[8] In 1894, sawmill operator W. B. Wright opened the 26-mile (42 km) Yellow River Railroad between Crestview and Florala, Alabama via Auburn, Campton, and Laurel Hill.

However, without significant shippers to sustain the line, it was eventually used for freight car storage in the early 1980s and was abandoned in May 1985, with 25.3 miles of track removed.

[12] The second and final public execution in Okaloosa County took place on September 23, 1921, when Putnam Ponsell and Jacob Benjamin Marin were hanged for the murder of John F. Tuggle.

[14] A modern bus terminal served by Greyhound Lines' Jacksonville-Los Angeles route, with connections north to Atlanta, Memphis, and New York,[15] opened on the corner of Ferdon and Pearl Streets on May 9, 1941.

[16] As nearby Eglin Field expanded into a major testing base, the Louisville and Nashville Railroad laid a long sidetrack in Crestview in the spring of 1941 to handle the influx of oil tank cars required for a vast paving project on ten new airfields.

[18][19] In January 1943, a misunderstanding involving Crestview’s constabulary led to the town being briefly off-limits to military personnel from Eglin Field.

The Pensacola News Journal reported on January 31, 1943, that the restriction had been lifted after a conference between town officials and Eglin authorities.

The incident was triggered when the town marshal attempted to arrest a soldier for reckless driving and an Eglin officer for interference.

[20] On July 31, 1949, the L&N inaugurated the Gulf Wind streamliner through Crestview, connecting New Orleans and Jacksonville in partnership with the Seaboard Air Line Railroad, replacing the heavyweight New Orleans-Florida Limited.

[21] As part of the 2005 Base Realignment and Closure (BRAC) round, Crestview experienced significant population growth when the U.S. Army's 7th Special Forces Group relocated from Fort Bragg, North Carolina to a newly built facility on the northern end of the Eglin Air Force Base reservation, about six miles south of the city.

In 2007, longtime mayor George Whitehurst resigned, leading to the election of David Cadle, a retired director of the Crestview High School band, The Big Red Machine.

The city lies within the USDA Hardiness Zone 8, where the coldest temperature of the season typically ranges between 10 °F (−12 °C) and 20 °F (−7 °C).

Sapp reported shipping blueberries from May 10 until the end of August, earning $605.85 for his crop, in addition to sharing some with friends and family.

Summer generally lasts from late April to early October, and winter extends from mid-December to mid-February.

In 2002, the Crestview Robert L. F. Sikes Public Library opened, named in honor of the local congressman.

However, service east of New Orleans to Jacksonville and Orlando was suspended due to damage to the rail line of CSX caused by Hurricane Katrina in 2005.

This was previously the route of the Gulf Wind streamlined passenger train, operated by the Louisville and Nashville Railroad.