Located on the banks of the Chester River, the historic town of Chestertown is the county seat of Kent County, Maryland. Chestertown, once a thriving port of entry for colonial settlers into Maryland, has court records dating back to the 1640's. Chestertown features many restored 18th century homes, lovely churches, the county courthouse, and several interesting shops. Grand houses built by wealthy merchants line the Chester River.
Chestertown's shipbuilding past has been revived by the Schooner Sultana project. The Sultana, a replica of a traditional 18th century schooner, was constructed locally by a non-profit organization using traditional ship building skills and launched in May of 2001.
For a selection of fresh produce and fine arts and craft, visit the Chestertown Farmer's Market and Artisan's Market, located on Park Row in the heart of downtown Chestertown. You'll find fresh breads and produce at the farmers market and work by local artists. Saturdays at 9:00 a.m. Open from the first Saturday in April to the last Saturday before Christmas.
The visitor center at the Kent County tourism office at 100 North Cross Street has information on self-guided walking, biking, and driving tours of the county, and a walking guide to the shady, brick streets of the Chestertown Historic District.
Chestertown is also home to Washington College. Washington College is the tenth oldest college in the United States. The college was founded in 1782 with the help of George Washington who gave his name and 50 guineas to the college. Washington served as a trustee and received an honorary degree.
Brampton Bed & Breakfast Inn. A romantic oasis, located on 20 wooded acres, just one mile outside the charming town of Chestertown, Maryland. Brampton B&B Inn brilliantly bends the grand elegance of a historical estate with the comforts and modern amenities today's stress-out travelers crave. 25227 Chestertown Road, Chestertown, MD 21620. Phone: 410-778-1860 or 866-305-1860 (toll free). Visit the Brampton Bed & Breakfast Inn Website.
May 22 - 24 -- Chestertown Tea Party. Come downtown to commemorate the local merchants' revolt against the British tea tax. A reenactment, parade, concessions, and crafts highlight the day on Saturday. Raft race on Sunday. More Information.
June through August on alternating Saturday Evenings -- Music in the Park. Fountain Park. 7:00pm.
September 12 -- Art in the Park. Original art and crafts for sale throughout Chestertown's Fountain Park. Activities for children, food, music.
October 3 -- Annual Chestertown House Tour. Spend an afternoon exploring a dozen of the most elegant historic hoes and buildings in Chestertown's historic district. More information.
October 16 - 17 -- Chestertown Wildlife Exhibition and Sale. Over 60 carvers, artists and craftsmen are on display throughout the historic district. More information.
October 29 - November 1 -- Schooner Sultana Downrigging. Traditional sailing vessels from around the Chesapeake will visit Chestertown to help the schooner Sultana celebrate the close of its season under sail. More Information.
Betterton Beach. Located 15 miles north of Chestertown near the mouth of the Sassafras River. Offers 300 feet of nettle free swimming beach, picnic pavilion, fishing jetty, and bath house.
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Located on the banks of the Chester River, the historic town of Chestertown is the county seat of Kent County, Maryland. Chestertown, once a thriving port of entry for colonial settlers into Maryland, has court records dating back to the 1640's. Chestertown features many restored 18th century homes, lovely churches, the county courthouse, and several interesting shops. Grand houses built by wealthy merchants line the Chester River. 
Chestertown is also home to 
Brampton Bed & Breakfast Inn
