Explore the best rated trails in Cambridge, MD. Whether you're looking for an easy walking trail or a bike trail like the Wayne Gilchrest Trail and Strawberry Lake Way Bicycle Path. With more than 28 trails covering 128 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.
Between 1900 and 1935, the Chesapeake Beach Railway whisked vacationers from Washington, DC, to the grand hotels, beaches and boardwalk of the resort town of Chesapeake Beach, Maryland. Now tourists...
Maryland's Cross Island Trail spans Kent Island, east to west, in Queen Anne's County, providing multiple points of access to everything from libraries and schools to ball fields and the waterfront....
The St. Michaels Nature Trail skirts the western edge of the scenic town of St. Michaels, Maryland, which was built on the site of a 17th century Anglican church that eventually lent the settlement...
Central Maryland's WB&A Trail occupies the former Washington, Baltimore & Annapolis Electric Railway corridor—hence its name—for its entire route. The railroad operated electric commuter trains...
The Mispillion River Greenway runs through historic downtown Milford on both sides of the Mispillion River. The greenway, which is surfaced primarily with brick and concrete, provides scenic views of...
Southern Maryland's Three Notch Trail is a work-in-progress under the guidance of St. Mary's County and other stakeholders. When complete, the recreational trail will extend 28 miles along an...
The Lone Wolf Trail is a 1-mile trail in Anne Arundel County Maryland. The trail is connected to two already existing trails: The Strawberry Lake Way Bicycle Path, and the WB&A Trail. Although the...
The Killens Pond Bike Trail provides non-motorized access from US 13 to Killens Pond State Park. The short trail parallels Killens Pond Road before turning south into the park along its main access...
The Wayne Gilchrest Trail, which opened on Earth Day in 2012, runs along the southern edge of the historic Maryland Eastern Shore community of Chestertown. The trail connects Washington College to the...
The Henson Creek Trail is located in the southwestern portion of Prince George's County, Maryland, and connects the growing District of Columbia suburbs of Fort Washington and Oxon Hill with the...
The Bob Trail (or simply, The Bob) in Trap Pond State Park loops around the perimeter of the 90-acre Trap Pond. The trail winds through hardwood forests, crosses a scenic dam at Raccoon Pond and...
A winding line of asphalt meanders between Glenn Dale Park in Lanham to Annapolis Road. The trail is sheltered amongst the riparian woodland of Folly Branch. At the north end of the trail can be...
Annapolis' Poplar Trail runs for nearly 1 mile on a section of the old Washington, Baltimore & Annapolis right-of-way in the heart of Maryland's capital city. Although short, the trail is a vital part...
The Strawberry Lake Way Bicycle Path is a 2.2 mile trail that is located between Laurel and Annapolis in Anne Arundel County Maryland. The trail starts at Piney Orchard Elementary School, and ends at...
The Kent Island South Trail is one of two popular recreational trails (along with the Cross Island Trail) on Maryland's Kent Island, the largest island in the Chesapeake Bay. The trail runs parallel...
The Easton Rails to Trails runs from Dutchmans Lane in southern Easton, Maryland, to North Easton Parka large sports complexover 2.5 miles away. The trail opened in 1998 and has been a popular local...
Phase 1 of the long-awaited Georgetown to Lewes Rail with Trail was officially opened to the public in October 2016. When completed, the trail, which parallels an active, but little-used freight...
The 3-mile separated multi-use path along Middletown Road allows for safe recreation and transportation along the western side of Waldorf, Maryland. The trail begins just south of State Route 228 and...
Located just 18 miles south of our nation's capital, the Indian Head Rail Trail offers a unique natural outdoor experience, seemingly far removed from urban development and its associated chaotic...
The Broadneck Peninsula Trail is 1.2 miles of asphalt walking and biking pathway in east Annapolis. The trail runs parallel to College Parkway, from Green Holly Drive to Old Cape St. Claire Road,...
The Easton Rails to Trails runs from Dutchmans Lane in southern Easton, Maryland, to North Easton Parka large sports complexover 2.5 miles away. The trail opened in 1998 and has been a popular local...
The Point Lookout Railroad Trail (also called Periwinkle Point Nature Trail) follows a corridor that was cleared in the early 1800s for a planned railroad line connecting Point Lookout, Maryland, to...
The Killens Pond Bike Trail provides non-motorized access from US 13 to Killens Pond State Park. The short trail parallels Killens Pond Road before turning south into the park along its main access...
