Chestertown, Maryland (MD) Trails & Maps

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  • Anacostia Tributary Trail System

    State: MD
    Length: 29.9 miles
    Surface: Asphalt

    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 ...
  • BWI Trail

    State: MD
    Length: 12.5 miles
    Surface: Asphalt

    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 ...
  • Baltimore and Annapolis Trail

    Rail-Trail

    State: MD
    Length: 14 miles
    Surface: Asphalt

    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 ...
  • Big Woods Trail-formerly Yelenoc Trail

    State: PA
    Length: 0 miles
    Surface:

    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

    Rail-Trail

    State: MD
    Length: 1 miles
    Surface: Dirt, Gravel

    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 ...
  • Chesapeake Beach Railway Trail

    Rail-Trail

    State: MD
    Length: 1.4 miles
    Surface: Boardwalk

    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 ...
  • Chestertown Trail

    Rail-Trail

    State: MD
    Length: 1.2 miles
    Surface: Asphalt

    The Chestertown Trail, which opened on Earth Day in 2012, runs along the southern edge of the historic Maryland Eastern Shore community of Chestertown. Development of the trail was made possible through a 2003 federal earmark by former Congressman ...
  • Christina Riverwalk

    State: DE
    Length: 1.3 miles
    Surface: Concrete

    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 ...
  • Cross Island Trail

    Rail-Trail

    State: MD
    Length: 6 miles
    Surface: Asphalt

    Maryland's Cross Island Trail spans Kent Island 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, beautiful community ...
  • Downs Park Trail

    State: MD
    Length: 5 miles
    Surface: Asphalt, Dirt

    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 ...
  • Easton Rails-to-Trails

    Rail-Trail

    State: MD
    Length: 2.5 miles
    Surface: Asphalt

    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 ...
  • Enola Low Grade Trail

    Rail-Trail

    State: PA
    Length: 28.9 miles
    Surface: Crushed Stone

    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 Enola Low ...
  • Grist Mill Trail at Patapsco Valley State Park

    Rail-Trail

    State: MD
    Length: 2.5 miles
    Surface: Asphalt

    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 ...
  • Gwynns Falls Trail

    State: MD
    Length: 15 miles
    Surface: Asphalt

    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 ...
  • Heritage Rail Trail County Park

    Rail-Trail

    State: PA
    Length: 22.8 miles
    Surface: Crushed Stone

    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. ...
  • Herring Run Trail

    State: MD
    Length: 2.5 miles
    Surface: Asphalt

    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 ...
  • Indian Creek Trail (MD)

    State: MD
    Length: 1.5 miles
    Surface: Asphalt

    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 ...
  • James F. Hall Trail

    Rail-Trail

    State: DE
    Length: 1.76 miles
    Surface: Asphalt

    The James F. Hall 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, this ...
  • John Overstreet Connector

    State: MD
    Length: 1.5 miles
    Surface: Asphalt

    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 ...
  • Jones Falls Trail

    Rail-Trail

    State: MD
    Length: 9.1 miles
    Surface: Asphalt

    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 ...
  • Junction and Breakwater Rail Trail Extension

    Rail-Trail

    State: DE
    Length: 16.8 miles
    Surface:

    Plans are on the table to develop a Rail-with-Trail that will connect Georgetown, Delaware to the existing trails outside Lewes, Delaware. DeDOT is scheduling public meetings to discuss possible routing for the trails which will parallel a section ...
  • Kent Island South Trail

    State: MD
    Length: 5.8 miles
    Surface: Asphalt

    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 ...
  • Killens Pond Bikeway

    State: DE
    Length: 1.8 miles
    Surface: Asphalt, Crushed Stone

    The Bike Trail begins outside of the park along Killens Pond Road passing Lake Forest High School. The trail crosses the main entrance, then turns into the Park. It is on an easy grade over a paved or crushed stone surface. Trail users will ...
  • Lake Artemesia Trail

    State: MD
    Length: 1.35 miles
    Surface: Asphalt

    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 ...
  • Little Jersey Trail

    State: DE
    Length: 7.2 miles
    Surface: Dirt

    The Little Jersey Trail loops through the park on packed earth surface. The trail is wide to accommodate shared-use among hikers, bikers, and equestrians. Trail users will traverse forested areas and the edges of fields and get a full appreciation ...
  • Lower Susquehanna Heritage Greenway Trail

    Rail-Trail

    State: MD
    Length: 2.5 miles
    Surface: Crushed Stone

    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 ...
  • Lums Pond State Park trails

    State: DE
    Length: 17.5 miles
    Surface: Dirt

    Lums Pond State Park is built around the largest freshwater pond in Delaware. The park features excellent fishing, sports facilities, hiking trails and more on its 1790 acres on the north side of the Chesapeake and Delaware Canal. Covering 200 ...
  • MA & PA Heritage Trail

    Rail-Trail

    State: MD
    Length: 5 miles
    Surface: Crushed Stone, Dirt

    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 ...
  • Michael Castle Trail

    State: DE
    Length: 6.2 miles
    Surface: Asphalt

    The Michael Castle Trail, named after the former Governor and U.S. Congressman, currently offers a scenic 6.2 mile route along the north shore of the Chesapeake and Delaware Canal in northern Delaware. The C&D Canal was built in the early 1800s ...
  • Mispillion River Greenway (east & west of Milford)

    State: DE
    Length: 1 miles
    Surface: Concrete

    The Mispillion River Greenway is located on South Washington Street along the Mispillion River. The greenway provides a peaceful view of the lovely Mispillion River. The greenway is surfaced with brick and concrete. For more information contact ...
  • New Castle Industrial Track

