Clear Creek Cowboys President Tim Kelley shows the Winslow council his new letter carrying bag he will be using for the ride.
Clear Creek Cowboys President Tim Kelley shows the Winslow council his new letter carrying bag he will be using for the ride. Photo by Shawn White

The Clear Creek Cowboys are preparing for their fourth annual ride along Territorial Road from Holbrook to Winslow next month. On Thursday, March 6, there will be a swearing in ceremony in front of the Winslow Post Office, followed by a hand-off demonstration in front of La Posada Hotel on Second Street.

Then on Saturday, March 8, the riders will set out at 9 a.m. from South Apache Drive and State Highway 77 in Holbrook and make their way down Territorial Road on horseback, passing mail items from one rider to the next until they reach the Standing on the Corner Plaza in Winslow at 2 p.m.

During the week leading up to the ride, members of the Clear Creek Cowboys will visit local elementary schools to share lessons about Old West history and the Pony Express. This educational outreach is a key part of the Cowboys’ mission, and they plan to continue their tradition of making a donation to the school district after the ride.

At last week’s Winslow City Council meeting, the council passed a proclamation in support of the upcoming ride and appropriated $2,000 to assist with event expenses. Clear Creek Cowboys President Tim Kelley and Vice President David Ramos addressed the council to thank the city for its ongoing support, highlighting the ease of working with city officials on street closures and coordinating police presence. Community members are invited to cheer on the riders along the route and welcome them at the finish line in Winslow.

In addition, the Clear Creek Cowboys Association is offering an opportunity for community members to participate in the ride by sending postcards or letters. Preprinted postcards and a sample letter will be available for purchase at several local businesses, including the Winslow Post Office, Standin’ on the Corner Route 66 Gift Shop, Winslow Chamber of Commerce, DeWitt Ranch Supply, Mi Pueblo Mexican Restaurant, Arizona 66 Trading Company, and Tom’s Store in Winslow. Cards can also be purchased directly from members of the association.

The cost for a stamped postcard is $1, with an unstamped postcard and sample letter costing 50 cents.