The best things to do in Bend in May
April 30, 2026
10 minute readJune is when much about Bend gets easier with all high-elevation roads open and river shuttles in full swing. Warm temps deliver sunshine and loads of activities. Float through town along the Deschutes River. Hike to sparkling high alpine lakes. Or just head out for a picnic with the family at First Street Rapids Park and watch the kayakers play in the waves.
June officially flips the switch to summer mode, with weekends packed with music, markets, and lots of family-friendly fun.
Concert season kicks off at Hayden Homes Amphitheater with artists like Bonnie Raitt, Bailey Zimmerman, and Lord Huron (it’s their third time playing in Bend). It’s easy to see why fans and artists keep coming back. Kids can dance around on the lawn while parents kick back with live music and a local beer. Celebrate the amphitheater’s silver season of music together and head to the Old Mill’s 25th Anniversary Dance Party on June 20, a free, all-ages show with DJ Eric Rhodes and special guest local SoMuchHouse!
Alpenglow Nights runs Thursday nights from 5-8 with free concerts at Alpenglow Park. Looking for a boot-kickin’ good time? Head to Sisters June 26-27 for the Big Ponderoo Music Festival, where bluegrass, folk, and country music pair perfectly with food carts and an art walk.
Beyond the bigger events, Bend’s breweries and patios start filling their summer evenings with live music. Stop by the Bend Visitor Center and grab a Bend Ale Trail or Drinkable Diversions passport, then collect stamps, earn prizes, and perhaps discover your new favorite local band while you’re at it.

Stay centered at the Bend Yoga Festival from June 11-14 with indoor and outdoor classes and wellness events. In Redmond, the Overland Expo PNW, June 26-28, is packed with tricked-out campers and adventure rigs, gear demos, and plenty of road trip inspiration.
Head to downtown Bend for strawberries, history, handmade art, and super-fast road cyclists. The Deschutes Historical Museum is hosting the Oregon Archaeology Roadshow on June 6. It’s a free, hands-on way to explore Central Oregon history and archaeology with the whole family. That same day is the Bend Handmade Market, where you can stroll through handmade art, jewelry, clothing, gifts, and more, all from local makers.
On June 14, the Cascade Cycling Classic Criterium race returns. Cheer from the sidewalk as high-speed cyclists rip through downtown Bend. The Bend Farmers Market also runs every Wednesday from 11-3 with local farm stands, fresh snacks, and plenty of picnic ideas.
Bend is a great place to learn standup paddleboarding and kayaking with forgiving lakes and currents and patient experts to teach you. Start off with a trip to Tumalo Creek Kayak and Canoe, where you can rent all the gear you need as well as take a lesson right from their storefront dock. You’ll also find an accessible kayak launch at Miller’s Landing. The slackwater of Mirror Pond at Drake Park downtown is a great DIY place for beginners to learn. Keep your distance from the spillway on the north end of the pond where the river plunges over a small drop and creates a recirculating water current.

A guided canoe or kayak tour from Wanderlust Tours makes it easy when transportation, gear, and expert local knowledge are all part of the experience. Their moonlight paddle tours are a must.
For splashy fun, June means time to go whitewater rafting with Sun Country Tours and Seventh Mountain Rafting on the Big Eddy section of the Deschutes River. Float by frozen-in-time lava flows, osprey nests, then punch through class II and III+ rapids. We dare you not to come out soaked and screaming, “Let’s do it again!”
Great places to swim in and near Bend include the newly accessible Miller’s Landing Park, McKay Park, Riverbend Park, and Farewell Bend Park.
For more ideas on where to cool off, follow the links on this page.

The Cascade Lakes Scenic Byway, colloquially known as Cascade Lakes Highway, is one of the prettiest drives around Bend, especially in June when snow still hangs on the Cascade peaks and wildflowers start popping up. All in all, about 14 lakes have direct road access, many of which are not paved. Check out this article for rules, maps, and other details. You’ll also want sturdy shoes and a couple extra layers, especially around higher-elevation spots like Sparks Lake and Todd Lake, where patches of snow can linger into early summer.
Most of these stops are easy to reach from Bend, making the highway perfect for a half-day drive or a full day outside. Resorts like Elk Lake Resort and Cultus Lake Resort rent kayaks, canoes, and boats, making it easy to get out on the water without hauling your own gear from town. They’re also great lunch stops (or grab picnic supplies from Wild Petals Provisions or Central Oregon Locavore ) before continuing farther up the highway.
Want to spend more time on the water? Book a guided fly fishing trip to Hosmer Lake with The Fly Fisher’s Place, where colorful brook trout cruise through crystal-clear water.

June is when Mt. Bachelor switches over to summer mode, with mountain bike trails, scenic chairlift rides, hiking trails, disc golf, and ziplining replacing ski runs and chairlift lines. The Evergreen Trail is especially great if you’re looking for an easier hike with huge Cascade views and no wilderness permit required. Book a sunset dinner mid-mountain for an unforgettable meal at a spectacular restaurant perched at 7,800 feet on the side of a volcano.
June in Bend works great for families, thanks to easy access to lakes, trails, river floats, and enough outdoor activities to wear everybody out.
The High Desert Museum is always a must in June when the outdoor exhibits and summer programs ramp up. Between the Raptors of the Sky demonstrations, river otters, and hands-on exhibits like the rad retro feel of Under Pressure: A Volcanic Exploration, it keeps kids and adults having equal amounts of fun.
If your crew still somehow has energy left after that, head to the Old Mill District for e-bike rentals and tours from Wheel Fun Rentals. Cruise along the river trail, downtown and the Old Mill District. Riders must be 14 years or older.
If your family’s into caves, volcanoes, and otherworldly landscapes, the Lava River Cave and Lava Lands Visitor Center make an easy stop south of town. Take a short, paved hike through ancient lava flows and reserve tickets for the self-guided 2-mile Lava River Cave hike. Walking through a giant lava tube tends to be the kind of thing kids talk about long after vacation ends. Wanderlust offers guided tours with naturalists who will blow you away with their knowledge.
For more ideas on family-friendly fun in Bend, check out this page.
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