Top Activities Downtown
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.
