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.
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...
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 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...
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...
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 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 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...
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 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...
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...
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 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,...
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 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...
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 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 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...
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...
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 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,...
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 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 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...
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...
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 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...
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 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 Loblolly Trail 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 travels over...
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...
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...
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 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...
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...
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...
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...
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 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 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...
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 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...
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 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...
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 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...
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...
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...
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...
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 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 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 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...
Short, not crowded, paved and a very nice flattish ride. Parking at senior center, or the beginning. Not at the library, not at Deborah Dr. Ride this if you are near by.
Have not ridden the Cross Island Trail in a couple of weeks, but drove by it on the way back home from Delaware today. The expansion which begins at the Kent Narrows near Harris' Crab House and ends at Long Point Park is complete and people were walking and riding this section. Beautifully done!
We parked at Pasadena and rode towards Annapolis. The trail is extremely well maintained and smooth. We stopped at 450, as we didn't want to ride on a busy road, and headed back to Pasadena. Great tacos at the Taphouse right next to the Pasadena parking lot!
Rode this trail on weekday. Very little traffic on the trail. Great paved surface. Pleasant countryside to ride through. Wonderful lunch and coffee at Clarity Coffee House in Indian Head.
Parked at route 224, rode to White Plains first then back to Indian Head for lunch. Final three miles back to the car afterwards.
We rode from Welcome center to the Laurel Grove / Baggett Park trail head. 17.5 mile round trip. Nice ride, some nice sights and some shade. Not crowded. Would recommend and will do it again.
Enjoyed a bike ride from Tall Pines campground all the way to Lewes for lunch! What a gem!
Rode it today on the last day of August under beautiful blue sky for the first time. I was delighted by this trail. It's well-kept and I really can't add any more than what others have written: party shaded, ride thru woods, wetlands and two spots of farmland. I started riding this Saturday morning, the Labor Day weekend, at 9:40 a.m. I expected the Village Green Park parking lot to be chock-full of people on such a great day and for a three-day weekend. Nope. There were about five other cars, with barely anyone around. While there were usually people in sight on the trail, it was not crowded at all, which made for a great ride if volume of trail traffic is a concern of yours. I think the signage is horrible if you start from the Village Green parking lot. There actually was one other person at the lot when I arrived who kindly offered to let me trail him as he biked to the trailhead. The web site for Chas. Co. Parks says to follow the signs from the park to the trail, but I saw none whatsoever. You bike to just in front of the naval air station entrance and take a left for a short ride up the street and the trailhead is on your left. I give it five stars b/c the scenery was varied and enjoyable; the trail is well-kept; and trail traffic is light.
Nice trail! Lots of bridges, overpasses and tunnels, if you enjoy seeing those things. I do! It goes through a lot of residential areas for easy access.
I got on the trail after starting at the airport overlook. From there I went 7.5 miles out and back. Not ready yet for the full length. Only drawback is that there are many street crossings where you need to stop. Very well maintained and cert well marked.
Nice flat trail, good for families with wildlife and decent shade. There is one tricky place to cross a busy road. Otherwise perfect.
Phase two of the new trail opened this past spring. They really did a fantastic job building it, and it is a pleasure to ride on. Now, you can go about 13 miles in one direction by connecting to the Junction-Breakwater trail towards Rehoboth. The road crossings are fairly frequent, but well marked. I'm happy to report that most drivers stop and waive bicyclists across. I'm excited about the prospect of the trail being completed all the way to Georgetown.
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