A portion of the route in the town center of Pomfret is on the National Register of Historic Places as Pomfret Street Historic District, and 32.10 miles (51.66 km) of the road is designated as the Connecticut State Route 169 National Scenic Byway.

In Canterbury, Route 169 continues north, generally parallel to the Quinebaug River although not actually along it, before crossing into Brooklyn.

It begins as North Woodstock Road, briefly overlaps Route 131 as part of East Main Street, then splits north on Mechanic Street at the American Optical rotary, bypassing Southbridge center.

A 32.10-mile (51.66 km) stretch of Route 169, running from Rocky Hollow Road in Lisbon to the Massachusetts state line, is a designated National Scenic Byway and state scenic road known for its vibrant autumn foliage and historic communities.

[5][6] The entire route within Connecticut is also designated the General Israel Putnam Highway.

By 1931, Highway 124 was relocated along roughly modern I-84 from the Connecticut state line in Holland via Sturbridge center to Charlton, then continuing along its original route to West Auburn.

At the same time, Massachusetts renumbered Highway 124A as Route 93 to maintain number continuity across the state line.