May

25 | Meredith Lodging Kids’ Day in May The Village at Sunriver, 11 am–4 pm, villageatsunriver.com/events

25–26 | Sunchaser Spring Finale Weekend and the 2nd annual Board, Bike and Brew Festival Mount Bachelor, Bend, 8:30 am–3:30 pm, mtbachelor.com

26 | Bennington Properties Dog Day in May The Village at Sunriver, 11 am–3 pm, villageatsunriver.com/events

31–June 1 | Sunriver Resort Brewfest The Backyard at Sunriver Resort, 4–9 pm, sunriver-resort.com

June

1 | Cascade Relays Bend Beer Chase Bend to Redmond and back, cascaderelays.com/beer-chases/bend-beer-chase

2 | Sunriver Music Festival Swings Fore Strings Golf Tournament Woodlands Golf Course, 11:30 am–7 pm, sunrivermusic.org

20th Annual Heaven Can Wait 5K Drake Park, Bend, 8 am, stcharleshealthcare.org/foundation/events/heaven-can-wait

7 | First Friday Art Walk Downtown Bend and the Old Mill District, 5:30 pm, visitbend.com/festivals-events/first-friday-art-walk

7–8 | The Butler Did It Sunriver Stars Community Theater, sunriverstars.org

8 | Second Saturday Party with the Artists Artists’ Gallery Sunriver, 4–6 pm, villageatsunriver.com

Deschutes Demolition The Village at Sunriver, 8 am–5 pm, nwfitgames.com/deschutes-demolition-2019

8–9 | Sisters Art in the Park Sisters Creekside Park, 10 am–5 pm, sisterscountry.com

9 | Jason Isbell & The 400 Unit + Father John Misty Les Schwab Amphitheater, Bend, 6:30 pm, bendconcerts.com

Sunriver Music Festival Young Artists Scholarship Concert Holy Trinity Church, Sunriver, 7 pm, sunrivermusic.org

14–15 | The Butler Did It Sunriver Stars Community Theater, sunriverstars.org

14–16 | Bite of Bend Downtown Bend, biteofbend.com

15 | The Roots Les Schwab Amphitheater, Bend, 6:30 pm, bendconcerts.com

Run for the Birds 5K and 1K Kids Dash 8 am, Sunriver Resort, sunriver-resort.com

La Pine Rhubarb Festival La Pine Senior Center, 9 am–4 pm, lapineseniorcenter.org

20–23 | 4 Peaks Music Festival Stevenson Ranch, Bend, 4peaksmusic.com

21–23 | Sunriver Solstice Junior Intermediate and Adult NTRP Tennis Tournament North Courts Complex, sunrivertennis.com

23 | Rebelution Les Schwab Amphitheater, Bend, 6:30 pm, bendconcerts.com

JuJu Eyeball Turf Tunes Sunriver Style, John Gray Amphitheater, SHARC, 4–6 pm, sunriversharc.com/turftunes

27 | Michael Franti & Spearhead + Ziggy Marley Les Schwab Amphitheater, Bend, 6:30 pm, bendconcerts.com

28–30 | Pacific Crest Weekend Sports Festival Sunriver, whyracingevents.com

29 | Lyle Lovett and His Large Band Les Schwab Amphitheater, Bend, 6:30 pm, bendconcerts.com

High Lakes Car Club Show and Shine La Pine Senior Center, 9 am–3 pm, highlakescarclub.org

30 | Code Red Turf Tunes Sunriver Style, John Gray Amphitheater, SHARC, 4–6 pm, sunriversharc.com/turftunes

July

3–6 | La Pine Frontier Days La Pine, lapinefrontierdays.org

4 | 4th of July 5K Fun Run and Bike Parade Sunriver Resort, 8:15 am and 11:30 am, sunriver-resort.com

First Interstate Bank 4th of July Festival The Village at Sunriver, 11 am–4 pm, villageatsunriver.com/events

Old-Fashioned July 4th Festival Drake Park, Bend, 8 am–4 pm

Pet Parade Downtown Bend, 10 am, bendparksandrec.org

Bend July 4th Fireworks Spectacular Pilot Butte State Park, Bend, 10 pm

4–6 | La Pine Rodeo La Pine Rodeo Grounds, lapinerodeo.com

5 | First Friday Art Walk Downtown Bend and the Old Mill District, 5:30 pm, visitbend.com/festivals-events/first-friday-art-walk

Trombone Shorty with Son Little Les Schwab Amphitheater, Bend, 6:30 pm, bendconcerts.com

7 | Hyatus Turf Tunes Sunriver Style, John Gray Amphitheater, SHARC, 4–6 pm, sunriversharc.com/turftunes

11 | Munch and Music Concert Series Drake Park, Bend, 5:30–9 pm, munchandmusic.com

Sisters Annual Garden & Home Tour 9 am–3 pm, Sisters, sistersgardenclub.com

12–13 | Sisters Artist Marketplace Downtown Sisters, 10 am–5 pm, sisterscountry.com

12–14 | COBA Tour of Homes Central Oregon, coba.org/tour-of-homes

13 | Slightly Stoopid Les Schwab Amphitheater, Bend, 5:30 pm, bendconcerts.com

Sisters Outdoor Quilt Show Downtown Sisters, 9 am–4 pm, sistersoutdoorquiltshow.org

Second Saturday Party with the Artists Artists’ Gallery Sunriver, The Village at Sunriver, 4–6 pm

