This enormous parcel of conservation land right in Litchfield is the go-to training zone for local cross country teams. With over 40 miles of paths, there are plenty of good running options here, although some are more technical than others. The most popular choice in the park is the Little Pond Loop, or “Boardwalk Trail,” which offers over a mile of running on a springy wooden boardwalk. The Little Pond Loop can be combined with the Mattatuck Trail for a roughly 5km “lollipop” route. Go west on the gravel road past the museum, then turn LEFT onto the Mattatuck Trail. Just after the Bissell Road crossing, turn right onto the black and white blazed Little Pond Loop which runs out to the Boardwalk, a fun track through a scenic marsh.
The accompanying map has lots of detail on trail features and distances.