Visitor Guide
Kent — Visitor Guide
Top attractions, trails, food and drink, history, seasonal activities, and everything you need to plan your visit to Kent, Rhode Island.
🧭 About Kent
Maryland's Least Populous County, One of Its Most Historic
Kent County is small — Maryland's least populous — but it holds one of the state's best-preserved 18th-century towns in Chestertown, a working watermen's village in Rock Hall, and a genuine tall-ship sailing experience on the Chester River. Tucked between the Chesapeake Bay and the Sassafras River, this is Eastern Shore Maryland at its most unhurried: brick sidewalks, sailboats, and a college town's worth of history.
⭐ Top Attractions
Chestertown Historic District
One of the largest and best-preserved collections of restored 18th-century homes in Maryland, founded in 1706 on the Chester River, with brick sidewalks and colonial architecture including the 1767 Hynson-Ringgold House.
Rock Hall
A historic Chesapeake Bay watermen's village turned sailing destination, with a working commercial fishing fleet and more than a dozen marinas.
Schooner Sultana
A hand-built, historically accurate reproduction of a 1768 Royal Navy schooner based in Chestertown, offering public sails on the Chester River through the Sultana Education Foundation.
Washington College
Founded in 1782, the first college chartered in the independent United States — George Washington personally permitted use of his name and served on its board until 1789.
Eastern Neck National Wildlife Refuge
A 2,285-acre island refuge at the confluence of the Chester River and Chesapeake Bay, with seven trails and more than 250 documented bird species including bald eagles.
Geddes-Piper House Museum
A circa-1784 Federal-period house museum and headquarters of the Historical Society of Kent County, with a Chinese export teapot collection and the county's historical archives.
🥾 Trails & Outdoors
🍺 Food & Drink Trails
Waterman's Crab House
A 40-plus-year waterfront seafood restaurant in Rock Hall, part of the Maryland Crab and Oyster Trail, known for jumbo lump crab cakes
Play It Again Sam
A popular casual coffee, bakery, and sandwich spot in downtown Chestertown, a favorite of locals and Washington College students
🏛️ History & Heritage
Chestertown Tea Party History
In May 1774, Chestertown residents adopted resolutions banning tea and, per local tradition, dumped tea cargo into the Chester River in protest — mirroring the Boston Tea Party
Geddes-Piper House Museum
A circa-1784 Federal house serving as the Historical Society of Kent County's headquarters and archive
Washington College
Founded in 1782, the only college George Washington personally allowed to bear his name during his lifetime
🗓️ Seasonal Guide
Spring 🌸
The Chestertown Tea Party Festival over Memorial Day weekend brings a Tea Toss Reenactment, colonial parade, raft race, and beer fest to downtown Chestertown.
Summer ☀️
Long days on the Chester River and Betterton Beach, with the Schooner Sultana offering public sails out of Chestertown.
Fall 🍂
Rock Hall FallFest brings a mid-October, oyster-centric community festival with live music and craft vendors to the harbor.
Winter ❄️
A quieter season for exploring Chestertown's historic district and the Geddes-Piper House Museum indoors.
🏨 Places to Stay
Browse all accommodations →🗺️ Plan Your Visit
Source: Maryland Mountain Side — Official Allegany County Tourism