City walking · Pennsylvania

Pittsburgh on Foot: The Strip, the Point and the Inclines day trip

Pittsburgh on Foot: The Strip, the Point and the Inclines

A car-free Pittsburgh day: breakfast and market browsing in the Strip District, the Andy Warhol Museum across the river, the fountain at the Point where three rivers meet, then up the Monongahela Incline for the walk along Grandview Avenue to the Duquesne Incline and dinner as the skyline lights up.

Time: 11–12 hour day
Driving: No driving; walking plus two incline rides
Best time: All year; best May–October
Updated: October 15, 2026 at 6:17 PM Pacific

$4 USD

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Downtown Pittsburgh's towers rising above the Monongahela River, seen from Mount Washington on a cloudy day — Dllu · CC BY-SA 4.0. October 2015 photograph; resized and displayed with crop. Some buildings may have changed.

Suggested times, not bookings

Your day at a glance

8:30 amThe Strip District
11:00 amThe Andy Warhol Museum
1:45 pmPoint State Park and the Fort Pitt Museum
3:30 pmSmithfield Street Bridge and the Monongahela Incline
4:00 pmGrandview Avenue to the Duquesne Incline
6:00 pmDinner on Mount Washington, then the overlook at dusk
8:30 pmRide down and walk back downtown

Highlights

Worth the trip

Penn Avenue's markets, cheese counters and fish market in the Strip District
Seven floors of Warhol on the North Shore
Grandview Avenue at dusk, from the Monongahela Incline to the Duquesne Incline

What’s in the guide

Detailed stop guidance, rules, practical pitfalls, a route map, Google Maps, Waze and Apple Maps links and weather alternatives. Read it online any time, or keep it offline in the Greg’s Guides app for iPhone and iPad. See an example guide →

Plan for the conditions

Expected seasonal weather

From May through October Pittsburgh is usually mild to warm. Summer afternoons are often humid, with passing thunderstorms, so plan a dry indoor hour around the Warhol and carry water for the open riverfront paths. September and October bring crisp, clearer days and cool evenings on Mount Washington, where the breeze makes it feel colder than downtown; the wooded hillsides start to turn in October. In winter expect cold, gray days, early darkness and some snow or ice on sidewalks and bridges. These are seasonal expectations, not a forecast for your travel date; check the NWS forecast before you go.

Admission and parking are separate. Check current conditions before departure.

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Harpers Ferry seen from a rocky cliff high above the Potomac: two railroad bridges cross the wide river toward the old brick town on its wooded point, with the Shenandoah curving in from the left

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Washington, DC → Harpers Ferry Visitor Center → Lower Town → Jefferson Rock → Shepherdstown → Antietam Visitor Center → Bloody Lane → Burnside Bridge

Harpers Ferry & Antietam

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10–11 hour day·About 3½–4 hours of driving in total, including the 8½-mile Antietam tour road

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Sunset over a calm Annapolis harbor, with moored boats and sailboat masts along the shore, a church spire against an orange and blue sky, and a small boat in the foreground water

History & waterfront

Washington, DC → Maryland State House → William Paca House & Garden → U.S. Naval Academy → City Dock and Main Street → Harbor cruise → Sandy Point State Park

Annapolis

A day in Maryland's small colonial capital, about an hour east of Washington: the State House where George Washington resigned his commission, a 1760s mansion and terraced garden, the Naval Academy's chapel and noon formation, crab cakes by Ego Alley, a short harbor cruise and the Chesapeake Bay Bridge at dusk.

9–10 hour day·About 2–2½ hours of driving in total, most of it on US 50

Best: All year; best April–May and September–October

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A Civil War-era cannon behind a low stone wall on Cemetery Ridge, aimed across a mile of open fields and fences toward a distant tree line and blue ridges under a clear sky

History & heritage

Washington, DC → Museum & Visitor Center → McPherson Ridge → Lincoln Square → Little Round Top → High Water Mark → National Cemetery

Gettysburg

A full day from Washington to Gettysburg: the film, Cyclorama and museum, then the battle in order across three days of ground, from McPherson Ridge to Little Round Top and the field of Pickett's Charge, with lunch on Lincoln Square and a quiet end at the cemetery where Lincoln spoke.

11–12 hour day·About 4 hours of round-trip driving from DC, plus about an hour on the battlefield roads

Best: All year; best April–June and September–October

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The long white mansion at Mount Vernon with its red roof, cupola and tall two-storey columned piazza, seen across a sloping green lawn under a blue sky with white clouds

History & heritage

Washington, DC → Mount Vernon → Washington's Gristmill → Carlyle House → Alexandria waterfront → King Street → Gravelly Point

Mount Vernon & Old Town Alexandria

A history day down the George Washington Memorial Parkway: Washington's Mount Vernon at opening time, his rebuilt gristmill and distillery on weekends in season, then an afternoon in Old Town Alexandria for Carlyle House, the river and King Street, with plane-watching at Gravelly Point on the drive home.

