


From Chestertown to...
Sanctuary on the Eastern Shore
Cross the Sassafras and the Chester or boat in on the Bay, Kent County is where waters meet the land. A rural county on Maryland’s Eastern Shore, it traces its roots back to the midseventeenth century. Chestertown, as the county seat, offers a thriving downtown district, which includes Washington College, one of the oldest liberal arts colleges in the country, as well as our local hospital, Chester River Health System of the University of Maryland. Our Historic District offers live theater at the Garfield Center, a multitude of art galleries, fine dining as well as casual fare, eclectic shops featuring clothing,
one of our many local resources for healthy living.
As you leave Chestertown and venture into the bucolic countryside, you’ll find an endless array of both land and water recreation - bike to Betterton Beach, kayak around Eastern Neck Island, feast on crabs at the harbor in Rock Hall, watch the eagles at Turner’s Creek, sail off of Quaker Neck Landing or join the local rowing club. Just inland play a round of golf at the Chester River Yacht & County Club, or maybe tennis at the College or Pickle Ball the YMCA or at one of many Parks. Learn to sculpt with RiverArts before dancing the night away at the Harbor Shack or Waterman’s or find your rhythm, funky or formal, at the Mainstay. Sunday brunch on the Chester River Packet will hit the spot after such a fun-filled weekend.
Artisans’ Market where patrons may purchase fresh flowers & produce, herb & garden plants, handmade soaps, fresh bread, homemade pies and many other locally crafted products. Most of which are readily available on a daily basis from our local shops & farms. The well established Natural Food Store is
The summer season begins on Memorial Day Weekend with the Tea Party Festival in Chestertown. In June we welcome the renown National Music Festival. The 4th of July features fireworks and more over the harbors at Rock Hall, Chestertown & Worton Creek. The Pirates & Wenches invade Rock Hall in August. Sultana wraps up the sailing season by greeting the tall ships for Downrigging Weekend then onward to Dickens of a Christmas Weekend and all the other events that happen throughout the year. For a “Taste of the Town” stop by the First Friday of any month... the Chestertown shops extend their hours into the evening and you can experience this vibrant community first hand!
40000 Acres Protected ,
343 Miles of Shoreline
These communities are prized throughout Kent County for water access, water views, and/or water frontage. Some have docks, boat ramps, or waterfront parks for the exclusive use of community residents.
Rock Hall/Tolchester/Fairlee
Fairlee
Rock Harbor
Hidden Acres
Huntingfield Estates
Kelley’s Park
Langford Bay Estates
Langford Farm
Little Neck Farm
Rock Hall Landing
Tilghmans Landing
Tolchester Estates
Chestertown/Worton
Barrett Lands
Byford Court
Chesapeake Landing
Chesmar
Chester River Landing
Cheerful Echos Clearview
Pleasant
Rivers
Shorewood Estates
Animal Care
Chestertown Animal Hospital
Kent Veterinary Center
The Visiting Vet
Education
Chestertown Christian Academy
Friendship Montessori School
Gunston School
Kent County Public Schools
Kent School
Open Doors Partners in Education
Radcliffe Creek School
Washington College
WC-ALL (Academy of Lifelong Learning)
Healthcare
Chester River Home Care
Compass Hospice
Eastern Shore Urgent Care
Kent Center
University of Maryland Shore Regional Medical Center
Holistic Wellness
Chestertown Natural Foods
Elevate444
Jacqui Von Voss
Park Row Floats
Slacktide
Retirement
Heron Point, a continuing care community on the Chester River
Upper Shore Aging
Whispering Pines
Cultural Arts
Chestertown RiverArts
Signature Events
A Dickens of a Christmas Weekend
Betterton Appreciation Day
Brews, Blues, & BBQ’s Festival
Chestertown Arts and Entertainment
District’s Art Walk
Chestertown Jazz Festival
Chestertown RiverArts Studio Tour
Chestertown Tea Party Festival
Crazy Days
Dogwood Festival of Galena
First Friday
Fourth of July in Kent County
Guardian of the Pearl Rock Fish Tournament
Kent County Poetry Festival
Legacy Day
National Music Festival
Paint the Town
Pirates and Wenches Weekend
Rock Hall Bike Fest
Rock Hall Fall Fest
Sultana Downrigging
Waterman’s Day
Witches Weekend
Outdoor Parks
Chestertown Dog Park
Cypress Branch State Park
Edesville Park
Ferry Park
Fountain Park
Galena Town Park
Still Pond Station Park
Toal Park
Ark & Dove Restaurant
Casa Carmen Wines
Flying Decoy
Little Lemon Leaf Diner
Modern Stoneage Kitchen
Watershed Alley
Exercise & Activity
Bocce
Chester River Rowing Club
Cycling (miles of flat, lightly traveled roads)
Fit Flock
Golf
Horseback Riding
Pickleball & Tennis
Sailing Lessons
Sporting Clays
WAC 1782 & YMCA
Wayne Gilchrest Trail
Fun in the Sun
Betteron Beach
Chester River Packet Cruise
Jelly Fish Joel’s
Kent County Community Center Pool
Rolph’s Wharf
The Shanty Beach Bar
Tiki Boat Cruise
Boating
30 Public Landings
30+ Marinas
Fishing
Turner’s Creek Park
Wilmer Park
Worton Park
Garfield Center for the Arts at the Prince Theater
Kent Cultural Alliance
MainStay Performing Arts Center
Washington College’s Gibson Center for the Arts
Birding
Chesapeake Farms
Eastern Neck National Wildlife Refuge
Millington Wildlife Management Area
Sassafras River NRMA
Turner’s Creek County Park
20+ Charter Fishing Companies
Hunting
11+ Hunting and Gunning Services/ Businesses
*For a full list of amenities and services, or to further explore Kent County, MD visit: www.kentchamber.org
…a boutique real estate shop comprised of a close group of local and talented Realtors with diverse areas of expertise including, but not limited to, Farms, Waterfront Real Estate, Hunting Properties, Residential, Historic Estates, Commercial Sales and Equine Facilities.
With a team of cohesive professionals, we differentiate ourselves by understanding the market to an unparalleled degree.
$650,000,000+ volume sold since 2010
10,000+ acres sold
12 Realtors
Time is prescious and, whether buying or selling, real estate is a journey. Who you choose to take this journey with matters.
Cross Street Realtors’ clients receive exclusive access to our Concierge Service, which enriches all aspects of their real estate experience. Whether you’re looking to book dinner reservations, need assistance with accommodations, or desire tickets to the Theatre, Cross Street Realtors is a team with established connections to produce results while providing the highest level of customer service, attention to detail, courtesy, and discretion.