Have you ever visited a place where you immediately felt welcome and just knew that you would come back again and again? The County of Kent, on Maryland’s Upper Eastern Shore, is that place, and is less than a two-hour drive from Philadelphia or Washington D.C.
The peaceful vistas, farms, vineyards and open space reminds us of a time past and where hustle and bustle are nowhere to be found. Enjoy the serenity and beauty, but be ready to have fun, for this quaint countryside is host to hundreds of events. Combine an event with attractions, recreational activities, local fresh foods, natural history, shopping, musical and theatrical performances, and you have the perfect escape in the historic towns of Chestertown, Rock Hall, Galena, Millington, Betterton, Kennedyville, and Georgetown.
Enjoy this 209 miles of shoreline scenic peninsula. Located directly on the Chesapeake Bay, Rock Hall has more than a dozen marinas, and trams that make it easy to get around town. The renovated Chestertown Marina and waterfront is host to a visitor center among a ship’s store, showers for slip holders and transient boaters. The Sassafras Harbor hosts a restaurant, an inn, marinas, and stunning sunsets. Anglers, look no further, for almost two dozen fishing captains are geared up and ready to set you on course to great fishing.
Passionate Paddlers will love the convenience of 30 public landings and the abundance of calm rivers and creeks. Kayak tours and rentals can be found in Chestertown or Rock Hall, or join one of Sultana’s themed guided tours.
For the Love of Nature, Eastern Neck National Wildlife Refuge, nestled along the Chesapeake Bay and Chester River, has seven unique hiking trails. Turners Creek and the Sassafras River Natural Resources Management Area has three miles of shoreline and 143-acres of woodlands, wetlands and agriculture fields.
Views from the Beaches. In Rock Hall at Ferry Park beachgoers can enjoy the charming strip of beach, complete with a quaint boardwalk, picnic tables and barbecue grills, and stunning Chesapeake Bay sunsets. Betterton Beach, known for its nettle-free swimming, has 500 feet of boardwalk, a picnic pavilion atop a bay view bluff, bath houses, picnic tables, a beach volleyball court, a fishing jetty, and a public pier.
Foodies will Love the local markets and restaurants brimming with fresh produce and meats, and straight-from-the-water seafood. The award-winning Chestertown Farmers and Artisans market begins every Saturday morning at 8:00 a.m. in Fountain Park. Nestled just outside of the town of Kennedyville is Crow Winery. This award-winning winery is also a vineyard, working farm, and Farm Stay B&B. Cassinelli Distilling and Bad Alfred’s, located in Downtown Chestertown, offers visitors a close up as vodka, gin and brandy are made, and then the tastings begin–directly from the stills. Continue your wine and spirits tour at Casa Carmen Wine Bar, also in Downtown Chestertown.
History buffs. Located on the banks of the Chester River, Chestertown has the second largest collection of 18th and 19th century structures in the state of Maryland. Washington College, located in Chestertown and founded in 1782, is the tenth oldest college in the Nation. George Washington personally gave use of his name and a founding gift of 50 guineas.
A Traditionally Friendly Shopping Experience awaits you in the quaint towns of Kent County. From the whimsical shops and antique stores of Rock Hall and Galena to boutique stores and art galleries in Chestertown, you will find one-of-a-kind gifts, sprinkled with old fashion, friendly service.
Body and Mind. Here visitors seeking relaxation and physical and spiritual renewal will find a wide variety of practitioners (more than 30) who together create a dynamic focal point for a holistic, healthy vacation experience.
There is something about the quiet of country that lends itself to a great night’s sleep. Many of the accommodations, ranging from luxury inns and bed and breakfasts to an award-winning campground, and everything in between, feature amenities like swimming pools, stand up paddle boards or kayaks, bicycles, and more. Many welcome your 4-legged family as well.
- First Fridays in Downtown Chestertown
- 2nd Saturdays Chestertown
- Chestertown Tea Party
May 24 through 26; throughout Downtown
- Rock Hall Spring Triathlon
June 1 & 2; Rock Hall Landing Marina
- National Music Festival
June 2-15; Throughout Kent County
- Rock Hall Rockfish Tournament
June 7th & 8th; Rock Hall Bulkhead
- 48th Antique Fly-In
June 8; Massey Aerodrome & Air Museum
- Music in The Park: Chestertown|
June 8-Aug. 31 – Every other Saturday
- 34th Bay to Bay Bicycle Ride
June 23; Begins at Betterton Fire Company
- Waterman’s Day
June 30; Rock Hall Harbor
- 4th of July in Kent County
– July 2; Great Oak Marina Fireworks
– July 3; Rock Hall Fireworks
– July 4; Rock Hall Parade
– July 4; Chestertown Fireworks
- Kent County Fair
July 19, 20 & 21; 4-H Park, Tolchester Beach Rd.
For more information and a complete list of events, visit kentcounty.com/events.