Upton State Forest Loop

This moderate route begins at the main Upton State Forest trailhead on Westboro Road. From the parking area, head east on Park Road and continue onto Loop Road through mixed hardwood forest. After three trail junctions, turn left onto Grouse Trail, which climbs gradually before transitioning into White Hall Road. Stay on White Hall Road as it curves south and rejoins Loop Road. Continue south toward Dean Pond, where the route follows the shoreline briefly and becomes Dean Pond Road. After a short stretch, Dean Pond Road merges back into Park Road—turn right here and follow it north to return to the trailhead. Expect a mix of wooded terrain, open meadows, and wet or muddy sections, especially near stream crossings and beaver-affected areas. Wildflowers are common in spring and summer, and Dean Pond offers a scenic spot to rest or observe wildlife. Historic structures from the Civilian Conservation Corps era add interest along the way, making this a rewarding day hike in Central Massachusetts.