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 (1) 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 (2) and descend over rocky trail and crumbling stone walls (old property lines) to MA 78 (3). Cross it and continue 1.8 miles to Richards Reservoir (4). Hugging the shoreline, you'll reach a side trail (5) 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 (6) and weave through hemlocks for 2.7 miles to Mayo Hill (7). In .6 mile, a small ridge yields a view of 3,165-foot Mt. Monadnock framed by pines. (Summit hungry? See "Locals Know," next page.) Descend into New Hampshire and rebound south to Bliss Hill Road (8), where the trail merges with the yellow-blazed Tully Trail. In .9 mile, reach MA 32 (9) and Newton Cemetery, an array of weathered tombstones dating back two centuries. Camp at Trustees Shelter (10) in .6 mile.
Start day two with a detour to Royalston Falls ("See This," next page), then hike north along Falls Brook past Buick-size boulders to a meadow (11). Cross Greenwood Road (12) at mile 13.5 and follow a 2.6-mile ridge to NH 119 (13). Go northwest along the road for .3 mile, turn right at Old County Road (14), then north at Grassy Hill Road (15). Reenter forest filled with a shag of primeval ferns and turn south down a cobblestone road (16). It's 1.1 miles to the top of Little Monadnock. Ease down a 30-foot rock slope to a dirt road (17). 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).
To trailhead From Troy, go south on NH 12 to NH 119 west. In 14.5 miles, go left on NH 10, then left on NH/MA 78 for 7 miles to Mt. Grace State Forest. 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