The Devil’s Trail: 11 Hikes for Halloween

September 18, 2015
Susan RoseLooking for a good Halloween-themed hike? The Devil’s Path in the Catskills is a real treat.

If you judge a hike by its name, you’re bound to be scared away from some unforgettable places. Why not embrace our region’s inner demons and explore the dozens of devil-themed trails, parks, and natural features scattered across New England and the Mid-Atlantic? Many of these spots earned their names by way of old legends or striking landmarks; others were so named because, well, they’re a devil of a hike. From Maine to Virginia, here are 11 hikes invoking the underworld, perfect for Halloween—or anytime you’re seeking a thrill.

Devil’s Den | North Berwick, Maine
Located in the Bauneg Beg Mountain Conservation Area, this impressive outcropping of large boulders and overhanging cliff faces forms the Devil’s Den. Named for the sense of enclosure created by the rocks and summit ledges, Devil’s Den sits between Bauneg Beg Mountain’s Middle and North peaks, along Linny’s Way Trail. Hike the easy North Peak Loop starting at the trailhead on Fox Farm Hill Road, about 7 miles northwest of North Berwick. The Bauneg Beg Trail starts at the back of the parking area behind an information kiosk and joins Linny’s Way Trail just before Devil’s Den. Follow the loop to Middle Peak and its lookout, descend into Devil’s Den, and pass over North Peak to finish the loop.
DISTANCE: 1.5 miles round trip
INFO: Best Day Hikes Along the Maine Coast (AMC Books)Great Works Regional Land Trust

Devil’s Hopyard | Stark, N.H.
This boulder-strewn ravine is filled with coniferous trees and covered in moss. Steep cliffs rise on all sides, creating a dark, moist environment that shelters year-round ice deposits and rare plant communities. Park on South Pond Road, about 15 miles outside of Berlin, and look for the Kilkenny Ridge Trail, a flat and wide road located beyond the bathhouse at the South Pond Recreation Area. After less than 1 mile, connect to the Devil’s Hopyard Trail and follow it into the gorge. A stream leaves some rocks in the Hopyard perpetually wet, so proceed with caution. In the off-season, park at the gate and walk about 1 mile to the Kilkenny Ridge Trail. Nearby, the Devil’s Slide, a massive imposing cliff face, towers over Stark’s famous covered bridge. Add it to your schedule for a particularly devilish afternoon.
DISTANCE: 2.6 miles round trip
INFO: Best Day Hikes in the White Mountains, 2nd ed. (AMC Books); White Mountain Guide, 29th ed. (AMC Books); White Mountain Guide Online

Devil’s Chair Trail | Charlotte, Vt.
This section of the relatively easy summit trail up Mount Philo is so named for a massive rock formation en route. For breathtaking views of the Champlain Valley, begin on the House Rock Trail, which features its own namesake rock formation before running into the Devil’s Chair Trail. Loop around to the peak of Mount Philo, continue along a carriage road for another 0.2 mile, then return to the House Rock Trail junction. The parking lot and trailhead for Mount Philo and the Devil’s Chair are located on State Park Road; take Route 7 from Charlotte.
DISTANCE: 2.4 miles round trip
INFO: Best Day Hikes in Vermont (AMC Books); Mount Philo State Park

Devil’s Gulch | Eden, Vt.
Part of Vermont’s famed Long Trail, Devil’s Gulch offers a huge return on a moderate hiking investment. An A-frame gateway formed by two large boulders stands at the mouth of this lush ravine; pass through it and follow the tall rock walls to Spruce Ledge, a gorgeous lookout. Continue on to summit Mount Belvidere then return the way you came, completing the loop by skirting the shore of Big Muddy Pond. The town of Eden and the Gihon River flowing through it are named for their biblical counterparts from the Book of Genesis. It is rumored that, upon discovering Devil’s Gulch, an early 18th-century settler gave the canyon its name due to the dank, dark, and eerie atmosphere.
DISTANCE: 5.2 miles round trip
INFO: Best Day Hikes in Vermont (AMC Books); Green Mountain Club

Purgatory Chasm State Reservation | Sutton, Mass.
This natural playground is more fun to traverse than its name suggests. A deep chasm with sheer rock walls and broken boulders strewn throughout, the reservation encompasses numerous dark caves and crevices, some with their own devilish monikers. Purgatory Chasm’s name can be traced back to the Puritans, who likened the route to a descent toward Hades, the mythological underworld. Hike the Chasm Loop Trail, which passes the Devil’s Corn Crib, the Devil’s Coffin, and the Fat Man’s Misery, a deep rift between two sheer rock faces with little wiggle room. To reach the visitors center and trailhead, follow MA 146 to Sutton, take Exit 6, and make a right onto Purgatory Road.
DISTANCE: 2 miles round trip
INFO: Massachusetts Trail Guide, 9th ed. (AMC Books), Purgatory Chasm State Reservation

