Wednesday, June 25 (last Wednesdays, monthly through September)
Pickin' & Paddlin'
The ultimate Wednesday summer evening. Seriously. Other towns dream of this sort of event: Free demos of kayaks and watercraft at an easy-flowing river just a stone's throw away, and fun-spirited Americana bands (starting with fast-picking quartet of The Blackberry Bushes) starting in the late afternoon and stretching past sundown.
4-10 pm. Tumalo Creek & Kayak's front yard, 805 SW Industrial Way. $5 (children under 12 free).
Wednesday June 25 – Sunday, June 29
Subaru of Bend Outside Games
Oh sure, you can treat this as a spectator event, but really you'd be missing the point. Whether a fearless mountain biker screaming down the single tracks on Mt. Bachelor's flank (Pickett's Charge Mountain Bike Race, 8 am–2 pm, Sun., June 29, Wanoga Sno Park), or learning some basics from mountain bike champ Lindsey Voreis (11 am–3 pm, Sat., June 28, Riverbend Park), the Outside Games is an all-comers, all-welcome weekend. Highly recommended: The 2nd Annual Meadow Camp kayak race, a brutal three-mile stretch of Class III-plus tumbling rapids (Sat., June 28, River Rim Park). For a smoother ride, try the Pepsi Freedom Float; homemade buoyancy (3 pm, Sat., June 28, Riverbend Park).
Various times and locations.
Friday, June 27
Oh sure, pros and masters and juniors pack in, shoulder to colorful jerseyed shoulder, and crank around the block, again and again. But the real race is the "Kids' Crit," with categories as young as 3 years old.
3:15 Kids' Crit; 4:30 pros, masters and juniors. Northwest Crossing.
Friday, June 27 – 29
Pacific Crest Sports Festival
With the tagline "sea level is for sissies," the long-standing event—the last weekend of every June—offers half and full marathons, and Olympic and sprint triathlons.
All day. Sunriver. Free to watch, fees to participate.
Sunday, July 6
Oregon Enduro Series
As much a sampler of the forests and mountains of Oregon, this is an amazing five-part series of mountain bike races; Bend is the second leg with miles of hair-raising turns and jumps. A one-day, four-stage race.
Friday, July 11
Opening of Mt. Bachelor Bike Park
Mountains aren't only good for wintertime.
Mt. Bachelor. $5-$34 for a single day ticket.
Saturday, July 12
Tour des Chutes
There are shorter options, but the real bragging rights come from completely the whole 100-mile loop. Starting in the Northwest Crossing neighborhood, the ride carves through ranch territory and traces nearly 20 miles along the Sisters-Smith Rock State Scenic Bikeway; although hilly, mercifully keeping the mountains as a beautiful backdrop to the ride.
100-mile ride starts at 6 am. High Lakes Elementary School, 2500 NW High Lakes Loop. $50.
Tuesday, July 15 – Sunday, July 20
Cascade Cycling Classic
Includes a four-stage pro race that covers the various terrains and challenges of Central Oregon, from Stage One's rolling mountain road (1:30 pm Friday), to Stage Two's time trail in the desert (8 am Saturday) and, most exciting, the downtown race (2:30 pm Sunday).
Various times. Across Central Oregon. Free to watch.
Saturday, July 26 – Sunday, July 27
Deschutes Dash Weekend Sports Festival
Olympic and sprint triathlons and duathlons, 5k, 10k, youth tri and kid's Splash 'N' Dash. Perfect for first time triathletes.
7 am. Riverbend Park, Old Mill District. Free to watch, fee to participate.
Saturday, August 23
Stream Stewardship Day
Because cleaning up and proper stewardship is part of the party, today is an end-of-summer (ah, say it ain't so) event picking up the bottles and debris left over for the previous months of fun, fun, fun.
10 am-1pm. Begins at Riverbend Park. Free.
Friday, August 29
U.S. All Girls Slackline Fest 2014
Trying to find a little balance in your life? (Ha! Get it?) The annual slackline festival (yes, like tightrope, but not so, um, uptight) is beginner-friendly and for females only.
8 am. Sisters. Free.