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 150 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 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 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...
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 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...
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 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...
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 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...
Built as a connector road on the outskirts of Dover, Kent County's POW/MIA Memorial Parkway also serves as a connector for cyclists and pedestrians, thanks to the paved sidepath trail constructed...
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 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...
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...
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...
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 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...
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 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...
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...
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 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...
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...
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...
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 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 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...
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 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 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...
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...
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...
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...
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 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 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...
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...
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 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...
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...
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 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...
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...
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 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 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 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 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...
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 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 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...
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...
Nice Ride through a State Park, I have been here on Many Weekday Afternoons after work & it has never been crowded. Main Trail Loops around Trap Pond & through the Campground, some Boardwalk, some Stone, Some narrower riding through the woods on Stone Dust. Plenty of other areas in the Park to ride as well. Easy to get 10 Miles in just cursing around the Park. Very Enjoyable
Really enjoy this Trail, have ridden it several times. Well laid out, enjoyable, plenty of great spots to eat on Kent Island. Always recommend it to Friends.
Asphalt appears to be new. Whole trail was smooth and well maintained.
Here's a note I received on 10/5/2021 from the Trail Development Program Manager for the Prince Georges County Department of Parks and Recreation.
Dawn Thomas is the Anne Arundel (AA) County Recreation and Parks point person for the project.
PG Parks is a partner in the project.
The latest news from AA County is that a Pre-Bid meeting was held by the Dept. of Public Works (AAC).
Contractors will be preparing bids for construction in October.
Contractor selection will happen in Nov-Dec. timeframe, and then a contract will need to be signed by the appropriate parties.
Depending on weather and the contractor’s planned schedule for construction activities, work will start in early 2022.
A planned construction schedule won’t be available until early 2022. In general, it will take at least 12 months, however weather will play a huge role in determining the actual timeframe.
Came from MI. To Baltimore, MD. to ride with my son. Awesome paved trail. Lots is things like the old ranger station to stop and see.
Visited the trail today at the chancellors run end after 0.36 of a mile the paved ground disappeared at the end of the Walmart (which put me in the street) and picked back up at the McDonald’s with no warning to trail users on how to connect to the other end. This was very confusing and interfered with my timed run. There are no proper signs welcoming you to the trail.
Recently relocated to the area and I couldn’t wait to explore the bike trails and learn a bit more about the area. This trail is magnificent!
Woke up this morning and decided to find one of the trails closer to me that people rave about. So with the Indian Head Trail being only an hour away I decided to give it a try. Only 2 months back on a bike after 30 something years I can say this trail was worth the drive. Scenic, clean and very well taken care of.
Even after almost two years (of no reviews), the barn kitties mentioned in a couple of the earlier reviews are still there! I couldn't believe it! In fact, I thought, "there's no way those cats are there now", but there was something in the middle of the trail ahead...I thought it might be a groundhog, but it didn't move as I got closer. In fact, it was a barn cat, lounging in the sun, and as soon as I stopped, it sauntered right up to me and gave me so much affection! Never even wandered away! *I* was the one who finally had to leave. Also, another barn cat came sauntering over; it was friendly enough, but was easily bored, lol, and just as soon walked back to the barn.
As for the trail itself, it is still well-maintained (maintenance was even going on that day) and a pleasant ride thru country. I parked at the Charlotte Hall Library, which has a bathroom (important!). I live an hour away and I'd say it's worth the drive. You are not just biking/walking thru woods, so there is some variation in scenery; woods, farms, backyards, a couple of places with horses.
The new section has been opened bringing the length of the trail to about 2 miles. The new section is quite hilly and will be a bit challenging for casual and older riders.
Not much shade. Other than that, a pleasant bike ride amidst the woodsy suburbs. Also, at the start in Annapolis, be forewarned that there is a hill to climb to get to the start of the actual trail; it's a doable hill, but I was suprised to encounter it. Best it be at the beginnig when one is fresh, tho! The bathroom (women's) at the ranger station was clean.
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