Henryetta is preparing to mark a milestone 125 years in the making with a spectacular blend of tradition and celebration. This year’s Labor Day festivities, scheduled for Aug. 28 through Sept. 1, will double as the city’s official quasquicentennial – honoring the founding of Henryetta in 1900 and the opening of its first post office on Aug. 28 of that year.

The week-long celebration promises something for everyone: pageants, parades, rodeos, concerts, games and an array of contests that showcase Henryetta’s unique hometown pride. With help from the Henryetta Lions Club, Chamber of Commerce and local partners, the event is shaping up to be one of the city’s largest and most memorable celebrations in decades.

— A Celebration 125 Years in the Making The anniversary highlights Henryetta’s journey from its roots in the Indian Territory era to becoming the tight-knit community it is today. In honor of the milestone, the Henryetta Chamber of Commerce is inviting all past Miss Labor Day queens to participate in a special anniversary float during Monday’s parade, offering a nostalgic glimpse at the city’s history.

In addition, Bruce Jones has created a special video series documenting the rich history of Henryetta. The series will be available for download, and anyone interested in pre-purchasing or learning more can contact the Chamber of Commerce directly.

— Festivities Begin with Pageantry Although the main celebration falls on Labor Day weekend, activities kick off early with the beloved Labor Day Baby Pageant at 10 a.m. on Friday, Aug. 23, followed by the Miss Labor Day Pageant that evening at 7 p.m. Both will be held at the Henryetta High School Auditorium, setting the stage for a week filled with tradition and community spirit.

— Carnival on Main

From Aug. 28 through Sept. 1, downtown Henryetta will be transformed with a bustling Carnival on E. Main Street. Open from 6 to 10 p.m. on weekdays and 6 to 11 p.m. on weekends, the carnival will feature rides, games and attractions. Admission options include $30 nightly bracelets or single tickets available at the gate.

— Saturday, Aug. 30: Cars, Contests & Cornhole Saturday kicks off bright and early with the 13th Annual First Family FCU Car and Bike Show at 8 a.m. on West Main Street. In the spirit of giving, entrants who bring a brand-new toy will have their registration fee waived, helping collect toys for America’s Guardians Club and their mission to fill a semi-trailer with donations for the Children’s Hospital.

The day also features the Smokin’ Hot Pinup Contest at 10 a.m. and the wildly popular Beard & ’Stache Competition at 11 a.m. at the Briefcase Event Center.

At 12:30 p.m., the Vets for Pets Costume Contest will take center stage, followed by the Jared Been Memorial Cornhole Tournament at 3 p.m., hosted by the Lions Club.

The evening lineup includes a Gospel Concert at 6 p.m. at First Baptist Church and the 32nd Annual Jim Shoulders Living Legends PRCA Rodeo at Nichols Park, beginning at 8 p.m. with Mutton Bustin’ at 6:30 p.m.

— Sunday, Aug. 31: Horseshoes, Disc Golf & Fireworks Sunday begins with PRCA Steer Roping at Nichols Park at 9 a.m., followed by the Birdie Derby Disc Golf Tournament at 9:45 a.m.

The afternoon features the 8th Annual Love Wins Horseshoe Tournament at 1:30 p.m. and the continuation of the cornhole showdown.

Evening festivities at the Henryetta Football Field include live music from The Bo Posey Band, the always- adorable Baby Crawling Contest and the Parade Awards Presentation, leading up to a dazzling fireworks show at dark, presented by Hwy 62 Fireworks.

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Monday, Sept. 1: The Grand Finale

Labor Day itself promises a whirlwind of activity, starting with live music at 9 a.m. downtown.

At 10 a.m., Main Street will burst to life with the Henryetta Labor Day Parade, one of the largest in the region, featuring community floats, marching bands and the special Centennial-themed entries.

Immediately following, a full slate of classic smalltown competitions awaits:

• Terrapin Race, Frog Hopping Contest and Fish Scramble on S. 6th Street

• Homemade Ice Cream Competition at Pocket Park, sponsored by the Rotary Club

• Labor Day Fun in the Sun at the Church of the Nazarene with free inflatables, slides, food and games

• Ruby Gooden Labor Day Games at Gazebo Park at 1:30 p.m.

The Okmulgee County Democratic Party will also host a traditional BBQ lunch at the Civic Center for $5 per plate, adding a tasty touch of community fellowship.

Capping off the weekend will be the highly anticipated LUV Fest at Gazebo Park, where families can enjoy food, fun and a community cookout featuring Schwab’s Made-in-Oklahoma hot dogs.

— Share the LUV in Henryetta

This year’s celebration carries a unique theme: “Share the LUV in Henryetta.” From engraved “Love Locks” at the Chamber of Commerce to the quirky toilet seat throw competition during the Love Wins Horseshoe Tournament, organizers are infusing creativity and fun into every aspect of the festivities.

With its blend of history, tradition and family- friendly entertainment, the 2025 Henryetta Labor Day and 125th Anniversary Celebration promises to be one for the history books.

– For more information, event updates or to pre-purchase Bruce Jones’ Henryetta history video series, contact the Henryetta Chamber of Commerce or follow their social media pages.