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Chestertown, Maryland (MD) Trails and Maps

Looking for the best trails around Chestertown, Maryland? Find the top rated trails in Chestertown, whether you're looking an easy walking path or a long bike trail, you'll find what you're looking for. Click on a trail below to find trail descriptions, trail maps, photos, and reviews.
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TRAIL LENGTH SURFACE TRAIL MAP

Anacostia Tributary Trail System

29.9 miles
The Anacostia Tributary Trail System includes a number of trails linked together and managed by the National Park Service. The trail include: the Anacostia River Trail, the Northwest Branch Trail, the Northeast Branch Trail, the Indian Creek ...
Asphalt

BWI Trail

12.5 miles
The 11-mile BWI Trail was primarily designed for area commuters; however, the trail also makes for a great recreation venue. Despite being close to BWI-Thurgood Marshall Airport, much of the trail is mercifully peaceful, especially the segment ...
Asphalt

Baltimore and Annapolis Trail

13 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 history lessons and boasts a solar system ...
Asphalt

Big Woods Trail-formerly Yelenoc Trail

0 miles
In Berks County, feasibility work has been started to design a trail section that will connect French Creek State Park to the Schuylkill River Trail. This is part of a Concept Plan for a trail called The Big Woods Trail that will connect the ...

Catonsville Short Line Trail

1 miles
When complete the Catonsville Short Line Trail will follow a 2.5-mile segment of the former Catonsville Short Line Railroad, which ran from Charlestown to Catonsville. As of 2013, the trail runs between Shady Nook Avenue and Charlestown Retirement ...
Dirt
Gravel

Chesapeake Beach Railway Trail

1.4 miles
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 and residents alike can enjoy a different ...
Boardwalk

Christina Riverwalk

1.3 miles
The Christina Riverwalk is short (1.3 miles) but pleasant pathway along the Christina River, between the Russell Peterson Wildlife Refuge and the end of S. Popular Street, just beyond Tubman-Garrett Riverfront Park. The trail offers access to ...
Concrete

Creek Road Trail

2.3 miles
The Creek Road Trail extends north from a connection with the Pomeroy and Newark Rail Trail in White Clay Creek State Park. The scenic park features over 37 miles of hiking trails through wooded valleys just north of Newark, home to the University ...
Dirt
Gravel

Cross Island Trail

6 miles
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. It's an impressively signed, well-maintained ...
Asphalt

Downs Park Trail

5 miles
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 of natural surface trail are offered. The ...
Asphalt
Dirt

Easton Rails-to-Trails

2.5 miles
The Easton Rails to Trails runs from Dutchmans Lane in southern Easton, Maryland, to North Easton Park—a large sports complex—over 2.5 miles away. The trail opened in 1998 and has been a popular local amenity since that time. Because it runs ...
Asphalt

Enola Low Grade Trail

28.9 miles
The Enola Low-Grade Trail (formerly the Atglen-Susquehanna Trail) is open for nearly 29 miles in disconnected segments between the Susquehanna River and Atglen in southeastern Pennsylvania. It follows an abandoned right-of-way of the old Atglen ...
Crushed Stone

Georgetown-Lewes-Cape Henlopen Trail

16.1 miles
Plans are on the table to develop a rail-with-trail that will connect Georgetown, Lewes and Cape Henlopen State Park in southern Delaware. The Delaware Department of Transportation has designed the first 1.1 mile segment in Lewes along the Delaware ...
Crushed Stone

Grist Mill Trail at Patapsco Valley State Park

2.5 miles
The Grist Mill Trail at Patapsco Valley State Park course for 2.5 miles through the heavily wooded park between Ilchester Road and Lost Lake. The trail is gentle and wheelchair accessible. It passes by the Swinging Bridge and Bloede's Dam. The ...
Asphalt

Gwynns Falls Trail

15 miles
The Gwynns Falls Trail is a 15-mile continuous corridor connecting dozens of west and southwest Baltimore neighborhoods with parks, historical and cultural landmarks and the urban business district. The trail leads a circuitous route through ...
Asphalt

Heritage Rail Trail County Park

22.8 miles
The Heritage Rail Trail County Park winds for more than 22 miles through urban and rural landscapes between the city of York and the Maryland state line. It connects Maryland's Torrey C. Brown Rail Trail with the historic district of York, PA. ...
Crushed Stone

Herring Run Trail

2.5 miles
Baltimore’s Herring Run Trail runs through scenic Herring Run Park, centered on a tributary of the Back River. The winding trail follows Herring Run through a woodlands environment so peaceful you're likely to forget you are in a major city ...
Asphalt

Indian Creek Trail (MD)

1.5 miles
Maryland's Indian Creek Trail is one of the shorter components of the Anacostia Tributary Trail System, but it serves as a vital link between the town of Berwyn Heights, Maryland, and scenic Lake Artemesia to its south. The trail runs entirely ...
Asphalt

