Donning their signature lavender blouses and white cowboy hats, the Main Street Sidesaddlers are the female counterparts to the Main Street Cowboys. With a focus on hospitality, they serve as ambassadors for Pendleton.

The group’s main fundraiser is the Twilight Breakfast. Calling it the “unofficial official start of Round-Up,” it’s on the Thursday prior to all the festivities.

The 2023 event is Thursday, Sept. 7, 4:30-7 p.m. at Stillman Park, 411 S.E. Byers Ave. In addition to a full plate of breakfast fare, the fundraiser features door prizes and live music. The cost is $10 for adults, $5 for children and free for ages 3 and under.

Sidesaddlers Treasurer Risa Riggen said there are about 30 members. And they’ve welcomed a handful of members each year in the past few years.

When the group was initially formed in 1959, membership was limited to those married to a Main Street Cowboy. However, by the 1970s, the Sidesaddlers welcomed all local women with a desire to serve.

As September rolls around, Riggen said the group is extra busy with behind-the-scenes preparation leading up to Pendleton Round-Up week. They offer a helping hand to Veterans of Foreign Wars Let ’er Buck Post No. 922 — cleaning grills and cutting ham. In addition, she said they spread Western hospitality by making appearances with Round-Up and Happy Canyon royalty for barbecues at area nursing homes and assisted living facilities.

And the Sidesaddlers get around — during Round-Up week, Riggen said they serve Cowboy Coffee during Tuesday’s slack at the Round-Up Grounds. And when the Cowboys transform South Main Street into “The Greatest Free Show in the West,” the Sidesaddlers serve in the vendor hospitality room and man the downtown information booth.

In addition to handing out brochures and answering questions from visitors, they help sell Main Street Cowboys promotional merchandise.

Riggen said the Sidesaddlers also participate in other activities throughout the year. One of the most enjoyable, she said, is going to parades with their signature calliope.

“We enjoy parades and watching the organization grow and develop,” she said. “We are looking for younger members that would like to be trained to play the calliope.”

In addition, they are involved with Pendleton’s Hometown Christmas celebration and serving in the coaches/referee hospitality rooms during the Oregon School Activities Association 2A state basketball tournament.

The group has made donations to Clearview Disability Resource Center, Domestic Violence Services, the Drug Abuse Resistance Education program and holiday giving trees. Riggen said the Sidesaddlers are in the process of gaining its own nonprofit status to “more thoughtfully give money” back to the community.