Waterfront towns & maritime history · Maryland

St. Michaels, Oxford and Easton day trip

St. Michaels, Oxford and Easton

Cross the Chesapeake Bay Bridge to Maryland's Eastern Shore for a loop of three old Talbot County towns: the Chesapeake Bay Maritime Museum and its 1879 lighthouse in St. Michaels, crab cakes by the harbor, the Oxford–Bellevue Ferry across the Tred Avon River, an ice cream on Oxford's quiet waterfront and dinner in Easton's brick downtown.

Time: 11–12 hour day
Driving: About 3½ hours of driving in total, roughly 150 miles, plus a 10-minute ferry
Best time: May–June and September–October
Updated: October 15, 2026 at 6:13 PM Pacific

$4 USD

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A white skipjack-rigged workboat with a tall wooden mast moored beside a weathered wooden boat shed with a red roof, on calm blue water at the Chesapeake Bay Maritime Museum — miketnorton · CC BY 2.0. September 2013 photograph; resized and displayed with crop.

Suggested times, not bookings

Your day at a glance

8:00 amChesapeake Bay Bridge
10:00 amChesapeake Bay Maritime Museum
12:45 pmLunch and a walk in St. Michaels
2:30 pmOxford–Bellevue Ferry
3:00 pmOxford
4:45 pmEaston
7:00 pmDrive back to Baltimore

Highlights

Worth the trip

Climb the screwpile Hooper Strait Lighthouse at the Chesapeake Bay Maritime Museum
Ride the Oxford–Bellevue Ferry, running across the Tred Avon since 1683
Three walkable towns: St. Michaels' harbor, sleepy Oxford and Easton's historic downtown

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

On the Eastern Shore in May and June, highs are usually in the 70s to mid-80s °F; in September they're near 80 °F, and in October in the upper 60s, with cool mornings. July and August are hot and humid, with highs near 90 °F and afternoon thunderstorms that can stop the ferry and close the lighthouse for a while. Breezes off the water make the ferry and waterfront feel cooler than inland. These are seasonal expectations, not a forecast for your travel date; check the NWS forecast the evening before and the morning of your trip.

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

Another good day

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Skyline Drive curving through a forest of gold, orange and red trees under a partly cloudy blue sky, with a low stone wall along the left shoulder

Scenic drive & short hikes

Washington, DC → Front Royal → Dickey Ridge → Range View Overlook → Stony Man and Skyland → Dark Hollow Falls → Big Meadows → Thornton Gap

Shenandoah's Skyline Drive

A full day from Washington, DC along the north and central Skyline Drive in Shenandoah National Park: the Dickey Ridge Visitor Center, the long view from Range View Overlook, the short climb up Stony Man with lunch at Skyland, the steep walk down to Dark Hollow Falls and an afternoon at Big Meadows before heading home through Thornton Gap.

11–12 hour day·About 5–6 hours of driving in total, including about 70 miles of Skyline Drive at 35 mph

Best: Late September to early November

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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

History & heritage

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

Harpers Ferry & Antietam

A Civil War history day out of Washington: the shuttle down to Harpers Ferry's Lower Town for John Brown's Fort and the meeting of the Potomac and Shenandoah, the Appalachian Trail steps to Jefferson Rock, lunch in Shepherdstown, then the Antietam battlefield from the Dunker Church to Bloody Lane and Burnside Bridge.

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

Best: All year; best late September to early November

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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

$4 USD

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

$4 USD

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

$4 USD

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

$4 USD

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

History & heritage

Philadelphia → Valley Forge Visitor Center → Muhlenberg's Brigade → National Memorial Arch → Washington's Headquarters → West Chester → Brandywine Battlefield Park

Valley Forge & Brandywine

The Revolution west of Philadelphia in one day: the film and exhibit at Valley Forge, the reconstructed huts, the Memorial Arch and the stone house where Washington spent the winter, then lunch in West Chester and the Brandywine battlefield, where the army lost the fight three months before it marched into camp.

8–9 hour day·About 3 hours of driving in all, including the 10-mile Encampment Tour loop

Best: April–June and September–October

$4 USD

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

A holiday-season day in the Brandywine Valley: Wyeth paintings and the model-train Brandywine Railroad in Chadds Ford, a mushroom-town lunch in Kennett Square, then Longwood Gardens' conservatories by daylight and A Longwood Christmas after dark.

