Chessie the Bear – Dismal Swamp Trail loop from Dollar Tree

If you're looking for a wonderfully flat and peaceful road cycling route, the Chessie the Bear – Dismal Swamp Trail loop from Dollar Tree is an easy 26.6-mile (42.8 km) ride with just 84 feet (26 metres) of elevation gain, taking about 1 hour and 45 minutes. It's an ideal choice for a relaxed outing, perfect for families or anyone wanting a smooth, car-free experience through unique natural scenery.

What to expect on Chessie the Bear – Dismal Swamp Trail loop from Dollar Tree

The route follows a former section of Virginia State Route 17, so you'll enjoy a consistently paved, wide, and smooth surface that's flat as a pancake. As you pedal, you'll be immersed in a remote and serene environment, cycling alongside the historic Dismal Swamp Canal and the extensive forested wetlands of the Great Dismal Swamp National Wildlife Refuge. Keep an eye out for the famous Chessie the Bear statue at the northern trailhead, and be prepared for potential wildlife sightings, from diverse bird species to butterflies, and even the occasional black bear. This minimal elevation ride is perfect for a comfortable, easy outing, suitable for beginners and families.

Planning your visit

The trail is car-free and well-maintained, offering a safe environment for cyclists. While the specific "Dollar Tree" parking isn't detailed, the northern trailhead is a popular access point and features amenities like restrooms, picnic areas, and a bike fix-it station at certain mile markers. The trail is generally accessible year-round, but spring and fall offer pleasant temperatures for cycling and increased wildlife activity. Always carry enough water, especially during warmer months.

Trail details

• Distance: 26.6 miles (42.8 km)
• Elevation gain: 84 feet (26 metres)
• Difficulty: easy
• Estimated time: 1 hours and 45 minutes