Peaks Island became famous for its summer entertainment in the late 1880's and earned the nickname “Coney Island of Maine.” Entertainment on Peaks Island has a long history, beginning with a picnic grove that visitors accessed by rowboat during the 1850s. After the Civil War, the grove was used as a respite for Maine Regiments, until the Regiments built their own Memorial Halls on Peaks (5th and 8th Maine) and other Islands. Starting in 1881, Jimmy Brackett transformed the area and shoreline into an amusement park, later known as Greenwood Garden, that featured an open-air roller skating/roller polo skating rink, later enclosed and converted to an Opera House, then a dance hall, and later a the famous Greenwood Playhouse. Greenwood Garden had many amusements including a merry-go-round, bandstand, restaurants, Beerhaus, Ferris wheel, midway, and observation tower. Just outside Greenwood Garden entrance on Island Avenue was a bowling alley and a shooting gallery. At one time, rumor has it that on opening day, Mr Brackett would lead an elephant on the road around the park, and the road was known as Elephant Avenue. Surrounding the amusement park, small gothic-style cottages were built on former camp sites along Adams Street and Oakland Avenue.
The growth in tourism was spurred in part by the growth of steamship travel and rising leisure time among the American middle class. Visitors traveled from New York and Boston by rail or ship to partake in the island’s many shows or to stay in one of several seaside resort hotels. By the 1920s island vacations began to decline as automobile touring grew in popularity. A series of devastating fires in 1918, 1934, and 1936 destroyed many of the Island hotels and entertainment facilities at Greenwood Garden. The Playhouse, along with the old bowling alley and shooting gallery (private residences now), and private cottages are all that remain.
Since 1955, Greenwood Garden is owned and operated by the volunteer members of the Peaks Island Lions Club. All of the proceeds from this event center are donated to charities, awarded as college scholarships, and used to restore or maintain this historic property.