All directions start at US Route 301 at White Plains, beginning with the eastern end of the Indian Head Rail Trail and proceeding to the western end at the town of Indian Head.
To parking at the eastern terminus in White Plains: From Route 301 in White Plains, turn west onto Theodore Green Boulevard. In approximately ¼ mile, trail parking is on the right side of the road at 10390 Theodore Green Boulevard. Weekend (only) overflow parking is available at the Charles County Health Department parking lot (intersection of Route 301 and Theodore Green Boulevard).
To the Middletown Road parking area (approximate address 4480 Middletown Road, Pomfret, MD): From US Route 301 just south of White Plains, turn west onto MD Route 227/Marshall Corner Road and go 1.8 miles, then turn right to go north on Middletown Road for 0.2 miles. The parking for the Rail Trail will be on the right (east) side of the road, immediately before crossing the Rail Trail itself.
To Bensville Park parking area (address 6980 Bensville Road, White Plains, MD): From US Route 301 just north of White Plains, turn west onto Billingsley Road. Drive west for 2.3 miles, then turn left to go south on Middletown Road. Drive south for just 0.2 miles, to a traffic circle; take the first exit to continue west on Billingsley Road. In 2.2 miles, turn left to go south on Bensville Road. The park will be on your right (west side of the road) in just 0.6 miles. The park has two big paved parking lots: a triangular one and a smaller square one that lies between three baseball diamonds. At the southeast corner of the square lot, there is a paved trail that heads east and then south, parallel to Bensville Road, providing access to the Rail Trail.
To Mason Spring Parking area (approximate address 4970 Livingstone Road, Indian Head, MD): From US Route 301 just south of White Plains, turn west onto MD Route 227/Marshall Corner Road and go 4.9 miles. Turn right to go northwest on Pomfret Road (still MD Route 227) for 3.2 miles, then turn left to go southwest on MD Route 224/Livingston Road. The Indian Head Rail Trail will be ahead in 2.5 miles. Carefully turn into the parking area on the right, at the intersection with the Rail Trail.
To parking near the western terminus of the Rail Trail in the town of Indian Head: There is no parking at the Rail Trail itself. Nearby parking is at Village Green Park, 100 Walter Thomas Road, Indian Head, MD. From US Route 301 just north of White Plains, turn west onto Billingsley Road. Drive west for 2.3 miles, then turn left to go south on Middletown Road. Drive south for just 0.2 miles, to a traffic circle; take the first exit to continue west on Billingsley Road. In 6.4 miles, turn right to go north on Warehouse Landing Road for just 250 feet, to the intersection with MD Route 210/Indian Head Highway. Turn left to go southwest on Indian Head Highway for 4.9 miles, to the town of Indian Head. Turn right onto Lackey Drive. The Village Green Park and its large paved parking lot will be on the left in just 0.1 miles. Follow signs to the start of the Indian Head Rail Trail about 3 blocks away, at Mattingly Avenue.
ALTERNATE PARKING IN INDIAN HEAD: Another option is to park at Mattingly Park, at 105 Mattingly Avenue in Indian Head. Although this parking lot is slightly farther from the start of the Rail Trail, access to the trail is a little more straightforward, and, as a bonus, you will be treated to a view of the Mattawoman Creek from the dock at the end of Mattingly Avenue. To reach Mattingly Park: Follow directions above to the western terminus of the trail in Indian Head, but instead of turning right onto Lackey Drive from Indian Head Highway, continue straight for another 600 feet and turn left to go south on Mattingly Avenue. Obey posted speed limits on this residential street. You will pass the start of the Indian Head Rail Trail on your left in just two blocks; continue straight ahead. Mattingly Park will be ahead on your left in 0.5 miles. Additional parking is at the city-owned Slavin’s Dock at the end of Mattingly Avenue, where there is a great view of Mattawoman Creek. Return north on Mattingly Avenue on foot or by bike to the start of the Rail Trail.