Chesapeake City to Cambridge, Crisfield and Smith Island, 271 miles plus a ferry trip, 7 days, 6 nights
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Smith Island ferry boat leaves Crisfield, Maryland City Dock.
From the Beach to the Bay Maryland’s Lower Eastern Shore is known for its traditional watermen culture, where locals rise with the sun and work the waters to bring in the day’s catch. Nestled between the vast, blue Chesapeake and the white, sandy beaches of the Atlantic, a tapestry of farms, woodlands, rivers and marshes paint an unparalleled landscape picture. Among the wide open spaces, watermen villages and towns, like Deal Island , Crisfield, Princess[...]
Spend A Day By The Water Ocean City is a perfect introduction to the Eastern Shore. You’ll find a party pretty much every season—from Winterfest to Springfest, Sunfest and beyond. While in Ocean City make sure you fit in a stroll along the award-winning Boardwalk. You’ll find amusements, arcades, and plenty of snacks—like Fisher’s famous caramel popcorn and Thrasher’s french fries. You’ll definitely want to stay the night in Ocean City so you can enjoy[...]
Day 1 A Day By The Bay Start your day in Annapolis, on the shores of the Chesapeake Bay. Let an Annapolis Tours by Watermark attired guide take you back to the 18th century. They will lead you through the Old Senate Chamber, in the Maryland State Capital Building, where in 1783 George Washington resigned as Commander-in-Chief. Travel through the gates of the United States Naval Academy, founded in1845, and home to 4,000 of our[...]
The Maryland Folk Festival Make your plans now to join us in Salisbury, Maryland, for the Maryland Folk Festival— a diverse celebration of arts, culture, and heritage. This large-scale multi-day outdoor event, celebrates the roots, richness and variety of American culture. It features hundreds of the nation’s finest musicians, dancers, craftspeople and other keepers of culture in performances, workshops, and demonstrations, plus children’s activities, non-stop participatory dancing, storytelling, parades, and more. Best of all, it’s[...]
When you shop along Maryland’s Main Streets, you’re supporting local businesses and the historic properties they steward. If window shopping by foot, dining at new spots, antiquing and collecting art sounds like a great day out, you’ll absolutely adore these Main Street destinations. Shop the Shore in Berlin’s Unique Stores With a population of about 4,900, Berlin is small but packs a lot of charm. This Eastern Shore gem, known for its great jewelry, gift[...]
Western Maryland Western Maryland is a great place for outdoor adventures. You can climb Maryland's highest mountain, swim in numerous lakes, hike the Appalachian Trail, brave white-water rapids or enjoy all kinds of winter sports from skiing to ice fishing. The three counties of Western Maryland, where fall foliage arrives first and winter usually stays the longest, were Maryland's last frontier. One of the most important events in Western Maryland in the early 1800s was[...]
BALTIMORE (March 10, 2021) Maryland’s Chesapeake Country Scenic Byway has been designated as an All-American Road by the U.S. Department of Transportation’s Federal Highway Administration (FHWA), the highest designation a road can receive. This honor was announced along with 49 new designations to the America's Byways® collection, including 15 All-American Roads (AAR) and 34 National Scenic Byways (NSB) in 28 states. "With elevation of the Chesapeake Country Scenic Byway to an All-American Road, Maryland is[...]