14 | The Junebugs Turf Tunes Sunriver Style, John Gray Amphitheater, SHARC, 4–6 pm, sunriversharc.com/turftunes

18 | Munch and Music Concert Series Drake Park, Bend, 5:30–9 pm, munchandmusic.com

19–21 | COBA Tour of Homes Central Oregon, coba.org/tour-of-homes

USTA PNW League Mixed 18 & Over Section Championships North Courts Complex and Tennis Hill, sunrivertennis.com

20 | 6th Annual Sunriver Antique & Classic Car Show The Village at Sunriver, 10 am–2 pm, villageatsunriver.com/events

21 | Jackwagon Blues Band Turf Tunes Sunriver Style, John Gray Amphitheater, SHARC, 4–6 pm, sunriversharc.com/turftunes

Sunriver Music Festival Annual Festival Faire Dinner & Auction Sunriver Resort Great Hall, 4:30 pm, sunrivermusic.org

24 | The Wine, Cheese and Brew Showcase Sunriver Resort, 5–8 pm, sunriver-resort.com

Melissa Etheridge John Gray Amphitheater, SHARC, 7 pm, sunriversharc.com/summerconcert

25 | Munch and Music Concert Series Drake Park, Bend, 5:30–9 pm, munchandmusic.com

26–28 | The Newberry Event Music & Arts Festival DiamondStone Guest Lodges, newberryevent.com

Balloons Over Bend Riverbend Park (Friday, 12–8 pm), and Sam Johnson Park, Redmond (Saturday Night Glow), balloonsoverbend.com

31–Aug 4 | Deschutes County Fair & Rodeo Deschutes County Fair & Expo Center, Redmond, expo.deschutes.org/fair

August

1 | Munch and Music Concert Series Drake Park, Bend, 5:30–9 pm, munchandmusic.com

1–3 | Flashback Cruz Bend, flashbackcruzbend.com

2 | First Friday Art Walk Downtown Bend and the Old Mill District, 5:30 pm, visitbend.com/festivals-events/first-friday-art-walk

2–3 | 12th Annual Cascade Lakes Relay Diamond Lake to Bend, cascaderelays.com

3 | 32nd Annual Sunriver Quilt Show The Village at Sunriver, 9 am–4 pm, mountainmeadowquilters.org

8 | Munch and Music Concert Series Drake Park, Bend, 5:30–9 pm, munchandmusic.com

Lord Huron and Shakey Graves Athletic Club of Bend, 6 pm, athleticclubofbend.com

9–11 | Sunriver Art Fair The Village at Sunriver, 9:30 am–6 pm (4 pm on Sunday), sunriverartfair.com

10 | Second Saturday Party with the Artists Artists’ Gallery Sunriver, The Village at Sunriver, 4–6 pm

Sweet Red and the Hot Rod Billies Sunriver Art Fair, The Village at Sunriver, 4–5:30 pm, villageatsunriver.com

B-52s with OMD and Berlin Les Schwab Amphitheater, Bend, 6:30 pm, bendconcerts.com

10–22 | 42nd Annual Sunriver Music Festival sunrivermusic.org

13 | The Avett Brothers with Lake Street Drive Les Schwab Amphitheater, Bend, 6 pm, bendconcerts.com

15 | Munch and Music Concert Series Drake Park, Bend, 5:30–9 pm, munchandmusic.com

15–17 | Bend Brewfest Les Schwab Amphitheater, Bend, bendconcerts.com

20 | Josh Groban Les Schwab Amphitheater, Bend, 6:30 pm, bendconcerts.com

22 | Fast Times Barrel Races Deschutes County Fair & Expo Center, expo.deschutes.org

23–24 | Airshow of the Cascades Madras Airport, cascadeairshow.com

23–25 | Art in the High Desert Old Mill District, Bend, artinthehighdesert.com

24 | The Wine, Cheese and Brew Showcase Sunriver Resort, 5–8 pm, sunriver-resort.com

31–Sept 1 | Sunriver Half Marathon for a Cause sunrivermarathon.com

September

6 | First Friday Art Walk Downtown Bend and the Old Mill District, 5:30 pm, visitbend.com/festivals-events/first-friday-art-walk

6–8 | Sisters Folk Festival Downtown Sisters, sistersfolkfestival.org

Team Cup Challenge Tennis Tournament Sunriver Resort, sunrivertennis.com

7 | 36th Annual High Desert Swap Meet & Car Show Deschutes County Fair & Expo Center, 7 am, coocc.net

Community Garage Sale SHARC, 9 am–12 pm, sunriverowners.org

8 | The Great Drake Park Duck Race Drake Park, Bend, theduckrace.com

12–15 | USTA Adult 65 & Over Section Championships sunrivertennis.com

13–14 | Uncorked, Sunriver Style Wine Festival Benham Hall, SHARC, sunriversharc.com

14 | Second Saturday Party with the Artists Artists’ Gallery Sunriver, The Village at Sunriver, 4–6 pm

Gary Clark Jr Les Schwab Amphitheater, Bend, 7 pm, bendconcerts.com

20–21 | Bend Oktoberfest Downtown Bend, bendoktoberfest.com

22–26 | Pacific Amateur Golf Classic Sunriver Resort, pacamgolf.com

28 | La Pine Lions Annual Oktoberfest Rosland Park, 10 am–6 pm