Devil’s Hopyard State Park | East Haddam, Conn.
This state park offers a bevy of trails and natural features, including waterfalls, rivers, and the well-known Devil’s Oven cave. The origin of the park’s name varies, depending on whom you ask, but one theory attributes it to the naturally occurring potholes in the rock. While science indicates these holes were formed over thousands of years by spinning eddies, lore has it that early settlers blamed the devil. Park in the lot on Foxtown Road and follow the Vista Trail Loop, which takes you past the Devil’s Oven and the picturesque Chapman Falls.
DISTANCE: 2.9 miles round trip
INFO: Best Day Hikes in Connecticut, 2nd ed. (AMC Books); Devil’s Hopyard State Park

Devil’s Den Preserve | Weston, Conn.
Fewer than 60 miles from New York City, this nature preserve protects more than 1,700 acres of land, wildlife, and solitude. According to legend, its name originated with the region’s former charcoal manufacturers, who saw the footprint of the devil in a cloven-shaped imprint on a boulder. Start your hike on the Laurel Trail toward Godfrey Pond and see the remains of sawmill machinery from 90 years ago, when timber was harvested in the area. Finish the loop along the Sap Brook Trail and the Deer Knoll Trail. From the Merritt Parkway (CT-15), take Exit 42 and travel north on CT-57 for about 5 miles. Turn right onto Godfrey Road then left onto Pent Road and continue on to the parking area at the road’s end.
DISTANCE: 3.3 miles round trip
INFO: Best Day Hikes in Connecticut, 2nd ed. (AMC Books)

Devil’s Path | Tannersville, N.Y.
Perhaps the most popular of all long routes in the Catskills, the Devil’s Path is famous for its rugged terrain and spectacular views. Dutch settlers to the region believed Satan lived beneath the jagged outcrops of these mountains, but the trail’s name can also be attributed to its punishing topography. The trail traverses five summits, dipping into deep valleys for an overall elevation change of 14,000 feet. You can conquer the Devil’s Path in its entirety, with overnights at lean-tos or at the Devil’s Tombstone Campground near the midpoint of the trail, or you can choose to tackle segments on day trips. Day hikers can reach the Devil’s Path by a number of offshoots. To start at the beginning, park at the trailhead off of Prediger Road, accessed by CR 16 and NY 23A from Tannersville.
DISTANCE: About 23 miles round trip
INFO: Catskill Mountain Guide, 3rd ed. (AMC Books); New York–New Jersey Trail Conference

Devil’s Pulpit | Slatington, Pa.
This loop hike through Pennsylvania’s Lehigh Gap will take you past Devil’s Pulpit, a rock formation that calls to mind a church pulpit. The trail starts on the northwestern side of the ridge, and the loop takes you all the way around Lehigh Gap. The Appalachian Trail links with the loop on the southeastern side. The result of geologic and erosional wear and tear, Devil’s Pulpit offers fantastic views of the Lehigh River. Start on the Northside Trail and follow it along the Kittatinny Ridge to Devil’s Pulpit, then continue on to the Appalachian Trail, which will return you to the trailhead. The parking area is located on Route 873, near the Lehigh River bridge.
DISTANCE: 6 miles round trip
INFO: Best Day Hikes Near Philadelphia (AMC Books)

Devil’s Marbleyard | Near Lexington, Va.
This Shenandoah Valley rock quarry boggles the mind in two ways: first with its location, appearing seemingly out of nowhere in the Virginia woods, and second with its scale. Some of the broken boulders in this 8-acre field are as large as cars and even buses. The Marbleyard was given its name in the 19th century by travelers unable to traverse it by wagon. Hike the short Belfast Trail to the bottom of the field then choose between climbing the Marbleyard itself—watch those ankles—or skirting its perimeter via a steep trail. The Belfast Trail meets a segment of the Appalachian Trail north of the Marbleyard, but hikers have the option of returning to the parking lot the way they came. Coming from VA 689 and US 11 south, the trailhead is on the left side of VA 781.
DISTANCE: 3.2 miles round trip
INFO: Best Day Hikes in the Shenandoah Valley (AMC Books)

Little Devils Stairs | Shenandoah National Forest, Va.
Located in the northern end of Shenandoah State Park, Little Devils Stairs is considered one of the more picturesque locations in the region. Strenuous early on before tapering off to moderate elevation gain, the route will take you past waterfalls, streams, and steep cliffs. Nearby is the hike’s less-traveled sibling, Big Devils Stairs, a 5.5-mile loop with views for miles. Pick up the Little Devils Stairs Trail from the parking lot on VA 614 (Keyser Hollow Road), accessible via VA 622 and US 211.
DISTANCE: 5.7 miles round trip
INFO: Best Day Hikes in the Shenandoah Valley (AMC Books)


Find hundreds of additional hikes and trip ideas throughout the Northeast and Mid-Atlantic in the Get Out archives.

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