The riverbank is a great place for fishing, and you’ll often find anglers casting their lines along the shore.
Lauter Park is especially beautiful in the fall when the foliage adds vibrant colors to the landscape. It’s a peaceful spot to escape the hustle and bustle, making it a great choice for anyone looking to connect with nature in Windham.
Address: 625 Jackson St, Willimantic, CT 06226
11. Visit the Third Thursday Street Fest
If you’re in Windham between May and September, don’t miss the Third Thursday Street Fest. Held on the third Thursday of each month, this lively festival transforms Main Street in Willimantic into a bustling celebration of local food, music, art, and culture. The street comes alive with vendors, food trucks, and entertainers, creating a vibrant atmosphere that’s fun for all ages.
The festival features live music on multiple stages, showcasing a range of genres from rock and folk to jazz and blues. Local artists and artisans set up booths to sell handmade crafts, artwork, and unique gifts. The festival is also a fantastic opportunity to try local food, with everything from classic fair treats to international flavors.
Kids will enjoy activities like face painting, balloon artists, and games, making this a family-friendly event. The festival has become a beloved tradition in Windham, bringing together locals and visitors for a night of fun and community spirit.
Address: Main St, Willimantic, CT 06226
12. Go Hiking on the Airline State Park Trail
The Airline State Park Trail offers an unforgettable hiking experience for outdoor enthusiasts visiting Windham. This scenic trail spans 50 miles across eastern Connecticut, with a significant portion running through Windham. Originally a railroad corridor, the trail is now a haven for hikers, cyclists, and nature lovers.
The trail features well-maintained paths surrounded by lush forests, quiet streams, and historic landmarks. As you hike, you’ll encounter remnants of old train trestles and bridges that hint at the trail’s railroad past. The gentle gradients make it accessible for all skill levels, while the peaceful surroundings create the perfect environment for relaxation.
One of the highlights is the section along the Willimantic River, where you can enjoy stunning views of the water. Wildlife sightings, including birds and small mammals, are common, adding an element of adventure.
Address: Route 66, North Windham, CT 06256
13. Explore Mansfield Hollow State Park
Mansfield Hollow State Park is a treasure trove of outdoor activities just a short drive from Windham. This sprawling park surrounds the Mansfield Hollow Lake, offering a serene setting for picnicking, fishing, and kayaking. It’s a popular spot for locals and visitors alike, providing a mix of recreational options and scenic beauty.
The park features several trails that wind through woodlands and along the lake’s edge. These trails are ideal for hiking and mountain biking, offering a mix of easy and moderate paths. For water enthusiasts, the lake is perfect for kayaking or paddleboarding, with rentals available nearby.
Fishing is another favorite activity here, with the lake being home to various fish species like bass and trout. Mansfield Hollow is also a bird-watching hotspot, especially during migration seasons. The park’s open spaces and picnic areas make it a great destination for families looking to spend a day outdoors.
Address: 151 Bassetts Bridge Rd, Mansfield Center, CT 06250
14. Discover History at the Windham Center Historic District
Windham Center Historic District
For a dose of history and charm, head to the Windham Center Historic District. This area is like stepping back in time, with beautifully preserved buildings that date back to the 18th and 19th centuries. Walking through the district, you’ll find a variety of architectural styles, from Colonial and Federal to Greek Revival, each telling a story of the town’s rich past.
The historic district is home to the Old Windham County Courthouse, an iconic landmark built in 1822. You can also see several old churches, houses, and the former town green, which was once a central meeting place for residents. Many of these buildings have historical plaques, providing interesting details about their origins and significance.
Visitors to the Windham Center Historic District often enjoy a self-guided walking tour, taking time to explore and appreciate the architecture and quiet beauty of the area. It’s a wonderful spot for history lovers and anyone interested in getting a deeper sense of Windham’s heritage. The district offers a peaceful yet enriching experience, perfect for an afternoon stroll.
Address: Windham Center Rd, Windham, CT 06280
15. Learn at the Charles H. Barrows STEM Academy
The Charles H. Barrows STEM Academy is a hub for innovation and learning in Windham. While primarily a magnet school, the academy also offers community events and workshops that visitors can enjoy. The school focuses on science, technology, engineering, and math, inspiring young minds and visitors alike.
