Just east of Old Greenwich and south of I-95, we’ve mapped a lovely 5-miler combining Bruce Park, Indian Harbor, and Grass Island. This route has a nice variety of park fields and water views from the coves and harbors. 

Start in Bruce Park, a classic older park featuring paths, fields, and ponds, and other recreational facilities. Continue west of the park on Davis Ave., and then take Indian Harbor Dr. (caution: no sidewalk), RIGHT on Oneida Dr. and LEFT on Steamboat Rd. to the water at Rocky Neck Point. Double back to Roger Sherman Park. Here, there’s an optional 1 mile add-on to Grass Island, which requires a slightly unpleasant crossing of I-95 to get to Shore Rd., which takes you to Grass Island. There are some worth-it views.