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Cambridge Trails and Maps

406 Reviews

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Indian Head Rail Trail

Looking for the best trails around Cambridge?

Explore the best rated trails in Cambridge, MD, whether you're looking for an easy walking trail or a bike trail like the Cross Island Trail and Strawberry Lake Way Bicycle Path . With more than 34 trails covering 154 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.

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Showing 9 of 34

4 Reviews

413 Rail to Trail

The 413 Rail to Trail is located in Somerset County, Maryland. The trail will be 12 miles point-to-point when complete. The trail parallels...

Length: 4.5 mi

State: MD

Surface: Asphalt, Crushed Stone

0 Reviews

American Holly Trail

Located in southern Delaware's Trap Pond State Park, the American Holly Trail provides a short and scenic alternative to some of the park's...

Length: 0.7 mi

State: DE

Surface: Crushed Stone

59 Reviews

B&A Trail

The paved 13-mile B&A Trail connects the Chesapeake Bay cities of Baltimore and Annapolis. Along with extensive historical markers, this...

Length: 13.3 mi

State: MD

Surface: Asphalt

9 Reviews

Bob Trail

The Bob Trail (or simply, The Bob) in Trap Pond State Park loops around the perimeter of the 90-acre Trap Pond for 4.5 miles. The trail...

Length: 4.5 mi

State: DE

Surface: Boardwalk, Crushed Stone

2 Reviews

Broadneck Peninsula Trail

The Broadneck Peninsula Trail is 2.43 miles of asphalt walking and biking pathway in east Annapolis. The trail runs parallel to College...

Length: 2.43 mi

State: MD

Surface: Asphalt

5 Reviews

Chesapeake Beach Railway Trail

Between 1900 and 1935, the Chesapeake Beach Railway whisked vacationers from Washington, DC, to the grand hotels, beaches, and boardwalk of...

Length: 1.3 mi

State: MD

Surface: Boardwalk

40 Reviews

Cross Island Trail

Explore the best of the Eastern Shore of Maryland on Queen Anne’s County’s Cross Island Trail, which runs the width of Kent Island for 9.3...

Length: 9.13 mi

State: MD

Surface: Asphalt, Boardwalk

16 Reviews

Downs Park Trail

Downs Park Trail is located in Downs Park on the Chesapeake Bay just north of Gibson Island. The 3.5-mile perimeter trail is paved, popular...

Length: 5 mi

State: MD

Surface: Asphalt, Dirt

9 Reviews

Easton Rails-to-Trails

The Easton Rails-to-Trails runs between Dutchmans Lane in southern Easton, Maryland, and North Easton Park—a large sports complex for 2.5...

Length: 4.6 mi

State: MD

Surface: Asphalt

Recent Trail Reviews

B&A Trail

Surprisingly Beautiful

August, 2025 by mehran.bayram

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.

Indian Head Rail Trail

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.

August, 2025 by kailarice2013

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.

Georgetown-Lewes Trail

J&B, Georgetown/Lewes and Cape Henlopen trails

July, 2025 by baarters

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.

Accordion

Kent Island South Trail

July, 2025 by carrollball99

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.

Wayne Gilchrest Trail

Small Town Trail With Regional Potential

July, 2025 by jmcginnis12@gmail.com

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.

B&A Trail

Smooth ride and well-infrastructured

May, 2025 by tnbpptw5x7

The trail is paved and easy to ride, and the water fountains that line the trail actually work! Great for beginners and experienced riders. Well-populated but not overcrowded.

WB&A Trail

Great Ride

May, 2025 by jackkboy

I just rode 28 miles round trip today (May 30, 2025) on the WB&A Trail and it was great!

Contrary to the narrative in the description, the bridge over the Patuxent River is now open.

Started in Odenton and parked on Railroad Ave just North of the trail entrance and rode all the way to Annapolis Road (Rt 450).

Lots of bikers and pedestrians out on the trail today.
Great day to ride!

WB&A Trail

The bridge is open and you're able to ride the full length of the trail. Great nature viewing throughout the ride. Surprisingly, over 1000 ft of elevation gain.

May, 2025 by hughes29187

The bridge is open and you're able to ride the full length of the trail. Great nature viewing throughout the ride. Surprisingly, over 1000 ft of elevation gain.

413 Rail to Trail

Nice trail. Parking at either end of the trail. 1 port-a-potty at the trailheads. All asphalt & level just watch for upheavals in the trail in a couple of different places.

May, 2025 by debkalnins

Nice trail. Parking at either end of the trail. 1 port-a-potty at the trailheads. All asphalt & level just watch for upheavals in the trail in a couple of different places.

Indian Head Rail Trail

Great Trail

March, 2025 by bf84rj842s

I’m a casual writer and I wrote the entire trail and one day.

Redden State Forest Headquarters Loop Trail

Free and accessible.

March, 2025 by mih28271

An amazing free resource for the lower eastern shore. Flat sand trail mostly covered with pine needles. I would not recommend this trail if your tires are less than 50mm (2 inch) wide. Minimal but effective main trail markings. Multiple unmarked side trails. Adequate parking. Pack a lunch and make a day of it. This is a state forest not a park, there are port-a-john's near the parking area.