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. 

Saturday, October 12, 2019
TRAIL RIDE 11:00am-3:00pm | After Ride Party 3:00pm-5:00pm

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!

Download 2019 Flyer

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.




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.


Register online, or Mail the Official 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.




Photos on SmugMug

doth 2015



View photos
from Day of the Horse. Photos are available for purchase or download 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.