Indian Head Rail Trail

The Indian Head Rail Trail loop from Brandywine offers a unique road cycling experience, blending the famously flat and smooth Indian Head Rail Trail with the varied terrain of connecting local roads. You'll pedal through mature forests and natural wetlands, enjoying views of the Mattawoman Creek stream valley, and might even spot wildlife like deer and wild turkeys. The rail trail itself is a paved, easy ride, but the full 59.2-mile (95.3 km) loop from Brandywine introduces 1191 feet (363 metres) of elevation gain, making it a moderate challenge that takes about 4 hours and 1 minute.

To tackle this route, you'll typically start from Brandywine and connect to the Indian Head Rail Trail. While there isn't a specific "Brandywine trailhead" for the rail trail, you can find parking at established access points like the White Plains trailhead or Bensville Park, which you'd integrate into your loop. The trail is open year-round, but spring and fall provide ideal cycling conditions, and you'll find amenities like water fountains and restrooms along the rail trail section.

This route is particularly notable for its rich natural beauty and history, as the Indian Head Rail Trail was built on an abandoned railroad corridor that once supplied the U.S. Navy's Indian Head Powder Factory. It's an excellent spot for birdwatching, situated within Important Bird Areas where nearly 150 species have been identified. The combination of easy rail trail and more challenging road cycling makes it a versatile option for exploring Southern Maryland's landscapes.