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Best Places to Try Winter Hiking

By Mike Boisvert.

I recommend you start winter hiking on trails that are close to home or familiar to you. I also advocate keeping the mileage and elevation modest. Short day hikes (no more than 3 miles) will help you adapt to the extra gear and energy needed for winter conditions. The following routes are easy or moderate treks that lead into the frozen backcountry. Organized GO winter trips are listed in our Events Calendar

Pleasant Mountain
Bridgton, Maine
Standing alone in the Sebago Lake Region, 2,006-foot Pleasant Mountain dominates the surrounding countryside and offers views of the Saco River Basin and the southeastern faces of Mount Washington and her sister peaks. From Mountain Road, take the 1.8-mile Ledges Trail, an old logging road that pierces overgrown hardwoods before a short, steep scramble onto rocky outcrops. Half the trip is spent along these ledges, where views abound. An old, boarded-up fire tower greets you on the summit. 

Distance: 3.6 miles round trip
Info: Loon Echo Land Trust

Mount Willard
Crawford Notch, N.H.
The Mount Willard trailhead is adjacent to Appalachian Mountain Club's Highland Center in Crawford Notch. The 1.6-mile trail climbs 900 feet to reach the 2,800-foot summit. Open ledges reveal jawdropping views of Crawford Notch’s U-shaped valley of steep slopes scarred by gullies and open slab. The trail has easy grades in most places and snow will often be packed down due to its popularity. Check conditions at the Highland Center before you go.

Distance: 3.2 miles round trip
Info: Our GetWinter Hike #2 this year is here: Click Here To Sign-Up

Yukon Ridge North
Lenox, Mass.
This 3.2-mile loop with an elevation gain of only 540 feet traverses a 407-acre section of ridge on the southern slopes of Lenox Mountain, in the central Berkshires. Begin on the Burbank Trail and go left to traverse the ridge through open woods and over two minor peaks—the latter has a westerly outlook of the surrounding hillsides. At the junction with Old Baldhead Road, remains of an 1850s farmhouse are visible. Stay on the Burbank Trail to loop back, passing by Monks Pond and a small dam.

Distance: 3.2-mile loop
Info: Berkshire Natural Resources Council

Devil's Den Nature Preserve
Weston, Conn.
A 20-mile trail system weaves through the largest nature preserve in southwestern Connecticut. One loop begins on the Laurel Trail and continues on the Godfrey, Sap Brook, Hiltebeitel, Deer Knoll, and Pent trails. Along the way, you will pass through forests of oaks, black birches, and red maples where tufted titmice, bobcat, and ruffed grouse live year-round. Gneiss boulders interrupt trees and punctuate open fields, and brooks cross wooden bridges and run along old stone walls.

Distance: 3.3-mile loop; other route options available
Info: The Nature Conservancy

Bonticou Crag
New Paltz, N.Y.
Located in the northern Shawangunks, the white sandstone face of Bonticou Crag rears up from the surrounding forestland. From its open-slab summit, the Catskills rise and fall against the northwestern horizon and the Hudson Valley lowlands ripple to the southeast. The approach is moderate, traversing open fields and hardwood forests before the crag’s base. A short, steep talus field requires scrambling over boulders. Bring ice cleats, or take the Northeast Trail to the Bonticou Ascent Path to bypass the talus and ascend from the north.

Distance: 3 miles round trip
Info: Mohonk Preserve

Merrill Creek Reservoir
Warren County, N.J.
In the mid-1970s, a 650-acre hole was carved atop Scotts Mountain, creating a 16-billion-gallon reservoir. Now, a 290-acre preserve encompasses the reservoir’s ridge-top north shore, and a shoreline loop hike passes through ecosystems both old and new. Ruins of the Cathers/Shafer farm and coves of drowned trees are contrasted against vibrant forests of sweet birch, beech, and oak and open vistas of the Appalachians and Kittatinny Ridge. Also look for a pair of bald eagles. They have been nesting at the reservoir since 1998.

Distance: 4.1 miles round trip
Info: Merrill Creek Reservoir

Mohican Outdoor Center
Blairstown, N.J.
Located on the road to AMC’s Mohican Outdoor Center, in the middle of the 70,000-acre Delaware Water Gap National Recreation Area, the Coppermines Trail descends from Camp Road into a ravine of rugged beauty and rich history. The trail passes Coppermine Falls before it reaches the Delaware River and the remains of two abandoned 18th-century copper mines. Several mine shafts and old mill foundations reflect how one industry once dominated the land. The return trip will climb steeply to recover the 700 feet of elevation lost on the descent.

Distance: 4 miles round trip
Info: Mohican Outdoor Center

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