Industrial Track Greenway Trail

3.7 miles
The Industrial Track Greenway Trail follows an abandoned rail corridor and will eventually link New Castle with the Wilmington waterfront. Already the trail spans nearly 4 miles in two disconnected segments between the Christina River and a ...
Asphalt

James F. Hall Trail

1.76 miles
The James F. Hall Trail—a rail-with-trail—packs a lot into a short stretch: Its paved surface is great for bicycling, inline skating and strolling, and there are multiple playgrounds, picnic areas and access points along the route. Best of all, ...
Asphalt

John Overstreet Connector

1.5 miles
The John Overstreet Connector is a 1.5-mile trail segment that links the Baltimore & Annapolis Trail and BWI Trail. The short—but vital—trail is named after Overstreet, a retiree from Glen Burnie, Maryland, and a great advocate for bicycle safety ...
Asphalt

Jones Falls Trail

9.1 miles
When complete, the Jones Falls Trail will extend 10 miles between Baltimore's Inner Harbor and the Mount Washington Light Rail Station. Currently, a paved, off-road section runs from Cylburn Arboretum south to Penn Station. A highlight of ...
Asphalt

Kent Island South Trail

5.8 miles
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 to Romancoke Road/State Route 8 for its entire ...
Asphalt

Killens Pond Bike Trail

2.3 miles
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 road. Note that the trail surface changes from ...
Asphalt
Concrete
Crushed Stone

Lake Artemesia Trail

1.35 miles
The Lake Artemesia Trail—one component of the larger Anacostia Tributary Trail System—completely encircles its scenic eponymous lake in Prince George's County, Maryland. The trail is also a great starting point for longer treks, as it directly ...
Asphalt

Little Jersey Trail

8.1 miles
The Little Jersey Trail loops through Lums Pond State Park on a wide, packed earth surface that accommodates hikers, cyclists and equestrians. The trail is the longer of two loops; the Swamp Forest Trail runs closer to Lums Pond at the center ...
Crushed Stone
Dirt

Lower Susquehanna Heritage Greenway Trail

2.5 miles
Maryland's Susquehanna State Park is recognized for challenging hiking and biking trails, camping facilities, rock outcroppings, boating, a museum and restored historical sites. But none of these outshines the Susquehanna River, which sweeps ...
Crushed Stone

MA & PA Heritage Trail

5 miles
The MA & PA Heritage Trail is found in two segments (about 2 miles apart) through the wooded parks of Maryland's Bel Air and Forest Hill communities. The folksy sounding name actually stands for the Maryland and Pennsylvania Railroad, which ...
Crushed Stone
Dirt

Michael Castle Trail

8.7 miles
The Michael Castle Trail currently offers a scenic 9-mile route along the north shore of the Chesapeake and Delaware Canal in northern Delaware. The trail is named after the former Governor and U.S. Representative whose efforts in Congress helped ...
Asphalt

Mispillion River Greenway

1.8 miles
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 peaceful waterway while linking city ...
Boardwalk
Concrete

Northeast Branch Trail

3.5 miles
The Northeast Branch Trail follows the levee along the—you guessed it—Northeast Branch of the Anacostia River from the Lake Artemesia Natural Area to Baltimore Avenue/US 1 (south of Hyattsville). The trail is one part of the Anacostia Tributary ...
Asphalt

Northern Delaware Greenway Trail

10.4 miles
The Northern Delaware Greenway Trail spans 10 miles of northern New Castle County from Bellevue State Park on the Delaware River to Brandywine Creek in Wilmington, Delaware’s largest city. The surface varies along the way from asphalt to crushed ...
Asphalt
Crushed Stone

Number Eight Streetcar Path

0.33 miles
The #8 Streetcar Path runs just a short distance (0.33 mile) along part of the route of the former streetcar system that once ran between Catonsville and Ellicott City. The streetcar operated from 1896 to 1963. Also part of the same line is ...
Crushed Stone

Paint Branch Trail (Montgomery County)

2.3 miles
Maryland is home to two Paint Branch Trails, this one in Montgomery County and another farther south in Prince George's County. This Paint Branch Trail offers a well-shaded, paved pathway stretching 2 miles through the northern end of Silver ...
Asphalt

Paint Branch Trail (Prince George's County)

3.5 miles
Prince George's County's Paint Branch Trail (not to be confused with Montgomery County's Paint Branch Trail farther north) runs for 3.5 miles between Lake Artemesia and Cherry Hill Neighborhood Park in the Washington, DC, suburb of College Park. ...
Asphalt

