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    Top Trail in North America - Click to view allBest Trail in MD - Click to view all (About Top Trails)
Published by Stackpole Books

#2. 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    Best Trail in MD - Click to view all (About Top Trails)
Published by Falcon Publishing

#3. 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    Best Trail in MD - Click to view allBestMountain Biking Trail - Click to view all (About Top Trails)
Published by Falcon Publishing

#4. 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    Best Trail in MD - Click to view all (About Top Trails)
Published by Stackpole Books

#5. 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    Best Trail in MD - Click to view all (About Top Trails)
Published by Falcon Publishing

#6. 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   
Published by Menasha Ridge Press

#7. 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    Best Trail in MD - Click to view all (About Top Trails)
Published by Falcon Publishing

#8. 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    Best Trail in MD - Click to view all (About Top Trails)
Published by Stackpole Books

#9. 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    Best Trail in MD - Click to view allBestRoad Biking Trail - Click to view all (About Top Trails)
Published by Falcon Publishing

#10. 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    Best Trail in MD - Click to view all (About Top Trails)
Published by Falcon Publishing

#11. 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    Best Trail in MD - Click to view all (About Top Trails)
Published by The Globe Pequot Press

#12. 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    Best Trail in MD - Click to view all (About Top Trails)
Published by The Globe Pequot Press

#13. 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    Best Trail in MD - Click to view all (About Top Trails)
Published by The Globe Pequot Press

#14. 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    Best Trail in MD - Click to view allBestRail-Trails Trail - Click to view all (About Top Trails)
Published by The Globe Pequot Press

#15. 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    Best Trail in MD - Click to view all (About Top Trails)
Published by Menasha Ridge Press

#16. Capital Crescent Ramble


This is a weekend favorite of many riders in the D.C. area, who know it as the “Yuri Ride”—named for a Guatemalan with a Russian cosmonaut’s moniker. Every Sunday for years, Yuri led a procession of b…
From the guidebook "Road Biking Washington, D.C."
Chevy Chase, MD - Road Biking - 22 miles    Best Trail in MD - Click to view all (About Top Trails)
Published by Falcon Publishing

#17. Schaeffer Farms


These trails are a perfect example of mountain bike advocacy at work. A group of dedicated mountain bikers approached Maryland's Department of Natural Resources in hopes of gaining access to some nea…
From the guidebook "Mountain Biking the Washington, D.C. / Baltimore Area"
Germantown, MD - Mountain Biking - 3.7 miles    Best Trail in MD - Click to view all (About Top Trails)
Published by Falcon Publishing

#18. Baltimore: Big Gunpowder Falls


The Big Gunpowder Falls is one of the finest wild trout tailwaters in the East. It is very challenging and exceptionally scenic, bordered by hemlocks and hardwoods, lilies, wildflowers, and ferns. I a…
From the guidebook "Trout Fishing near American Cities"
Hereford, MD - Fly-Fishing
Published by Stackpole Books

#19. Loch Raven Reservoir: Glen Ellen–Seminary Road


Follow the natural contours of the southeastern edge of Loch Raven Reservoir before ascending the hills above to come back through upland forest. At the trailhead, you’ll see a bulletin board explaini…
From the guidebook "60 Hikes within 60 Miles: Baltimore"
Lutherville, MD - Hiking - 9 miles   
Published by Menasha Ridge Press