Drive time: 2 hours
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, crowfarmmd.com.
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, bluecrabcharters.com.
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, twotreerestaurant.com.
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. Rockhallpirates.com.
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, mdschool.com.
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.
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, mainstayrockhall.org.
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, crumptonauctions.com.
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, ortizstudios.com.
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, rockhallmd.com/pastaplus.
Chestertown Arts League. Members and invited artists exhibit in themed group presentations and solo showings. 312 Cannon St., Chestertown; (410) 778-5789, chestertownartsleague.org.