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 34 trails covering 148 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 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...
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 will extend 17 miles west to Georgetown, making it 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 Milton Rail-Trail is a short, paved pathway in the small town of Milton, allowing local residents to get out and take a quick ride or walk along a flat, off-road corridor. The newest section of...
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...
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....
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...
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 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...
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 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 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 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 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 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 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 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...
Traversing the western edge of Dover, the Hazlettville/North Shared-Use Path is a sidepath trail that follows the southern side of Hazlettville Road and W North Street, providing a wide asphalt...
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...
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...
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...
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 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 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...
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 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...
Part of an emerging network of trails in the Dover area called the St. Jones River Greenway, the Isaac Branch Greenway Trail offers over three miles of completed, paved trail, providing a mixture of...
The Milton Rail-Trail is a short, paved pathway in the small town of Milton, allowing local residents to get out and take a quick ride or walk along a flat, off-road corridor. The newest section of...
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...
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 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 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 413 Rail to Trail is located in Somerset County, Maryland. The trail will be 12 miles point-to-point when complete. The trail parallels State Route 413, which lends it its name, and is built in...
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 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...
If you are looking to augment your physical workout with some intellectual exercise, look no further than the Baltimore & Annapolis Trail. The scenic, paved, 13-mile community trail is brimming with...
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 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 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...
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 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 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...
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 will extend 17 miles west to Georgetown, making it the...
Traversing the western edge of Dover, the Hazlettville/North Shared-Use Path is a sidepath trail that follows the southern side of Hazlettville Road and W North Street, providing a wide asphalt...
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 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 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...
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 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 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...
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 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 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...
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...
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...
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 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 413 Rail to Trail is located in Somerset County, Maryland. The trail will be 12 miles point-to-point when complete. The trail parallels State Route 413, which lends it its name, and is built in...
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 longer pathways. Trail users can start their journey from...
A wonderful ride if you’re looking for a casual, relaxed experience. Pulled my three year old in a trailer and he loved it. Smooth riding experience. The beach and playground make this a great destination for kids. Definitely going to return. Bring a map because the loop isn’t well marked.
We rode the trail today with our Schnauzer behind in a pet carrier. The trail is in excellent condition and the massive trees and beautiful flowers and honeysuckle fragrances make it a tremendous experience. When finished it will definitely be a Rail Trail Hall of Fame nominee. Don’t miss doing this trail if you are visiting the quaint town of Lewes. The parking lot next to the Lewes library has beautifully clean restrooms and a fix-it station with a pump for minor repairs.
Rode the entire trail yesterday as an out-and-back from Lewes. The trail is in perfect shape and is certainly popular based on the traffic of cyclists and walkers.
As noted in the description, at the northern end there is an easy connection to the Breakwater trail and "downtown" Lewes. The current endpoint is at busy Log Cabin Hill Road but there are multiple possible on-road loop routes back to Lewes.
Best trail in the area. The ride from White Plains to Indian Head and back (or vice versa) is a good workout, (26 miles total). This trail is a nature lover’s dream. Very clean and immaculate. I’ve ridden quite a few trails throughout the US and this is easily in the top two or three. Rest areas all along the way.
Rode the trail from Annapolis to BWI and back with my husband and our two kiddos (one in a bike seat, one on a tag-along) last weekend. It was such a great experience! The trail offers very nice views of the backyards and little towns, lots of trees, not a lot of busy roads to cross and those couple have cross walks with lights. The trail is well paved and maintained, there are some joggers and many cyclists but overall it didn't seem busy. There is a cool section with something called "Planet walk" where the planets are spaced proportionately to how they are in the solar system, we really enjoyed looking out for the planets on the way! There are a few places to stop and get food but no public bathrooms till you get to BWI where there were a couple of port-o-potties. We used the bathrooms in Severna but then felt obligated to buy the frozen yogurt.
We ride many different trails on the shore, but this one is my favorite. I've logged hundreds of miles on my app riding my bike on The Cross Island Trail. Not too long and not to short.
Nice smooth ride through quiet marshes and trees. One of the best-kept trails I’ve ridden.
This trail was simply beautiful. All paved and nestled through amazing forest and along the water. So worth the hour drive from my home and the $6.00 entrance fee.
This trail was very beautiful. Nicely paved and winds through woods with breathtaking scenery along the way. Was about an hour drive from my home and entrance was $6 per car, but I will absolutely go back.
Easy parking at small clean park, then hop on paved flat trail. A couple of nice water views and a covered bridge. Crosses several neighborhood streets with minimal car activity. Very nice.
TrailLink is a free service provided by Rails-to-Trails conservancy
(a non-profit) and we need your support!
TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!
Map Search
