Bend and the Old Mill District: Step Into Summer With Memorial Day Weekend Events, Outdoor Excursions, Patio Dining and Concert Season Kickoff!

It’s almost Memorial Day weekend, the unofficial start of summer, marked by backyard barbecues, road trips, river floats and lake days. Beyond the seasonal celebrations, the holiday also carries a deeper meaning that deserves recognition. Memorial Day is a time to honor fallen service members as communities come together through ceremonies and parades, reflecting on their sacrifice and legacy.

For a meaningful tribute, join the community for the 18th annual Bend Memorial Day reading, “We Are Remembering — Not Just a Number,” from 8 to 11:30 a.m. at Troy Field in downtown Bend. Now in its 18th year, the event features a continuous, chronological reading of the name, age and hometown of every U.S. service member killed in Afghanistan since 2001 and in Iraq since 2003, ensuring each life is honored and remembered.

While the weekend is rooted in reflection, it also offers plenty of ways to gather, explore and celebrate across Bend.

Events & Community Gatherings:

At Drake Park, the second annual Bend Brews & Beyond brings together more than 50 breweries alongside food vendors, live music, DJ appearances and a new Hempgarten featuring hemp-derived beverages. Guests can also join the interactive Drinking Pants Pageant, where participants showcase their most creative pants in an onstage fashion show for a chance to win concert tickets to Jimmy Eat World or O.A.R. at Hayden Homes Amphitheater this summer. Whether you come for craft beer, live music or the fashion spectacle, the event delivers a lively kickoff to the holiday weekend.

The High Desert Museum is a well-loved spot in Bend for a daytime family outing offering both indoor and outdoor exhibits that spotlight Oregon’s most important history and a peak at some of its indigenous wildlife. With four revolving exhibits, 11 permanent exhibits and even virtual experiences, there is always something new to explore and something reliable to look forward to.

Outdoors & Adventure:

For nature lovers, McKenzie Pass is open and ready for wanderers and adventure seekers, with plenty of hiking trails to explore throughout the area. The McKenzie River Trail remains a favorite among Central Oregon locals and visitors alike. With three different routes to explore by foot or bike, the trail features views of O’Leary Mountain, high desert forests, Cascade lava rock formations and scenic riverside landscapes. For an extra memorable stop, visit Sahalie Falls Viewpoint for breathtaking waterfall views. The accessible viewpoint is welcoming for visitors of all abilities, including furry friends.

Locals and visitors know Bend’s craft beer scene is a big part of the community, so why not turn brewery hopping into a game? The Bend Ale Trail invites beer lovers to explore more than 30 breweries across Bend, Sisters, Prineville and Redmond while discovering new favorites, meeting fellow enthusiasts and earning fun prizes along the way. Getting started is easy. Pick up a free passport at the Bend Visitor Center or download the Bend Ale Trail app, then set out to collect stamps across seven tasting room territories. Complete each territory to redeem prizes back at the Visitor Center. The rules are simple. Explore, have fun and always drink responsibly!

Old Mill District: Movies, Dining & Concert Season Kickoff

At Regal Old Mill ScreenX & IMAX, the “Music Mayhem” series continues with classic musical favorites all month long. Weekday screenings feature beloved films, while weekends bring family-friendly titles, all for $4.99 tickets. Featured films include “Pitch Perfect,” “Baby Driver,” “Blues Brothers,” “Rocketman” and “Sing 2,” offering something for every moviegoer over the holiday weekend.

Beyond the big screen, the Old Mill District comes alive with patio dining, riverfront views and the return of concert season at Hayden Homes Amphitheater. With the Deschutes River running through the heart of the district, patios become natural gathering places for pre-show dinners, post-show drinks and everything in between.

Photograph by: Nate Wyeth

Va Piano Vineyards Wine & Champagne Bar offers a relaxed, dog-friendly patio for wine flights and light pairings before Brandi Carlile takes the stage on Wednesday, May 20 and Thursday, May 21, starting off the holiday weekend early with a special two-night performance.

Stacks Dinner and Delicatessen brings lively New York-inspired dining featuring brisket pastrami, corned beef, house-made pickles and specialty cocktails just steps from the amphitheater footbridge, making it a prime pre-show stop ahead of Yellowcard on Saturday, May 23. The performance is sure to add a nostalgic flare and pop-punk singalongs to the holiday weekend lineup.

Anthony’s at the Old Mill District pairs Pacific Northwest seafood with a relaxed happy hour menu, offering an easygoing stop for clam chowder, ahi poke and shrimp and crab dip, all sourced fresh from the Oregon Coast in the heart of the riverfront scene.

Greg’s Grill remains a longtime favorite among Bend locals for its sought-after riverside patio, where diners can catch views and sounds from Hayden Homes Amphitheater across the water. Arrive early for a pre-show cocktail, signature Yellowstone burger or slice of New York-style cheesecake before Claypool Gold brings an electrifying performance to Bend on Friday, May 22.

Pastini offers Italian-inspired comfort dishes alongside Oregon wines during May’s Oregon Wine Month, inviting guests to sip and dine while taking in sunset views over the Deschutes River.

To close out the night, Lady Bird Cultural Society delivers vintage-inspired cocktails and a stylish patio atmosphere, making it a go-to spot for a late-night toast as a final stop before heading home.

Memorial Day weekend in Bend offers a balance of remembrance, community and the unofficial start of summer. From ceremonies and concerts to outdoor meals and adventures across Central Oregon, the weekend honors both sacrifice and freedom. However you spend the holiday, carry that spirit of gratitude into the summer season.