Why You Need to Visit Maryland’s Eastern Shore after the Holidays

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The holidays are over. The past few weeks were spent decorating the tree, baking cookies, squinting at the computer screen as you searched Amazon or Wayfair for the perfect gifts, reminding your (grand)children that Santa is watching them, shopping for holiday food, gift wrap, and other supplies, and wrapping an endless pile of presents. The list of holiday tasks is endless and now that they are finally over, you deserve a break!
Come on… you know you do! So, treat yourself to a few days on the Chesapeake Bay.


Chestertown Waterfront

  • Chestertown is a unique, historic town with great restaurants, tons of shopping, and a rich history. Its brick sidewalks, elaborate architecture, and antique stores beckon visitors all year long.
  • First Fridays in Chestertown are like a little party for the town. Enjoy the festivities as you eat, drink, and shop at the charming stores and boutiques.
  • The Chesapeake Wine Trail, which can be quite busy over the summer, has quieted, leaving you with plenty of time to chat with the winemakers and other staff at the vineyards. Crow Vineyard and Winery, Clovelly Vineyards, and Cassinelli Winery & Vineyards are all located in Kent County and are a short driving distance from the Manor.
  • Eastern Neck National Wildlife Refuge is a 2285 acre island that provides habitat for various wildlife including small mammals and more than 240 species of birds, one of which is the Tundra Swan. These graceful creatures arrive in late November for a visit before traveling more than 4,000 miles in the spring.

    Tundra Swan

  • No matter the season, the Chesapeake Bay has the most glorious sunsets!
  • There are great events in Chestertown and Kent County all year long. Check out some of these great events:
    • First Friday – January 5
      Enjoy Chestertown after dark! Visit the gallery exhibits and unique shops, watch special performances, participate in kids’ activities and enjoy a variety of dining options. 
    • Martin Luther King Jr. Commemorative Concert – January 13
      The Garfield Center for the Arts presents its annual Martin Luther King Jr. Commemoration Concert.
    • Celebrate Love – February
      Great Oak Manor will celebrate love all month long! Guests staying two nights will receive complimentary chocolate and flowers! You can also add a delicious dinner for two for an additional $100. Dinner includes: choice of filet, crab cake or salmon entree plus side, salad, dessert, and a bottle of wine!
  • Great Oak Manor has the following specials:

New Year’s
Enjoy a peaceful retreat after the hustle and bustle of the holidays. Guests staying three nights receive a complimentary dinner with wine.

Martin Luther King Jr. Weekend – January 12-15
Stay two nights, get one night 50% off. Stay three nights, get one free!

Mid-Week Special*
Buy one night, get the second 50% off!
Code: BOGO

Buy two nights, get the third free!
Code: Fireside





*Sunday to Thursday only. New reservations only. Not to be combined with other offers. Second-floor rooms and Carriage House only; rooms subject to availability. Offer valid December 2017 – January 2018.

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