The Mispillion River Greenway runs through historic downtown Milford on both sides of the Mispillion River. The greenway, which is surfaced primarily with brick and concrete, provides scenic views of...
The 3-mile separated multi-use path along Middletown Road allows for safe recreation and transportation along the western side of Waldorf, Maryland. The trail begins just south of State Route 228 and...
Central Maryland's WB&A Trail occupies the former Washington, Baltimore & Annapolis Electric Railway corridor—hence its name—for its entire route. The railroad operated electric commuter trains...
Located just 18 miles south of our nation's capital, the Indian Head Rail Trail offers a unique natural outdoor experience, seemingly far removed from urban development and its associated chaotic...
The Broadneck Peninsula Trail is 1.2 miles of asphalt walking and biking pathway in east Annapolis. The trail runs parallel to College Parkway, from Green Holly Drive to Old Cape St. Claire Road,...
A winding line of asphalt meanders between Glenn Dale Park in Lanham to Annapolis Road. The trail is sheltered amongst the riparian woodland of Folly Branch. At the north end of the trail can be...
Nestled amongst the trees of St. Mary's River State Park, trail-goers will find an 8-mile path that loops around St. Mary's Lake, offering beautiful natural scenery and the chance to catch a glimpse...
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 for walkers and cyclists alike, and an additional 1.5 miles...
The Marshyhope Creek is a 37-mile tributary of the Nanticoke River running from Delaware to Maryland. One of the towns it passes through is Federalsburg, Maryland, where a 2.5-mile multiuse greenway...
Annapolis' Poplar Trail runs for nearly 1 mile on a section of the old Washington, Baltimore & Annapolis right-of-way in the heart of Maryland's capital city. Although short, the trail is a vital part...
The St. Michaels Nature Trail skirts the western edge of the scenic town of St. Michaels, Maryland, which was built on the site of a 17th century Anglican church that eventually lent the settlement...
The Henson Creek Trail is located in the southwestern portion of Prince George's County, Maryland, and connects the growing District of Columbia suburbs of Fort Washington and Oxon Hill with the...
Between 1900 and 1935, the Chesapeake Beach Railway whisked vacationers from Washington, DC, to the grand hotels, beaches and boardwalk of the resort town of Chesapeake Beach, Maryland. Now tourists...
Maryland's Cross Island Trail spans Kent Island, east to west, in Queen Anne's County, providing multiple points of access to everything from libraries and schools to ball fields and the waterfront....
The separated multi-use Rosewick Road Sidepath provides a direct link for both recreation and transportation between the southern Maryland communities of St. Charles and La Plata. The path runs...
The Strawberry Lake Way Bicycle Path is a 2.2 mile trail that is located between Laurel and Annapolis in Anne Arundel County Maryland. The trail starts at Piney Orchard Elementary School, and ends at...
The developing South Shore Trail will one day stretch 14 miles between Annapolis and Odenton. It's also part of the larger East Coast Greenway, a widespread network connecting trails from Maine to...
The Easton Rails to Trails runs from Dutchmans Lane in southern Easton, Maryland, to North Easton Parka large sports complexover 2.5 miles away. The trail opened in 1998 and has been a popular local...
Redden State Forest, located just north of Georgetown in Sussex County, offers more than 44 miles of trails for hiking, mountain biking, birdwatching and hunting on several thousand acres. The most...
The 3-mile separated multi-use path along Middletown Road allows for safe recreation and transportation along the western side of Waldorf, Maryland. The trail begins just south of State Route 228 and...
Southern Maryland's Three Notch Trail is a work-in-progress under the guidance of St. Mary's County and other stakeholders. When complete, the recreational trail will extend 28 miles along an...
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 for walkers and cyclists alike, and an additional 1.5 miles...
The Lone Wolf Trail is a 1-mile trail in Anne Arundel County Maryland. The trail is connected to two already existing trails: The Strawberry Lake Way Bicycle Path, and the WB&A Trail. Although the...
The Bob Trail (or simply, The Bob) in Trap Pond State Park loops around the perimeter of the 90-acre Trap Pond. The trail winds through hardwood forests, crosses a scenic dam at Raccoon Pond and...
Located just 18 miles south of our nation's capital, the Indian Head Rail Trail offers a unique natural outdoor experience, seemingly far removed from urban development and its associated chaotic...
The Kent Island South Trail is one of two popular recreational trails (along with the Cross Island Trail) on Maryland's Kent Island, the largest island in the Chesapeake Bay. The trail runs parallel...
The Henson Creek Trail is located in the southwestern portion of Prince George's County, Maryland, and connects the growing District of Columbia suburbs of Fort Washington and Oxon Hill with the...
