Grass Rides Loop

Starting from the parking area off Highland Street, head southeast on a broad trail, then turn left to begin the Grass Rides Loop. After a short distance, take the next right to climb gently over Pigeon Hill, one of the few notable rises along the route. Continue downhill and turn right, entering a scenic stretch flanked by meadows and woods. Pass two junctions, then stay left at a Y-intersection as the loop bends toward Round Point—a central clearing marked by granite pinnacles from the former Harvard College Library. At Round Point, turn right and continue through several trail crossing, staying on the Grass Rides Loop. The route closes gently through open fields and woodlands before returning to the trailhead. This trail is open year-round and offers an easy walk through varied landscapes with opportunities for wildlife viewing. Granite landmarks and broad, grassy paths make this route especially enjoyable in any season.