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      • Destination Maryland Magazine Order a free Destination Maryland magazine
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Chesapeake Bay Maritime Museum
Courtesy of CBMM

Chesapeake Country - Middle

From Kent Island to Tilghman Island

Chesapeake Bay Maritime Museum
Courtesy of CBMM

American Byways logoTake your time experiencing the special beauty of this tidewater region with its pristine waterways and vibrant historic waterfront villages.

  • Drive the central section of the Chesapeake Country Scenic Byway
  • View local wildlife on the 6-mile Cross Island Trail
  • Paddle, kayak or canoe the Kent Island River Trail
  • Dine on Maryland crab at a Kent Narrows restaurant
  • Bird watch at the Pickering Creek Audubon Center
  • Learn maritime history at the Chesapeake Bay Maritime Museum
  • Set sail on the Winnie Estelle in St. Michaels
  • Check out the award-winning spirits at Lyon Rum
  • Learn about oystering on Tilghman Island
  • Travel on the Oxford-Bellvue Ferry
  • Ride a bike on the St. Michaels to Oxford Bike Trail
  • Enjoy house-made ice cream at Scottish Highland Creamery
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Places Mentioned

Chesapeake Photo
Attractions, Accommodations, & Dining

Scenic Byways-Chesapeake Country

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Cross Island Trail Photo
Attractions, Accommodations, & Dining

Cross Island Trail

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The Narrows Restaurant view of the Bay Photo
Dining

The Narrows Restaurant

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Chesapeake Bay Maritime Museum Photo
Attractions, Accommodations, & Dining

Chesapeake Bay Maritime Museum

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Attractions, Accommodations, & Dining

LYON RUM Distillery & Golden Hour Rum Room

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A fishing boat docked at a pier in Tilghman Island Photo
Attractions, Accommodations, & Dining

Tilghman Island

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Oxford Bellevue Ferry Photo
Attractions, Accommodations, & Dining

Oxford-Bellevue Ferry (Oxford)

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A couple riding bikes together Photo
Attractions, Accommodations, & Dining

Oxford/St. Michaels Bike Trail

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Find Your Adventure on the Open Road

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Sleep Inn and Suites Cumberland/LaVale Photo
Cumberland

Stay 3 nights and receive 20% off your stay!

Now Through May 31, 2025
[…]
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