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Windham County Area Guide

Windham County is a delightful part of Connecticut, known for its natural beauty and rich cultural heritage. The county features a myriad of charming towns and villages, each with its unique character and attractions, that make it an ideal destination for visitors looking to explore small-town New England.

Ashford CT

Ashford, a pastoral and picturesque town, is a perfect destination for those looking to immerse themselves in nature. The town boasts some of Connecticut's most beautiful natural scenery, along with several historic sites such as the Ashford Meeting House and the Knowlton Memorial Hall. Ashford's location near the Connecticut and Massachusetts borders, makes it an excellent spot for those looking to visit both states in one fell swoop. Ashford is close to several ski resorts, making it an excellent destination for winter sports enthusiasts. The town is also home to the Ashford Oak, a historic tree that has stood since the Revolutionary era.

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Brooklyn CT

Brooklyn is a quaint and charming town with a rich cultural heritage. Visitors can spend time exploring its beautiful parks and historic landmarks, including the Brooklyn Green Historic District and the Old Brooklyn Burying Ground. The town boasts several excellent restaurants and cafes, making it a perfect destination for a foodie trip. Brooklyn's historic downtown district comprises a wide range of unique shops, restaurants, art galleries, and other cultural attractions. The town boasts several outdoor recreation areas such as the Bigelow Hollow State Park, which encompasses a lake and a range of trails for hiking and biking. Finally, no visit to Brooklyn would be complete without experiencing the Brooklyn Fair, a quintessential Connecticut agricultural fair held every August since 1809.

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Canterbury CT

Canterbury is another idyllic village known for its charming downtown area and excellent recreational facilities. It is also home to the Prudence Crandall Museum, which highlights the life of the abolitionist teacher who opened the first academy for African American girls in New England. Canterbury's picturesque downtown area features a variety of charming shops and boutiques, restaurants, and cafes. Moreover, the town boasts several well-equipped parks and fields for various recreational activities, including a dog park, playgrounds, and basketball courts. Finally, those interested in nature and hiking will marvel at the striking vistas of the Quinebaug River in nearby James L. Goodwin State Forest.

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Chaplin CT

Chaplin is a hidden gem of Windham County, known for its tranquil atmosphere and picturesque scenery. Visitors can enjoy the town's stunning natural beauty, which includes breathtaking views of the countryside and hiking trails through its many parks. Those looking to explore the town's cultural heritage can visit its various historical landmarks, such as Chaplin Museum and the Elisha Payne House, which dates back to the 1700s.

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Eastford CT

Eastford is a charming town located in northeast Connecticut, surrounded by beautiful natural landscapes. Visitors can enjoy hiking, fishing, and camping in the Natchaug State Forest or explore several historical landmarks, including the Union Society of Phoenixville meetinghouse and the Lauren Risley Potter Schoolhouse. The town also features a vibrant cultural scene, with numerous art galleries and studios showcasing local talent.

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Hampton CT

Hampton is a quintessential New England village located in Windham County, Connecticut. The town boasts a rich cultural heritage, with several historic landmarks such as the Hampton Congregational Church and the Nathan Hale Schoolhouse Museum, commemorating the area's past. Visitors can also enjoy the town's beautiful parks and excellent outdoor recreational facilities, including the Hampton Reservoir and Natchaug State Forest. Several excellent restaurants and cafes are also located in Hampton, making it a perfect destination for a foodie trip.

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Killingly CT

Killingly is a charming village known for its breathtaking natural scenery and historic sites. Those interested in history should visit the Killingly Historical Society Museum. It offers several engaging exhibits that detail the village's role in shaping Connecticut's political landscape. In addition to the Killingly Historical Society Museum, visitors can enjoy many other historical sites throughout the village of Killingly. The Colonel Daniel Putnam Homestead is a fascinating example of colonial architecture that is open to the public from May through October. Visitors can explore the homestead's various rooms and learn more about life in the 18th century. Moreover, the village's old mill buildings have been repurposed into shops and businesses, allowing visitors a glimpse of how these structures were repurposed for modern use.

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Plainfield CT

Plainfield is another charming New England village renowned for its stunning natural beauty and excellent schools. Visitors can admire some of the area's oldest buildings, such as the Plainfield Village Historic District and the Congregational Church of Plainfield. Plainfield has bountiful opportunities for visitors to explore the town's rich cultural heritage. The Plainfield Historical Society features exhibits that detail the town's fascinating history, while the Central Village District is home to numerous historic buildings, including the Elisha Payne House, which dates back to 1790. Moreover, the town's several parks and natural areas are perfect for hiking, biking, and picnicking.

