Things to Do on the Chesapeake Bay
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 email@example.com
…On the Water:
- Blue Crab Chesapeake Charters
- We highly recommend the sunset cruises.
- Chester River Kayak Adventures
- East Neck Boat Rentals
- The Chester River Packet Company, LLC
…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:
- Eastern Neck Wildlife Refuge has several different trails to explore and is great for biking or kayaking.
- Copper Pearl Confections is a fantastic local spot to get hand crafted chocolates and other fun confections.
- Garfield Center for the Arts at the Prince Theater
- The Mainstay
- Church Hill Theatre
- Music in the Park: held every other Saturday in Chestertown’s Fountain Park (starts in June)
- Chester 5 Movie Theater
- National Scenic Byway
- Chesapeake Wine Trail
- Great Oak Manor happens to be in the middle of the Chesapeake Wine Trail, putting us within minutes of several wineries
- Crow Vineyard & Winery
- Tasting Room is open each day 12 noon to 5 pm. To contact the Tasting Room call: 302-304-0551.
- Cassinelli Winery
- Clovelly Vineyards
- Call ahead, 410-708-1775, to arrange tours and tastings.
Local Annual Events: