Local Guides | Nature

Explore Our Favorite Hikes


Falling on November 17 this year, National Take a Hike Day is all about exploring the over 60,000 miles of trails throughout the United States. We’re sharing our favorite paths from each of our Outposts. Wear some sturdy shoes, pack extra water and snacks, and bring along a friend to celebrate with us.

Best Hike around DC


Hightop Mountain, around Mile 68 of Skyline Drive, VA

Hightop Mountain is a pleasant 3.2 mile round trip hike that offers a 180-degree southwest view of Shenandoah National Park. Follow the Appalachian Trail for a slow and steady climb with switchbacks that build anticipation until the end. Even in cloudy conditions, the view at the peak reveals layers of the Blue Ridge mountains extending into the distance. Especially beautiful during steamy sunrises or during autumn months, Hightop Mountain is one of those hikes that even the most experienced climbers return to over the years.

Best Hike around NY

Overlook Mountain hike

Overlook Mountain, 335 Meads Mountain Road, Woodstock, NY 12498

After a gradual 2.5-mile uphill trek, the skeletal ruins of an 1920s-era hotel await hikers before they continue towards the summit of Overlook Mountain. Breathtaking views of the Hudson River Valley and infinite swaths of foliage await. If you’ve got the energy and your quads aren’t burning too badly, climb the stairs to the top of the old fire tower for an unobstructed 360-degree perspective of the surrounding scenery.

Best Hike around Boston

Bear Brook hike

Bear Brook State Park, 61 Deerfield Road, Allenstown, NH 03275

As one of the largest developed parks in New Hampshire, Bear Brook State Park’s 10,000 acres contain over 40 miles of trails at varying difficulties for every kind of hiker. Many lead to quiet summits, marshes, bogs, and ponds, where you can fish, swim, or boat. Mountain bikers and equestrians are also welcome to practice their sport. Our favorite path is Catamount Trail, about 2.2 miles roundtrip. It’s a difficult uphill climb along a rocky and steep trail. However, after winding through a red pine forest, the reward is one of the best lookouts in the entire park.

Backpack packed and boots laced? Book a cabin and explore these local hikes.