Look in any direction and you’ll spot a peak just begging to be bagged. South Sister, Broken Top, Mount Jefferson: These magnificent summits take planning and preparation to climb. Yet, there are many mountaintops that are easily crested within a few hours, and with a whole lot of snacks.
Cue the Big Butte Challenge, a go-at-your-own pace event put on by Cascade Relays. This all-ages adventure offers community spirit while tackling peaks within driving distance of Bend. For each summit achieved, hikers receive a token that can be redeemed at the local brewery sponsoring each butte.
The idea came about in 2021, when gathering for races and other big athletic events wasn’t feasible. Realizing there were more than a handful of attainable buttes to climb—while maintaining social distance—the team at Cascade Relays started the Big Butte Challenge (named after a creative Cascade Relays team, I Like Big Buttes). Scott Douglass, co-founder of Cascade Relays, wanted this event to both challenge those who joined and support businesses within the Central Oregon community.
“Everything at Cascade Relays revolves around community,” said Douglass. “People come to Central Oregon to feel connected, and when hikers see someone else wearing the green Big Butte Challenge hat, it draws them into a sense of togetherness.”
This year, roughly 500 people are hiking, running or even biking the trails, which runs from May through October. The one who finishes bagging all nine peaks first gets a prize, but the real reward comes with each mountain conquered: stunning views of the mountains, lakes and stretches of land that make Bend such a magical place to call home. The ice cold brew is the cherry on the top.

The Buttes to Climb
Barnes Butte
Distance: 2.72 miles round trip | Brewery: Wild Ride Brewing | The volcanic landscape of Central Oregon unfolds in front of climbers when they get to the top of this butte, with the Cascades to the west and Ochocos to the east.
Black Butte
Distance: 3.8 miles round trip | Brewery: Van Henion Brewing | A steep and exposed trail makes this hike best tackled early in the day, but once at the top, climbers are treated to views of Mount Jefferson, Mount Washington and even Mount Hood to the north.
Misery Ridge
Distance: 3.6 miles round trip | Brewery: Kobold Brewing | An iconic Central Oregon hike in Smith Rock State Park, the trail takes you along rocky ledges and offers views of the Crooked River and rock climbers scaling the side of the ridge below.
Overturf Butte
Distance: 5.58 miles round trip | Brewery: GoodLife Brewing | Although it takes challengers through neighborhoods, this easy meander from Phil’s Trail to the top of Overturf is an easily tackled butte, and welcoming for dogs.
Paulina Peak
Distance: 6.12 miles round trip | Brewery: Bend Brewing Company | The push to this rocky mountain top is one of the more challenging, but well worth it. Once there, find a reward to scan views of Paulina and East lakes framed by the Cascade Range.
Pilot Butte
Distance: 2.06 miles round trip | Brewery: Worthy Brewing | It’s a popular spot in the center of town, but when Mount Hood is visible on a clear day, the top of this butte is anything but ordinary.
Tumalo Mountain
Distance: 4.04 miles round trip | Brewery: Cascade Lakes Brewing | With Broken Top and the Three Sisters standing magnificently in the distance, the view from the top of this two-mile climb just might be the best look at Mount Bachelor in Bend.
Tam-a-lau
Distance: 6.6 miles round trip | Brewery: Initiative Brewing | The Peninsula, a lava plateau at the end of a trail winding through old-growth juniper and sagebrush, offers views of the Deschutes and Crooked River canyons below.
Vista Butte
Distance: 4.3 miles round trip | Brewery: UPP Liquids | This relatively quick and mild jaunt is a popular spot to get to easy views of Mount Bachelor and the Three Sisters, and is a great option for hikers just getting their trail legs.