Sat., May 18, 2019
POLE PEDAL PADDLE
Six events that span Central Oregon's outdoor scene. Contestants race in teams or do all the events, including Alpine skiing, Nordic skiing, cycling, paddling and a sprint to the finish. Worth a watch, or for a major training goal. Starts at Mt. Bachelor. pppbend.com
First Fridays
ART WALK
Stroll the streets of downtown Bend the first Friday of every month, when local artists roll out special works and downtown businesses feature live music and drinks 5-9pm. Downtown Bend, various locations. Free. downtownbend.org
Sat., May 25, 2019
HAPPY GIRLS RUN – BEND
Women of all levels of fitness and achievement come together for a race that many racers say is nothing short of life changing. Half Marathon, 10K & 5K distances. Riverbend Park, 799 SW Columbia St., Bend. Registration varies. happygirlsrun.com
Sun., May 26, 2019
SISTERS STAMPEDE
Oregon's largest cross-country mountain bike race, right in the heart of Sisters Country! Ride Petersen Ridge with hundreds of your bikey friends. Starts at Three Creeks Brewing, 721 S. Desperado Ct., Sisters. sistersstampede.com
Wed., May 29-Sun. Jun. 2, 2019
CASCADE CYCLING CLASSIC
North America's longest running stage race happens right here in Central Oregon, drawing participants from the PNW as well as from all over the U.S. and Canada. Stages will take place in Tumalo, the Painted Hills, Cascade Lakes Highway and on the top of Awbrey Butte. The jewel of this year’s CCC is the Sul Fiume Criterium Festival June 1—an all-day family-friendly bike festival overlooking the Whitewater park on the Deschutes and featuring the iconic CCC Criterium. Cycling-related events for kids from “2 to 92” (Strider Adventure Zone, the annual Hutch’s Kids’ Race, a Middle/High School Grand Prix, a Gravel Grinder, a Family Ride and a Community Ride), a vendor expo, and live music from Oregon darlings High Street featuring Precious Byrd, ¡Chiringa! and G Bots and the Journeymen.
Various locations in Bend. cascade-classic.org
Sat., June 1, 2019
BEND BEER CHASE
Six people. 50 miles. One day. This running relay from Bend, to Redmond, Sisters and back consists of 12 legs, with each team member running a portion. Includes stops at seven local breweries. Starts at Worthy Brewing, 495 NE Bellevue Dr., Bend. Registration varies. bendbeerchase.cascaderelays.com
Fri., June 14- Sun.,16, 2019
BITE OF BEND
The region's largest food festival and a three-day party on the streets of downtown Bend showcases the best bites that area restaurateurs have to offer, as well as a Mixology Showcase featuring local distilleries and a Top Chef competition. Bite Week follows with special dinners and workshops. Downtown Bend. Free entry. biteofbend.com
Sun., June 16, 2019
BITE OF BEND BEER RUN
Sends participants along a 5K race loop through Drake Park along the Deschutes River and back through Columbia Park, stopping for brews from local breweries. Bonus prizes are awarded to participants in the best costumes! Get the kids in the action as well—check out the Little Hopper Root Beer Run Sat., June 15! Early Bird (until June 13): $20, Day of Event: $30. biteofbend.com/beer-run
Thur., June 20 – Sun., June 23, 2019
4 PEAKS MUSIC FESTIVAL
A family-friendly, music-filled weekend. Over 20 bands, three stages, two bars, silent disco, yoga, Kidlandia and more. Headlining this year are The Wood Brothers, Billy Strings, Los Lobos, The Lil Smokies and many others. Stevenson Ranch, 21085 Knott Rd. Bend. $225/weekend pass. 4peaksmusic.com
Fri., July 12 – Sun., July 14, 2019
BEND SUMMER FESTIVAL
The First Interstate Bank Bend Summer Festival draws upward of 75,000 visitors to downtown Bend. Featuring fine artists and craftspeople, artisans and performers, and two stages of some of the best regional and national blues, rock and jazz. The First Interstate Bank Bend Summer Festival draws upward of 75,000 visitors to downtown Bend. Featuring fine artists and craftspeople, artisans and performers, and two stages of some of the best regional and national blues, rock and jazz. Downtown Bend. Free admission. bendsummerfestival.com
Fri., July 26-Sat., July 27
SISTERS RHYTHM & BREWS FESTIVAL
A two-day blues festival and so much more. Great blues musicians, as well as great local craft beers, all in the cozy town of Sisters. Also a benefit for local nonprofits. Fri., July 26-Sat., July 27
Fri., July 26-Sun., July 28
NEWBERRY EVENT
A small, family friendly festival that includes full camping, located south of Sunriver. With an eclectic lineup of blues, jazz, rock, reggae and bluegrass, and a free admission for kids under 13, this is a great way to spend a weekend. Early bird $75; full adult ticket $120. Fri., July 26-Sun., July 28
Fri., July 26 - Sun., July 28, 2019
BALLOONS OVER BEND & CHILDREN'S FESTIVAL
An awe-inspiring weekend where you can see hot air balloons take flight. Also take part in the Children's Festival, including a bike rodeo and bounce houses, as well as launches, meet and greets with pilots and a Night Glow. Children's Festival: Friday, Noon-8pm, Riverbend Park. Launches: Fri-Sun. at various locations in Bend & Redmond. balloonsoverbend.com
