These woods have drawn wilderness pilgrims since long before Henry David Thoreau made escapism stylish—and this 23.6-mile point-to-point offers enough deep forests and waterfalls to inspire another back-to-nature movement. Start in the parking lot in Mt. Grace State Forest, and climb to Mt. Grace’s 1,621-foot summit. On top, a five-story fire tower presents a three-state view over rolling hills.
Turn north onto the white-blazed New England Trail and descend over rocky trail and crumbling stone walls (old property lines) to MA 78. Cross it and continue 1.8 miles to Richards Reservoir. Hugging the shoreline, you’ll reach a side trail to a bed of moss 30 feet above the water and open to a breeze. Nap time.
Back on the trail, climb to Richmond Road and weave through hemlocks for 2.7 miles to Mayo Hill. In .6 mile, a small ridge yields a view of 3,165-foot Mt. Monadnock framed by pines. Descend into New Hampshire and rebound south to Bliss Hill Road, where the trail merges with the yellow-blazed Tully Trail. In .9 mile, reach MA 32 and Newton Cemetery, an array of weathered tombstones dating back two centuries. Camp at Trustees Shelter in .6 mile.
Start day two with a detour to Royalston Falls, then hike north along Falls Brook past Buick-size boulders to a meadow. Cross Greenwood Road at mile 13.5 and follow a 2.6-mile ridge to NH 119. Go northwest along the road for .3 mile, turn right at Old County Road, then north at Grassy Hill Road. Reenter forest filled with a shag of primeval ferns and turn south down a cobblestone road. It’s 1.1 miles to the top of Little Monadnock.
Ease down a 30-foot rock slope to a dirt road. Turn right and descend gently for .7 mile to Prospect Street. Having fronted the essential facts of life (to paraphrase Thoreau), find your waiting ride in one mile.
SHUTTLE: From Troy, go south on Prospect St., and park in .8 mile. Let the Troy police know (603-242-7992).
PARKING: Tell the Warwick Police dispatch (978-544-2244) you’re parking overnight.
GEAR UP: Trail Head, 1 S. Main St., Orange, MA. (978) 249-8500; trailheadonline.net
-Mapped by Charlie Wood
- Distance: 37.9
Location: 42.689139, -72.341
Start in the parking lot in Mt. Grace State Forest, and climb to Mt. Grace's 1,621-foot summit.
Location: 42.693386, -72.353044
The trail turns left on the saddle between Bennetts Knob and Mt. Grace.
Location: 42.705508, -72.348597
Cross Warwick Road (MA 78)
Location: 42.6998, -72.320939
Turn left, and trek north along Richards Reservoir.
Location: 42.707547, -72.319164
Turn left (east).
Location: 42.708442, -72.315358
Cross Richmond Road.
Location: 42.715661, -72.298989
After you Crest Mayo Hill, descend north.
Location: 42.715403, -72.272503
Road crossing: pass over Bliss Hill Road and follow the trail east.
Location: 42.715756, -72.256
Cross Athol-Richmond Road (MA 32).
Location: 42.719211, -72.248069
camp at Trustees Shelter. Turn right for an out-and-back detour to Royalston Falls.
Location: 42.723975, -72.248836
Location: 42.726733, -72.251889
At mile 13.5, turn right at Greenwood Road and follow a ridge toward NH 119
Location: 42.757211, -72.235744
Turn left at Fitzwilliam Road.
Location: 42.759608, -72.239608
Turn right at Old County Road.
Location: 42.759764, -72.232172
Trail turns to the left, heading north.
Location: 42.778978, -72.212528
Turn right as the trail heads south.
Location: 42.807572, -72.199808
Turn right and begin a gentle descent for .7 miles.