Maryland's Cross Island Trail spans Kent Island, east to west, in Queen Anne's County, providing multiple points of access to everything from libraries and schools to ball fields and the waterfront....
The Killens Pond Bike Trail provides non-motorized access from US 13 to Killens Pond State Park. The short trail parallels Killens Pond Road before turning south into the park along its main access...
The developing South Shore Trail will one day stretch 14 miles between Annapolis and Odenton. It's also part of the larger East Coast Greenway, a widespread network connecting trails from Maine to...
The separated multi-use Rosewick Road Sidepath provides a direct link for both recreation and transportation between the southern Maryland communities of St. Charles and La Plata. The path runs...
Phase 1 of the long-awaited Georgetown to Lewes Rail with Trail was officially opened to the public in October 2016. When completed, the trail, which parallels an active, but little-used freight...
The Strawberry Lake Way Bicycle Path is a 2.2 mile trail that is located between Laurel and Annapolis in Anne Arundel County Maryland. The trail starts at Piney Orchard Elementary School, and ends at...
Nestled amongst the trees of St. Mary's River State Park, trail-goers will find an 8-mile path that loops around St. Mary's Lake, offering beautiful natural scenery and the chance to catch a glimpse...
The Broadneck Peninsula Trail is 1.2 miles of asphalt walking and biking pathway in east Annapolis. The trail runs parallel to College Parkway, from Green Holly Drive to Old Cape St. Claire Road,...
Between 1900 and 1935, the Chesapeake Beach Railway whisked vacationers from Washington, DC, to the grand hotels, beaches and boardwalk of the resort town of Chesapeake Beach, Maryland. Now tourists...
The Wayne Gilchrest Trail, which opened on Earth Day in 2012, runs along the southern edge of the historic Maryland Eastern Shore community of Chestertown. The trail connects Washington College to the...
While scenic, this trail is not marked at all. Even while on the outside trail loop, it was difficult to tell which direction to go at major trail intersections. Trail markings are essential to communicate where a hiker is currently, and where you need to go next. If you don't have WiFi, you can't count on referencing GPS or TrailLinks online map--which can be downright unsafe if you're a novice hiker or have young children.
Taking a “leisurely stroll” on a sunny morning may have it’s challenges, considering the often groups of 5, 10, 15 — or more — cyclists pedaling past you at 10 or 15 MPH. And that the cyclists lack bells or horns doesn’t help matters much. C’mon, cyclists... give “Ma and Pa Kettle” a break, will ‘ya?
Pushed my dad in a manual wheelchair. The boardwalk is well maintained. There were 2 or so slight inclines on trail but they weren't too difficult for me to push him and he is 200 lbs. Maybe the angle of inclines were 15 - 20 degrees. Dad is 82 and didn't mind the vibration of the wheels rolling over the surfaces with the grooves in the boardwalk and then the surface turns into a poured concrete with stamped brick design. The stretch with the stamped brick caused a bit more vibration for the wheelchair . Not difficult to push across it and dad still didn't mind. The tranquility and beauty of the marsh and the water was perfect and so close up that it was a perfect way to immerse in nature with the wheelchair. The trail starts behind the Waterpark. There is a small water canal that separates the waterpark parking from the trail start and a long white fence that separates the two. So it is closer to park in the "Tot Lot" a small playground area. There is a handicap parking spot there. Definitely enjoyed the trail, just wish it were longer but definitely worth going!
I chose the south trail b/c I thought it might be quieter than the other trail on a fall Sat afternoon. It was perfect. New asphalt path, light traffic, lots of pretty scenery, and a stop at Kentmorr Restaurant for their crab pretzel. I also appreciated the flat, wide path away from the cars. I parked free where it says to park on the map, and hopped right on the path.
Enjoyed the ride. Nicely paved path. Not many people on trail. Would recommend this to anyone.
Good trail for all riding types.
Nice mix of wooded and open trail, good views of the waterfront. Will do this ride again.
We enjoyed the trail on a beautiful October afternoon. Trail traffic was very light and the trail's new pavement made the ride very nice. It's about 12 miles round trip and the pier at Romancoke is a nice stop. Just wish the trail was a few miles longer or connected to the Cross Island Trail.
9/27/20. Was just on this trail. Yes, there is a bit of maintenances work underway, but now there is a clearly marked detour. The detour is on the adjacent road, but it is short (less than 300 yards), clearly marked, and on a wide shoulder.
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TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!
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