Glen Riddle Farm

Ocean Downs is a casino and harness racing track in Berlin, Maryland, near Ocean City. It is owned and operated by Churchill Downs Inc. Construction started in 1947 as a harness racetrack, and it opened in 1949 with Ocean Downs Racing Association (ODRA) as owner. After two failing years, ODRA began to speculate about switching to thoroughbred racing, but that did not happen. In 1986, the Maryland Racing Commission was hesitant to approve race days at Ocean Downs due to the track's management. Hence, the owners of Rosecroft Raceway, a competing harness track in Maryland, purchased Ocean Downs and renamed it Delmarva Downs. In 1987, real estate developer Mark Vogel purchased the racetrack. However, Ocean Downs went into bankruptcy in 1991, and it was sold to Fred Weisman, a California entrepreneur. Weisman died in 1994, and the track was sold again to Cloverleaf Standardbred Owners Association (CSOA) in partnership with Bally Entertainment. After the purchase, the racetrack returned to its former name, Ocean Downs. Two years later, CSOA sold Ocean Downs to Bally Entertainment because the track continued to lose money, and Bally Entertainment expected slot machines to be legalized in the state. That did not happen, and William Rickman purchased Ocean Downs from Bally Entertainment in 2000. Maryland voters approved slot machines in 2008 for five locations, including Worcester County. In 2010, construction of a $45-million casino began and opened the following year.

Sherwood Forest is an unincorporated community in Worcester County, Maryland, United States. Sherwood Forest is located in the southern portion of Ocean Pines.

Ocean Pines is a census-designated place (CDP) in Worcester County, Maryland, United States. The population was 11,710 at the 2010 census. It is part of the Salisbury, Maryland-Delaware Metropolitan Statistical Area. It shares the same ZIP code as Berlin. The community began as a small resort in 1968 and today is the largest residential community in Worcester County. It is the largest concentration of retirees on the Eastern Shore. During the summer months, Ocean Pines' population swells by more than 50 percent.

Sinepuxent or Sinepuxent Town was a village in Worcester County, Maryland, located on Sinepuxent Neck across Sinepuxent Bay from the barrier island of Assateague. The village was destroyed by a hurricane in 1818 and never rebuilt. Its location arose in large part from its convenience to ocean-going ships: an inlet—Sinepuxent Inlet—allowed access through Assateague Island from the Atlantic Ocean to Sinepuxent Bay, until it was closed by the same hurricane that destroyed the village. Sinepuxent was the birthplace of U.S. Navy officer Stephen Decatur in 1779.

West Ocean City is a census-designated place (CDP) in Worcester County, Maryland, United States. The population was 4,375 at the 2010 census. It is part of the Salisbury, Maryland-Delaware Metropolitan Statistical Area.

Stephen Decatur High School (commonly Stephen Decatur, Stephen Decatur High, SDHS) is a four-year public high school in Berlin, Worcester County, Maryland, United States. With the grades of 9–12 the school is a part of Worcester County Public Schools. It is one of four public high schools in Worcester County along with Pocomoke High School, Worcester Technical High School, and Snow Hill High School. The school was opened in 1954.

Dog and Bitch Island is depending on the sources one or two islands in Worcester County, Maryland, in the United States. It is located within the Isle of Wight Bay. The island is small in size and marshy. In 2014 the federal Army Corps of Engineers pumped 18,000 cubic yards of material from navigation channel dredging operations onto the island to improve migratory bird habitat.

The St. Martin River is a tributary of Isle of Wight Bay in Worcester County, Maryland. Approximately 4.4 miles (7.1 km) long, it drains the northernmost part of Worcester County. A short river, the St. Martin broadens rapidly to enter Isle of Wight Bay where the bay is crossed by Maryland Route 90. Most of the river is a tidal estuary. Its two main tributaries are the Bishopville Prong and the Shingle Landing Prong. The St. Martin forms the northern boundary of Ocean Pines, Maryland; Bishopville, Maryland is on the Bishopville Prong of the river.

Isle of Wight Bay is a lagoon that separates part of mainland Worcester County, Maryland from the midtown part of Ocean City, also in Worcester County. To the north, it connects to the Assawoman Bay just south of the Assawoman Bay Bridge, and to the south it connects to the Sinepuxent Bay at the north end of West Ocean City where the bay narrows between the Thoroughfare channel and Mallard Island. The major tributary of Isle of Wight Bay is the St. Martin's River; other tributaries include Turville Creek, Manklin Creek, and Herring Creek.

The Harry W. Kelley Memorial Bridge is a bridge in the U.S. state of Maryland. It carries 4 lanes of U.S. Route 50, plus two sidewalks, across Sinepuxent Bay, connecting the downtown area of Ocean City, Maryland to the mainland of Worcester County, Maryland within West Ocean City, and is mere feet from the national eastern terminus of said route. It is one of four entrances to the resort town, and the southernmost of them all; the others are Maryland Route 90, Delaware Route 54, and Delaware Route 1. The bridge features a drawbridge span near the Ocean City end. The bridge is named for Harry W. Kelley, a former mayor of Ocean City. The current bridge in this location, built in 1942, replaces an earlier bridge that was slightly downstream of the current site, which used what is now Maryland Route 707 (Old Bridge Road) to cross the Sinepuxent Bay and connect to downtown Ocean City as Worcester Street. At the time of its construction, the bridge carried U.S. Route 213; it was changed to its current number in 1948 when the extension of US 50 replaced US 213 south of Queen Anne's County. Currently the bridge is a busy center of activity in the city, and is utilized by many fishermen, joggers, and cyclists. The bridge is the target of much discussion due to its age and structural issues, as well as its antiquated design. In August 2010, the Maryland State Highway Administration decided to construct a new drawbridge to replace the current structure. The new drawbridge was selected over a higher fixed span, which would have cost more and have displaced more properties. The bridge is not expected to be constructed until at least 2035, with $300 million in funding for planning of the bridge. When the new bridge is complete, the existing structure is planned to be turned into a fishing pier with the central part of the bridge removed.

Lewis Corner is an unincorporated community in Worcester County, Maryland, United States. Lewis Corner is located at the junction of Maryland routes 376 and 611, 4.3 miles (6.9 km) east-southeast of Berlin.

Caleb's Discovery is a historic home located two miles west of Berlin, Worcester County, Maryland. The house consists of two sections, the 1+1⁄2-story kitchen wing, dating from the early 18th century, and the 2+1⁄2-story living room wing, dating from about 1820. It is a good illustration of the incorporation of an early house into a later structure without the loss of the earlier building's identity.It was listed on the National Register of Historic Places in 1975.