Patuxent Branch Trail

4.6 miles
The Patuxent Branch Trail is part of a 20-mile trail system over and around the rolling hills of Howard County that follows a former Baltimore and Ohio Railroad line along the Patuxent River. The trail begins in Savage Park. Follow signs ...
Asphalt
Concrete
Crushed Stone

Pomeroy and Newark Rail Trail

4.4 miles
The Pomeroy and Newark Rail Trail offers urban connections to the University of Delaware campus, Newark Shopping Center, DART Transit Hub and the downtown area, as well as the recreational amenities of White Clay Creek State Park. To further ...
Asphalt
Gravel

Poplar Trail

0.9 miles
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 of Annapolis' trail system, as it links ...
Asphalt

Redden State Forest Headquarters Loop Trail

4 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 popular trail is a four-mile loop around ...
Dirt

Rhode Island Avenue Trolley Trail

2 miles
The Rhode Island Avenue Trolley Trail provides a safe pathway for students, from kindergartners to doctoral candidates, to walk and bike to school in College Park, Riverdale Park and Hyattsville. The short, paved trail (currently open in three ...
Asphalt

Riverview Trail

1.4 miles
The Riverview Trail makes a loop through Fox Point State Park along the Delaware River in Wilmington. The trail circles an open field along the west bank of the river.
Concrete

Savage Mill Trail

1 miles
The Savage Mill Trail in Savage Park travels along the rolling Patuxent River through the grounds of an old cotton mill. In the early 1800s, Savage was a major manufacturing center, harnessing power produced by the falls on the Little and Middle ...
Asphalt
Dirt
Gravel

Seashore Line Trail

10 miles
Dirt

Seneca Creek Greenway Trail

22.1 miles
Seneca Creek Greenway Trail was built by a coalition of organizations and follows the meandering Seneca Creek near Germantown, MD, from the Potomac River to State Route 355 (Frederick Road). NOTE: Only parts of the trail are multi-use; horses ...
Dirt

South Shore Trail

0.6 miles
The South Shore Trail will one day stretch 12 miles between Annapolis and Odenton. It’s also planned to be part of the East Coast Greenway, a widespread network connecting trails in more than a dozen states. The trail’s first phase—a half-mile ...
Asphalt

Springlawn Trail

2.1 miles
The Springlawn Trail travels on what was once Springlawn Road, connecting Chesterville Road (Rt. 841) and Strickersville Road. The 2-mile trail is comprised of dirt and gravel and makes for a good walk or hike. Cycling and equestrian use is ...
Dirt
Gravel

St. Michaels Nature Trail

1.3 miles
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 its name. Now the town is a popular tourist ...
Asphalt

Stony Run Trail

2.9 miles
Baltimore’s Stony Run Trail follows an old Maryland and Pennsylvania Railroad line through nearly 3 miles of wooded stream valleys and small parks, providing a quiet escape from the hustle and bustle of city life. The unique urban trail sits ...
Asphalt
Crushed Stone
Dirt
Grass
Gravel
Woodchips

Swamp Forest Trail

6.4 miles
The Swamp Forest Trail loops through Lums Pond State Park on a packed earth surface that accommodates hikers and cyclists. The trail is the shorter of two loops; the Little Jersey Trail runs closer to the perimeter of the park, and the wider ...
Crushed Stone
Dirt

Torrey C. Brown Rail Trail

21 miles
The Torrey C. Brown Rail Trail, completed in 1984, is one of the best hiking and biking trails in the Mid-Atlantic region. It allows for more than 20 miles of flat travel on the crushed-stone surface, punctuated by a number of access points ...
Crushed Stone

Trolly Line #9 Trail

1.5 miles
The first thing you may notice about the Trolly Line #9 Trail is the boardwalk that curves between the bluffs of massive rock. The granite was hand cut in the 1890s when the electric streetcar rails were built from Ellicott City to Catonsville. ...
Asphalt
Boardwalk

Valley Forge to Heinz Refuge (aka Forge to Refuge)

0 miles
a proposed 18 mile shared use pathway is envisioned by area residents in Delaware and Chester counties of Pennsylvania. The Bicycle Coalition of Greater Philadelphia is leading the preliminary work of envisioning a trail that could connect Valley ...

WB&A Trail

10.25 miles
Central Maryland's WB&A Trail occupies an abandoned Washington, Baltimore & Annapolis Electric Railway corridor—hence its name—for its entire route. The railroad operated electric commuter trains between its three namesake cities from 1908 to ...
Asphalt

Wayne Gilchrest Trail

1.2 miles
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 Chestertown business district and is named ...
Asphalt

Windsor Hills Conservation Trail

0.9 miles
The Windsor Hills Conservation Trail is a short hiking trail through the Windsor Hills neighborhood of Baltimore. Built partially on a former streetcar line that once connected the area with the nearby neighborhood of Dickeyville, the trail ...
Dirt