🏛️ CulturalDay trip · from Philadelphia, PA
Colonial Charm & Waterfront Heritage
Discover Revolutionary-era streets and waterfront elegance in Chestertown's timeless colonial charm just beyond Philadelphia.
Day 1 — Chestertown
Day 1 — Chestertown
Day 1 — Chestertown
🚗 2 hr 8 min driving📍 5 stops
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Morning
🚗
Drive
Philadelphia, PA → Chestertown
2 hr 6 min8:00 AM → 10:06 AM
Chestertown — Washington College & High Street
Tour the historic 1782 campus, then stroll High Street's colonial architecture and local shops.
10:06 AM📍 See location
🍽️
Lunch
☀️
Afternoon
🚗
Drive
Chestertown → Chestertown Maryland
1 min12:06 PM → 12:07 PM
Chestertown Maryland
★ 4.6Stroll the brick-lined streets of this 18th-century port town, touring colonial homes and the riverside Washington Square. Visit the Geddes-Piper House museum or browse local shops before watching the sunset over the Chester River.
12:07 PM📍 See location
🌙
Evening
🚗
Drive
Chestertown Maryland → Luisa's Cucina Italiana
1 min5:00 PM → 5:01 PM
🍽️ Dinner5:01 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 without leaving the Philadelphia area.
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Consider staying overnight
The drive home from Chestertown is 2h 6m — consider staying overnight and driving back in the morning.
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