Top 10 Hikes in the Greater Monadnock Region

I've been hiking in the Monadnock Region for decades, and on most outings, I've been fortunate to have a good friend, Curtis Carroll, accompany me. Curtis and I have logged hundreds of miles that have taken us to wilderness sanctuaries, cliff outlooks, waterfalls deep in the woods and, of course, the top of Mount Monadnock. Although I now live on the fringe of the Monadnock Region in Ashburnham, Mass., and Curtis resides in Halifax, Vt., we continue to explore Southwest New Hampshire almost every weekend. The goal — as always — is to enjoy the simple pleasures of the great outdoors: watch a porcupine lumber down a woods road, observe interesting patterns of low-angle sunlight falling on the forest floor or listen to the croak of a raven's call. Some of our favorite hikes are located just outside the region — in southern Vermont or North Central Massachusetts. However, these hikes are close enough in location and in spirit so that they are included on our list. Here are our ten favorite hikes in the greater Monadnock Region — not including Mount Monadnock — with one extra mountain thrown in for good luck. Mount Wantastiquet and Mine Ledge. Moderate to difficult. Mount Wantastiquet in Hinsdale rises 1,335 feet from the banks of the Connecticut River across from Brattleboro. It's a 3.5-mile (round trip) switchback climb to the top where there are wide views of Brattleboro and the Green Mountain ski peaks to the west. A short walk from the summit of Wantastiquet brings you to Mine Ledge — a cliff promontory on the east side of Wantastiquet where there are even wider views. A trail to Mine Ledge, a 2.5-mile round trip hike, can be accessed from the Madame Sherri Forest in Chesterfield. Mount Wantastiquet access: Mountain Rd., Hinsdale. Mine Ledge Access: via Mount Wantastiquet or Gulf Rd., Chesterfield. See ELF July 10, 2024. North Pack Monadnock Mountain. Moderate. A 1.4-mile segment of the Wapack Trail brings you to the open ledgy summit (2,276 feet) of North Pack Monadnock where there are good views. From the east side of the summit, the blue Cliff Trail leads to an outlook on the southeast side where the view — stretching from Pack Monadnock all the way down to Mount Watatic in Ashburnham, Mass — is considered one of the finest of all vistas on the Wapack Trail. North Pack Monadnock Mountain access: Old Mountain Rd., Greenfield. Farley Ledge. Moderate-to-difficult. This is a premiere rock-climbing destination where you'll see climbers scaling the ledges, looking like spiders suspended on silken threads. But there is a 2.5-mile ridge line loop trail that safely skirts the edge of the cliffs and offers stunning views of the Millers River Valley. Farley Ledge access: Holmes Rd. off of Massachusetts Route 2, Erving, Mass. There is also a Western Massachusetts Climbers' Coalition parking lot 0.3 mile west of Holmes Rd. on the cliff side of Route 2. See ELF Sept. 10, 2020. Taylor Hill. Moderate. Taylor Hill is part of the Franconia Mountain Range, a chain of hills located in Richmond. It has nothing to do with the famous peaks in the White Mountains. An FAA (Federal Aviation Administration) radio beacon sits on top of 1,376-foot Taylor Hill, but there is also a sweeping view of the Green Mountains of Vermont to the west and Mount Monadnock to the northeast. The juxtaposition of the sweeping view of hills and mountains and what seems to be a spaceship from a science fiction movie set is a weird vibe. But it works. Taylor Hill access: Taylor Hill Rd., Richmond. See ELF Sept. 14, 2023. Stratton Mountain. Moderate-to-difficult. No, this mountain is not the famous ski area in Vermont. Rather, a 1,219-foot mountain in Northfield, Mass., that offers a spectacular 180-degree view — that includes Mount Monadnock — from its summit. The one-way, 3.3-mile trail follows a section of the white blazed New England Trail. Stratton Mountain access: Gulf Rd., Northfield, Mass. See ELF July 29, 2021. Temple Mountain (South). Moderate. A short climb (about 15 minutes) on the Wapack Trail from parking area on Temple Road leads to the Sharon Ledges where there are great views. You can continue the Wapack Trail for approximately one mile to Burton Peak with more great views along the way. Burton Peak (2,020 feet) is a prominent elevation, along with Holt Peak, on the north-south ridge known as Temple Mountain. Temple Mountain (South) access: Temple Rd., Sharon. Loverens Mill Cedar Swamp. Moderate. A three-mile loop trail that includes a rare Atlantic white cedar swamp situated at 1,040 feet. There are also the remnants of an old sawmill and frontage along the North Branch of Contoocook River. Dogs are not allowed. Loverens Mill access: Lovern Mill Rd., Antrim. See ELF Oct. 13, 2017. North Round Pond, Pisgah State Park. Moderate. A six-mile loop trail hike to a remote pond. You'll see giant trees and lots of mushrooms along the way. The trail starts at Horseshoe Road and continues on Old Chesterfield Road, the Reservoir and North Round Pond trails. After reaching North Round Pond, your return route is via the Reservoir and North Ponds trails, and Old Chesterfield Road. North Round Pond access: Horseshoe Road Trailhead, Pisgah State Park, Chesterfield. See ELF Oct. 21, 2021. Black Mountain. Moderate to difficult. Black Mountain rises abruptly from the banks of the West River in Dummerston, Vt., to a horseshoe ridge with a summit of 1,280 feet. The mountain originated as a mass of molten rock beneath the earth almost 400 million years ago. Erosion has exposed the granite that forms the core of the mountain. There is pitch pine-scrub oak on the summit along with a great view of Mount Monadnock. Black Mountain access: Rice Rd., Dummerston, Vt. See ELF February 24, 2022. Otter Brook Preserve. Moderate. A three-mile loop hike through a sprawling, northern hardwood forest with a stop at a remote pond (Bolster Pond) along the way. The nearly 5-mile-long trail system at Otter Brook wends past long forgotten stone walls, cellar holes and abandoned pastures that give the property a frontier feel in places. Dogs are not allowed. Otter Brook Preserve access: Bowlder Rd., Sullivan. Round Mountain. Moderate. A 1.2-mile trek up this small mountain (1,475 feet) leads to a spectacular two summit vista. H. P. Lovecraft, the American horror fiction writer, frequented the Brattleboro area and was familiar with Round Mountain. "I've never seen no country niftier than the wild hills of West Brattleboro. The nearness and intimacy of the little domed hills become almost breathtaking," he wrote to a friend. Round Mountain access: Abbott Rd., West Brattleboro. See ELF Sept. 1, 2022.