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Tolchester Beach is an unincorporated community located on the eastern shore of the Chesapeake Bay in Kent County, Maryland, United States. Established in 1877, it was formerly a popular resort. Tolchester Beach is located just north of Rock Hall. The resort was closed in 1962.In the late 1800s, Tolchester Beach was a popular tourist destination for residents of Baltimore and other areas served by the Chesapeake Bay steamships. The beach had hotels, restaurants, games, picnics, horse-racing, and an amusement park with a merry-go-round and a roller coaster.Some of the steamships that served Tolchester Beach were the Emma Giles and Louise.

The Whirl Pool Dips was a roller coaster located at Tolchester Beach Park in Tolchester Beach, Maryland. It operated from 1913 until 1959.

Tolchester is a census-designated place in Kent County, Maryland, United States. Its population was 329 as of the 2010 census. The CDP covers the unincorporated community commonly known as Tolchester Beach.

Edesville is an unincorporated community and census-designated place in Kent County, Maryland, United States. Its population was 169 as of the 2010 census.

Rock Hall, is a waterfront town located directly on the National Chesapeake Scenic Byway in Kent County, Maryland, United States. The population was 1,310 at the 2010 census.

Georgetown is an unincorporated community and census-designated place in western Kent County, Maryland, United States. Per the 2020 census, the population was 117. It should not be confused with the community of the same name 22 miles (35 km) to the northeast on the Kent/Cecil County border.

Sharpstown is an unincorporated community in Kent County, Maryland, United States.

Gobbler Hill is a historic home located at Chestertown in Kent County, Maryland, United States. It was built in 1858 and is a center-hall plan frame house on a foundation of local fieldstone and brick. It is five bays wide, two bays deep, and two stories tall with late Greek Revival / early Italianate style details. It features a shallow hip roof surmounted by a tall belvedere and a full-width porch.It was listed on the National Register of Historic Places in 2009.

The Fairlee Manor Camp House is a historic home located near Fairlee, Kent County, Maryland, United States. It is a "telescoping house" composed of a two-story, three-bay-long brick structure with a 1+1⁄2-story brick wing and a 1+1⁄2-story, 3-bay-long plank wing on each side in decreasing height and width. The oldest sections of the house date to 1825–1840. In 1953 Louisa d'Andelot Carpenter donated Fairlee Manor to the Easter Seal Society for Crippled Children and Adults of Delaware, Inc.The Fairlee Manor Camp House was listed on the National Register of Historic Places in 1973.

St. Paul's Church is an historic Episcopal church located near the village of Fairlee, southwest of Chestertown, Kent County, Maryland. St. Paul's Church is one of the original thirty parishes created in 1692 by an Act of the General Assembly declaring the Church of England as the established religion of the Province of Maryland. The Georgian-styled building, completed in 1713, is the second-oldest Episcopal church on the Eastern Shore of Maryland (after Trinity Church in Church Creek, built in 1675).

The Battle of Caulk's Field was fought during the War of 1812 in Kent County, Maryland between a small British Army force commanded by Captain Sir Peter Parker and American militia forces commanded by Lieutenant Colonel Philip Reed. Parker, who was operating in the Chesapeake Bay region as part of the British campaign against Baltimore, Maryland, landed on the eastern shore of the Chesapeake Bay to move against Reed's militia encampment. The British attacking force encountered American skirmishers, who conducting a fighting retreat, drawing the British towards the main American line. Parker was mortally wounded during the fight, and the British force withdrew after Parker fell. Later British setbacks at the Battle of North Point and the Battle of Fort McHenry led the British to abandon their campaign against Baltimore. In 2012, the battlefield was the site of an archaeological survey.

Carvill Hall, also known as Carvill's Prevention, Salter's Load. or Packerton, is a historic home located at Chestertown, Kent County, Maryland. It is a 2+1⁄2-story Flemish bond brick house, with exterior corbeled brick chimneys at each gable end. The main block was built between 1694 and 1709. Additions to the main block date to the 19th century. It was listed on the National Register of Historic Places in 1973.