Explore the best rated trails in Chestertown, MD, whether you're looking for an easy walking trail or a bike trail like the Ben Cardin C&D Canal Recreational Trail and Pomeroy and Newark Rail Trail . With more than 85 trails covering 390 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.
I start at Red Hill Road parking lot in Pequa and do the 20 mile round trip to Turkey Hill and back, it is flat, no potholes or surprises and glorious. Two bridges, 5 miles each way along the river, often a train, many groups of rock climbers on the weekend. Just glorious. If you want to add miles, going west is level and wooded. Some might say boring however I find it cool, refreshing and safe. My favorite trail!
A lot of trail damage from storms in July 2025 makes for a very rough ride. Rough hard gravel, very bumpy ride. Could be dangerous if riding fast. My friends and I have moved to the Pa Heritage Rail Trail. NCR is more beautiful though rough. Would love to know if/when trail damage will be smoothed out. Got to be a budget for repair
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.
We started this path from the Conowingo dam parking lot. We had to move through a group of turkey vultures to get to the trailhead. It was a beautiful fall day and the trail was clear of most debris. There are quarter mile markers. While we were out, several bikers were also on the trail. We took several side trails to the river to see other wildlife and to get some sun. The deep canopy of the trail blocks much of the sun making this an easy stroll in 80 degree weather.
My first time on this trail today and I was not disappointed! Each trail has a personality and I would say that the WB&A is the back country cousin of the the more metro B&A trail over by Annapolis. Lots of tunnels and bridges make this interesting, and the steep, serpentine descent on pristine new blacktop going south to the new bridge was exhilarating and frightening at the same time. A super ride out and back. I parked at the Electric Ave Lot at mile 1. The map shows a restroom (Jiffy John), but I didn't see any on my trip today. The closest one starting at the southern end was at the parking lot at 8609 Race Track Rd, Bowie, MD. The splash park did not have an external restroom that I could find.
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.
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.
We Loved this trail. We got on at the Brillhart Road Parking lot went down the trail through the Howard tunnel, all the way down to the Hanover Junction. It was pretty much all in the shade. There were sections with very low grade ups and downs but the grade was so low you couldn’t see the hills visually, you just felt the difference in your legs. There was also minimal street crossings and they were all super small back roads with minimal traffic, which was great for my kids.
This was the second time I visited this trail. But the change in parking location from Quarryville the first time to Red Hill Road in Pequa this time made all the difference. From the that trailhead, you can choose what direction you’d like to enjoy the trail. But I would highly recommend going west towards the Martic Forge Trestle and the beginning of the spectacular views of the Susquehanna to River
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.
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