Things to Do

Our 7 Favorite Nearby Hikes to Do in the Fall

Bucket-list-worthy: Hiking Old Rag. Photograph by Jeff Mauritzen.
Fall Weekends 2019

About Fall Weekends 2019

Whether you want to get out of town for just the day or for a few, here are some great ideas for colorful autumn trips. Hit a hiking trail, stomp grapes at a festival, stroll a historic small town, and more.

Seven great hikes where you can get some exercise and see fall foliage, all in one step.

Old Rag


This is the Mid-Atlantic’s premier hike—and not to be undertaken lightly. Round-trip, the Old Rag hike is more than nine miles, with an elevation gain of 2,400 feet. After some initial switchbacks through the woods, the path climbs above the tree line. At several points, you have to use your hands and feet to scramble over rocks. The reward at the summit? A breathtaking panorama of the peaks along Skyline Drive and the forested foothills of the Virginia Piedmont. You can relax at the top—the return trip is easier, mostly along an old fire road. Be sure to have plenty of water and snacks for the hike, which can last more than seven hours. It can get crowded on fall weekends, so consider a midweek climb. Distance from DC: 86 miles.

Big Meadows


Atop the mountains of Shenandoah National Park and about a mile off Skyline Drive, Big Meadows Campground is the hopping-off point for several trails and scenic views. The best trail descends deep into a thicket clad in fall colors to Dark Hollow Falls. The short, 1.4-mile out-and-back trip is often busy, but worth risking the possibility of a crowd. The beautiful waterfall cascades 70 feet over a series of moss-covered boulders. In the early morning, it’s often shrouded in a foggy mist. You half expect a hobbit to appear. The campground includes more than 200 campsites for those who want to enjoy a starry sky free from light pollution. Not into camping? Big Meadows Lodge is next door. Distance from DC: 102 miles.


Easy to strenuous

If you’d like a hike with creature com­forts, consider a stay at Virginia’s Wintergreen Resort. The property, along the Blue Ridge Parkway, offers access to more than 30 miles of hiking trails. One favorite in the fall is Raven’s Roost, whose scenic overlook along the Blue Ridge Parkway not only gazes out onto a colorful sea of trees but also is an ideal spot to watch raptors soaring along the mountain ridge during the fall migration. Distance from DC: 183 miles.

Loudoun Heights


This hike, also in West Virginia, can start in downtown Harpers Ferry or farther along the trail, at a parking lot outside town. After you cross a bridge, the trail winds upward three miles, through the woods, to a view of where the Potomac and Shenandoah rivers meet. It’s a postcard-perfect scene of not just the water but also forested mountains, bridges, rocky outcroppings, and the historic hamlet. The out-and-back hike is either 6.3 miles or 8.5 miles, depending on your starting point. Distance from DC: 60 miles.

Dolly Sods

Moderate to strenuous

Is your style more to rough it, maybe with a bit of camping and backpacking? Dolly Sods, a West Virginia wilderness area encompassing 17,000-plus acres, offers 47 miles of trails of varying difficulty. Fall comes earlier here, with elevations ranging from 2,500 to 4,700 feet. It’s a magical place to appreciate nature: The diverse ecosystem includes forested valleys, grassy plains, sheer cliffs, and views of Canaan Valley. Distance from DC: 157 miles.

Annapolis Rock


The Annapolis Rock overlook in Maryland is reached by trekking a shady, shallow incline for 2.7 miles. It’s a literal walk in the woods on the Appalachian Trail—and it breaks out of the tree cover to the top of jagged cliffs and a view of Greenbrier State Park and Greenbrier Lake. You’re facing west, and the autumn colors as the sun begins to set can be mesmerizing. The site is popular with rock climbers, so don’t be surprised if a head pops up over the rocks while you’re enjoying the view. You return via the same path. Distance from DC: 62 miles.

Chimney Rock

Moderate to strenuous

This hike in Maryland’s Catoctin Mountain State Park is often done as a loop trail including Wolf Rock. But don’t bother with Wolf Rock—there’s no view. Instead, start at the visitor’s center for this 3.9-mile out-and-back hike, which follows a sometimes steep trail to a series of gigantic flat boulders that resemble a chimney. The view from these white rocks is fantastic—undulating mountain ridges covered in trees for days. Distance from DC: 65 miles.

This article appears in the September 2019 issue of Washingtonian.