Woodstock Tower Hike
Length: Two miles out and back (about 1½ hours).
Difficulty: Easy.
Distance from DC: 90 miles.
Why this is a great fall hike: Avoid the hordes of leaf-peepers on Sky-line Drive and head one ridge to the west, to the Massanutten Mountain range in the George Washington National Forest. The easy and never crowded trail leads to a fire tower maintained by the Capital Hang Gliding and Paragliding Association. The tower’s three-story observation deck provides a 360-degree view, with the seven bends of the Shenandoah River to the west and Fort Valley to the east. As the sun begins to set, the red, orange, and yellow trees along the ridge appear to glow as if on fire. An eating area is directly be-low the structure.
If you go: For trail details and directions, visit hikingupward.com and search for Woodstock Tower.
Post-hike: In the town of Woodstock, you’ll find antiques shops and the delightful Spring House Tavern (325 S. Main St.; 540-459-4755), with 14 beers on tap.
Stony Man
Length: 3.7-mile loop (about three hours).
Difficulty: Moderate.
Distance from DC: 89 miles.
Why this is a great fall hike: Skyline Drive has more than 500 miles of hiking trails. This short loop is the best bang for your buck, with three of the park’s most stellar views in less than four miles. Each of the overlooks is atop a rocky outcropping, with wide vistas of tree-covered peaks and valleys stretching to the horizon. The trail also passes the base of a 90-foot-high, sheer vertical wall that’s popular with rock climbers.
If you go: For trail details and driving directions, see hikingupward.com and search for Stony Man.
Post-hike: Quench your thirst with a Stony Man Camper Cooler or other specialty cocktail at the Mountain Taproom at Skyland Lodge (around mile 42 on Skyline Drive; 540-999-2212), a few miles down the road from the trailhead.
Annapolis Rock
Length: About five miles out and back (about three hours).
Difficulty: Moderate.
Distance from DC: 63 miles.
Why this is a great fall hike: The Appalachian Trail runs 2,200 miles from Maine to Georgia. This little stretch of Maryland is about 2,190 miles shorter but makes a great way to sample the AT. The well-trod path gradually ascends a few hundred feet through a dense forest before becoming an easy walk in the woods. Follow the white blazes—the official blaze color for the AT—for two miles to a short blue-blazed connector trail to the gleaming cliffs of Annapolis Rock. (They’re actually in Boonsboro, a long, long way from the state capital.) The cliffs, which are a popular spot for rock climbers—you may see them while you’re coming up from below—offer a 180-degree west-facing view of spectacular colors in fall, with Greenbrier Lake visible to the south.
If you go: For more details on the trail and for directions, see alltrails.com and search for Annapolis Rock.
Post-hike: Grab a delicious ice-cream cone at the Potomac Street Creamery (9 Potomac St.; 301-432-5242) in Boonsboro.
Loudoun Heights
Length: 6.3 miles out and back, starting at the secondary Harpers Ferry parking area at the intersection of US 340 and Shenandoah Street and following a different section of trail part of the way back (about four hours).
Difficulty: Moderate.
Distance from DC: 68 miles.
Why this is a great fall hike: The little-known hike is unrivaled for its views of the confluence of the Shenandoah and Potomac rivers, Harpers Ferry, and the soot-coated cliffs of Maryland Heights. Start at the Shenandoah Street lot to save a couple of miles of walking through town. The pathway crosses a small stream and follows the mountain ridge up past the remains of an old fort. It then opens to a view of the Potomac River and crests at an overlook of the historic town and, in season, the thick autumn foliage draping down to the banks of the rivers.
If you go: For more trail details and directions, see hikingupward.com and search for Loudoun Heights (although we suggest skipping the first 1.1 miles of that route).
Post-hike: Returning to Harpers Ferry, explore the historic town’s museums, monuments, shops, and restaurants. Don’t miss Jefferson Rock for a view from the opposite side of the Shenandoah River.
Sugarloaf Summit and White Rocks Overlook Hike
Length: 6.8-mile loop (about four hours).
Difficulty: Moderate.
Distance from DC: 40 miles.
Why this is a great fall hike: The closest mountain to DC, Sugarloaf has a variety of scenic overlooks, several accessible by car. For those who want to hoof it all, a seven-mile loop starts in the East View Parking Area. Head up a steep trail to the 1,282-foot summit. Here the view spreads out toward the southwest, to a sea of trees interrupted by islands of farmland. A stair-step path returns to a lower view toward the west and then down into the woods. After a couple of miles, you come upon two rocky outcroppings—the White Rocks overlooks—for more fall-foliage vantage points. Then it’s mostly uphill to finish the loop.
If you go: For trail details and driving directions, visit hikingupward.com and search for Sugarloaf Mountain.
Post-hike: Reward your efforts with a stop at Sugarloaf Mountain Vineyard (18125 Comus Rd., Dickerson; 301-605-0130) on the drive home.
Wolf Rock/Chimney Rock Loop and Cunningham Falls
Length: Five-mile loop plus 2.8 miles out and back to the falls (about three hours plus two hours).
Difficulty: Moderate to strenuous.
Distance from DC: 67 miles.
Why this is a great fall hike: It can still be hot in the fall. These two hikes may be combined in one day in Catoctin Mountain Park to enjoy a bit of fresh mountain air and cool mountain water. The loop hike is best done counterclockwise, with a stop first at the striking Wolf Rock, which erupts from the ground in huge horizontal slabs. While there’s no overlook here, the rocks make for a fun place to scramble. Continue on to Chimney Rock and to take a small leap over a crevice if you dare. It would be easy to spend an entire day here marveling at the view from the flat white boulders, perched on the edge of the mountain. Finish the loop and then, if you’ve got the time and energy, take a short drive to the Cunningham Falls trailhead. The easy 1.4-mile path ends at the cascades of the 78-foot waterfall, Maryland’s highest.
If you go: For a PDF with trail details and a map, go to nps.gov and select Maryland under Find a Park. Click on Catoctin Mountain, then hiking trails, then Wolf Rock/Chimney Rock Loop.
Post-hike: The pool at the bottom of the falls is a wonderful spot to cool off your feet.
Old Rag
Length: 9.2-mile loop (about six hours).
Difficulty: Strenuous.
Distance from DC: 86 miles.
Why this is a great fall hike: It’s hands down the best day hike in the Mid-Atlantic,so it can be crowded on weekends. The trailhead begins a quarter mile from the parking area. A couple of miles of moderate grade through the woods lead to a variety of harder rock scrambles—up and down narrow chutes, over and under boulders. Atop the rocky cliff, you can look out on breathtaking views of Shenandoah National Park and verdant Virginia countryside. The return trip follows an easy trail to a fire road.
If you go: For directions, parking in-formation, and other trail details, see nps.gov and search for Old Rag hike.
Post-hike: Go winetasting at Sharp Rock Vineyards (5 Sharp Rock Rd., Sperryville; 540-987-8020), two miles from the parking lot.
This article appears in our September 2016 issue of Washingtonian.
