The Cowboy Cup

05/29/2026

Winners Announced!!

Thank you all for entering the giveaway.

Winner #1 -
Winner #2 - Poboy Cheadle

These two have won 2 Saturday passes to Rocklahoma and the Cowboy Cup. This is going to be a year not to miss. Awards show will be held on the Roadhouse Stage at Rocklahoma’s 20th Anniversary Saturday September 6th in Pryor, Ok.

Congratulations to the winners and we hope to see all of you in Pryor Labor Day weekend!!

thinkhigher









elevated





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05/21/2026

Ticket Giveaway!

Want to win two free passes to Rocklahoma and The Cowboy Cup? We got you!

Here’s how you enter.
1. Follow and
2. Tag your favorite Oklahoma Cannabis Brands in the comments.

For each brand tagged you will receive one entry to win.

We are stoked to bring this cosmic collaboration to Oklahoma. Rocklahoma’s 20th anniversary will definitely be its dankest! The Cowboy Cup will be held in all its glory, including a vendor tent with the Rawsin Lounge, games, seminars and giveaways all weekend long right in the heart of the country’s biggest Labor day Rock Festival.

Cowboy Cup’s award ceremony will be held at 4:20 on Saturday with a smoked out Cypress Hill show to follow. You’re not gonna wanna miss this one.

Cowboy Cup is presented this year by Dime Industries. “Think Higher”

thinkhigher



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elevated

05/20/2026

05/20/2026

Grizzly has always been about culture first. Real people. Real energy. Real community. That’s why we’re beyond excited to be part of Cowboy Cup this year! Big respect to Daniel Lewis and the entire Cowboy Cup team for continuing to push the culture forward. We’re proud to be part of something this special. See y’all at Cowboy Cup.

Labor Day Weekend 2026 - Rocklahoma - Pryor, Ok

thinkhigher








elevated

05/10/2026

Happy Mother’s Day from the Cowboy Cup 💐

Today we’re celebrating all the moms, grandmas, bonus moms, and strong women who keep showing up with love, grit, and compassion every single day. We hope your day is filled with laughter, relaxation, and a little time to enjoy what makes you happy. 💚

02/03/2026

We’re beyond honored 🤠🏆
Cowboy Cup was voted BEST EVENT in Best in Herbage!

From the competitors and vendors to the judges, sponsors, and every single attendee — YOU made this happen.

We work all year to build an event that’s authentic, competitive, educational, and unforgettable — and this recognition means the world.

Thank you for riding with us. 🔥

01/18/2026

George is keeping his ears warm with The Cowboy Cup!

12/29/2025

2025 Grand Champion