Explore Kent County
Kent County, Maryland
The Eastern Shore’s undiscovered gem, Kent is Maryland’s smallest county by population. Its charming small towns of Chestertown, Rock Hall, Galena, and Millington, and miles of Chesapeake, Chester and Sassafras River waterfront are set in a timeless landscape of farm fields and wooded stream bottoms.
Kent’s small towns offer a slower pace of life in their close-knit communities. Chestertown, the riverfront County seat, is home to Washington College, established in 1782, and the colonial downtown has shops and restaurants in its Arts and Entertainment District, as well as an award-winning farmer’s market an annual events like Downrigging, pictured left. Boaters will be drawn to the marinas, harbors, and maritime history of Rock Hall, located right on the Chesapeake Bay. A slower pace of life can be found in the villages of Millington and Galena, where neighbors still wave to each other in the evenings from their front porches.
Conveniently located within an hour of Philadelphia, and hour and a half to Baltimore, and two hours to Washington, D.C., County residents can access urban amenities and culture while enjoying the laid-back pleasures of the Upper Eastern Shore lifestyle. Kent County is home to those who value a connection to the land and water, seek meaningful ways to contribute to their communities, and above all, don’t mind a little peace and quiet.
Meet the Towns of Kent County
The restored Clam House in Rock Hall celebrates the community’s maritime and seafood past.
Set within the unspoiled scenic beauty of Kent County, the county’s small towns are known for their historic charm, and rich cultural heritage, each with its own unique character and attractions.
Boaters will naturally seek to set down roots in Rock Hall or Betterton for immediate Bay access, while those in search of cultural events and a bustling downtown will find amenities and a close knit community in Chestertown. For a slower pace of life and an appreciation for the traditions and beauty of the rural landscape, Galena, Millington, or Kennedyville suit residents who value knowing their neighbors and the quiet atmosphere of the towns.
Chestertown: As the county seat, Chestertown is the largest town in Kent County and offers a vibrant blend of history, culture, and natural beauty. Its colonial-era streets are lined with beautifully preserved homes, churches, and brick sidewalks. Chestertown is also home to Washington College, the tenth oldest college in the United States. The town hosts numerous festivals and events throughout the year, including the popular Chestertown Tea Party Festival.
Rock Hall: Situated on the westernmost part of Kent County overlooking the Chesapeake Bay, Rock Hall is a charming waterfront town known for its fishing and boating opportunities. With its marinas, seafood restaurants, and picturesque harbor, it attracts many visitors who come to enjoy water activities, such as sailing, kayaking, and fishing. Rock Hall also has a welcoming small-town atmosphere and hosts the annual Pirates and Wenches Fantasy Weekend.
Galena: Galena is a small hamlet located in the northern part of Kent County. It has a rich history as a former agricultural and industrial center. Today, Galena offers a peaceful and rural ambiance, with beautiful farmland surrounding the town. Visitors can explore the Galena Historic District, which features well-preserved Victorian homes and historic buildings.
Betterton: Nestled along the Chesapeake Bay, Betterton is a small town known for its sandy beach and waterfront access. An historic beach resort during the Bay’s steamboat era, Betterton today provides a quiet and relaxing getaway for visitors seeking sunbathing, swimming, and picnicking opportunities. Betterton is a popular spot for birdwatching, and its beach offers stunning views of the Upper Chesapeake.
Millington: Tucked away in the northeastern part of the county, Millington offers a serene and peaceful atmosphere. Surrounded by rolling farmland and picturesque landscapes, the town provides a charming retreat from the hustle and bustle of city life. With a close-knit community, Millington exudes a friendly and welcoming vibe. The town's main street features a few small businesses, including shops and local eateries, where visitors can experience the warm hospitality of the area.
Plan your visit to Kent County
Explore Kent County’s Parks & Outdoor Spaces
From large, inviting NRMA’s just begging to be explored, to community hubs with concert series and playgrounds, Kent County’s parks and outdoor spaces offer a range of recreational activities and opportunities to connect with nature. Whether you enjoy birdwatching, hiking, boating, or simply relaxing by the water, there are plenty of options to enjoy the county's natural surroundings.
