Best Trails of Maryland

This list represents the most popular trails in Maryland (learn more about Top Trails). Use this list to plan your next Maryland outdoor trip. Select a state and/or activity below to find even more top trails.

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#1. Appalachian Trail: Crampton Gap to Harpers Ferry, WV

The 9.8-mile stretch of Appalachian Trail leading from Crampton Gap to Harpers Ferry, West Virginia, is one of the most popular and rewarding AT day hikes in this region, with good reason. It feature…

From the guidebook "Exploring the Appalachian Trail: Hikes in the Mid-Atlantic States"
Burkittsville , MD - Hiking - 10.2 miles

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#2. Catoctin Mountain Park and Cunningham Falls State Park

Located scarcely 60 miles northwest of Washington, Catoctin Mountain Park and Cunningham Falls State Park let arriving visitors know immediately that they’re far removed from the urban plains. The air…

From the guidebook "60 Hikes within 60 Miles: Washington, DC"
Thurmont , MD - Hiking - 11 miles

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#3. Gunpowder Falls North and South Loop, Gunpowder Falls State Park

A walk through mixed hardwood and conifer woodlands along and above scenic Gunpowder Falls. You can make a day of hiking in the wooded stream valley of Gunpowder Falls and the ridges above it, or you…

From the guidebook "Hiking Maryland & Delaware"
Hereford , MD - Hiking - 9.6 miles

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#4. Patapsco Valley State Park: Glen Artney / Avalon / Orange Grove / Hilton Areas

One of the area's most popular off-road cycling destinations in the region, the Avalon Area offers the experienced rider some of the best singletrack in town. Often severe and unforgiving, the Avalon…

From the guidebook "Mountain Biking the Washington, D.C. / Baltimore Area"
Ellicott City , MD - Mountain Biking - 20 miles

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#5. Appalachian Trail: Pine Knob to Pen Mar County Park

The three fine, west-facing vistas of Annapolis Rock, Black Roc, and High Rock plus a peculiar river of stone called the Devils Racecourse are the highlights of this hike through northern Maryland. T…

From the guidebook "Exploring the Appalachian Trail: Hikes in the Mid-Atlantic States"
Hagerstown , MD - Hiking - 17.8 miles

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#6. Sugarloaf Mountain

Sugarloaf Mountain looms above rolling farmlands about 30 crow-miles northwest of Washington. Privately owned, it’s managed as both a nature preserve and public recreation area. Although it attracts m…

From the guidebook "60 Hikes within 60 Miles: Washington, DC"
Dickerson , MD - Hiking - 8.1 miles

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#7. Appalachian Trail: Interstate 70 to Turners Gap

This AT hike focuses on the part of South Mountain that lies roughly 20 miles north of the Potomac River and some 60 miles or so northwest of Washington. The hike route extends southward from where I-…

From the guidebook "60 Hikes within 60 Miles: Washington, DC"
Myersville , MD - Hiking - 10.2 miles

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#8. Wildlands Loop, Gunpowder Falls State Park

This loop follows the upland forests of the fall zone, crossing a few streams and visiting a pleasant waterfall, then meanders downstream along Big Gunpowder Falls as it leaves the piedmont. Watching…

From the guidebook "Hiking Maryland & Delaware"
Baltimore , MD - Hiking - 5.2 miles

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#9. C&O Canal National Historic Park

This ride's general location is between Georgetown in Washington, D.C., and Cumberland, Maryland, along the Potomac River. Scenery includes splendid views of the wide Potomac River, forests, and moun…

From the guidebook "Mountain Bike! Virginia"
Georgetown , VA - Mountain Biking - 185 miles

#10. C&O Canal Towpath: Carderock to Great Falls

From 1850 to 1924, the 185-mile Chesapeake and Ohio Canal carried boat traffic between Washington, DC, and Cumberland, Maryland. Mule teams plodding along a towpath powered the boats. The US governmen…

From the guidebook "60 Hikes within 60 Miles: Washington, DC"
Bethesda , MD - Hiking - 11.7 miles

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#11. Blue Ridge Summit - Hog Rock, Catoctin Mountain Park

A ramble through hardwood forests and over ridges of Catoctin Mountain, with views of the Blue Ridge and the Monocacy Valley. In spring, dogwoods and other flowering trees are abundant. In about two…

From the guidebook "Hiking Maryland & Delaware"
Thurmont , MD - Hiking - 5.1 miles

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#12. Appalachian Trail: Crampton Gap, Fox Gap, & Turners Gap

On a warm, sunny Sunday in 1862 a force of 9000 Rebels used the ramparts of South Mountain as a natural fort from which to stage a delaying action against 30,000 Yankee soldiers. Although they lost t…

From the guidebook "Exploring the Appalachian Trail: Hikes in the Mid-Atlantic States"
Burkittsville , MD - Hiking - 12.3 miles

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#13. Escape to the Maryland Countryside Challenge

This is a route suggested by a person who knows more about biking than almost anyone around the Beltway: Mike Dornfield, a former associate bicycling coordinator for Washington, D.C. Mike developed th…

From the guidebook "Road Biking Washington, D.C."
Rockville , MD - Road Biking - 57 miles

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#14. Cabin John Regional Park

Located in Montgomery County Maryland, Cabin John Regional Park is a great destination for any local mountain biker who can't get away to more remote locations, or it's great for the visitor looking f…

From the guidebook "Mountain Biking the Washington, D.C. / Baltimore Area"
Bethesda , MD - Mountain Biking - 10.9 miles

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#15. Historic Annapolis Ramble

This little town by the Chesapeake Bay is known not only for its port city history, but by its stately structures, narrow brick-lined streets, and classic village architecture. It is home to the Mary…

From the guidebook "Best Bike Rides in Delaware, Maryland, Virginia, Washington, D.C., & West Virginia"
Annapolis , MD - Road Biking - 19.2 miles

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#16. Farmer's and Fisherman's Ramble

For more than 300 years farmers have plowed the thin strips of land and fishermen have navigated the narrow channels of water slicing through this isolated section of Maryland's Eastern Shore. And as…

From the guidebook "Best Bike Rides in Delaware, Maryland, Virginia, Washington, D.C., & West Virginia"
Easton , MD - Road Biking - 29.2 miles

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#17. Three Covered Bridges Cruise

Be sure to pack your camera for this jaunt into the northern part of Frederick County. Rolling, lightly traveled roads take you through a valley from which you can gaze at the distant Blue Ridge Moun…

From the guidebook "Best Bike Rides in Delaware, Maryland, Virginia, Washington, D.C., & West Virginia"
Frederick , MD - Road Biking - 44 miles

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#18. Chesapeake & Ohio Canal National Historical Park

The Chesapeake & Ohio Canal was built between 1828 and 1850 with the intention of linking Chesapeake Bay ports with the Ohio Valley. Rendered obsolete by the railroad even before it was completed, the…

From the guidebook "Rails-To-Trails: Maryland, Delaware, Virginia, West Virginia"
Cumberland , MD - Rail-Trails - 184.5 miles

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#19. Loch Raven Reservoir: Merryman Trail

Arguably the prettiest trail in the Loch Raven Reservoir watershed. Follow it to Merryman Point, where the reservoir spreads out in several directions. From the parking area, you have several options…

From the guidebook "60 Hikes within 60 Miles: Baltimore"
Timonium , MD - Hiking - 9.8 miles

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