🏛️ CulturalLong weekend · from Washington, DC
Historic Riverbanks & Colonial Charm
Discover centuries of American heritage while wandering charming riverside towns steeped in colonial history and authentic local character.
Day 1 — ShepherdstownDay 2 — Maryland Center for History and CultureDay 3 — Chestertown
Day 1 — Shepherdstown
Day 1 — Shepherdstown
🚗 2 hr 7 min driving📍 5 stops
🌅
Morning
🚗
Drive
Washington, DC → Shepherdstown
1 hr 39 min8:00 AM → 9:39 AM
Shepherdstown — Shepherdstown & German Street
Tour the Shepherdstown Foundation's historic sites, then stroll German Street's 18th-century architecture and local cafés.
9:39 AM📍 See location
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Lunch
🍽️ Lunch10:39 AM
Alma Bea
A Washington DC–area restaurant with a focused menu and strong local reviews. The kind of neighborhood spot that rewards diners who venture past the obvious tourist stops.
3 options · tap to switch
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Afternoon
🚗
Drive
Shepherdstown → Harpers Ferry National Historical Park
14 min12:00 PM → 12:14 PM
Harpers Ferry National Historical Park
★ 4.8Walk the cobblestone streets and tour John Brown's Fort, then hike to Maryland Heights for sweeping views of the Potomac and Shenandoah rivers converging below.
12:14 PM📍 See location
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Evening
🚗
Drive
Harpers Ferry National Historical Park → Bistro 112
14 min5:00 PM → 5:14 PM
🍽️ Dinner5:14 PM
Bistro 112
Indulge in refined French-inspired cuisine in a charming West Virginia setting that perfectly captures European elegance in a historic small-town atmosphere.
4 options · tap to switch
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Tru by Hilton Martinsburg
A highly-rated Tru by Hilton in the West Virginia Eastern Panhandle — bright, modern rooms, free parking, and a convenient base for historic Shepherdstown, Antietam National Battlefield, and the Harpers Ferry corridor. Strong value for the region.
Day 2 — Maryland Center for History and Culture
Day 2 — Maryland Center for History and Culture
🚗 2 hr 3 min driving📍 6 stops
🌅
Morning
🚗
Drive
Shepherdstown → Maryland Center for History and Culture
1 hr 55 min8:00 AM → 9:55 AM
Maryland Center for History and Culture
★ 4.7"The Star-Spangled Banner" manuscript is on display at this history museum & library.
9:55 AM📍 See location
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Lunch
R. House
★ 4.5A Baltimore food hall in a converted auto repair shop in the Remington neighborhood — chef-driven stalls in an energetic, high-ceilinged space. One of the city's best lunch destinations.
10:55 AM📍 See location
☀️
Afternoon
🚗
Drive
Maryland Center for History and Culture → Fort McHenry National Monument and Historic Shrine
5 min12:00 PM → 12:05 PM
Fort McHenry National Monument and Historic Shrine
★ 4.8Explore the star-shaped fortress where the national anthem was born, climb the ramparts for harbor views, and watch the flag ceremony at sunset.
12:05 PM📍 See location
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Evening
🚗
Drive
Fort McHenry National Monument and Historic Shrine → Ekiben
3 min5:00 PM → 5:03 PM
🍽️ Dinner5:03 PM
Ekiben
Savor authentic Japanese-inspired cuisine in the heart of Baltimore — inventive onigiri, braised meats, and bold Asian flavors that have made this Charm City spot a cult favorite among food lovers up and down the East Coast.
3 options · tap to switch
Rusty Scupper Restaurant & Bar
★ 4.5Local landmark serving upscale regional seafood dishes in a waterfront setting for over 30 years.
6:03 PM📍 See location
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Four Seasons Hotel Baltimore
The Four Seasons Baltimore sits above the Inner Harbor with views across the water toward Federal Hill — exceptional service, a spa overlooking the harbor, and the brand's reliably executed rooms. The best full-service hotel in Baltimore.
Day 3 — Chestertown
Day 3 — Chestertown
🚗 2 hr 35 min driving📍 4 stops
🌅
Morning
🚗
Drive
Maryland Center for History and Culture → Chestertown
54 min8:00 AM → 8:54 AM
Chestertown — Washington Square & High Street
Tour the Geddes-Piper House museum, then stroll High Street's colonial architecture and local shops.
8:54 AM📍 See location
🍽️
Lunch
🍽️ Lunch9:54 AM
Modern Stone Age Kitchen
A New Jersey/Pennsylvania restaurant with a menu focused on whole foods and bold flavors. One of the more distinctive dining concepts in the mid-Atlantic region.
4 options · tap to switch
☀️
Afternoon
Chestertown Maryland
★ 4.6Stroll this Colonial waterfront town's brick-lined streets, tour the 18th-century Geddes-Piper House, and browse antique shops along the Chester River.
12:00 PM📍 See location
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Evening
🍽️ Dinner5:00 PM
Luisa's Cucina Italiana
This intimate Italian restaurant celebrates authentic culinary traditions and regional Italian culture through expertly crafted dishes that transport diners straight to the heart of Italy — handmade pastas, wood-fired flavors, and warm Sicilian hospitality.
4 options · tap to switch
🚗
Drive
Luisa's Cucina Italiana → Washington, DC
1 hr 41 min6:00 PM → 7:41 PM
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