Main Street in Ramona was lined with cheering spectators on May 16 for the long-awaited return of the Ramona Main Street Parade.
Families gathered early to find the perfect viewing spot to watch parade entries, local groups, businesses and community organizations make their way down the street on a variety of decorated floats. A total of 40 entries participated in the parade’s return after six years.
Four-year-old Kennedy Willeford said she was “excited to see the horses and the fire trucks” as she waited with her mom, sister, and nana for the parade to begin.
BackCountry Heroes, the parade grand marshal, led the parade through town in an authentic Old West-style carriage pulled by a four-horse team of Clydesdales. The organization was recognized for its dedication and service to veterans, first responders and the backcountry community.
A team of Clydesdale horses from Temecula Carriage Company pulls the 2026 Ramona Main Street Parade Grand Marshal, BackCountry Heroes, through downtown Ramona. (Stephanie Ogilvie)
Ramona residents Terra Willeford, 4-year-old Kennedy Willeford, 2-year-old Collette Willeford and Deena “Nana” Willeford sat along Ramona’s Main Street enjoying fresh smoothies as they waited for the parade to begin. (Stephanie Ogilvie)
Sixteen-year-old Ramona resident Madelyn Kennedy carries the Turquoise Barn Cider flag in the Ramona Main Street Parade held on Saturday, May 16, 2026. (Stephanie Ogilvie)
Ramona High School’s Jazz Band entertained parade crowds with classic jazz music as they performed their way down Main Street during the return of the Ramona Main Street Parade. (Stephanie Ogilvie)
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A team of Clydesdale horses from Temecula Carriage Company pulls the 2026 Ramona Main Street Parade Grand Marshal, BackCountry Heroes, through downtown Ramona. (Stephanie Ogilvie)
“It is an honor to be selected as the Grand Marshal of the Ramona Main Street Parade, especially since it is the first one in years. It is truly an honor for myself, my family, and BackCountry Heroes to be a part of such a great community event,” said Kaleb Weakly, founder of the group.
Sarah Kennedy, a member of the Ramona Main Street Parade Committee, said she was overwhelmed with gratitude by the turnout for this year’s parade.
Madison Kirkman, a sixth-generation Ramona resident, rides his pre-1900s 56-inch-wheel Penny Farthing bicycle representing the McKeen Motor Car Company Historical Society, a Ramona-based nonprofit organization dedicated to preserving and restoring historic McKeen railcars and railroad history. (Stephanie Ogilvie)
Ramona Rodeo royalty wave to the crowd as they ride down Main Street during the return of the Ramona Main Street Parade. From left: 2026 Ramona Rodeo Queen Stella Erb, 2026 Ramona Rodeo Young Miss Carrie Vincent, and 2026 Ramona Rodeo Junior Queen Jessie James. (Stephanie Ogilvie)
Chancelor Jaeger, owner of Red Tail Ranch SD, drives his vintage 1952 John Deere Model A tractor while pulling family and friends in a restored 1950s wagon during the return of the Ramona Main Street Parade on Saturday, May 16. Red Tail Ranch SD offers tours of its rural ranch homestead, where visitors can meet and interact with a variety of ranch animals. (Stephanie Ogilvie)
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Madison Kirkman, a sixth-generation Ramona resident, rides his pre-1900s 56-inch-wheel Penny Farthing bicycle representing the McKeen Motor Car Company Historical Society, a Ramona-based nonprofit organization dedicated to preserving and restoring historic McKeen railcars and railroad history. (Stephanie Ogilvie)
“We appreciate the overflowing support from the community, the sponsors, the participants, the volunteers and the audience,” Kennedy said. “We couldn’t have done it without them. This was the first year back since COVID, and it was a huge success. Thank you, Ramona!”
“Pat Donovan, Bonnie Kirkland and their families helped make the return of the parade possible by passing down their expertise, along with support from the Ramona Rodeo Foundation,” Kennedy said. “We also could not have done it without the help of Pro Traffic, all of the amazing volunteers, Pete Lavelle and Neil Kennedy for their organization, and especially Lavelle for handling the permits and logistics that made the parade possible.”
The committee is already planning for the 2027 parade.