Cross Island Trail

Chester is a census-designated place on Kent Island in Queen Anne's County, Maryland, United States. The population was 3,723 at the 2000 census.

The historic Stoopley-Gibson Manor is a stately three-story, 18th-century Georgian brick manor home along the Chester River on the north shore of Kent Island in Maryland. The original 150 acres (61 ha) land patent was first issued to Henry Stoupe and John Gibson in 1656. According to the local tax assessment, the property had increased to 176 acres (71 ha) by 1798 with the initial reference to the building structure. The manor was enlarged in the mid-19th century, with secondary restorations and expansions in the 20th and 21st centuries. Of particular note is the original header bond brick on the south façade, common in period Annapolis and Chestertown homes and two-story north-facing veranda reminiscent of Mount Vernon. Significant local history includes fugitive slave, Henry Massey, who escaped from the home in 1854, and the multi-generation family cemetery that was lost to shoreline erosion.<

Kent Island High School (KIHS) is a public high school in Stevensville, Maryland, United States that first opened in 1998 to accommodate the growing population of Queen Anne's County. The school takes its name from Kent Island, the location of the school (and the entire census-designated place of Stevensville). The school is often seen as the successor to Stevensville High School, which closed in 1966, and was renovated and reopened as Stevensville Middle School. The two schools have similar school colors and mascots (SHS's colors and mascot were blue and gold and the Pirates, compared to navy blue and silver and the Buccaneers of KIHS). Between 1966 and 1998, residents of Kent Island attended Queen Anne's County High School. Grades 10-12 are located at Kent Island High School, while 9th graders instead attend at an annex of the high school located at Matapeake Middle School. Kent Island High School's sports teams are members of the Bayside conference and 2A East region in Maryland.

The Kent Island Research Facility is a U.S. National Security Agency facility located on Kent Island, Maryland, near the town of Chester.The facility was established in 1961 to conduct research on very high frequency and microwave antenna systems—specifically, on problems associated with anomalous propagation in communications interception. According to James Bamford in 1983, the location consists of the NSA Propagation Research Laboratory, a single-story, white, windowless building that houses automatically operating, unattended equipment, as well as a small, white cinder-block "control" building surrounded in a barbed-wire fence. Near the control building are a number of unusual antennas.In 2016, the United States government shuttered various Russian diplomat vacation facilities, including one that, according to Australian security expert Des Ball, was well positioned to spy on the NSA’s "Propagation and Research Laboratory" on Kent Island.

The Stevensville Historic District, also known as Historic Stevensville, is a national historic district in downtown Stevensville, Queen Anne's County, Maryland. It contains roughly 100 historic structures, and is listed on the National Register of Historic Places. It is located primarily along East Main Street, a portion of Love Point Road, and a former section of Cockey Lane.

Christ Church refers to both an Episcopal parish currently located in Matapeake, Maryland and the historic church building located in the Stevensville Historic District in Stevensville, Maryland, which the parish occupied from 1880 to 1995, and that is now a Lutheran church. Christ Church Parish was one of the original 30 Anglican parishes in the Province of Maryland.

The Episcopal Diocese of Easton is a diocese of the Episcopal Church in the United States of America that comprises the nine counties that make up the Eastern Shore of Maryland. It is in Province III (the Middle Atlantic region) and was created as a split from the Diocese of Maryland in 1868. The diocese consists of the Eastern Shore of Maryland (the nine counties of Caroline, Cecil, Dorchester, Kent, Queen Anne's, Somerset, Talbot, Wicomico, and Worcester), and has a total membership of about 9,750 people, out of a total population of 420,792, according to a 2004 census estimate. There are 39 parishes and missions in the diocese. Its largest cities are Salisbury, Ocean City, and Easton, the centrally located city from which the diocese takes its name and where Trinity Cathedral, the bishop's seat, is located. Camp Wright, the diocesan camp, is located in Stevensville. Christ Episcopal Church of Kent Island, the oldest Christian congregation in Maryland, is a part of the diocese, and is also located in Stevensville.

The Stevensville Bank is a historic bank building located near the center of Stevensville, Maryland, United States, and is in the Stevensville Historic District. The building's name is a reference to Stevensville Savings Bank which once occupied the building. The classically detailed bank is now used as a law office.It was listed on the National Register of Historic Places in 1985.

The Cray House is a two-room house in Stevensville, Maryland. Built around 1809, it is a rare surviving example of post-and-plank construction, and of a build of small house which once dominated the local landscape. For these reasons it was listed on the National Register of Historic Places in 1983.

Stevensville is a census-designated place (CDP) in Queen Anne's County, Maryland, United States, and is the county's most populous place among both CDPs and municipalities. The community is the eastern terminus of the Chesapeake Bay Bridge. The Stevensville Historic District is one of two registered historic districts in the county, the other being the Centreville Historic District.

The James E. Kirwan House and Store is a living museum located south of the village of Chester on Kent Island, Queen Anne's County, Maryland. It served as a general store, lumber mill, cooper's mill, and blacksmith shop between 1889 and 1955 and facilitated local trade as a port on Kirwan Creek. The estate was donated to the Kent Island Heritage Society in 1998 to be run as a museum.

Broad Creek was a town on western Kent Island, Maryland that existed from the 17th century to the 19th century. The town once served as the eastern terminus of a trans-Chesapeake Bay ferry line that was part of an early route between Annapolis and Philadelphia. In the mid 19th century, with the rise of steamboat travel, much of Kent Island's activity shifted to the towns of Stevensville, Chester, and Dominion, and in 1880, Christ Church, the main congregation on the island, moved to Stevensville, cementing the new town's position as Kent Island's main center of activity. Today, the area once occupied by Broad Creek is widely considered part of Stevensville. All that remains of the town today is the Broad Creek Cemetery and Christ Church, which are being restored.