The facility features state-of-the-art labs, interactive exhibits, and outdoor learning spaces, including a garden and a weather station. Community programs often include science fairs, STEM challenges, and lectures on topics ranging from robotics to environmental science. These events are designed to engage both kids and adults, making learning a fun and inclusive experience.
The academy’s architecture is modern and inviting, reflecting its mission to foster creativity and innovation. Visiting during an open house or special event offers a glimpse into the cutting-edge education Windham provides. It’s a great stop for families with children or anyone curious about STEM education.
Address: 141 Tuckie Rd, North Windham, CT 06256
16. Visit the Connecticut Eastern Railroad Museum
The Connecticut Eastern Railroad Museum is a must-see for history buffs and train enthusiasts alike. This outdoor museum is dedicated to preserving the region’s rich railroad history, showcasing a fascinating collection of vintage locomotives, railcars, and historical artifacts. Visitors can explore fully restored railcars and even step inside an authentic caboose, getting a firsthand feel of what rail travel was like in past eras.
One of the museum’s highlights is the recreated Columbia Junction Roundhouse, which offers insight into the operations of railroads in the 19th and early 20th centuries. Volunteer staff, often dressed in railroad attire, share captivating stories about Connecticut’s railroad past and are happy to answer questions. The museum also hosts seasonal events, including rail-themed fairs and model train displays, making it a fun and educational visit for families.
The museum is open seasonally, so it’s best to check the schedule before planning your trip. Visiting the Connecticut Eastern Railroad Museum provides a unique glimpse into the golden age of rail travel in New England.
Address: 55 Bridge St, Willimantic, CT 06226
17. Discover the Old Mills in Willimantic
Exploring the old mills in Willimantic is like stepping into the industrial past that shaped this vibrant town. During the late 19th and early 20th centuries, Willimantic was a thriving mill town, known for its textile production. Today, many of the mill buildings remain, serving as a reminder of the town’s rich heritage. These mills once produced vast quantities of cotton thread, earning Willimantic the nickname “Thread City.”
Visitors can take a walking tour of the mill district to view these historic structures, which have been carefully preserved. Some buildings now house local businesses, art studios, and even apartments, blending old-world charm with modern functionality. The American Thread Company mill complex is particularly iconic and gives a sense of the scale and importance of Willimantic’s industrial past.
The nearby Willimantic River was a vital resource for powering the mills, and visitors can still enjoy scenic views of the river as they explore. These historic mills are a powerful symbol of Willimantic’s identity and serve as a fascinating piece of Connecticut’s industrial history.
Address: Along the Willimantic River, Willimantic, CT 06226
18. Try the Local Eateries in Downtown Windham
Windham’s downtown area is a treat for food lovers, with a variety of eateries that showcase the local flavor. From cozy cafes to lively pubs, the dining options here offer something for every taste. Start your culinary tour with a stop at Cafemantic, a popular eatery known for its farm-to-table menu and relaxed atmosphere. Their dishes are crafted from fresh, locally sourced ingredients, with seasonal menus that highlight New England flavors.
For a unique dining experience, try Willimantic Brewing Company, located in a former post office. It’s one of the area’s favorite spots, known for its house-brewed beers and pub fare. Here, you can pair a locally brewed craft beer with a hearty burger or a plate of fish and chips, all while enjoying the building’s historic charm.
Those looking for international flavors will enjoy dining at local spots that serve Mexican, Italian, and Asian cuisines, adding diversity to Windham’s food scene. Each restaurant and cafe brings a unique taste to the town, making Windham’s downtown a delightful destination for food lovers.
Address: Main St, Willimantic, CT 06226
19. Browse the Willimantic Public Library
The Willimantic Public Library is more than just a place to borrow books. It’s a community hub that brings people together and offers a quiet, inviting space for readers of all ages. Founded in 1897, the library has grown into a beloved local institution with a variety of resources, programs, and events.
Inside, you’ll find a well-curated collection of books, from classic literature to the latest bestsellers. The library also offers an impressive selection of local history materials, making it a great stop for those interested in learning more about Windham and its past. If you’re traveling with kids, don’t miss the children’s section, which features a cozy reading nook and regularly scheduled story hours.
The library hosts numerous community events, including author talks, craft workshops, and book clubs. Visitors are always welcome to stop by and browse or participate in a scheduled event. With free Wi-Fi and a comfortable reading area, it’s also a great spot to relax or catch up on some work during your visit to Windham.