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Pomfret CT

Pomfret, a picturesque town with a thriving arts scene, offers visitors numerous outdoor recreational activities to enjoy, including hiking, fishing, and camping. Those interested in history should head over to Pomfret Street Historic District to take in some of the area's most significant colonial and post-colonial structures. Pomfret has a long history of fostering the arts, and this tradition continues today with several galleries and studios that offer workshops and classes for aspiring artists. Among the many outdoor recreational options, the Sharpe Hill Vineyard is a beautiful spot to admire the stunning scenery and sample some delicious wines. Additionally, those looking to hone their culinary skills can sign up for classes at the Woodstock Hill Preserves Culinary Center, offering hands-on training in cooking, baking, and wine education.

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Putnam CT

Putnam is a bustling community with an exciting cultural scene and a rich history. The town's downtown area is home to several excellent restaurants and shops, along with several historic sites like the Putnam Town Crier that dates back to the late 18th century. The Putnam Town Crier is an excellent example of the town's commitment to preserving its history. Visitors can take a step back in time and see how local news was disseminated in the region, with information about everything from public meetings to notices about missing farm animals. Furthermore, the town's outstanding recreational facilities and scenic landscape, including the Airline Trail, are perfect for those looking to spend time outdoors.

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Scotland CT

Scotland, a small and picturesque town, is a great destination for anyone interested in the arts, thanks to its thriving cultural scene. The town is also known for its stunning parks and natural attractions, making it an ideal place for outdoor enthusiasts. Scotland is the location of the famous Scotland Highland Games, which takes place during Memorial Day weekend every year. The festival includes traditional Scottish sports and games, such as the caber toss and bagpipe competitions. Scotland is also known for its pristine parks and scenic natural beauty, including the Wells State Park and Emily Dickinson Trail.

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Sterling CT

Sterling is a charming New England village renowned for its stunning parks and excellent recreational facilities. Visitors can explore the Sterling Hill Historic District and the Sterling Opera House while appreciating the area's natural beauty. Sterling is an excellent destination for history enthusiasts, thanks to its numerous historic sites and landmarks, including the Sterling Hill Historic District and the Sterling Opera House. Furthermore, the town's abundant parks and natural attractions offer a variety of outdoor recreational opportunities. Visitors can enjoy boating or fishing on Pachaug Pond, exploring the Natchaug State Forest, or hiking the nearby trails of the Mohegan State Forest.

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Thompson CT

Thompson is another idyllic New England village that offers visitors an opportunity to explore its charming downtown area and excellent recreational facilities. The town is home to several historic sites, including the West Thompson Dam, which features some of the region's best hiking and biking trails. Thompson's downtown area offers a range of shops, boutiques, and restaurants for visitors to enjoy. For book lovers, the French Memories bookstore is a must-visit destination. The bookstore offers a vast selection of used books, and visitors can enjoy a cup of coffee or tea while browsing through various titles and genres.

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Windham CT

The town of Windham, located in the heart of the county, has a vibrant cultural scene and a rich history. For example, visitors can explore the town's downtown area, which offers many excellent restaurants and shops, as well as the Windham Textile and History Museum, which showcases the history and significance of the area's textile industry and is a must-see for anyone interested in the history of the textile industry. The museum's collection includes over 6,000 artifacts, ranging from looms and spinning wheels to finished products such as fabrics and garments. Visitors can explore exhibits that showcase the development of textile manufacturing in Windham and how it contributed to the town's growth and prosperity. Furthermore, visitors can view many historic photographs, audio recordings, and videos that provide an in-depth look at the industry's impact on the area.

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Woodstock CT

Woodstock, one of Connecticut's most scenic and picturesque towns, offers plenty of opportunities to explore some of the state's oldest structures, including the Roseland Cottage and the Woodstock Academy. Visitors can also enjoy hiking, fishing, and camping, thanks to the town's abundant outdoor recreational opportunities. Woodstock is one of Connecticut's most significant tourist destinations, attracting visitors with its stunning beauty, rich history, and delicious cuisine. The Golden Lamb Buttery, one of the town's popular restaurants, features a menu of classic New England cuisine and fresh farm-to-table fare. Hikers can enjoy miles of trails in the Mashamoquet Brook State Park, while golf enthusiasts can challenge themselves at the nearby Wallingford Golf Course.

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Learn More About Our Communities

For more information, see our Connecticut area guide and discover more counties like Hartford, New Haven, Middlesex, New London, and Tolland.

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