🥾 ActiveLong weekend · from Baltimore, MD
Western Maryland — Cumberland, the Paw Paw Tunnel & the Great Allegheny Passage
Three days deep in the Maryland panhandle, where the Appalachian ridges fold tight and two great trail systems — the C&O Canal towpath and the Great Allegheny Passage — meet at the old railroad city of Cumberland. Day one explores Cumberland itself, the western terminus of the C&O Canal, with its canal boat replica, restored depot, and the wooded trails of the surrounding Narrows gap. Day two heads into the vast, wild Green Ridge State Forest to walk to the Paw Paw Tunnel, an astonishing 3,118-foot canal tunnel bored straight through a mountain in the 1830s. Day three splits Rocky Gap State Park's mountain lake with a stretch of the Great Allegheny Passage rail-trail before the drive home. It's a trip built on canals, tunnels, rail-trails, and ridge-and-valley forest — the industrial and natural history of Appalachian Maryland on foot and by bike.
Day 1 — Cumberland & the C&O Canal western terminusDay 2 — Green Ridge State Forest & the Paw Paw TunnelDay 3 — Rocky Gap State Park & the Great Allegheny Passage
Day 1 — Cumberland, MD
Day 1 — Cumberland, MD
🚗 2 hr 30 min driving📍 4 stops
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Morning
🚗
Drive
Baltimore, MD → Cumberland, MD — C&O Canal Terminus
2 hr 30 min8:00 AM → 10:30 AM
C&O Canal Terminus & Cumberland Visitor Center
★ 4.6Cumberland is Mile 184.5 — the western end of the Chesapeake & Ohio Canal, whose towpath runs unbroken all the way back to Washington. The National Park Service visitor center in the restored 1913 Western Maryland Railway Station is the essential first stop: exhibits trace the canal's mule-drawn heyday, and a full-size replica canal boat sits in the rewatered basin outside. This is also the southern terminus of the Great Allegheny Passage, meaning you can literally stand where the towpath from D.C. hands off to the rail-trail to Pittsburgh — 335 continuous car-free miles. Get oriented here before exploring the town and its trails.
10:30 AM📍 See location
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Lunch
🍽️ Lunch11:30 AM
Ristorante Ottaviani
On Cumberland's walkable downtown pedestrian mall, Ristorante Ottaviani serves classic Italian cooking in a warm brick-walled dining room a short stroll from the canal terminus. Fresh pasta, veal, and seafood make a substantial midday meal to fuel an afternoon of walking. The surrounding Baltimore Street mall is closed to cars and lined with Victorian storefronts, cafes, and the twin church spires that give downtown Cumberland its distinctive skyline.
2 options · tap to switch
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Afternoon
The Cumberland Narrows & Lovers Leap Trail
★ 4.8Just west of downtown, Wills Creek slices a dramatic 1,000-foot gap through Wills Mountain known as the Cumberland Narrows — the historic gateway west, followed in turn by the Native trail, the National Road, the canal, and the railroads. Trails climb the ridge to the Lovers Leap overlook, a rocky perch high above the gap with a sweeping view down onto Cumberland's rooftops, church spires, and the winding creek and rail lines below. The climb is steep and the summit exposed, but the panorama is the finest in the city. It's a punchy afternoon leg-stretcher that puts the whole ridge-and-valley landscape into perspective.
12:30 PM📍 See location
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Evening
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Cumberland lodging
Stay in Cumberland tonight to be close to tomorrow's Green Ridge and Paw Paw drive. The historic Fairfield Inn at Canal Place sits right at the trailhead by the visitor center, and several chain hotels and bed-and-breakfasts occupy the restored downtown and the ridges above it. Downtown's pedestrian mall offers easy dinner and evening strolling within walking distance. Book ahead in fall, when foliage and the Great Allegheny Passage draw cyclists to town.
Day 2 — Green Ridge State Forest & Paw Paw Tunnel
Day 2 — Green Ridge State Forest & Paw Paw Tunnel
🚗 1 hr 45 min driving📍 4 stops
🌅
Morning
🚗
Drive
Cumberland, MD → Paw Paw Tunnel, Green Ridge State Forest
50 min8:00 AM → 8:50 AM
Paw Paw Tunnel
★ 4.7The Paw Paw Tunnel is the engineering marvel of the C&O Canal: a 3,118-foot tunnel bored straight through the mountain to bypass the tortured Paw Paw Bends of the Potomac, lined with roughly six million bricks and taking fourteen years to complete in the 1830s. Walking the towpath through it is unforgettable — the tunnel is pitch black inside, cool and dripping, with only a wooden walkway and a wobbly railing between you and the canal water, so a flashlight or headlamp is essential. The approach cuts through a deflection wall and dramatic rock deep-cut. Combine it with the mile-long Tunnel Hill Trail over the top of the ridge for a loop that shows both the tunnel and the forest it pierces.