Sassafras NRMA offers stunning clifftop views of the Sassafras River and Chesapeake Bay.
Eastern Neck National Wildlife Refuge: Located near Rock Hall, the Eastern Neck National Wildlife Refuge is a haven for birdwatchers and nature enthusiasts. The refuge spans over 2,285 acres, including forests, marshes, and grasslands. Visitors can explore the various trails and boardwalks, which offer excellent opportunities for birdwatching, wildlife observation, and hiking. The refuge is known for hosting a diverse range of bird species, including bald eagles, ospreys, and migratory waterfowl.
Sassafras NRMA: Situated near Kennedyville, Sassafras NRMA is a hidden gem for outdoor enthusiasts. The park covers over 630 acres and offers a range of recreational activities, including hiking, fishing, and kayaking. There are several trails that wind through woodlands and meadows to cliff overlooks, providing opportunities to explore the diverse natural landscapes. The park provides multiple points of access to the Sassafras River, a popular spot for fishing, birding and boating.
Betterton Beach: Situated in the town of Betterton, Betterton Beach is a beautiful sandy beach along the Chesapeake Bay. It provides a picturesque setting for sunbathing, swimming, and picnicking. The beach offers stunning views of the bay and is a popular spot for residents and visitors to relax and enjoy the waterfront ambiance. There are also facilities like picnic tables, grills, and a playground for families to enjoy.
Wilmer Park: Located in Chestertown, Wilmer Park is a scenic waterfront park along the Chester River. The park offers a serene atmosphere and features walking paths, benches, and picnic areas. It is a great spot for leisurely strolls, picnics, and enjoying views of the river. Wilmer Park is also a popular venue for community events and festivals throughout the year.
Chestertown Marina: Located on the Chester River in Chestertown, the Chestertown Marina provides access to the water for boaters and offers a scenic place to relax and enjoy the waterfront. Boaters can take advantage of the marina's facilities, including slips, boat ramps, and fuel services. The marina area features a park with benches and picnic tables, where visitors can watch boats go by or simply take in the beautiful river views.
Kent County’s Annual Events
From small town parades to community-wide festivals, Kent County’s annual calendar is full of lively events that celebrate the region’s abundance and sense of fun.
A colonial atmosphere and a festival spirit bring the community together during the annual Chestertown Tea Party Festival, where parades, vendors, food and entertainment are all part of the fun.
SPRING: May, Chestertown Tea Party Festival
This annual colonial-flavored street festival celebrates Chestertown’s 18th century history with a parade, colonial costumes, music, artisans, local food, and craft beer. The highlight of the day is the reenactment of the alleged 1774 Tea Party, with Chestertown’s costumed patriots dumping bales of tea into the Chester River. Other events throughout the weekend include a wine and beer festival on Sunday and a community Raft Race, where racers on vessels of non-nautical materials compete for wacky awards.
https://www.chestertownteaparty.org/
SUMMER: August, Pirates and Wenches Weekend
Rock Hall’s waterfront gets taken over by scurvy dogs, buccaneers, and pirates-at-heart in this fantasy weekend with a hometown spirit. Music, rum tasting, sea shanty singalongs, a dinghy parade, a treasure dig and more peg legs and parrots than you can count are all part of this fun in this family-friendly event.
https://www.rockhallpirates.com/
FALL: October, Downrigging Festival
Chestertown’s Downrigging Weekend Festival, hosted by Sultana Education Foundation, is one of the largest annual tall ship gatherings in North America. Held on the Chester River and throughout the historic downtown, the festival features a long-weekend of tall ship sails, tours, live bluegrass music, lectures, exhibits, family activities, local oysters, fireworks, and more. Proceeds benefit the Foundation’s environmental literacy programs and the other nonprofits participating in the festival.
WINTER: December, Dickens Festival
“Dickens of a Christmas” (or just Dickens to locals) celebrates the season with live music, carriage rides, Victorian food and drink, costumed characters, and entertainment all inspired by Dicken’s classic story, A Christmas Carol. The spirit of the season comes to life in several days of themed events, vendors, music and artisans throughout the historic downtown and shops.