In the early years, the fare for the round trip train ride from District Line station at the eastern corner of Washington to Chesapeake Beach was 50 cents. Express trains took about 60 minutes to make the trip..locals took about 90 minutes. At the resort, there was a mile of boardwalk lined with concession stands and amusement booths. Other attractions included a carousel complete with Wurlitzer organ, a roller coaster, a band shell, various other popular entertainments, and dancing in the pavilion to the music of J. Worthington Krunkley's orchestra. But the the greatest attraction was the water of the Chesapeake Bay, where hundreds of bathers took the plunge every day.
Extending out into the Bay was a long pier that visitors used for strolling, fishing, and crabbing. Steamboats carrying excursionists from Baltimore docked at the end of the pier. The elegant Belvedere Hotel catered to Washington's tired and jaded for two decades until it was destroyed by fire on March 20, 1923.
The hotel was not rebuilt. Patronage had been declining for several years; affluent Washingtonians now had automobiles that carried them swiftly to ocean beaches. In 1933, a hurricane irreparably damaged the resorts facilities. On April 15, 1935, the last train left Chesapeake Beach. The Chesapeake Beach Railway Company shut down, and the rails were torn up.
The town of Chesapeake Beach was left behind, but it survived. Charter fishing gained popularity. In 1946, a group of entrepreneurs refurbished the amusement park and added a salt water pool. In 1948, slot machines were legalized in Southern Maryland, and business boomed.
Remnants of the old resort are still visible today. The Chesapeake Beach Railway Station on Mears Avenue, for example, has been renovated to house the Chesapeake Beach Railway Museum.
In the summer of 1995, the town opened the Chesapeake Beach Water Park, complete with water slides and a hydraulically controlled flowing river. The Northeast Community Center has been built to provide regional recreation and meeting facilities. The faces have changed and buildings have been rearranged, but Chesapeake Beach is still a pleasant home for its residents and a welcome sight to visitors arriving by car or boat.
Overnight visitors could stay in the luxurious Belvedere Hotel, which was built about 1900. It was located on the north side of 17th Street overlooking the bay before it was destroyed by a fire on March 30, 1923. The resort consisted of a boardwalk over the water and a pleasant park and picnicking area on the nearby land. On the boardwalk, one could find a bandstand, performing bears, games of chance, a carousel, casino, theaters, and many restaurants.
A roller coaster, called "The Great Derby," was constructed over the boardwalk about 1900 and operated until the late 1920's.