8:50 AM📍 See location
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Lunch
Picnic at the Paw Paw Tunnel campground
★ 4.5Green Ridge is remote back-country with essentially no restaurants, so lunch today is a packed picnic — spread it at the shaded C&O Canal picnic area beside the tunnel's southern portal, with the Potomac and the canal at hand. Stock up in Cumberland before setting out. The riverside setting, with the great brick tunnel mouth behind you, makes an atmospheric midday break between the tunnel walk and the afternoon's forest driving.
9:50 AM📍 See location
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Afternoon
Green Ridge State Forest & Banner's Overlook
★ 5At nearly 47,000 acres, Green Ridge is Maryland's second-largest state forest — a rumpled expanse of oak-hickory ridges and hollow-carved valleys laced with backcountry roads and the long Green Ridge Hiking Trail. Drive the forest's gravel roads to overlooks like Banner's, where the ridges of the Ridge-and-Valley Appalachians roll away in parallel waves toward the Potomac and West Virginia beyond. Short spur trails lead to quiet vistas and the forest's pine barrens. It's a place to feel genuinely remote — cell service is patchy and the roads are unpaved — so keep an eye on the time and your fuel before winding back toward Rocky Gap for the night.
12:00 PM📍 See location
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Evening
🚗
Drive
Green Ridge State Forest → Rocky Gap / Cumberland lodging
55 min5:00 PM → 5:55 PM
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Rocky Gap Casino Resort or Cumberland lodging
Tonight, position yourself for tomorrow's Rocky Gap and Great Allegheny Passage. The Rocky Gap Casino Resort sits right inside the state park on the shore of Lake Habeeb, with a golf course, spa, and lakeside rooms — the most convenient base for the final day. Alternatively, return to Cumberland's downtown hotels for more dining choices, a short fifteen-minute drive from the park. Either way you'll be at the trailhead early for the last day.
Day 3 — Rocky Gap State Park & the Great Allegheny Passage
Day 3 — Rocky Gap State Park & the Great Allegheny Passage
🚗 3 hr driving📍 3 stops
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Morning
🚗
Drive
Rocky Gap / Cumberland lodging → Rocky Gap State Park — Lake Habeeb
15 min8:00 AM → 8:15 AM
Rocky Gap State Park — Lake Habeeb & the Evitts Homesite Trail
★ 4.6Rocky Gap wraps around the clear, spring-fed Lake Habeeb, cradled in a gorge below Evitts Mountain where Rocky Gap Run cuts through a mile-long chasm of hemlock and rhododendron. Start with the Lakeside Loop, an easy 5-mile trail circling the water with a swimming beach and boat rentals, or take on the steeper Evitts Homesite Trail up the mountain flank for ridgetop views over the lake and the surrounding forest. The turquoise water, backed by wooded ridges, is among the prettiest in the state park system. A morning swim or paddle before the last hike makes a fine start to the closing day.
8:15 AM📍 See location
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Lunch
🍽️ Lunch9:15 AM
Lakeside Restaurant at Rocky Gap
The resort's lakeside dining room overlooks Lake Habeeb and serves a full lunch menu — sandwiches, salads, and regional entrees — with a broad view over the water and Evitts Mountain. It's a convenient sit-down meal between the morning at the lake and an afternoon on the rail-trail, without leaving the park. The terrace is a pleasant spot to rest tired legs before the final leg of the trip.
2 options · tap to switch
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Afternoon
🚗
Drive
Rocky Gap State Park → Great Allegheny Passage — Cumberland trailhead
15 min12:00 PM → 12:15 PM
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Great Allegheny Passage — The Cumberland Approach
Cap the trip on the Great Allegheny Passage, the 150-mile rail-trail that climbs from Cumberland over the Eastern Continental Divide to Pittsburgh on a gentle, near-flat railroad grade. Rent a bike in town and ride the scenic opening miles out of Cumberland, following Wills Creek up through the Narrows past old rail bridges and the ridge scenery, then turn back for an easy coast home. It's a fitting finale that ties together the canal, the tunnel, and the trails of the whole trip — the same corridor that carried goods and travelers west for two centuries, now given over entirely to walkers and cyclists. Ride out as far as your legs allow and return before the drive back to Baltimore.
12:15 PM📍 See location
🌙
Evening
🚗
Drive
Cumberland, MD → Baltimore, MD
2 hr 30 min5:00 PM → 7:30 PM
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