The Progressive Trail Ride is one of the only events that is multi generational and brings together riders of varied interests and disciplines. Riders come from as far away as Southern California and everyone is invited to bring their horses to tour the town trails of Woodside, stopping at barns and local landmarks along the way. 


Horses are spoiled by delicious treats, and stops will be designated where finger-food, beverages, restrooms and water will be provided. Maps will be mailed to you in advance as part of your registration package. Each year, rides have a unique theme and costumes are encouraged!


Event Date This Year! (October 14, 2017)
Event Theme: Casino Royale (It's a POKER RIDE!)

Goodies and Prizes:  There are many ways to win prizes this year including up to $1000. See more

How Does it Work?

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.


Riders completing a minimum numbers of stops will receive a goody bag when they turn in their map after the ride. Stops include both public and private horse-friendly locations, concentrating in the areas near central Woodside.

Pre-Register (Download 2017 Registration Form)

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. Your “Ticket to ride” maps will sent to you.


Mail the Official Registration Form by September 30 2017 to Horse-shoeS.jpg 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).



Other Logistical Information:

WHOA! Operations and Prize Desks will be set up at the Mounted Patrol Grounds where riders turn in their maps and exchange them for their Goody Bags. Goody Bags are designed so that they may be carried on horseback.


The WHOA! Desk will be open until 4pm. If you finish your ride at the other end of town, or have to put away your horse, you may come by foot or car to pick up your prizes.

Need Accomodation During
the Event?

For those trailering in for the event, directions are included for trailer parking in your rider packet.


There is limited off site overnite stabling/trailer hookups. First come/first serve after completed registration. 

If you need overnight accommodations, please note this request on your registration form or email WHOA! At at least three weeks prior to the event.




Resource Guide-2016


Day of the Horse Resource Guide 2016

Download PDF

Event Documents

Trail Ride

RIDER Registration



FAIR Flyer



Become a Sponsor


Map to Woodside & Mounted Patrol



Photos on SmugMug

doth 2015



View photos from Day of the Horse. Photos are available for purchase or diwnload through Smugmug!



For general donations or Day of the Horse sponsorship you may process the payment online through the Woodside Community Foundation - the fiscal umbrella for WHOA!




(for Day of the Horse sponsorship, please put "DOTH" in the message field on the form)


Bay Area Equestrian Network


Board Your Horse in Woodside

Many boarding opportunities exist, ranging from small private facilities to larger and public options.

Please fill out a brief online form and we will contact you shortly.