The Latgawa Native American tribe was present in the early 1850s when the sudden influx of non-indigenous settlers resulted in the Rogue River Wars.

After acquiring a large amount of land from the Lions Club and the federal government between 1930 and 1933, the city created the 1,740-acre (700 ha) Prescott Park in 1937.

The oldest layer, the 35 to 50-million-year-old Payne Cliffs Formation, forms the base of the peak and consists of sedimentary sandstone, shale, and conglomerates.

[8] At the summit, younger basalt dikes and intrusions K–Ar dated to 30.82 ± 2 million years ago form a relatively erosion-resistant cap,[7] likely contributing to the peak's isolation and familiar conical shape.

[6][15] The first European Americans to visit the area were a group of fur trappers led by Peter Skene Ogden who traveled north through the Rogue Valley on February 14, 1827.

[13][14][17][18] In October 1883, construction of the Oregon and California Railroad was begun through the center of the Rogue Valley, bypassing Jacksonville, the county seat.

[6] In 1929, the Lions Club purchased two sizable portions of land on the peak, and deeded 200 acres (81 ha) to Medford for recreational use the following year.

[25][26] The park was dedicated in 1937 to George J. Prescott, a Lions Club leader and Medford police officer who was killed on duty on March 16, 1933.

Park maintenance ceased due to municipal budget problems, and gasoline rationing caused the number of visitors to drop markedly.

[6][27] During the late 1990s, the park experienced a surge in vandalism, littering, and wildfires caused by off-roading,[27][30] and Roxy Ann Road became nearly impassable because of lack of maintenance.

[32][35] Prescott Park and Roxy Ann Peak's upper slopes remain relatively undeveloped, being outside of Medford's city limits and urban growth boundary.

Oregon House Bill 3375 required that new construction on slopes of 20 percent or greater with unstable soil undergo increased regulation and an extended approval process.

[40][41] On September 21, 2009, a wildfire broke out on Roxy Ann Peak's western slopes and consumed approximately 633 acres (256 ha).

[49] At higher elevations, the vegetation transitions to mixed coniferous forest, dominated by Douglas fir, ponderosa pine, incense cedar, western juniper, and Pacific madrone trees.

[50] Mammals that inhabit the mountain include black-tailed deer, cougars, bobcats, skunks, raccoons, coyotes, bears, weasels, and squirrels.

The herd swelled to over 100 individuals in the mid-2000s, causing traffic problems and severe damage to local pear orchards, but shrank to about 40 members by 2009 after an Oregon Department of Fish and Wildlife relocation effort.

[14] Roxy Ann Peak and Prescott Park serve as Medford's most important viewshed, open space reserve, and recreational resource.

[37][40] Popular recreational activities on the peak include picnicking and hiking, mountain biking, and horseback riding on the 4 miles (6 km) of designated trails in Prescott Park, which range in difficulty from moderate to steep.

[14][34][54] In August 2013, the city of Medford and the International Mountain Bicycling Association released a conceptual plan detailing future improvements to the park's trail system.