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Weekend Roundup: June 5-9

The Sisters Rodeo is happening this weekend along with Art in the Park, Maupin Madness, Pride Golf Day and some live music to kick off the summer concert season.

Jason Isbell and the 400 Unit

Sisters Rodeo
June 5-9 | Sisters | $14-$22

The Sisters Rodeo is one of the most popular events in Central Oregon each year. Now in its 79th year, the rodeo draws the top riders and ropers to the high desert to compete. Bring the whole family to experience the region’s Western heritage and community spirit.

Maupin Madness Poker Run, Bike Show & Chili Cook-Off
June 8-9 | Maupin | Prices vary

Maupin Madness is an annual event that benefits veterans. Join the 200-mile scenic ride through Central Oregon that ends at the Imperial River Company with a chili cook-off, beer garden and live music.

Art in the Park
June 8-9 | Creekside Park, Sisters | Free

This is the fifteenth year of Art in the Park, a festival that takes place in Sisters during the Sisters Rodeo weekend. There will be local vendors with fine arts and crafts, artisan goods, and local food and drinks.

Pride Golf Day
June 8 | Juniper Golf Course, Bend | $80

This is the first annual Pride Golf Day, an event created by Out Central Oregon. The LGBTQ+ community is invited to Juniper Golf Course for a day of activities that will include an instruction clinic, rounds of golf, lawn games, and more. The evening will be capped off with dinner and dancing.

Live Music

On Friday night, Longbeach Dub Allstars will be headlining at Midtown Ballroom. At McMenamins, Moody Little Sisters takes the stage Wednesday and Toast and Jam will be play on Thursday. And finally, end the weekend with a concert by the Deschutes River. Jason Isbell and Father John Misty kick off the concert season at the Les Schwab Amphitheater on Sunday evening.


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