20 Old Towns to Explore in Connecticut

The Broad Street – Davis Park Historic District in Windham, Connecticut, stands as a significant architectural and historical area showcasing the town's heritage. Designated as a historic district, it encompasses a collection of well-preserved homes and structures, reflecting various architectural styles prevalent during the late 19th and early 20th centuries.

The Brooklyn Green Historic District, located in Windham County, Connecticut, is a designated historic area that preserves the architectural and cultural heritage of Brooklyn, Connecticut. Centered around the picturesque town green, this district showcases a collection of well-preserved buildings representing various architectural styles from the 18th and 19th centuries.

The Bush Hill Historic District encompasses a historic rural landscape in central northern Brooklyn, Connecticut. It extends along parts of Bush Hill Road, Connecticut Route 169, and Wolf Den Road. The area has a remarkable concentration of farmhouses and agricultural outbuildings dating to the early 19th century or earlier. The district was listed on the National Register of Historic Places in 1987.

Downtown Putnam, Connecticut, is a vibrant and historic area known for its quaint charm, rich history, and revitalized downtown district. Nestled in northeastern Connecticut, Putnam's downtown has undergone significant revitalization efforts, transforming it into a hub for shopping, dining, arts, and cultural experiences.

Essex, Connecticut, nestled along the banks of the Connecticut River, exudes a quintessential New England charm that captivates visitors and residents alike. This historic town, often referred to as the "Best Small Town in America," seamlessly blends rich maritime heritage, scenic beauty, and a vibrant community.

Nestled within the idyllic landscapes of Litchfield County, Connecticut, Goshen stands as a charming town that seamlessly combines rich historical roots with a serene rural ambiance. With a backdrop of rolling hills, historic architecture, and a strong sense of community, Goshen invites visitors to experience the timeless beauty and warm hospitality of a quintessential New England town.

Haddam, situated in Middlesex County, Connecticut, embodies a picturesque blend of historic charm, scenic landscapes, and a close-knit community. This town, nestled along the Connecticut River, offers a serene setting with a rich historical heritage and a range of recreational opportunities.

Nestled within the scenic beauty of Litchfield County, Connecticut, the town of Kent stands as a quintessential example of New England charm. Steeped in history and surrounded by picturesque landscapes, Kent invites visitors to step back in time while enjoying the warmth of a welcoming community and the allure of its natural surroundings.

Killingworth, nestled in Middlesex County, Connecticut, is a picturesque town characterized by its rural beauty, historical landmarks, and tight-knit community. This tranquil and scenic area offers residents and visitors a serene environment with a blend of historical charm, natural landscapes, and recreational opportunities.

Middletown, nestled in Middlesex County, Connecticut, stands as a vibrant city blending historical charm, cultural diversity, and a thriving community. This dynamic city offers a mix of historical landmarks, educational institutions, recreational opportunities, and a lively downtown scene, making it a multifaceted destination.

New Haven Green, situated in the heart of downtown New Haven, Connecticut, serves as a historic and cultural centerpiece of the city. This iconic public park, dating back to the early 17th century, embodies a blend of history, community gatherings, and urban green space, making it a beloved destination for locals and visitors alike.

North Grosvenordale, located in the town of Thompson within Windham County, Connecticut, is a village known for its historical significance and community heritage. Originally established as a mill village in the 19th century, North Grosvenordale flourished around textile manufacturing and mill operations along the French River.

Old Saybrook, nestled along the Connecticut shoreline in Middlesex County, Connecticut, is a historic and picturesque town known for its coastal beauty, rich history, and vibrant community. This charming town offers a unique blend of waterfront allure, cultural heritage, and a range of recreational activities.

Old Sturbridge Village isn't in Tolland; it's actually located in Sturbridge, Massachusetts. Nevertheless, it's a captivating living history museum that authentically recreates an early New England village from the 1830s. This immersive destination offers visitors a journey back in time to experience daily life as it was in rural New England during the 19th century.

Nestled within the scenic landscapes of Litchfield County, Connecticut, Plymouth is a charming town that reflects the essence of New England living. Steeped in history, adorned with historic architecture, and surrounded by natural beauty, Plymouth invites visitors to explore its quaint streets, experience its cultural richness, and appreciate the warmth of a close-knit community.

The Pomfret Street Historic District, situated in the town of Pomfret, is a captivating enclave steeped in historical significance and architectural splendor. This district encompasses a collection of residences and structures dating primarily from the late 18th to the early 20th centuries, showcasing an eclectic mix of architectural styles including Federal, Greek Revival, and Victorian designs.

Prospect Hill Historic District, is a designated historic area that preserves a significant portion of the town's architectural and cultural heritage.The district comprises a collection of well-preserved historic homes, buildings, and landmarks that reflect various architectural styles prevalent from the late 18th century to the early 20th century. It encompasses residential, commercial, and institutional structures, providing a glimpse into the town's evolution and development over time.

Nestled in the picturesque northwest corner of Connecticut, Salisbury is a charming town that embodies the quintessential New England experience. Steeped in history, surrounded by natural beauty, and graced with a vibrant community spirit, Salisbury invites visitors to explore its historic streets, scenic landscapes, and cultural offerings.

Wauregan, Connecticut, nestled in the northeastern part of the state, holds a distinct place in local history and community life. This small village, part of the town of Plainfield, has a heritage steeped in industry and the development of the region. Wauregan was historically known for its mills and textile production during the 19th and early 20th centuries, contributing significantly to the area's economy.

The Woodstock Hill Historic District, situated in Windham, Connecticut, is a captivating area renowned for its rich history and architectural significance. This district encompasses a collection of meticulously preserved structures, homes, and landmarks predominantly dating from the late 18th to the early 20th centuries.