Experience Bend Like a Local: 10 Best Events in Bend, OR

There’s always something fun to do in Bend, Oregon. The city is best known for its easy access to scenic mountains, high desert, and rivers. Outdoor enthusiasts enjoy skiing, climbing, hiking, or boating.

You may not realize that Bend’s community festivals give you a chance to participate in the local culture, shop for unique gifts, or taste delicious food and craft beverages. When you visit, be sure to attend some of the events in Bend to get to know the community.

These Bend events are well worth a trip to central Oregon. Please check the event’s website for the exact date and event details since everything is subject to change.

1. Cascade Wedding Show

Large marquee lights spelling “BRIDE ERA” glow warmly against a stylish backdrop of balloons and soft lighting. The display creates a romantic, Instagram-worthy scene that celebrates love and modern bridal trends.

Photo Credit @cascadeswedding

Mid-January at the Riverhouse Lodge Conference & Events Center

Are wedding bells in the air? The Cascade Wedding Show is a must for anyone planning a destination wedding in Bend.

With over 60 vendors under one roof, it’s the perfect spot to get inspired, sample ideas, and chat with vendors dedicated to helping plan an unforgettable wedding day. See the latest wedding fashion trends in action or sample food prepared by the region’s caterers. The event even features a live music showcase, giving attendees a chance to shop for wedding entertainment.

2. Bend Winterfest

A lively crowd watches a man and his dog perform at an outdoor winter show surrounded by frisbees on the ground. Families bundled up in winter coats enjoy the entertainment at Bend’s WinterFest celebration.

Photo Credit @oregonwinterfest

Mid-February, on the streets throughout the Old Mill district

Bend knows how to enjoy winter, and its unique Winterfest celebrates the season. Skiers and snowboarders converge to compete at the WinterFest Pump Bump Jam! Artists celebrate fire and ice by creating ice sculptures as well as fire pit sculptures.

This three-day festival also features a wine walk where attendees sample the region’s wines while browsing Old Mill District shops. Runners of all ages can warm up with the Hot Cocoa 5K run, enjoying a hot chocolate bar with their choice of toppings after the finish line. While you are there, don’t miss the live music and entertainment.

3. Alpenglow Concert Series

People relax on lawn chairs and wooden benches while enjoying live music under a modern outdoor pavilion surrounded by tall pines. The casual setup, sunshine, and laid-back crowd capture the welcoming vibe of Bend’s Alpenglow Concert Series.

Photo Credit @alpenglownights

Selected Thursdays and Fridays in late May through June at Alpenglow Park

Alpenglow Nights is a free summer concert series in Alpenglow Park featuring live both local and touring bands. Relax on your picnic blanket and enjoy food from local vendors including beer from Worthy Brewing.

The whole vibe is family-friendly and welcoming. Kids may enjoy the family fun zone with activities like a bounce house or even the Glow Run.

4. Bend Summer Festival

A cheerful summer crowd strolls through vendor booths on a tree-lined street as two adults swing a young child playfully between them. The warm weather, live music, and local food stands capture the joy of Bend’s Summer Festival.

Photo Credit @bendsummerfestival

Mid-July in Downtown Bend

Downtown Bend is a three-day party zone during Bend’s Summer Festival. The community comes together to enjoy music, art, and family fun. Listen to live music or watch a pop-up performance.

If you are looking for art or a unique gift, browse the artisan vendors in the marketplace. With a family fun zone, kids will have a place to play. If you get hungry, grab a bite from one of the local food and beverage vendors. It’s free to attend and is located in the heart of downtown. Feel free to stroll, socialize, and enjoy summer under the Central Oregon sun.

5. Munch & Music

Aerial view of a large outdoor crowd enjoying live music in a park surrounded by tall trees. Blankets, food stalls, and colorful tents create a fun, laid-back summer evening atmosphere at Bend’s Munch & Music event.

Photo Credit @munchandmusic

July and early August in Drake Park

Bring a lawn chair, find a comfy spot, and enjoy a night of music and food under the stars.

Munch & Music is a free summer concert series in Drake Park by the Deschutes River. The atmosphere is relaxed and fun, with live music from local and touring bands.

Grab dinner from one of the local food trucks. If you feel like shopping, wander through Artisan Row to find something special. There’s also a Kids Zone with games, an inflatable playground, and activities.

