Things to Do on the Chesapeake Bay

Boat.  Bird. Shop. Visit local Wineries. Golf. Fish. Swim. Walk. Hike. Kayak. Nap.

The options for your vacation on the Chesapeake Bay waterfront at Great Oak Manor are endless. You can do everything, or do nothing at all. In fact, relaxing is the point.

While Great Oak Manor offers serene views and quiet relaxation, the surrounding area is full of attractions ready to be explored! Don’t forget to visit our Events Calendar to find out about upcoming events around and at Great Oak Manor.

Let us know your favorite experiences exploring the area so we can include your comments about our wonderful setting on the Eastern Shore. Contact us at

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Going Out?

…On the Water:

 …to 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:
    • 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.
    • The Stam Drug Company: Full service pharmacy, old fashioned soda fountain & ice cream, and gifts.
    • Twigs and Teacups: Gifts, toys, cards, soaps, linens, apparel, amusements useful and useless.

…to Rock Hall:

…for Entertainment/Arts:

…Driving Tours/Trails:

Local Annual Events: