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Your Dream Vacation in Kent County

Your Dream Vacation in Kent County

Betterton Beach in Kent County

There are so many great reasons why you should enjoy a vacation in Kent County, Maryland. This Upper Eastern Shore peninsula has endless water access, pristine landscapes, few stoplights, and close-knit villages. Everything beckons sightseers to that quintessential Bay way of life. My favorite: it’s a short enough drive to make for an easy weekend trip while still being far enough from home to be a true vacation. Ready to plan your dream vacation in Kent County? Here are my suggestions:


  • Chestertown
    Founded in 1706 as a royal port, Chestertown preserves colonial character with a dash of contemporary appeal. Art and entertainment venues dot the brick-lined downtown, and imaginative dining and shopping options await. If you’re feeling a little “revolutionary,” drop by the long-running Tea Party Festival on Memorial Day weekend.
Actor in period clothing at festival
Photo Credit: Chestertown Tea Party Festival
  • Washington College
    In 1782, George Washington gave 50 guineas and the use of his name and signature to the founding of this Chestertown-based liberal arts college. The campus makes for a postcard-perfect stroll. The world-class National Music Festival is held here every June.
  • Rock Hall
    Nicknamed the “Pearl of the Chesapeake,” Rock Hall is bejeweled with quirky character and beachy boutiques. It hosts a teeny
    Watermen’s Museum, a strict competition muskrat cook-off, and celebrated sunsets.
Rock Hall
Photo Credit: Auni Gelles
  • Tallulah Bankhead’s grave
    A star of stage and screen, Tallulah Bankhead (1902-1968) was known for her colorful language and personal life. Her gravestone at St. Paul’s Kent Episcopal Cemetery is adorned with empty vodka bottles, playing cards, and other tokens of her infamous habits.
  • Outdoor adventures
    The Eastern Neck National Wildlife Refuge and the Sassafras Natural Resources Management Area are premier birding, paddling, and hiking destinations. Kayak outfitters and boat cruise operators are numerous and can help you explore any part of the county. 
Kayaking close to Eastern Neck National Wildlife Refuge during early fall before colors have started to pop.
Kayaking close to Eastern Neck National Wildlife Refuge during early fall before colors have started to pop. Photo Credit: Dylan Taillie
  • Beaches
    Before the Chesapeake Bay Bridge was built, massive steamboats ferried people to resorts along the shores of Kent. Today, excellent public-access beaches with quality amenities remain. I recommend the well-kept sands at Betterton and Fairlee.

Eat & Drink

  • Crow Vineyard & Winery
    This Kennedyville vintner knows how to make good wine – the owner, Judy Crow, once led the Maryland Wineries Association – and how to curate an ecotourism experience bar none. The estate hosts celebrity chef dinners, wine seminars, and more. Crow has several standout wines, with the Berbera variety being our favorite. We regret not taking a case home. Consolation: we saw a calf being born on the adjoining farm!
  • Java Rock & Sweet Cheeks (Rock Hall)
    First, visit Sweet Cheeks for fresh cakes, pies, pastries, and handmade chocolates and candies. Then, head next door to sister spot Java Rock and chase your treat down with a fresh brew.
  • Evergrain Bread Company (Chestertown)
    A sign of a good bakery is when it sells out early in the morning. That’s certainly the case with Evergrain. Luckily, I was able to grab the most tempting baked good ever to tickle my taste buds: the buzz bar. You must try one, then buy 11 more. 
Evergrain Bread Company in Chestertown, MD. Photo Credit: Chelsea Milko McCallister
  • Procolino’s Pizza (Chestertown)
    This pizza is widely hailed as some of the best in the state. The locals call it “Proc’s.” My husband calls the affordably priced pizzas “three meals for the price of one.” A Proc’s pie is not only an excellent deal, it’s a memorable meal.
  • Seafood
    There are too many local seafood shanties to list. I advise you to find any dock bar and dig into some fresh catch. You’ll love the vibe in the summers, especially. With more boat landings than any other county on the Chesapeake, Kent is an understandable magnet for the dock n’ dine crowd.


  • Twigs & Teacups (Chestertown)
    The backbone of every small town is made of small businesses – a principle fully supported by this Chestertown tradition. Housed in a former ice cream factory, the sweeping retail emporium sells imaginative gifts found nowhere else. What they really do best is brighten everyone’s day. I’ve never visited a shop quite like it. Make sure to pet Jonathan, the shop cat, and grab a sticker with his face on it! 
Twigs & Teacups in Chestertown, MD. Photo Credit: Chelsea Milko McCallister
  • Chestertown Farmers Market
    Locals gather near the village square every Saturday to exchange fresh food and gossip. While you’re there, get a closer look at the “Lady in the Park” fountain, the towering aqua centerpiece of Fountain Park.
  • The Hickory Stick (Rock Hall)
    Friendly shop owner Sandy has orchestrated one of the best Eastern Shore gift shops I’ve seen. The shelves are stacked with tempting beach and Maryland flag decor.


Dozens of historic countryside homes serve as bed and breakfasts. The Inn at Mitchell House, a dreamy 18th-century manor, is a McAllister family favorite.

The Inn at Mitchell House in Chestertown, MD. Photo Credit: Chelsea Milko McCallister

It’s tucked away but still easily accessible to major points of interest. Visitors will find elegant rooms, fine home-cooked breakfasts, and, hopefully, the time to read a book and drink sherry in the library. The innkeepers are excellent itinerary planners, too!

Enjoy your vacation in Kent County!

Feature Photo Credit: Kent County, Maryland Tourism

About the Author

Chelsea Milko McAllister

A native of Las Vegas, NV, Chelsea Milko McAllister resides in the historic Baltimore neighborhood of Charles Village with her new husband and stepson. Her foreign policy career and travel obsession have taken her to over 50 countries, including Uganda, where she served as a U.S. Peace Corps Volunteer. Chelsea loves documenting her Maryland adventures through writing and photography. Follow her on Instagram @themilkoway.

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