Explore the best rated trails in Middletown, MD, whether you're looking for an easy walking trail or a bike trail like the Torrey C. Brown Rail Trail and Grist Mill Trail at Patapsco Valley State Park . With more than 102 trails covering 4612 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
The path in some areas were easily accessible and shown however coming from takoma the signage was not very well maintained…the bike trail was on side and the signage on the opposite side. Luckily I know the area to get to the actual trail. Other than that, it was a pleasant bike trail.
The Washington & Old Dominion is the best trail hands down. It is also one of the busiest trails that hosts running clubs, cycling clubs, nature walkers, neighborhood walkers, walking and biking commuters and is at its busiest before 7 am in extreme heat.
What makes this 44 mile trail so unique is the amenities that sit along side of it making it the best trail to plan an activity on with family and friends. Just pick a city that you want to visit and you can find convenience stores adjacent to the trail within walking distance as well as myriad of restaurants for all ages, ice cream parlors, grooming services, bike shops and over the past few years breweries have been added to the scenery right on the trail.
The location is prime to the cities of Northern Virginia with access to getting into Washington DC to see the monuments and Hains Point. Nothing beats the W&OD Trail!
Level, thin tiny crush stone on packed earth trail. Rolls easily, just a step below paved. From small old town of Newville through woods and farmland 10 mile ride to small university town of Shippensburg, with a couple small villages on the way. Horse path is next to bike/pedestrian path. You may see horses and riders on path. You will see farms, barns, cows, sheep, horses, cats, birds, assorted other animals, louse distant mountains. You will smell manure. It is not 15.8 miles. It is 10 miles from park at Newville to Shippensburg. You can add a couple miles by going east from Newville to a dead end. It's a nice ride. In Newville you can park at the park at Cherry & McFarland Streets
Parked at Carroll Park to get on the trail and I’ll never do that again. Credit to the numerous homeless people gathered around and the guy actively infecting drugs into his arm for not breaking into my car for the 90 minutes I was on the trail. Graffiti everywhere and quite a bit of trash. Once you get to Leakin Park it’s actually pretty nice. I’m pretty new to Baltimore and I’m really hoping it has better bike trails to offer than this.
This is probably the most I could handle on a bike ride. We rode the GAP and C&O back to back like many do in 8 days. It was great fun but the C&O is noticeably rougher, fewer port-a-Johns and very scarce potable water sources. On our 7th day from Williamsport to Brunswick we ran out of water midway and rode the remaining 25 miles without water. Fortunately the shade offered by the beautiful canopy of trees made it bearable. We made sure to load up on extra water on our final day. The mix of loose sand that caught us by surprise & the larger stones on the trail made for a more challenging ride than expected. On the one rainy day we had from Cumberland to Little Orleans, some of the puddles we encountered offered a new sense of “oh dear” as we didn’t know how deep the hole we were riding thru when there was no room to go around the puddle.
Biked from Hancock to Little Orleans and return on August 30, 2025. Distance: 34.5 miles. Stopped for lunch at Bill's Place in Little Orleans and got good food and friendly service. The paved portion of the trail is in excellent condition -- thanks to the Maryland Park Service for recently repaving the trail. The only negative is the 3-mile detour on the C & O Canal towpath around the abandoned Indigo tunnel. The towpath detour is unpaved and has a rougher surface than the trail. The nearly one-mile long tunnel was closed in 2010 to protect a handful of bats allegedly living inside. The tunnel is an engineering marvel that should be seen and experienced by humans. Opening it to trail users would help the economically depressed Western Maryland area. For example, the equally-long Blue Ridge Tunnel in Afton, Virginia, draws about 50,000 visitors annually since it was reopened in 2020.
This is a great trail. Shaded and flat. It could use some more signage, though, to help identify right and lefts.
We camped at Indian Rock Campground right along this trail. It was a lovely comfortable ride with our mountain bikes. The Howard Tunnel was neat too. We highly recommend this trail.
Beautiful quiet rail trail that we have added to our favorites list.
We started at Lake Needwood which had great parking. The trail is not well maintained. It is bumpy most of the way south. It looks like there has been some attempt to patch the asphalt but the transitions were not smoothed out so many jarring bumps. Also tree roots have pushed up the trail which is not unusual but given all the other bumps it was annoying. Also be aware that from Lake Needwood - it is downhill so if you are returning to the same spot, you will have an uphill climb which is not too bad.
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