Wed., July 31 - Sun., Aug. 4, 2019
DESCHUTES COUNTY FAIR & RODEO
Celebrating its 100th year this year! The fair and rodeo has all the classic family fun: five days of carnival rides, tasty food, live music and a rodeo and ag expo. Deschutes County Expo Center, 3800 SE Airport Way, Redmond. expo.deschutes.org/fair
Sat., Aug. 10, 2019
HAULIN' ASPEN
A 6.5-mile course (dubbed the "Half As"), a half marathon and a full marathon in a gorgeous Cascades trail setting. A points qualifier for the Trail Runner Magazine Trophy Series and Central Oregon's only full trail marathon. Trails wind through Wanoga Sno-Park and forestland. Wanoga Sno-Park, Cascade Lakes Highway, Bend. Registration varies. bendraces.com/haulin-aspen
Thu., Aug. 15 – Sat., Aug. 17, 2019
BEND BREWFEST
More than 60 breweries bring their wares to this event that includes three days of tasty craft beer, cider and wine along the banks of the Deschutes River. Taste some of the 150 beers, ciders and wines and X-taps with limited-release small batch beers. Les Schwab Amphitheater, 344 SW Shevlin-Hixon Dr., Bend. Free admission; $20/mug + 5 tasting tokens. bendbrewfest.com
Sat., Aug. 24, 2019
VOLCANIC BIKE & BREW FESTIVAL
Free bike demos, live music and vendors, all located in the West Village Base Area. Visit the beer garden for brews, and watch enduro mountain bike racers do their thing. Mt. Bachelor, 13000 SW Century Dr., Bend. mtbachelor.com
Fri., Aug. 23 & Sat., Aug. 24, 2019
THEATER IN THE PARK
Dinner and a show, right in the heart of Bend! This year's production is the musical, "La Cage aux Folles." Drake Park, 777 NW Riverside Blvd, Bend. $25-45/GA. $55-$75/VI, including dinner and beverages. theaterbend.com
Fri., Aug. 30 & Sat., Aug 31, 2019
THE LITTLE WOODY
Celebrating craft wood-aged beers from across the Northwest, along with small-batch whiskeys. Taste selections from over two dozen local and regional brewers and distillers. Deschutes Historical Museum, 129 NW Idaho Ave. Bend. $12-$15. thelittlewoody.com
Fri., Sept. 6 – Sun., Sept. 8, 2019
SISTERS FOLK FESTIVAL
Artists perform in many small venues scattered throughout Sisters, creating an intimate atmosphere. The lineup includes stars from the folk, Americana, bluegrass and other genres. A rockin' good time! Various locations in Sisters. $170/weekend pass. sistersfolkfestival.org
Fri., Sept. 27-Sun., Sept 29, 2019
BEND ROOTS REVIVAL
A free, family friendly music and arts festival in the heart of Bend, with local music from nearly every genre you can think of. With seven stages next to the Deschutes Brewery Warehouse, it's like an end-of-summer block party for the community. Deschutes Brewery, 901 SW Simpson Ave., Bend. bendroots.net
Sat., Sept. 28
SISTERS FRESH HOP FESTIVAL
If you're not already in the know about fresh hop beers, this is your chance to try them out from a host of local and statewide breweries. Three Creeks Brewing pulls out all the stops to celebrate the harvest of one of Oregon's best-loved crops. Three Creeks Brewing, 721 S. Desperado Ct., Sisters. sistersfreshhopfest.com
Fri., Oct. 4 – Sun., Oct. 6, 2019
BEND FALL FESTIVAL
This family friendly weekend includes pumpkin carving, gourmet food and wine, a Harvest Market, live music and more. Downtown Bend. Free admission. bendfallfestival.com
Sat., Nov. 2, 2019
HAPPY GIRLS RUN – SISTERS
Bringing together women of all levels of physical fitness and achievement. The half-marathon winds along a challenging trail on Peterson Ridge and the 5K takes runners through downtown Sisters. Five Pine Lodge, 1021 Desperado Trail, Sisters. happygirlsrun.com
December 2019
DIRKSEN DERBY
An event put on by pro snowboarder Josh Dirksen, bringing the international snowboard and sit-ski communities together to raise funds for a host of local nonprofits. Competitors get into the competition by lottery, so check their site for updates! dirksenderby.com
Sat., Jan 18, 2020
CASCADES WEDDING SHOW
A one-day event for Central Oregon event professionals to connect with future brides and grooms! An elegant bridal experience, including collaborative vendor booths, educational presentations and workshops. Riverhouse on the Deschutes Convention Center, 3075 N Hwy 97. Bend. cascadesweddingshow.com
Fri., Feb. 1 – Sun., Feb. 16, 2020
OREGON WINTERFEST
Join thousands of spirited locals and visitors President's Day weekend for three days of live music, delicious food and drink and activities for the whole family. The fire pit artist installations and ice sculptures are a must-see. Les Schwab Amphitheater, 344 SW Shevlin Hixon Dr, Bend. oregonwinterfest.com
Sun., April 5, 2020
SALMON RUN
Run along the gorgeous Deschutes River Trail in the Old Mill District in either a half-marathon, 10K or 5K. Register the kiddos for the Little Fry Run, part of the Kids Rock the Races Series. Athletic Club of Bend, 61615 Athletic Club Dr, Bend. Registration varies. bendraces.com/salmon-run
