Canyonville Pioneer Days

At 5:15 on the Thursday evening, the Canyonville Lions Club serves its Old Time BBQ in the pavilion at Pioneer Park, and Pioneer Days begins. The 2026 festival, counted as the 60th, ran August 27 through 30. After the barbecue came a “First Pioneer Days” presentation at 5:45. At 6:30 the Chamber of Commerce held its pie auction, which the organizers advertised as “The best pies in the west!” The Eddy Ross Band played from 8:00 to 10:00. Earlier that afternoon, at 2:00, a jam contest had been judged at the Pioneer Stage.

The Canyonville Pioneer Days Committee runs the festival. Two days before the 2026 opening, the committee thanked the Lions Club and Tamara Hoff for “Keeping the Pioneer Days Tradition alive!” Bob Chaney, a board member, gave the reason so many families come in 2024: “It’s one of the last celebrations of the summer before we all get back to this grind of school for a lot of kids and everything. And it’s family-oriented, and there aren’t many of those things left anymore and it’s free.”

Three stages and a midway

The festival spreads across the park on three stages, the Pioneer, the Creekside and the Lumberjack, with a midway, vendor booths, food and a beer garden. In 2026 the midway ran from 5 to 10 p.m. on Thursday and from 10 a.m. to 11 p.m. on Friday and Saturday.

The 2026 Friday opened at 10:00 with the Downstream Drum Team on the Creekside Stage. At 10:30 the Bergin College of Canine Studies gave a demonstration at the Pioneer Stage. The afternoon held Bigfoot races and watermelon eating contests. Borrowed Time and Bruce Knowlton played the Creekside Stage, and Toyz took the stage at 6:00. The headliner that night was The Sweet. “Canyonville! SWEET has arrived! Can’t wait for 8:00!” the committee posted that afternoon. VIP seats up close to the Pioneer Stage cost $20 a day, cash only. The bleachers were free, and the committee called the show “our treat to the community.”

Saturday is the parade day, and Dawn Cartwright, president of Pioneer Days in 2024, said it draws the most people. In 2026 Saturday also held Pioneer Life Demos in the pavilion, a dog show, the Lions Club cake walk and a donut eating competition. On the music side were Steve’s Country Music Roundup and Steve Kelly’s CHERRY CHERRY, a Neil Diamond tribute, and Main Street, a Bob Seger tribute band, closed the night at 9:30. A tractor show and the 2026 Queens Court were also on the program. On Sunday came a horseshoe competition and Christian music from Open Bible Church and The Solid Rock Band. The News-Review’s schedule put the close at noon on Sunday. A regional events listing gave 5:00 p.m.

The grease pole and the frog

The contests change from year to year, but a few return. Cartwright’s favorites in 2024 were both on Saturday. “I’m kind of kid-orientated, so I love watching the kids try to do the grease pool and the frog,” she said. “Both of these are classics that I don’t think anyone else does.” The frog jumping contest was billed as the 47th annual in 2018, and contestants brought their own frogs. The bed race that year was in its 16th year. Teams built a bed from a frame, wheels and a mattress, put someone on it, and pushed it a block down Main Street.

The 2018 festival, then three days long, also offered mechanical bull rides, fry bread, a Dutch oven cook-off, an antique tractor show, kids’ tractor pulls, a dachshund derby, a cribbage tournament and a magic show. In 2022, the 56th year and four days long, Spallino chainsaw art was carved at the Lumberjack Stage, the Old Time Fiddlers played, and square dancers performed at the Pioneer Stage. In 2024 the Lumberjack Stage held a frisbee challenge and a beard, mustache and hair contest. That year’s Pioneer Life Demonstrations included wool spinning and wash tubs.

“We try to include a lot of things about the pioneers, because (Canyonville) is the third oldest town in the state, and it was a big pioneer stop,” Cartwright said. “It was a big supply town, so we’re really big on pioneers here.”

In 2018 the parade began at 10 a.m. at Seven Feathers Casino Resort and wound through town for about 45 minutes with cars, horses, floats and drill teams. In 2024 it started on Main Street, with a car show after it. Misty Boye, a Canyonville business owner and the event coordinator in 2018, remembered the festival as her last carefree weekend before school. “It really was the big event of the summer,” she said. “We have people that have never missed a Pioneer Day ever. It’s a time where they come out and see people they haven’t seen in a while.” Chaney’s version, in 2024, was the kids’ “last fling, that last corndog, whatever it might be.”

A museum lot that became a park

The ground under the stages was meant for something else. Lawrence Boyle gave the city the part of Pioneer Park east of Canyon Street and south of East Fourth Street in 1967, on the condition that a museum be built there. According to the city, the site was judged too small, so Boyle proposed a park. He named it the John and Mary Rose Jackson Pioneer Memorial Park and asked for a board drawn from the Lions Club, the city and the Historical Society.

In 1969 the city sought a grant to buy a little over half an acre from Clyde and Verneta Marriott. The option to buy was running out, so the Lions Club took out a loan for the whole price. The federal money finally arrived in June 1972. The Lions Club bought a last wedge by the highway and the creek from the estate of Archie and Sonia Kindred and gave it to the city.

Volunteers did most of the building that followed: the barbecue, the picnic pavilion, a fire department kitchen, the stage, the bleachers, the entrance logs and an Applegate Trail kiosk. A covered footbridge over Canyon Creek was finished for the Bicentennial in 1976. On the back of the restrooms hangs a circular saw donated by C&D Lumber Company. In 1993 Charles Buehner, an artist from Riddle, painted the covered wagon trek to Oregon on its blade. Beside the Tiller-Trail Highway stands a section of a Douglas fir 110 inches across, which held 10,640 board feet of wood. The city says the tree was 142 years old when Columbus reached America.

Down the dread canyon

Pioneer Days was started in 1966 to celebrate Canyonville as the third-oldest town in Oregon and a main supply town on the Oregon Trail. The town sits on the Applegate Trail, the southern route into the state. Jesse and Lindsey Applegate camped here in 1846. The city’s history describes the “dread canyon” as feared by most travelers. Wagons were often taken apart and let down the steep inclines on ropes, and the canyon was littered with equipment left behind when the animals gave out.

By 1851 Joseph Knott kept the first store in a dirt-floored log cabin where Fifth Street is now. His stock was tobacco, overalls and whiskey, “mostly whiskey.” Knott and Joel Perkins ran a ferry across the South Umpqua and called the settlement Kenyonville. Jesse Roberts bought the place in 1858, platted the town site and named it Canyonville. That same year the town’s first wedding joined Phoebe Thrush and Isaac Boyle. Lawrence Boyle, who gave the park its land, descended from that family. Some of the pioneers who came down the trail stayed, and their descendants remember them during Pioneer Days.

The festival has its own small books, Pioneer Days in South Umpqua Valley, published as part of the celebration with recipes, pictures and local history. Volume 56 carries “The Barber of C’Ville” by Susan Waddle and Jerry McKinney. Its cover shows McKinney at his Canyonville barber shop in 1998, “42 years in by the number on the window.”