Explore the best rated trails in St Michaels, MD, whether you're looking for an easy walking trail or a bike trail like the Silver Lake Park Trail and Custis Trail . With more than 94 trails covering 4458 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.
This is a great trail. Shaded and flat. It could use some more signage, though, to help identify right and lefts.
I actually started at the fishing pier and went through the pond-side trail. Was on a bicycle. Realized I wasn’t supposed to ride on the trail half-way through. Oops. Anyhow I enjoyed that part of the trail on my bicycle as it was good for my beginner trail skills. Did end up on the gravel road towards the end. Anyhow I enjoyed it, not thrilling, but was nice none-the-less.
there are some really old bridges that go over the C&O. the highlight is the paw paw tunnel. better to walk through it. once you hit little orleans, i suggest going on the western maryland trail. it is fully paved and nice.
hancock is a great town
Even though the trail is in an urban setting it is surprisingly lush and beautiful. There is actually a marsh land half way that is a gorgeous place to rest and take some photos. The trail is smooth and pretty flat. Nice enjoyable easy ride.
Multiple spots to stop. Most of the trail is shaded. There are some beautiful spots to stop on either end of the trail. Never over packed. I always see a ton of wildlife, which my kids love. It's not hard to bike, mostly flat.
If you visit Lewes or Rehoboth Beach plan to take your bike and check out these trails. The J&B combined with Cape Henlopen SP is my favorite, be sure to ride it in both directions as well. This year I added the Georgetown section (it's a fair distance out and back from Lewes, ends up somewhere near Rt. 9 and Cool Spring Rd). The very straight, very flat paved Georgetown/Lewes Trail was busy close to Lewes on a warm Saturday in May, I expect summers are even more crowded. There are more road crossings than I like but cars were courteous. The J&B twists through both Lewes and Rehoboth with everything from paved residential areas to gravel paths through wooded and open field sections in between. The signage is adequate but it is easy to get misdirected in Rehoboth. If you make your way through Rehoboth on whatever route you choose, continue to the southern entrance of Cape Henlopen. You can't miss the Gordon Pond Trail which takes you through the park and back to Lewes. Cape Henlopen trails are well marked, there are multiple other trails within the park also. There are many places to stop and rest and bathrooms along all 3 sections.
I started riding this trail in 2018 and rode it 3-5 times a summer. It was a great trail that allowed you to get 12 miles in before riding the Cross Island Trail just 3 miles away. The tree roots have been bulging the asphalt for the past 7 years and now it is so bad I don't know if I will ride it again. For the first 1-2 miles from the start of either end the roots have the asphalt bulged up over two inches. Even riding with a suspension seat post the trail jars your spine unless you are standing on the foot pegs. Since the roots are so numerous this means you would be on the pegs 50 percent of the time. With the financial state that Maryland is in I doubt this trail will be repaired any time in the foreseeable future.
I kept hearing how beautiful this "trail" was. Most of the "trail" was city streets even before you get in to Baltimore. It was also poorly marked. Keep a GPS handy, or just give up on the trail and ride through whatever Baltimore streets you feel like riding.
It does take you past the Baltimore Zoo which was nice. It also takes you right in to Inner Harbor which is also a good place to hang out for a bit.
Stretching for more than 2 miles across Chestertown on MD's Eastern Shore, the Wayne Gilchrest Trail is a scenic greenway that has the potential to connect to more communities.
Like many town-based trails, the paved, multi-use path allows residents to walk or bike between communities with minimal street crossings. It links Washington College with the north and south sides of town and the southern terminus along Cross Street is just a short distance from the waterfront at Wilmer Park as well as the historic downtown. Also notable is a spur of the trail that branches from the main path on the grounds of an office building and parallels High Street, connecting to the northwest side of town and ending at the former Radcliffe Mill, which has been restored and now houses a restaurant and microbrewery.
The trail also serves as an outdoor museum of sorts and features several sculptures and murals along the route, while the old train station, vintage passenger coaches and caboose at the southern end off Cross Street are a testimony to the rail line that used to run here.
Last, but not least, the lush vegetation that lines most of the trail's route provides a serene atmosphere and is a great place to observe local wildlife. The section from Mill Street south to Cross Street forms a greenbelt between residential communities and the Lawrence Preserve nature area, whose wetlands can be further explored through a network of paths extending from the trail. The ravine that forms the trail's route through the Washington College campus and the embankment on the portion north of Morgnec Road are also notable for their beauty and serenity.
My only caveats with this premier small town trail are the busy crossings on Morgnec Road and High Street, though flashing signal lights that warn motorists when trail users are crossing reduce the danger to a degree and the lack of any direct connection to Washington College. It would also be nice if a separate connector path or sidewalk could be built along Morgnec Road that would link the NW Spur of the trail with the main route on the north side of town so that trail users don't have to use the shoulder of that busy road.
Although currently confined to Chestertown, local officials are exploring plans to extend the Wayne Gilchrest Trail further north along the old RR towards Worton, forming part of a bigger network of greenways on the Eastern Shore.
The trail is 100% paved and takes you along the Anacostia River. I like that this trail has a good mix of city elements and natural beauty. The Kenilworth aquatic gardens are a wonderful stop early in the trail, you get to see a lot of swamp flowers. Later, closer to Dc you are taken up to the Fredrick Douglas memorial bridge. The large white arches of the bridge are breathtaking. There are many places to eat diner once you make it to Dc. I stopped at Gordon Ramseys fish and chips. Great trail!
I have used this trail a few times to commute from the Arlington, VA area into the district. It is convenient but could use a repaving. The paved path is bumpy (It looks like tree roots grew to create the wavy in the path). The first time I rode it I was pulling my dog and the wavy ness of the trail actually broke the bike rack connecting the dog trailer from the bumps. 3 years later from when by rack broke, the path has only gotten more wavy.
This trail is also hilly so you will get a workout. Going from Ballston to DC it was more downhill and rather easy, coming back the hills were somewhat steep. A good workout but not overly difficult.
On a side note: If you are visiting DC, I strongly suggest using the bike trails in DC, around DC, and all the trails in the surrounding areas. Every Smithsonian has bike racks to lock up your bike while visiting the museums. It is a great way to see the monuments, museums, and the mall without miles of walking. Today I first went to Library of Congress (to do some research), then to National African American Museum, and to the Native American Museum. I rode about a mile between the two museums which was much easier than walking.
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