Recorded history begins with the construction of the Orange Grove House of Refuge in 1876. The house derives its name from the grove of mature sour oranges and other tropical fruit trees found at the site chosen for the house of refuge. No record or evidence of who planted the trees has survived.

In 1894 William Seelye Linton, postmaster of Saginaw, Michigan, bought a tract of land just west of the Orange Grove House of Refuge, and began selling plots in what he hoped would become a farming community. Initially, this community was named after Linton. In 1896 Henry Flagler extended his Florida East Coast Railroad south from West Palm Beach to Miami, with a station at Linton.

In 1911, the area was chartered by the State of Florida as an incorporated town. In the same year, pineapple and tomato canning plants were built. Pineapples became the primary crop of the area. This is reflected in the name of the present day Pineapple Grove neighborhood near downtown Delray Beach.

Downtown Delray Beach is a retail, cultural, and residential hub. The area offers restaurants, retail, nightclubs, and art galleries. The city presents a pedestrian-friendly atmosphere.

In 2009, expansion of the Downtown Delray Beach Arts District was established that features galleries and numerous cultural organizations of South Florida.

The Delray Beach Garlic Fest is a three day music, food, and art festival held annually on the grounds of Old School Square. The Delray Affair is a three day long art and street fair, in the Downtown Delray Arts District annually. Art & Jazz on the Avenue, held six times a year, is produced by the Delray Beach Downtown Marketing Cooperative. Gallery Walk held every Friday night 7pm to 10pm is where downtown galleries, art studios, and showrooms open their doors to the public for an evening of art, music, & refreshments along Atlantic Avenue in the Downtown Delray Arts District.

Nearby is the Town Center at Boca Raton that the Simon Property Group bought and redeveloped in 1991. They improved upon it and built an outdoor lifestyle center, which is popular among Delray residents. Town Center Mall is an important tourist attraction and the largest indoor mall in Palm Beach County.