Maryland's Upper Eastern Shore: Kent County

As laid-back or lively as you want it to be.

Kent County: Chestertown and Rock Hall

Drive time: 2 hours

Stay here

Crow Farm Farmstay B&B. You can’t help but feel like family in the three-guestroom home, set on a 365-acre working cattle farm. Check out the on-site winery, as well. $145. 12441 Vansants Corner Road, Kennedyville; (410) 648-5687,

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Blue Crab Chesapeake Charters. Take a private sunset cruise, then spend the night aboard a yacht ($300 for two) and wake to champagne and a continental breakfast. Rock Hall, (410) 708-1803,

Eat here

Two Tree Restaurant. At this tiny treasure, the New Orleans-style spicy shrimp and grits small plate ($12) makes a satisfying meal. 401 Cypress St., Millington; (410) 928-5887,

To-do list

Pirates and Wenches Weekend. Aug. 10-12, the town of Rock Hall shivers all of its timbers for the biggest beach party of the year.

Maryland School of Sailing and Seamanship. Head out onto the Chesapeake for a full-day sailing course on a 32-foot yacht. $250. Lankford Bay Marina, 22978 McKinleyville Road, Rock Hall; (410) 639-7030,

Eastern Neck Boat Rentals. The peace of the waters, the thrill of the catch, a perfect day in Rock Hall. Rental prices vary. Eastern Neck Island Road, Rock Hall, (410) 639-7100.

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The Mainstay. Like a concert in your own living room. The venue also hosts a series of outdoor musical performances. $15-$20. 5753 Main St., Rock Hall; (410) 639-9133,

Crumpton Auction. People come from all over the Eastern Shore every Wednesday to bid on consignment home furnishings and to enjoy the spectacle. 1921 Dudleys Corner Road, Millington; (410) 928-3006,

Ortiz Studios. Chat with furniture-maker Robert Ortiz in his workshop as he creates one-of-a-kind pieces in his signature contemporary Shaker-meets Japanese style. 207C S. Cross St., Chestertown; (410) 810-1400,

For thrifty types

Pasta Plus. A $12 stromboli is big enough for two, and the soups are great. Even better is the banter between veteran server Annie and her watermen customers. Most dinners are under $10. 21356 Rock Hall Ave., Rock Hall; (410) 639-7916,

Chestertown Arts League. Members and invited artists exhibit in themed group presentations and solo showings. 312 Cannon St., Chestertown; (410) 778-5789,

Click here to read about Maryland’s Middle Eastern Shore.

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