Wolcott Hill Loop

This moderate hiking route begins at the Trailside Museum’s north parking area on Canton Avenue in Milton, MA. From the trailhead kiosk, follow the green dots east onto Wolcott Path, which gradually climbs through shady pine and hemlock forest. At marker 1100, turn left onto Border Path. After a short distance, turn right at marker 1135 onto Five Corners Path and continue following the green dots as the route curves around the base of Wolcott Hill and onto Coon Hollow Trail. Near a vernal pool around marker 1092, veer right onto Wildcat Notch Path, where a break in the trees offers views of the northeastern slope of Great Blue Hill. Turn left onto Puddle Path to rejoin Wolcott Path and return to the museum parking area. The eastern side of the route includes uneven footing and loose rock—use caution, especially when conditions are wet. This woodland route offers a satisfying mix of rolling terrain, peaceful forest scenery, and occasional views within Blue Hills Reservation.