Go here: Locals call Easton in Talbot County the "Hamptons of the Chesapeake Bay" because of its eclectic arts scene. Throughout the year, you can check out live music, performing arts and gallery events. There's even a film festival. Summer is a fabulous time to rent a bike and cycle the triangle formed by Easton, St. Michaels and Oxford, and to catch a ride on the Oxford-Bellevue Ferry. All around are boat races, kayaking and nature preserves.
Stay here: The Inn at 202 Dover, 202 E. Dover St.; 866-450-7600. The historic mansion with afternoon tea and a Cordon Bleu-trained chef is posh and pampering. Rates start at $275 midweek and $375 on weekends.
Eat here: Start off at Easton's Little Ashby Vineyard, 27549 Ashby Drive; 410-819-8850. The first licensed winery on the Eastern Shore can be reached by boat, car or bicycle. Open by appointment only, Little Ashby produces vintages of merlot, pinot noir, chardonnay and a varietal light red "spring wine." Then visit Restaurant Local, 101 E. Dover St.; 410-819-8088. The restaurant in the Historic Tidewater Inn offers seasonal bounty from neighboring waterways, farms and orchards. Want to dine al fresco? The garden at the Talbot County Historic Society is the perfect place for a picnic.
Don't miss this: The Academy Arts Museum, 106 South St., 410-822-2787. This nationally recognized museum, which has a permanent collection that consists largely of works on paper and contemporary art, operates as the anchor of a downtown district that includes galleries, retail shops, restaurants, antiques dealers and the Avalon Theatre, a performing arts venue for lectures, films, plays and music.
Get here: Cross the Bay Bridge and follow U.S. 50 toward Ocean City. Then take Md. 322/Easton Parkway to Bay Street. Make a left and then a right onto Washington Street.