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A little more information on the Indian Head rail trail (I lived in Indian Head for 12 years and am still in the area; this is my “home trail”).
There is parking at Indian Head (but not next to the trail, you have to ride a bit on roads to get there), Livingston Road, Bennesville Road, Middleton Road, and the trail head at White Plains. Here’s a map: https://www.charlescountyparks.com/sites/charlescountyparks.com/files/parks/Trails/IHRT/railtrailmapApril2013.pdf Middletown is listed as a small parking area, but they’ve enlarged it since this map was created.
The section between IH and Livingston tends to be the most crowded because there’s a lot of homes right next to the trail. The crowds in this section are often teens who take up the whole trail and are oblivious to other folks using the trail. If you’re on a hybrid, this section is a difficult climb going towards IH and for all riders heading away from IH, racing down the incline and into the crowds is a bad idea.
Between Livingston and Bennesville the trail is very flat and straight and lightly traveled. I use clip on aerobars and am very comfortable dropping into them for most of this distance; there’s not a lot of need to change gears and you can see kids/dogs in plenty of time to go back to the handlebars in case you need brakes. There’s a section near Bumpy Oak where people fish a lot, but they tend to stay off the trail (and it’s right by a road crossing, so you’re not likely to have the hammer down when you encounter them).
To get from the Bennesville parking lot to the trail is an off-road path, but it’s VERY steep (the trail is lower than the parking lot). I don’t like parking here and climbing that hill at the end of a ride. I don’t think I’ve ever been able to climb it on a hybrid either.
From Bennesville to White Plains is uphill, but not terribly so. It’s longer and more gradual than the hill on the IH side. It’s more crowded between Middletown and White Plains, but they tend to be folks working out (and more aware of their surroundings than the crowd in IH).
I highly recommend the Livingston to Bennesville section for new hybrid riders looking to avoid hills, and for folks looking for a long, straight, flat place to put the hammer down. If you’re likely to be tired at the end of your ride, park at Livingston. The section to IH is the prettiest, but the worst for crowds. Even at its worst it’s leaps and bounds less crowded than Mount Vernon (the only other off road trail I’ve ridden).