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 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...
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 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 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...
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....
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...
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 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...
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...
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...
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 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 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 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...
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 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 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 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...
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...
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...
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 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...
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 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...
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...
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...
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 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 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...
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...
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 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...
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,...
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...
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...
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 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 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...
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...
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 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...
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 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 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 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...
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 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 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...
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 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...
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 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 mostly flat, completely paved trail makes it ideal for beginners. It also connects (on the eastern end) to bike lanes that can take you into Annapolis and (on the western end) to more paved trails (via the John Overstreet connector, itself a paved trail). Although there are many surface street crossings, my experience has been that most drivers are courteous and will often yield right of way to cyclists.
Very pleasant and clear, wide trail.
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!
A gorgeous day for a ride, with a bit of a snag early on. One leg of the trail (Arthur Ross to Rte 225, about 2 miles from the Indian Head trailhead) is closed due to asphalt maintenance. They expect to open again by tomorrow. You can work around the closure riding through the neighborhood streets that parallel the trail.
Aside from that one unexpected detour, a beautiful ride on a flat, well marked and maintained trail.
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.
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