Welcome to Windham County

Windham County is Connecticut’s quintessential countryside—think rolling hills, historic villages, and picture-perfect colonial homes surrounded by old stone walls and open land. Located in the northeast corner of the state, this area is often called the “Quiet Corner” for good reason—it offers a serene, rural lifestyle with surprisingly easy access to larger cities like Hartford, Providence, and Worcester. This makes it a hidden gem for those who want the peaceful pace of country life without giving up weekend trips to museums, concerts, or city shopping.

The real draw here is its authentic New England feel. With its classic town greens, white church steeples, and tree-lined country roads, Windham County offers a refreshing sense of calm and connection. It’s a place where historic charm and natural beauty come together in everyday life, and where homes often come with spacious yards, scenic views, and a true sense of privacy. The local culture is rich with creativity, tradition, and community pride, making it a truly special place to call home.

What to Love

Beautiful New England architecture and open landscapes

• Spacious properties and a more rural lifestyle

• Easy access to MA and RI

• Locally owned shops, farms, and restaurants

• Active arts, culture, and historical attractions

Local Lifestyle

Living in Windham County feels like stepping into a slower, more intentional rhythm. Mornings often begin with fresh coffee from a local café and views of the countryside, while weekends are filled with farmers markets, scenic hikes, or visits to historical landmarks. There's a deep appreciation for nature, craft, and community here—residents take pride in supporting local businesses and preserving the area’s heritage. It’s a lifestyle rooted in simplicity, where quality of life is measured more by connection and experience than by speed or scale.

Dining and Shopping

The culinary scene in Windham County is quietly impressive, with local chefs and restaurateurs creating destination-worthy meals that highlight farm-fresh ingredients and creative flair. In Putnam, 85 Main stands out for its elevated take on American cuisine and seafood, served in a stylish yet relaxed setting. Just a few blocks away, The Stomping Ground offers live music and artsy ambiance alongside its hearty, eclectic menu—perfect for a night out with friends.

In Woodstock, Inn at Woodstock Hill provides an elegant dining experience in a historic setting, complete with fine wines and seasonal menus crafted to perfection. For something casual and cozy, Victoria Station Café in Putnam blends charm with freshly made pastries, sandwiches, and locally roasted coffee, making it a beloved daytime hangout.

Shopping leans local and artisanal here. Downtown Putnam is known for its walkable streets lined with antiques, boutiques, and art galleries. Arts & Framing, Antiques Marketplace, and Celebrations Gallery offer everything from one-of-a-kind vintage finds to fine art and handmade gifts. Throughout the year, seasonal craft fairs and open studios bring even more opportunities to discover local talent and treasures.

Things to Do

A must-see attraction in the area is the iconic Roseland Cottage, a striking pink Gothic Revival mansion in Woodstock. Known for its stunning architecture, lush gardens, and rich history, the cottage hosts guided tours, concerts, and events throughout the year. Its vibrant facade and impeccably preserved interiors offer a unique glimpse into 19th-century life and style, making it a favorite for locals and history buffs alike.

Outdoor enthusiasts will find no shortage of fresh-air adventures in Windham County. From hiking and kayaking in Bigelow Hollow State Park to scenic drives along Route 169—one of the state’s most beautiful byways—there’s always something to explore. Local vineyards, like Taylor Brooke Winery, offer a relaxing way to spend an afternoon with a glass in hand and a view of the vines. The area’s blend of nature, culture, and heritage creates a lifestyle that’s both invigorating and enriching.