Location: From the Connecticut/Massachusetts state line south to Newent, Connecticut
Length: 32 miles (51 km)
Time To Allow: 1 day

Description/Highlights/Points of Interest

Traverse one of the last unspoiled areas in the northeastern United States, with forests, open spaces, rustic farmsteads and historic structures and features. This 25-town route winds its way through history, passing colonial homesteads, churches, stone walls, meeting houses and private schools as its connects several classic New England towns. You'll see nearly 200 structures built before 1855, as well as maple and pine stands and glacially deposited rocks and boulders that lie strewn throughout green fields.

Suggested Itinerary

Your driving tour of Connecticut State Route 169 begins in the town of Lisbon, Connecticut. The route itself is accessible from all sites along the route by various state routes and local highways. To reach Lisbon and the beginning of the byway, take exit 83A off I-395, go north on Route 169 for 0.9 miles (1.4 km) to Lisbon.

The town of Lisbon was originally part of Norwich and was named in 1786, probably after Lisbon, Portugal since residents and commercial shippers Hezekiah and Jabez Perkins traded with the European port. In Lisbon, tour the Bishop House Museum, a circa 1810 Federal farmhouse that features both colonial and federal architecture. Nearby is the Rev. David Hale House, built in 1795 by Nathan Hale's younger brother, David, who was the minister of the nearby Congregational Church from 1795–1802.

On Route 14 just off the byway is Canterbury, which was settled in 1697 as part of Plainfield. The town was incorporated in 1703 and was named for Canterbury in Kent, England. Be sure to visit The Prudence Crandall Museum, operated by Prudence Crandall, it was the first academy for young black women in New England (1833–34). Crandall, who faced arrest, harassment and mob violence was designated Connecticut's State Female Hero in 1995. The circa 1805 Federal/Georgian-style house is a notable example of the "Canterbury style."
(Hours: February to mid-December: Wednesday–Sunday, 10am-4:30pm. Admission fee is required for adults.)

Between the towns of Canterbury and Brooklyn, there are several points of interest that merit a visit, including the Finnish American Heritage Hall, which was built by members of the town's large Finnish population in 1924. The Moses Cleaveland Birthplace honors the founder of Cleveland, Ohio. Cleaveland surveyed Connecticut's Western Reserve (northeast Ohio) in 1796. The site offers an outstanding vista.

Trinity Episcopal Church in Brooklyn was built in the Gothic Revival style in 1866. The church boasts four stained glass windows made in New York by Louis Comfort Tiffany, a descendant of the store's founder and the family that had owned the Tiffany Mill in East Brooklyn, Connecticut. Beyond Brooklyn as you head toward Pomfret, stop by the Friendship Valley B&B Inn. This Georgian-style house was a stop on the Underground Railroad. In the 1830s, it was the home of George Benson, a Quaker, who sheltered and supported Prudence Crandall during the time of her trial. Crandall gave the house its name in appreciation for the kindness shown her by the Benson family. The New England Center for Contemporary Art is a four-story barn featuring changing exhibits of contemporary art from around the world. And if you're ready to stretch your legs, the C. Vaughan Ferguson, Jr. Conservancy is 78-acre preserve with red-blazed walking trails through marshlands and hilly terrain.

Between Pomfret and Woodstock, there are many more miles of hiking trails to be explored at Connecticut Audubon-Pomfret Farms and along the Air Line Trail, which follows an old railroad bed. Christ Episcopal Church in Pomfret was built in 1882 as a memorial to the Rev. Alexander H. Vinton by his daughters. Five of the windows in the nave and the rose window were designed at the turn of the century by Louis Comfort Tiffany. The Roseland Cottage/Bowen House Museum is a striking Gothic Revival structure built in 1846, that was the home of Woodstock native Henry Bowen. The grounds feature a 100 year-old boxwood parterre garden, bowling alley and ice house. Colorful Fourth of July celebrations, with U.S. Presidents in attendance, were held on the property. The house contains its original furnishings.
(Hours: June – October 15: Wednesday–Sunday 11am–5 pm, tours on the hour. An admission fee is charged for adults and children.)