Chesapeake Beach Resort: 1900-1929

The Great Derby Roller Coaster, c.1915

The early 1900s were the golden days of the resort when everything was new and innovative.  Imagine riding a giant roller coaster that extended out over the water; jumping on a fabulous carousel for a spin to the music of a Wurlitzer organ; strolling down a 1,600-foot boardwalk lined with games of chance, souvenirs, and refreshments; visiting the bowling alley or the theater. Visitors enjoyed various entertainers or dancing at the boardwalk pavilion while well-known bands played in the bandshell. When it got too hot, there were beaches for swimming. For something more active, there was fishing, crabbing or boating. Local restaurants would even cook your catch. 

For those wanting to extend their visit, they could stay at the elegant Club House, later known as the The Belvedere Hotel. More pocket-friendly choices were the High View Hotel, the Water Edge Hotel or one of the many rooming houses available. The campgrounds were a popular and fun option for families. Many organizations found the Chesapeake Beach Resort an attractive venue. Typical group events included shad bakes, group picnics, and organized games.

From 1900 through the 1920s, the resort was highly popular. On October 31, 1926, the original Dentzel carousel burned, but by 1930, a replacement including some Dentzel figures was built on shore next to the Casino restaurant. By the end of the 1920s, the boardwalk and other structures had suffered the ravages of time and weather.  The upkeep was too costly, and in 1930, the decision was made to recreate the amusement park on land, creating a new chapter.

Gambling, though not sanctioned, was available in many forms on the boardwalk as described in The Calvert Journal, July 8, 1916 article titled “Sunday at Chesapeake Beach”.