While you’re visiting our Eastern Shore B&B, why not make a visit to downtown. An area steeped in history, Chestertown is host to a wide variety of activities sure to keep you busy for an entire day or more! Pick out farm fresh fruits and veggies at the farmers market, visit a local museum and learn all about the history of the area, browse a used bookstore at your leisure, or go wine-tasting. Conveniently located near the Inn, there’s no shortage of fun activities for those venturing into historic Chestertown, MD.

Historic Downtown Chestertown

  • Farmer’s Market – Saturday mornings from 8 a.m. to noon beginning about the third Saturday in March through the last Saturday in December. Located at Fountain Park in Chestertown.
  • First Fridays in Chestertown – Held every first Friday of the month. Extended shop hours, arts, and entertainment. 5-8pm.
  • Kent County is home to several antique shops in Chestertown, Galena, Rock Hall, and Crumpton.
  • Visit the museums and art galleries
  • Take an audio tour of historic Washington College

Noteworthy Shops

  • Twigs and Teacups – Gifts, toys, cards, soaps, linens, apparel, amusements useful and useless.
  • Bookplate – Used books, local and regional history, signed first editions, imported Mediterranean ceramics and tiles.
  • Chester River Wine & Cheese Co – Wonderful selection of wines, cheeses, meats, and other great things for your kitchen.
  • Houston’s Dockside Emporium – Has gifts, clothing, accessories, and more.
  • Mimi’s Closet – Fine & fun ladies clothing.