The historic Westwind Community Barn dates back to the 1940's when Frank Ellithorpe built the first six stalls and raised Morgan and Arabian horses. The original barn resembled the gambrel-roofed barns of New England. Ellithorpe sold the land in 1965 to Robert D. Clement who added 17 stalls, a tack room and an arena.

Hungarian Countess Margit Bessenyey purchased the property in 1971 as a California extension of her Montana stud farm where she raised Hungarian thoroughbred horses. The Countess was the granddaughter of Marcus Daly, the Anaconda Copper Company tycoon, daughter of a Hungarian count, and widow of the Hungarian ambassador to the United States. The Countess and the well-known horsewoman, Linda Tellington-Jones, moved the nationally known Pacific Coast School of Horsemanship to Los Altos Hills and combined the training of Hungarian horses with the total education of horsemen in the equine industry. Under Linda's management and Jim Forderer's instruction, the Pacific Coast School grew – drawing students from all over the country and Europe.

The Countess added a third wing to the barn and other elegant touches, which included the ornate double oak door entry, carved in Mexico, and the elaborate spiral stairway which was imported from France. A full-sized dressage ring was built and a cross-country course was added.

In 1976, the Countess donated over 13 acres of land to the Town of Los Altos Hills and the Town bought Westwind Community Barn for $25,000. This complemented the earlier donation of 55 acres by Dr. Albert Byrne, known as Byrne Preserve. The purchase of a hiking and wildlife corridor, enabled by Lucile Packard and The Packard Foundation, connects the barn and preserve to Hidden Villa, Black Mountain, and the Pacific Ocean beyond.

In 1977, the Town Council approved the proposal presented by a local group, the Friends of Westwind, to lease and manage the barn as a cooperative stabling facility. The barn is one of the few community owned barns in the country.

To meet the Town Council's wishes that the Westwind Community Barn serve "the broader community," a therapeutic horse riding program for physically handicapped children was established. Under the supervision of Jim Forderer, Westwind 4-H Riding for the Handicapped began operating in 1978. Over 500 children with physical handicaps have been served since the inception of the riding program. Thousands of volunteers have given countless hours, many of these high school students fulfilling community service requirements.

Westwind Community Barn is home to the Pacific Ridge Chapter of the United States Pony Club. Many youngsters who live in Los Altos Hills have been given the opportunity to learn good horsemanship, team skills and leadership. The rigorous program is widely acclaimed and nationally has been the starting point of many members of the US Olympic Equestrian Team.

The barn is also the center for many of the recreation programs offered by the Los Altos Hills Parks & Recreation Department, including summer horsemanship camps, Ohlone nature camps, horse management classes, and a new year-round riding program. Other recent activities include Earth Day celebrations, schooling horse shows, and a guided hike to local private vineyards.

Both the Town and the Friends have contributed financially over the years towards the regular upkeep and improvement of the premises. Additional major capital expenditure is required to restore the buildings and provide an endowment for future maintenance. This is beyond the scope of what the Town is able to provide. In 2002, the Town Council adopted a Citizens' Initiative prohibiting the barn's sale without voter approval. This expression of confidence and long-term support encouraged Supporters of Westwind Community Barn to create a charitable 501(c)(3) organization to raise the necessary funds.