"Montana's Biggest Weekend" is a bold claim. Many towns and cities across the Treasure State have pretty epic weekends, from the big music festivals in Western Montana to the Bucking Horse Sale in Miles City; we aren't shy when it comes to good times, especially in the summer.

Labor Day marks the unofficial end of summer, and the folks in Dillon, MT are ready to back up their claim of hosting Montana's Biggest Weekend. To be fair... it does sound pretty epic. Hosted by the Dillon Jaycees, here's what to expect.

Read More: How To Enter The Billings Firefighters Local 521 Gun Raffle

Credit Michael Foth, TSM
Credit Michael Foth, TSM

PRCA Rodeo

Rodeo action is scheduled for both Saturday and Sunday, and you can expect all the classics, including bull riding, bronc riding, steer wrestling, barrel racing, breakaway roping, and team roping.

Some of the best competitors from across the country will be in Dillon looking to leave town with a little extra cash and bragging rights.

Scott Lewis
Scott Lewis

39th Annual Labor Day Concert

Sunday night brings the music, with the 39th Annual Labor Day Concert happening September 6. Michael Armstrong will open the show, followed by special guest Redferrin before country star Kameron Marlowe takes the stage as the headliner.

Cat Country 102.9 logo
Get our free mobile app

If you're a fan of country music, that's a pretty solid way to spend a Sunday night.

Yobro10
Yobro10

Dillon Labor Day Parade

The fun wraps up Monday morning with the Labor Day Parade, beginning at 10 AM on September 7.

The parade starts on East Glendale Street and travels through Dillon to Montana Street. There will also be a cash prize for the Best Use of Theme.

Virginia City and my copy of The Bad Old Days of Montana. Credit Michael Foth, TSM.
Virginia City and my copy of The Bad Old Days of Montana. Credit Michael Foth, TSM.

From hot springs to Vigilantes, Southwest Montana is fun.

The Southwest corner of Montana is one of my favorite places. My wife and I spent a long weekend in the area last summer, visiting Virginia City, Ennis, Ruby Reservoir, and other fun stops along the way.

If you haven't been in the Dillon area for a while, give it a revisit. If you've never been, go! After all, who wouldn't want to be a part of Montana's Biggest Weekend? VisitMT.com has a great itinerary HERE.

Montana's First Frost Dates 2026

Montana's first frost dates for 2026, according to the Old Farmer's Almanac.

Gallery Credit: Chris Wolfe

The New Fastest Growing Towns In Montana For 2026

According to census data, these Montana towns had the most population growth in 2025.

Gallery Credit: Nick Northern

More From Cat Country 102.9