Almost every town in the Litchfield Hills has a quaint New England vibe, but one of the best towns for a run is Litchfield itself, situated about one hour west of Hartford. The stretch of Route 202 (West Street) through downtown is a scenic highway lined with pretty houses, trees, and a well-kempt sidewalk.
We’ve mapped two routes in downtown Litchfield. The 3.6 mile loop starts a the high school and utilizes West Street, plus some side streets including the lovely residential Meadow Street. The 6.8 mile loop loosely follows the course of the Litchfield Hills Road Race, starting in the town center and incorporating Gallows Lane, which is widely considered one of the most heartbreaking hills in Connecticut.