US-44 Litchfield Hills Corridor

Built in 1842, Bull's Bridge is one of only two remaining covered bridges in Connecticut open to vehicular traffic. The single-lane 109-foot lattice-truss span carries Bull's Bridge Road over the Housatonic River near the New York border, flanked by whitewater rapids and a small gorge. A riverside parking area at the southeast end provides access to falls, pools, and a stretch of the Appalachian Trail.

A 28-mile route running roughly parallel to the western bank of the Connecticut River from Old Saybrook north through Essex, Deep River, Chester, and Haddam to Higganum. The 9-mile Haddam section carries a state scenic road designation for its river-view corridor along the Middlesex Turnpike, a toll road since 1802. The southern stretch passes through the historic villages of Essex and Chester — both well-preserved small towns with independent restaurants — before opening onto river panoramas near the Haddam Swing Bridge and Gillette Castle environs. Works well paired with CT-148 and the Chester-Hadlyme ferry (seasonal) for a full valley loop.

A federally designated National Scenic Byway running 32 miles north-south through the "Quiet Corner" of northeastern Connecticut, from Lisbon near the Rhode Island border up to the Massachusetts state line north of Woodstock. The road threads through well-preserved 18th- and 19th-century villages — Canterbury, Brooklyn, Pomfret, and Woodstock — across rolling farmland with apple orchards, stone walls, and historic commons largely unchanged since the colonial era. Pacing is unhurried; the reward is pastoral immersion rather than lean-angle entertainment.