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

$4 USD

Downtown Pittsburgh's towers rising above the Monongahela River, seen from Mount Washington on a cloudy day

City walking

Downtown Pittsburgh → Strip District → Andy Warhol Museum → Point State Park → Monongahela Incline → Grandview Avenue → Duquesne Incline

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.

11–12 hour day·No driving; walking plus two incline rides

Best: All year; best May–October

$4 USD

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

Flight 93, Johnstown and Ligonier

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.

12–13 hour day·About 4½–5 hours of driving in total

Best: May to October; Friday to Sunday

$4 USD

A long, wide sandy beach curving along calm blue Lake Erie, with a line of green trees behind it and a few beachgoers and umbrellas in the distance

Lake & beach day

Pittsburgh → Erie Maritime Museum → Bicentennial Tower → Tom Ridge Center → Presque Isle Lighthouse → Beach 11 → Perry Monument

Erie and Presque Isle Beaches

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

$4 USD

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

Pittsburgh → Wellsboro → Leonard Harrison → Pine Creek Rail Trail → Colton Point → Cherry Springs → Kinzua Bridge → Pittsburgh

Pennsylvania Grand Canyon Weekend

A two-night fall weekend in the Pennsylvania Wilds from Pittsburgh. Drive to gas-lit Wellsboro on Friday. Saturday is the big day: the east rim of Pine Creek Gorge and the Turkey Path, a ride on the Pine Creek Rail Trail along the canyon floor, the west rim at Colton Point, then the dark skies of Cherry Springs after dinner in Coudersport. Sunday loops home past the Kinzua Bridge Skywalk.

2-night weekend·About 11–12 hours of driving in all: roughly 4½ hours to Wellsboro on Friday, 2½ hours around the canyon and west to Coudersport on Saturday, and about 4½ hours home by way of Kinzua Bridge on Sunday

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

History & waterfront

Inner Harbor → Fort McHenry → Federal Hill → Inner Harbor → Fells Point

Baltimore Harbor and Fort McHenry

The star fort that inspired the national anthem, a market lunch in Federal Hill, the harbor view from the hilltop, and a waterfront walk past the USS Constellation to the cobblestones of Fells Point.

8–9 hour day·No driving; a free bus to the fort, then walking

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

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The stacked gray rock column of Chimney Rock above a ridge of orange and green fall trees, with Catoctin's wooded hills rolling away under a soft cloudy sky

Mountain hike & small town

Baltimore → Catoctin Mountain Park → Cunningham Falls → Catoctin Mountain Orchard → Frederick's Carroll Creek

Catoctin Mountain and Frederick in Fall

A fall day west of Baltimore: a rocky ridge hike to Chimney Rock and Wolf Rock in Catoctin Mountain Park, Maryland's largest cascading waterfall at Cunningham Falls, pies and apples at an orchard below the mountain outside Thurmont, and an evening stroll and dinner along Carroll Creek in downtown Frederick.

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

Baltimore → Great Falls Overlook → Great Falls Tavern → Billy Goat Trail Section A → Old Angler's Inn → Glen Echo Park

Great Falls and the C&O Canal

A day on the Maryland bank of the Potomac, an hour from Baltimore: the boardwalk to the Great Falls Overlook, the old canal tavern beside Lock 20, a rock scramble above Mather Gorge on the Billy Goat Trail, a late lunch across from the towpath and a stroll through Glen Echo's old amusement park.

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

Baltimore → Bay Bridge → Berlin → Assateague Island → Assateague State Park → Ocean City Boardwalk → Baltimore

Assateague and Ocean City Weekend

A two-night beach weekend on Maryland's Atlantic coast from Baltimore. Cross the Bay Bridge on Friday afternoon and spend the evening in historic Berlin. Saturday belongs to Assateague Island: wild horses on the bayside at dawn, the three short nature trails, a beach afternoon at Assateague State Park and an optional paddle on Sinepuxent Bay, then the Ocean City Boardwalk at dusk. Sunday is lighter, with a morning on the boards to the Inlet, the Life-Saving Station Museum and an early start home.

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