Connecticut: Discover historic towns nestled in beautiful landscapes in the Litchfield Hills

From Watertown’s colonial buildings to Canaan’s picturesque stone canals, this hour-long route is a study in historic New England charm. You won’t want to leave the region’s rolling hills and scenic vineyards.

Drive 42.5 miles, 1 hour, 20 minutes

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1. Bristol

Starting Point

Visit in September to see Bristol’s in bloom during the town’s famed chrysanthemum festival. Thousands join in the celebration, which include a parade, gala and Miss Mum competition. The town is also home to the Witches’ Dungeon Classic Movie Museum, a one-of-a-kind ode to horror films. Open during the Halloween season, this quirky destination displays wax figures of classic characters in set pieces.

2. Watertown

12.9 miles, 28 minutes

Dating back to the early 18th century, Watertown’s historic district is a veritable living museum of early-American architectural styles. A visit to Main Street yields numerous colonial buildings, Italianate and Victorian homes, as well as classic general stores, monuments and cemeteries. It’s charming New England at its finest, and the perfect stopover on this historic route.

3. Litchfield

10.7 miles, 19 minutes

Known for its historic homes and perennial gardens, Litchfield is especially welcoming to the visitor with an eye for architecture. Tours are available to many historical homes, and the downtown district is a picturesque throwback to the olden days. After exploring downtown, head to one of the nearby wineries for a vineyard tour and tasting. A stop on the Connecticut Wine Trail, Litchfield is home to some of the state’s original wineries.

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4. Canaan

18.9 miles, 33 minutes

Don’t let Canaan’s small-town serenity fool you. There is plenty to see and do in this riverside hamlet. Located on the banks of the Housatonic, Canaan is home to Great Falls, a powerful waterfall that thunders throughout town when, in early spring, water spills over the nearby dam. The area is also dotted with scenic stone canals, a legacy of the hydropower that fueled a booming 19th-century iron industry.