The Farmington Canal Heritage Trail is the best option for a long off-road run in New Haven. This paved multi-use trail runs for 58 miles in Connecticut toward the Massachusetts border, and then another 20 miles in Massachusetts. It’s a combination of  abandoned rail corridors and canal tow paths through urban, suburban and rural areas of Southern Connecticut and the Farmington Valley. There are historic buildings, canal locks, the remains of canal aqueducts and other landmarks.

A good section in New Haven is to start at the trail head off Temple St. (near Yale Campus), and run for 2 miles to Morse St., for a 4 mile out and back. Or, continue for longer! It’s 18 miles from New Haven to Meridian.

Note: As of May 2021, there’s a 9-mile gap from southern Farmington, through all of Plainville into northern Southington.