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Day of the Horse

October 8-10, 2021

Friday, October 8

Equestrian Art Show
Time TBD 

Saturday, October 9

Progressive Trail Ride
Time TBD

Sunday, October 10

Horse Fair
Time TBD

A Fun-Filled Celebration for All

The Woodside Day of the Horse celebrates the unique equestrian heritage of Woodside and the extraordinary contribution horses make to the quality of life throughout San Mateo County. Made possible by a public-private partnership of Woodside-area Horse Owners Association (WHOA!), The Town of Woodside and our generous Sponsors and Volunteers.

Art of the Horse Exhibit

Friday October 8, 2021

Online and in person events in 2021

In 2021, the Art of the Horse exhibit will be in person and online for your year round viewing pleasure!

Stay Tuned for Details


The exhibit includes original equestrian themed art created by Bay Area residents.  

Artwork must be the artist’s original design, and may be in oil, acrylic, watercolor, pastel, pen and ink, graphic and charcoal, colored pencil, photography, sculpture, miniatures, or mixed media, as long as the artwork celebrates the horse.

Progressive Trail Ride

Saturday October 9, 2021
Time TBD

Historically, participants from all over California enjoyed this legendary trail ride that gives riders a glimpse of rural America right in the heart of Silicon Valley. 

  • The route will be “Take Your Own Line” within the time allowed and will encourage an efficient path to all stops.
  • Riders may start at any point. The official route will use only town trails without gates.
  • Stop locations will be annotated on the map with directions as needed and well-marked signs.
  • Stops include both public and private horse-friendly locations, concentrating in the areas near central Woodside.
  • All riders must pre-register, sign a liability release, and make a minimum donation per rider.
  • You must bring your own horse.
  • The ride is open to the public; all participants must be mounted on the trail ride.
  • Boots and helmets are strongly advised.
  • No stallions or dogs are permitted.

 WHOA!2995 Woodside Road, #400-466

Woodside, CA 94062

Checks should be payable to: Woodside Community Foundation- WHOA!
The Woodside Community Foundation is a 501(c)(3)

The theme for 2021 is OKTOBERFEST

Costumes reflecting the 2021 theme are encouraged, though any costumes are welcome and are optional!


Horse Fair

Sunday October 10, 2021
Time TBD

There’s equestrian fun and information for everyone in the family.

Details TBD


Woodside Town Hall
2955 Woodside Rd
Woodside CA 94062
view map>

Stay Tuned for Details

Learn more about the history of Day of the Horse!

Receive an Art of the Horse 2021 Calendar

Donate $15 or more to WHOA! and
receive yours today!

For additional funds, you can specify how many calendars you would like to receive, in the “comments” section on the donation form.

If you are local, we will contact you to arrange for pick up. 

Contact WHOA!

2995 Woodside Rd. Suite 400-466, Woodside CA 94062

We will respond as soon as we can!