West Hopkinton-Upton trail loop (total distance ~ 13 miles) Trail maps of Hopkinton Town Forest/Cameron Woods, Lake Whitehall State Park and Upton State Forest can be useful if you aren't already familiar with these trails.
Hopkinton Town Forest/Cameron Woods Red trail. Start at the trailhead on Pond Street, opposite Erika Drive. Follow the red trail markers up the hill, down to cross Pond Street, and through the woods toward Woodville. Pass a junction with the Green trail (or take the Green trail until the Red trail rejoins) and continue on the Red trail to the junction with the Yellow trail (near some houses on Wood Street, look for a Cameron Highlands sign on a tree). Go left on the Yellow trail.
Cameron Woods Yellow trail. Follow the yellow trail markers. The path joins the Green trail for a bit, then heads to the right toward the Sylvan Way neighborhood. Approaching the neighborhood, the path turns left (south), climbs a hill, turns right toward the houses, left again, and finally right to descend toward Sylvan Way/Winter Street.
Lake Whitehall State Park trail. From Sylvan Way, cross Winter Street to get to the blue-blazed trail around Lake Whitehall. Go to the right (east/north, toward the dam). Follow the trail all the way around the northern shore of the lake, passing through through the boat ramp parking lot, to the site of the old Hopkinton Springs (near Lyford Road). Go right to exit to Lyford Road.
Lyford exit. Follow the Public Access path up to Lyford Road, then continue on Lyford out to Spring Street. Turn right on Spring Street and continue a short distance to the entrance for the old oxcart path. The path is on the left (north side of Spring Street), opposite the mailbox for 135 Spring Street. In the summer it will likely be hidden by vegetation.
Old Oxcart path. Follow this unblazed but obvious path to a junction with a much more obvious path. Go left, and follow that path southwest along the Hopkinton/Upton town line. Pass by several paths entering from the right, and a granite post on the left marking the western-most point in Hopkinton (“U” and “H” carved on the sides to indicate Upton & Hopkinton). At this point you are back on an Upton State Forest trail. Soon after, the path exits to the left to go down to Southboro Road (continuation of Spring Street in Upton). Directly across the street will be the Upton State Forest (USF) Mammoth Rock trailhead. Go right on the road. Or follow the Mammoth Rock trail to the USF Loop Road, turn right, and jump to step 8 below .
Southboro Road. Follow a short distance to the USF Swamp Trail. Turn left onto the trail.
USF Swamp Trail. Follow to the end on the USF Loop Road. Turn right on Loop Road.
USF Loop Road. Follow to the USF Park Road. Turn left onto Park Road.
USF Park Road. Follow up hill and back down to the Dean Pond Trail. Go left on Dean Pond trail.
USF Dean Pond trail. Follow to the Dean Pond, where the USF Loop Road comes in from the left.
USF Loop Road. Follow this path until the USF Bridge Road junction on the right. Go right to follow Bridge Road.
USF Bridge Road. Follow the trail over a bridge and then past signs for Tamarack Farm until it ends at a T junction. Go left at the junction.
USF/Whitehall connector. Follow the path until it exits the woods. Hopkinton’s Stonegate neighborhood will be up on the hill to the right. Continue straight ahead (north), passing retention ponds on the left, and re-enter the woods through some barrier rocks. Follow the path to its end on Pond Street, at the southern end of Lake Whitehall.
Lake Whitehall State Park trail. Cross Pond Street and head to the lake shore to pick up the blue blazed path around the lake. Go the the right (north) to follow the western shore of the lake. After the Three Peninsulas trail enters on the left, the path starts to head back toward Winter Street. Continue to a junction where the Snake Hill access path joins on the right. Go right to follow that path.
Snake Hill access path/Winter Street. Follow the Snake Hill path out to Winter Street, then go left on Winter Street a short distance to an overgrown road/trail on the right. A chain between two posts marks the entrance.
Phipps property trails. Follow the path up into the woods. At a four way junction, go to the right and descend to a small stream crossing in a hemlock grove. Follow the path over the stream. It turns right, goes up a small hill, then turns left and continues to ascend somewhat to a junction with the Town Forest Red trail. Continue to the right, toward Pond Street.
Town Forest Red trail. Follow the trail a short distance to Pond Street. End here, or cross Pond Street and continue on the Red trail back to the Start.