Historic Route 169, Connecticut
While picturesque, this route is best for the history buff. Bring along passengers who also enjoy exploring historical sites.
Stop in Canterbury for a visit to the Prudence Crandall Museum. Continue on to Brooklyn for a stop at the Brooklyn Green, a site on the National Register of Historic Places. Next, don't miss the Friendship Valley Inn, a stop on the Underground Railroad.
Take a recess from the history lesson in Pomfret with a visit to the Lapsley Orchard for apple picking, and end your break at the Sharpe Hill Vineyard and Winery. Once you make it to Woodstock, don't miss the Roseland Cottage (also known as the Pink House).
Find your way: Our route runs through the "Quiet Corner" of rural northeastern Connecticut. Begin on Route 169 in Lisbon and continue toward Woodstock.