9–10 hour day·About 1–1½ hours of driving in total on the George Washington Memorial Parkway

Best: All year; best April–May and October

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A white Lancaster County farmstead with two stone silos, barns and a farmhouse among green fields and trees, with a wooded ridge beyond under a cloudy summer sky

Countryside day

Philadelphia → Lancaster Central Market → Amish Farm and House → buggy ride → Intercourse → Leaman Place Covered Bridge → Strasburg Rail Road

Lancaster County Amish Country

A respectful day in Lancaster County's Plain country from Philadelphia: breakfast at Lancaster Central Market, a guided look inside an 1805 farmhouse, a buggy ride on back roads, lunch in Intercourse, a covered bridge over Pequea Creek, and an optional steam train through the farms.

10–11 hour day·About 4 hours of driving in all, most of it Philadelphia to Lancaster and back

Best: All year (Fridays and Saturdays); best late April–June and September–October

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Low sun shining between reconstructed log huts along a gravel company street at Valley Forge

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Valley Forge & Brandywine

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Best: April–June and September–October

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Bare trees wrapped in blue and white holiday lights over a dark garden path, with a few visitors walking away from the camera

Gardens & art

Philadelphia → Chadds Ford → Kennett Square → Longwood Gardens

Longwood Christmas and the Brandywine Valley

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11–12 hour day·About 2½ hours driving

Best: Weekdays, late November to mid-December

$4 USD

Fallingwater's cream-colored concrete terraces and stone chimney rising above a waterfall on Bear Run, framed by dense green summer forest

Architecture & waterfalls

Pittsburgh → Fallingwater → Kentuck Knob → Cucumber Falls → Ohiopyle Falls → Ferncliff Peninsula

Fallingwater, Kentuck Knob and Ohiopyle

A Laurel Highlands day from Pittsburgh: a timed house tour at Frank Lloyd Wright's Fallingwater, lunch on site, his hilltop Kentuck Knob in the afternoon, then Cucumber Falls, the Ohiopyle Falls deck and the Ferncliff Peninsula loop along the Youghiogheny before the drive home.

11–12 hour day·About 3½ hours of driving in total

Best: May to October

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The long, pale concrete wall of the Flight 93 National Memorial visitor center along a hilltop, above a broad meadow of grasses and yellow wildflowers under a clear sky

History & heritage

Pittsburgh → Flight 93 National Memorial → Johnstown Flood National Memorial → Johnstown Inclined Plane → Ligonier

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A long, reflective Laurel Highlands day from Pittsburgh: the Flight 93 National Memorial in the morning, the remains of the South Fork Dam and the story of the 1889 Johnstown Flood after lunch, a ride on the Johnstown Inclined Plane, then dinner on the Diamond in Ligonier before the drive home.

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Best: May to October; Friday to Sunday

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Lake & beach day

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A summer day on Lake Erie from Pittsburgh: the Erie Maritime Museum and the restored U.S. Brig Niagara, the view from Bicentennial Tower on Dobbins Landing, then Presque Isle State Park's free environmental center, its 1873 lighthouse, an afternoon on a guarded beach and the Perry Monument on Misery Bay.

13–14 hour day·About 4½ hours of driving in total

Best: June to Labor Day

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Pine Creek winding through a deep, steep-sided gorge covered in orange, red and gold autumn forest, framed by green pines on the rim

Weekend getaway

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Pennsylvania Grand Canyon Weekend

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Best: Late September to mid-October

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Baltimore's Inner Harbor at dusk from above, with downtown towers, the National Aquarium and a tall ship at its pier

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11–12 hour day·About 2½–3 hours of driving in total

Best: Late September to early November

$4 USD

White water pouring through channels between dark, jagged rocks at the Great Falls of the Potomac, with a wooded ridge and blue sky beyond

Hiking & history

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Great Falls and the C&O Canal

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9–10 hour day·About 2½–3 hours of driving in total, most of it on I-95 and the Beltway

Best: March–November; best April–May and late September–early November

$4 USD

Four wild horses, brown and pinto, wading across a shallow channel through the salt marsh at Assateague Island, with marsh grass and pine woods behind

Weekend getaway

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2-night weekend·About 6½–7 hours of driving in all: roughly 3 hours each way from Baltimore over the Bay Bridge, plus short hops between Ocean City, Berlin and Assateague

Best: September to mid-October (or late May–June)

$5 USD