Your Ultimate Guide to Exploring the Chesapeake Bay
Embark on an unforgettable journey through Maryland and Virginia along the shores of the Bay. Discover hidden gems, scenic drives, and local favorites.
36 Breathtaking Destinations
Favorite Places
Destination
St Michaels MD
Destination
Cambridge MD
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Cape Charles VA
Destination
Urbanna VA
2025 Events Around the Bay
Jan
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Feb
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Mar
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Apr
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May
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Jun
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Jul
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Aug
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Sep
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Oct
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Nov
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Dec
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Start Your Chesapeake Bay Adventure Today!
Join us on a road trip around Chesapeake Bay, a region of the U.S. teeming with history, culture, and natural beauty surrounded by Bay waters. This book is designed to make your journey one you won’t forget with colorful photographs, detailed maps of the 36 iconic harbor towns and cities, and a distance chart that tells you how far everything is from everything else. Make it a major trip and circumnavigate the Bay, or take shorter hops for a weekend getaway. The Chesapeake Bay Bridge (Annapolis MD → Kent Island MD) and the Chesapeake Bay Tunnel Bridge (Cape Charles VA → Tidewater VA) provide options to explore both sides of the Bay. If you get bored or have kids who need something to do, try the regional word puzzles on the companion website www.chesapeakebayroadtrip.com.