6. Balloons Over Bend

Colorful hot air balloons float gracefully above Bend, Oregon, during sunrise. The bright stripes and mountain backdrop make for a breathtaking view over the city.

Photo Credit @balloonsoverbend

Late July in the Athletic Field at Central Oregon Community College (COCC)

Balloons Over Bend is a colorful weekend featuring hot air balloons that fill the sky each morning at sunrise. Attendees may start the day by watching the balloon launches.

Live music, entertainment, and food vendors round out the schedule. Kids may compete in the Balloon Blast obstacle course race. In the evening, the whole family may relax and enjoy the Bend Night Glow Celebration. Nearby Redmond gets in on the action that weekend with their own sister celebration, the Redmond Brewfest & Night Glow.

7. Theatre in the Park

Rows of white chairs face an outdoor stage set with a brick backdrop and turquoise doors surrounded by tall pine trees. Guests relax under umbrellas before showtime, creating a peaceful and inviting atmosphere at Bend’s Theatre in the Park.

Photo Credit @Bend Festivals

Mid-August in Drake Park

Enjoy lively musical theatre in Drake Park. Forget Broadway, you can enjoy that perfect mix of fresh air, live music, and great storytelling in downtown Bend.

Bring your picnic blanket or lawn chairs and settle in for a relaxing night under the stars. With local food and craft beverage vendors, enjoy dinner or a drink. They also have VIP ticket options that include a full dinner and drinks.

8. Little Woody

Festivalgoers enter through a whimsical archway decorated with hops vines at The Little Woody Beer, Cider, and Whiskey Festival. The relaxed outdoor vibe sets the stage for tastings and community fun.

Photo Credit @bendfestivals

Labor Day Weekend at Deschutes Historical Museum

The Little Woody is a quirky beer festival celebrating gnomes, all things wood and beer, especially barrel-aged beers and tree-themed brews. If you fancy tastings of unique stouts, sours, and whiskey cocktails, then you won’t want to miss it.

Festival highlights include live music, two comedy shows, including a locals-only showcase, and a gnome costume contest. Runners may also enjoy the Bend Beer Run, where participants run a 5K with beer stops along the way. Oregon and the city of Bend are both known for their vibrant craft beer scene and Little Woody is an ideal introduction.

9. Bend Fall Festival

owntown Bend comes alive with colorful vendor tents, fall decorations, and crowds strolling under sunny skies. Locals and visitors browse handmade crafts, enjoy seasonal treats, and soak in the festive harvest atmosphere of the Bend Fall Festival.

Photo Credit @bendfestivals

Early October in downtown Bend

The Bend Fall Festival celebrates the colors and spirit of fall with a lively weekend of music and art. Held in downtown Bend, the festival features hands-on activities for the family in the Art in Action Avenue, with activities like pumpkin painting. With pop-up music and performers, you will always be entertained.

Attendees also enjoy local food, craft beers, and wines. Get a running start on your holiday shopping by browsing the marketplace for art, jewelry and handcrafted items. The Harvest marketplace also offers a selection of the area’s delicious bounty.

10. Winter Nights

The illuminated entrance sign of the High Desert Museum glows warmly at dusk, surrounded by pine trees and desert brush. It sets the scene for an evening of art, wildlife, and living history during the museum’s Winter Nights event.

Photo Credit @highdesertmuseum

Thursdays in December at the High Desert Museum

Bend’s High Desert Museum is a must-visit for anyone traveling to the area. If you happen to be there in December, Winter Nights is an after-hours experience. The museum stays open until 7:30 pm and each night has a theme. Each night features a fun theme, such as ugly sweaters, flannel, animal-inspired outfits, and cozy pajamas.

Activities may include simple arts projects like making your own watercolor bookmark or printmaking gift wrap. Photo booths and cookie decorating are also popular activities, depending on the night. Attendees may sample local craft beverages or shop. Experience holiday spirit and creativity in a beautiful museum setting with plenty to see and do for all ages.

Make your visit to Bend feel like a special occasion by choosing memorable accommodation. Whether you plan to enjoy the outdoors or attend one of Bend’s festivals, our partner Jennifer Mucha of Arrived Vacation Rentals offers homes conveniently close to downtown Bend or Mt. Bachelor. Depending on the home you choose, you can enjoy special touches like fireplaces, hot tubs, spa-like bathrooms, or even private pools.