    Rail-Trail

    State: DE
    Length: 3.7 miles
    Surface: Asphalt

    New Castle Industrial Track 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 Christina River and the Delaware River. The ...
  • Northeast Branch Trail

    State: MD
    Length: 3.5 miles
    Surface: Asphalt

    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 ...
  • Northern Delaware Greenway

    Rail-Trail

    State: DE
    Length: 9 miles
    Surface: Asphalt, Crushed Stone

    The Northern Delaware Greenway Trail spans 9 miles of northern New Castle County from Fox Point State Park on the Delaware River to the Brandywine Creek and the City of Wilmington. This urban trail connects with Wilmington's Walkway System and ...
  • Number Eight Streetcar Path

    Rail-Trail

    State: MD
    Length: 0.33 miles
    Surface: Crushed Stone

    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 ...
  • Paint Branch Trail (Montgomery County)

    State: MD
    Length: 2.3 miles
    Surface: Asphalt

    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 ...
  • Paint Branch Trail (Prince George's County)

    State: MD
    Length: 3.5 miles
    Surface: Asphalt

    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. ...
  • Patuxent Branch Trail

    Rail-Trail

    State: MD
    Length: 4.5 miles
    Surface: Asphalt, Concrete, Crushed Stone

    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 along ...
  • Pineland Trail - Cape Henlopen State Park

    State: DE
    Length: 2 miles
    Surface: Sand

    The Pineland Trail is a two-mile loop that meanders on a gentle grade through coastal upland pine forest over packed and loose sand. Nature enthusiasts will discover four species of pine, including loblolly, Virginia, pitch, and black, as well ...
  • Pomeroy Rail-Trail

    Rail-Trail

    State: DE
    Length: 4.4 miles
    Surface: Asphalt

    The Pomeroy Rail-Trail offers both 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 enjoy ...
  • Poplar Trail

    Rail-Trail

    State: MD
    Length: 0.9 miles
    Surface: Asphalt

    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 ...
  • Redden State Forest Headquarters Loop Trail

    State: DE
    Length: 4 miles
    Surface: Dirt

    Redden State Forest is located just north of Georgetown in Sussex County. The state forest offers more than 44 miles of trails for hiking, mountain biking, birdwatching and hunting on several thousands acres. The most popular trail is a four-mile ...
  • Rhode Island Avenue Trolley Trail

    Rail-Trail

    State: MD
    Length: 1.8 miles
    Surface: Asphalt

    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 ...
  • Riverview Trail

    State: DE
    Length: 1.4 miles
    Surface: Concrete

    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.
  • Savage Mill Trail

    Rail-Trail

    State: MD
    Length: 1 miles
    Surface: Asphalt, Dirt, Gravel

    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 ...
  • Seashore Line Trail

    Rail-Trail

    State: NJ
    Length: 10 miles
    Surface: Dirt

  • Seneca Creek Greenway Trail

    State: MD
    Length: 22.1 miles
    Surface: Dirt

    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 ...
  • South Shore Trail

    Rail-Trail

    State: MD
    Length: 10.3 miles
    Surface:

    The South Shore Trail is part of the Grand History Trail concept. For more information, visit www.railstotrails.org/grandhistorytrail: From the Maryland Department of Natural Resources Greenway Commission: The South Shore Trail is a planned ...
  • St. Michaels Nature Trail

    Rail-Trail

    State: MD
    Length: 1.3 miles
    Surface: Asphalt

    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 ...
  • Stony Run Trail

    Rail-Trail

    State: MD
    Length: 2.9 miles
    Surface: Asphalt, Crushed Stone, Dirt, Grass, Gravel, Woodchips

    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 ...
  • Torrey C. Brown Rail Trail (formerly North Central or Northern Central)

    Rail-Trail

    State: MD
    Length: 21 miles
    Surface: Crushed Stone

    The Northern Central Railroad 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 ...
  • Trap Pond State Park Trail

    State: DE
    Length: 5 miles
    Surface: Cinder, Crushed Stone

    Very nice multi use trail system in an underused & understaffed State Park. Five mile loop around Trap Pond is accomplished by following the Loblolly & American Holly trails. Plenty of other side trails & Park Roads give the user plenty of options. ...
  • Tri-Valley Trail

    Rail-Trail

    State: DE
    Length: 0.8 miles
    Surface: Dirt

    The Tri-Valley Trail begins at Hopkins Road, near the nature center in White Clay Creek State Park, and travels south just shy of a mile to Wedgewood Road. The natural-surface trail parallels the west side of White Clay Creek and is surrounded ...
  • Trolley Line #9

    Rail-Trail

    State: MD
    Length: 1.1 miles
    Surface: Asphalt, Boardwalk

    The first thing you may notice about Trolly Line #9 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. Today ...
  • Valley Forge to Heinz Refuge (aka Forge to Refuge)

    Rail-Trail

    State: PA
    Length: 0 miles
    Surface:

    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

    Rail-Trail

    State: MD
    Length: 10.25 miles
    Surface: Asphalt

    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 ...
  • White Clay Creek State Park trails (part of the Northern Delaware Greenway)

    State: DE
    Length: 40 miles
    Surface: Ballast, Crushed Stone, Dirt

    White Clay Creek State Park was created in 1968 when the state purchased 24 acres of land. The park has since grown to almost 2,500 scenic acres in the continuing effort to preserve and protect the natural resources of the valley. The park has ...
Explore urban trails in and around Chestertown, Maryland.Find detailed trail guides for Chestertown bike trails, Chestertown walking paths and much more.Click on a trail below to find trail descriptions, trail maps, photos and reviews. Once you find the trail you’re looking for,plan a trip there and use one of our partners to book your hotel, bed and breakfast, or campground near Chestertown.