Jamaica Avenue became Jamaica's main shopping street after growing out of a trail Native tribes once used to trade furs for wampum, then a toll road called the Brooklyn and Jamaica Plank Road. The stretch through downtown Jamaica is still often compared to Brooklyn's Fulton Street, cheap and crowded. Macy's and the Valencia movie theater were the last of the avenue's big stores to close, in 1969. The 1980s crack epidemic hollowed the corridor out further. Hair salons and 99 cent stores took over many of the storefronts left behind. A steel elevated train ran above the avenue from 1918 until local merchants pushed for its removal in the 1970s. The three easternmost stations closed in 1977. The rest closed by 1985, and the structure was gone by 1990. Merchants are said to have lost business once the el was actually gone.
The elevated train that still runs nearby today is a mile west, above Jamaica Avenue in Richmond Hill, outside the neighborhood itself. Downtown Jamaica's own elevated structure is , an automated guideway that opened in 2003 and meets the Long Island Rail Road at Sutphin Boulevard and Archer Avenue, next to the JFK Airport stop. The stands a block from that hub, seven stories of white Alabama limestone with a row of Corinthian columns across its front, funded partly by a WPA grant that Mayor La Guardia secured in 1938.
East along Jamaica Avenue, surrounds King Manor, a wood frame farmhouse built around 1730 and expanded by Rufus King in 1755 and again in the early 1800s. The former First Reformed Dutch Church stands directly across the avenue from the house, now used as the . Farther east, near 164th Street, the Jamaica Main post office is brick with a granite base and marble trim. Its portico is lined with four Ionic columns.
