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Baltimore and the Eastern Shore Road Trip

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90.8 miles: 2 hours, 29 minutes
History and water are the defining characteristics of this route. Baltimore was a thriving port more than 350 years ago and played a leading role in events associated with the American Revolution and the War of 1812, while Spanish explorers sailed into Chesapeake Bay way back in the 1520s. And Maryland’s culinary side (namely seafood) is well worth exploring, too.
1
Baltimore to Annapolis
36.1 miles: 1 hours, 1 minutes
You'll want to spend at least a day hanging out at the Inner Harbor, Baltimore’s spiffy downtown waterfront that’s chock full of tourist attractions, restaurants and souvenir shops against a backdrop of boats—everything from cargo tankers and tugboats to yachts and pleasure craft. Then zip down I-97 to the treasure trove of Colonial-era Americana that is Annapolis.
2
Annapolis to Easton
43.5 miles: 1 hours, 5 minutes
Annapolis is known as “a museum without walls” for a preponderance of carefully preserved 18th-century buildings. And the downtown waterfront surrounding City Dock is picturesque with a capital “P.” Have crab cakes for dinner—local restaurants vie for best crab cake bragging rights—or press on to Easton by way of the impressive Bay Bridge spanning Chesapeake Bay.
3
Easton to St. Michaels
11.3 miles: 0 hours, 21 minutes
Woods alternate with small farms on the short drive to St. Michaels, which is small enough to be totally relaxing but has plenty of tourist amenities. Watch skipjacks (a traditional boat used for oyster dredging) sail on Eastern Bay, stroll side streets lined with gingerbread houses, go antique hunting or feast on Chesapeake blue crabs (they turn red when cooked).