Address: 905 Main St, Willimantic, CT 06226
20. Tour the Dr. Chester Hunt Office Historic Site
Step back in time at the Dr. Chester Hunt Office, a beautifully preserved historic site that offers a glimpse into 19th-century life in Windham. This small office, built in the early 1800s, served as the workspace of Dr. Chester Hunt, a prominent local physician. The site provides an authentic look at how medical professionals of that era practiced medicine and served their communities.
Inside, you’ll find original furnishings, medical tools, and artifacts that were once used by Dr. Hunt. Each item tells a story of the medical practices and challenges of the time, from handmade instruments to old books filled with medical knowledge. Guided tours are available, and knowledgeable docents share fascinating details about Dr. Hunt’s life and work, as well as the history of the town during that period.
The office is small but packed with history, making it an intriguing stop for anyone interested in medicine or local history. A visit here offers a unique, educational experience that sheds light on Windham’s past and the everyday lives of its early residents.
Address: 116 Windham Center Rd, Windham, CT 06280
21. Walk around the Main Street Historic District in Willimantic
Main Street Historic District in Willimantic
Wandering through the Main Street Historic District in Willimantic is like stepping into a well-preserved snapshot of 19th-century New England. This district offers a collection of historic architecture, charming shops, and unique eateries. Many of the buildings date back to the height of Windham’s textile era, featuring beautiful facades and intricate architectural details that reveal the town’s affluent past.
Key highlights include the Victorian-era buildings and the Frog Bridge, a distinctive local landmark adorned with whimsical frog sculptures. The bridge itself serves as a symbol of Willimantic’s character and creativity. You’ll also find murals and sculptures that celebrate the town’s heritage and bring color to the streets.
The district’s locally owned cafes and shops are perfect for a leisurely afternoon. Stop by for a coffee or pick up handmade goods from local artisans. The Main Street Historic District is a prime example of how Windham has preserved its history while fostering a vibrant, community-oriented present.
Address: Main St, Willimantic, CT 06226
22. Celebrate the Annual WILI Boom Box Parade
One of Windham’s most beloved and quirky events is the WILI Boom Box Parade, held every Fourth of July. This unique celebration is known for its creativity and community spirit. What sets it apart is that it features no marching bands or live music—participants and spectators rely entirely on boom boxes to broadcast synchronized patriotic tunes.
The tradition began in 1986 when no live bands were available for the town’s Independence Day parade. Local radio station WILI-AM came to the rescue by broadcasting parade music, and residents were encouraged to bring their boom boxes to join in. The result was a one-of-a-kind celebration that has continued to grow and attract visitors.
Participants dress in festive costumes, decorate floats, and march along Main Street carrying their boom boxes tuned to the same station. The event is open to everyone—there’s no need to register, and the focus is on having fun and showing creativity.
The Boom Box Parade is more than just a parade; it’s a reflection of Windham’s sense of community and ingenuity. It’s a perfect way to experience the town’s personality while celebrating Independence Day in a truly unique style.
Address: Main St, Willimantic, CT 06226 (parade route)
23. Take Scenic Drives Through Windham’s Countryside
Windham’s countryside offers some of the most scenic drives in Connecticut. With rolling hills, open fields, and tree-lined roads, the landscape provides a picturesque escape from urban life. These drives are especially beautiful in the fall, when the foliage transforms into vibrant shades of red, orange, and yellow.
One popular route takes you along Route 14, winding through North Windham and Ashford. This stretch is filled with rural charm, including farms, historic barns, and old stone walls. For those looking to explore the Willimantic River Valley, follow Route 66 for scenic river views and quaint roadside stops.
Another recommended route is Route 203, leading through the countryside’s lush greenery and dotted with small farms and local markets. This route provides a mix of nature and rural architecture, making it a relaxing drive that also showcases Windham’s farming heritage.
These scenic drives are perfect for a leisurely afternoon or a weekend escape, giving you a chance to enjoy the beauty of Connecticut’s quiet countryside. Just roll down the windows, breathe in the fresh air, and enjoy the ride.
Address: Start from Main St, Windham, CT 06226
Final Thoughts
Windham, Connecticut, offers a delightful blend of history, culture, and natural beauty. This charming town invites visitors to immerse themselves in its vibrant community, explore its rich heritage, and experience its tranquil countryside.
Its welcoming atmosphere and authentic New England charm make it a memorable destination. Take the time to explore, connect with locals, and enjoy all that this picturesque town has to offer.