Summerland's first inhabitants were the Syilx (Okanagan Salish), with the First Nations boundaries extending from Kamloops to southern Washington state.

Summerland's proud and diverse past includes hunting and fur trading, ranching, orchards and fruit industries, transportation hubs and more recently, tourism.

Immigration to the Summerland area commenced in the late 1880s when the first settlers arrived and began diverting water to irrigate orchards.

The upper benches continued to be an important transportation route and a number of small communities were constructed or were planned for development.

By 1907, Summerland had access to Peachland and Penticton with a well-established road system, and a ferry service connecting the community with the eastern shore of Okanagan Lake (Naramata).

[15] Summerland is popular because of its situation on Okanagan Lake and sandy beaches, a destination for three major Canadian population centres (Vancouver, Calgary, Edmonton).

Agriculture, featuring fresh tree fruits (peaches, cherries, apricots, apples and pears), and canneries, were the economic engine of the region until the late 20th century.

The railway takes tourists on a trip around the Dale Meadows region of Summerland and further, eventually ending at the famous Trout Creek Trestle.

Football Club (FC) Detonate, founded in 2024, competes in the South Okanagan Men’s Soccer League (SOMSL).

In the summer of 2003, a severe drought nearly rendered the town's reservoir incapable of ensuring a water supply through to the beginning of the next annual replenishment cycle.

Summerland is home to an extinct volcano, known locally as Giant's Head Mountain – so-named for its gigantic facial profile as viewed from the southeast.

This hill dominates the town's land features and provides an hour's hike to the top for an expansive view up and down the Okanagan Valley.

The hills surrounding Summerland is the natural habitat for black bear, white-tailed deer, moose, cougars and bobcats, California big-horn sheep, mountain goats, and rattlesnakes.

These warm nights in a dry climate means that Summerland has the lowest morning relative humidity in Canada from May through September.