Ventura Boulevard is one of the primary east-west thouroughfares in the San Fernando Valley; as it was originally a part of the El Camino Real (the trail between Spanish missions), Ventura Boulevard is the oldest route in the San Fernando Valley. It was also U.S. Route 101 before the freeway was built.

Route of Ventura Boulevard

(Other main streets in the San Fernando Valley shown above include Victory Boulevard, Vanowen Boulevard, Roscoe Boulevard, Topanga Canyon Boulevard, and Mulholland Drive.)

Ventura Boulevard has a bit of a snobbish attachment to it as a class-delineator: houses "South of the Blvd." are in rolling hills, with large lots and views. Houses "North of the Blvd." are in The Flats, and belong to less wealthy people.

Ventura Boulevard begins in Woodland Hills, passes through Tarzana, Encino, Sherman Oaks, and finally in Studio City changes into Cahuenga Blvd. and wends through the Cahuenga Pass toward Hollywood.

It has always been the most concentrated location for mom-and-pop shops and small businesses in the Valley; nowadays it has pockets of housing, mini-malls, and boutiques, along with a wide assortment of Bagel, Chinese, Delicatessen, Indian, French, Italian, and Mexican restaurants, book stores, camera stores, car washes, and supermarkets.

Due to natural springs, one of the first inhabited areas of the San Fernando Valley was the land around what is now known as Los Encinos State Historic Park , at the corner of Balboa and Ventura Blvd., which was inhabited by the Tongva Indians possibly for thousands of years. This five acre (20,000 m²) park now includes the original nine-room De La Osa Adobe (built in 1849) and a reservoir shaped like a Spanish guitar that collects the spring water.

The Valley's first golf course opened at the corner of Ventura and Coldwater Canyon in 1922 (now this is site of the Sportsmens Lodge).

Also in 1922, around the area of Cangoa Avenue south of Ventura Boulevard, Victor Girard purchased 2,886 acres (12 km²) of land and planted over 120,000 pepper, sycamore, and eucalyptus trees, later resulting in the appropriately named Woodland Hills.

In 1928, just a couple blocks east of Laurel Canyon, Mack Sennett created his 38 acre (154,000 m²) Keystone Studios, which produced silent movies with stars such as Fatty Arbuckle, W.C. Fields, Stan Laurel, and the Keystone Kops. After talkies, Keystone became Republic Pictures, and then in 1963 CBS Studio Center. Although closed to the public, this complex just a couple blocks off Ventura Boulevard probably makes more TV sitcoms than any other studio.

Ventura Boulevard is also mentioned in Tom Petty's song "Free Fallin'" ("All the vampires walkin' through the valley, Move west down Ventura Boulevard..."), although there is no freeway through Reseda.