This weekend in Bend, OR

Designed for those seeking a true Central Oregon trail adventure, this all-trail race explores the Deschutes National Forest with wide-open views, rolling terrain, and signature high-desert singletrack. Each course begins and ends at Wanoga Sno-Park at roughly 5,500 feet, guiding runners through shaded forest, rocky stretches, and short, steep climbs. The marathon features a late 700 foot ascent that rewards steady pacing and grit. Come prepared for varied footing and elevation, and take on a scenic, challenging day on the dirt.

Enjoy the Sunriver Art Fair, featuring around 90 booths filled with fine art and crafts. You can browse a wide mix of one-of-a-kind works, including ceramics, glass, jewelry, painting, photography, sculpture, textiles, woodworking, drawing, and mixed media, all set in the Village at Sunriver. Admission is free, and parking is also free. Proceeds support the Sunriver Women’s Club Community Grant Program.

A casual meetup centered on bikes and friendly conversation. The focus is simply chatting about anything bike related or relaxing with kind company. The tone is welcoming and low pressure, so even a brief hello fits the spirit of the gathering.

Learn the responsibilities of concealed carry in a focused four hour class held at Sportsman’s Warehouse Bend in Bend, OR. This combined Oregon Concealed Handgun License and Arizona Concealed Weapons Permit course explains when and how force may be used, reinforces safe firearm practices, and covers correct handling and secure storage. Instruction also reviews the legal steps and qualifications for permits in Oregon, Arizona, and Utah. Schedule details may change, so check the provider’s website for the most current information.

A community marketplace highlights local creators with a variety of vendors. Enjoy offerings from food trucks as you browse unique goods and pick up fresh Pacific Northwest produce.

Join TrueLeah's Art Studio for a relaxing, in-person Bob Ross inspired painting workshop at TEAL Tea + Art Lounge. You’ll follow the joyful wet-on-wet oil painting technique to create a beautiful landscape called “Towering Peaks.” No experience is needed, and all painting supplies are included, including brushes and a 12x16 canvas. Doors open at 9:45 AM, and there’s free parking. This workshop is for ages 14 and up.

Enjoy a relaxed yarn meetup at American Legion Park in Redmond. Bring a chair and your own yarn, settle in, and chat with others who share an interest in crafting. It is a simple, social chance to unwind in the park with your projects and friendly conversation.

Step into Central Oregon’s 1940s past at the Hollinshead-Matson Homestead Museum in Hollinshead Park. Take a complimentary guided visit and hear firsthand stories about farming and everyday life in Bend from Sharron Rosengarth, a Matson family member who grew up in the homestead house. No reservations are required. Presented by Sharron Rosengarth and Bend Park and Recreation District, with support from volunteers and the Deschutes County Historical Museum. Private tours for small groups may be available by appointment.

Enjoy open DIY hours designed for creative exploration at your own pace. Choose from projects like drawing, printmaking, or collage. All materials are provided, and helpful guidance is available so you can focus on creating. No reservation is required, walk in whenever it suits you.

Chained to Stone brings a three hour set of heavy 90s rock to Hardtails Outlaw Country Dive Bar & Grill during the Iron and Thunder Run biker rally. The performance features covers spanning Stone Temple Pilots, Alice in Chains, Nirvana, Pearl Jam, Soundgarden, Smashing Pumpkins, Silverchair, and more. Expect a loud, high energy show with motorcycles in the mix and cold drinks on hand, creating an electric evening at a lively Central Oregon summer rally weekend.

Tedeschi Trucks Band brings the Future Soul 2026 Tour to Hayden Homes Amphitheater. The venue is an open lawn without permanent seating. Depending on the show, some sections may be reserved and low-profile chairs may be available to rent, so check the venue for seating options specific to this concert. All events take place rain or shine. The amphitheater is cashless. Outside food and beverages are not allowed, and professional cameras or recording equipment are prohibited. Only clear bags up to 12 by 12 by 6 inches are permitted, with small clutches up to 6 by 9 inches as the only exception. To ease travel, the amphitheater is partnering with Commute Options to promote walking, biking, transit, carpooling, and other alternatives that help reduce traffic and parking demand. Concertgoers can take part in the Summer Commute Challenge for chances to win prizes and concert tickets during the season. For maps, directions, parking details, permitted and prohibited items, accessibility information, and other FAQs, consult the venue’s official resources.

Experience a family friendly karaoke gathering that welcomes all ages. Singing is free, giving everyone the chance to sing their hearts out and enjoy time together.

This introductory meditation workshop offers clear guidance for getting started and support for those returning to practice. It addresses frequent roadblocks, including the belief that the mind must be completely blank, that long sessions are required, that a wandering mind means failure, or that you must sit cross legged and remain perfectly still. The session highlights how meditation can lift mood, improve sleep, spark creativity, support brain health, and build resilience. Participants create a personal practice that feels realistic and sustainable. Instruction focuses on developing steady concentration to relate skillfully to thoughts, emotions, and body sensations. You will learn practical ways to cultivate qualities like joy, kindness, equanimity, gratitude, compassion, and self compassion, along with methods for bringing mindful awareness into everyday activities and communication. The experience blends information, journaling, discussion, and guided meditation. Seating is arranged in a circle to encourage community and open sharing of insights and reflections. It suits complete beginners and also serves practitioners who want to refine their approach. The cost is $35 per person, or two people for $50. The workshop is led by Sadie Barr, who has guided mindfulness and meditation students for more than a decade. Her training includes study with Tara Brach and Jack Kornfield, and she explores the intersection of neuroscience and contemplative practice through the work of Rick Hanson. Her guided sessions on Insight Timer have been played over 350,000 times, and she teaches a ten week foundational mindfulness course at Central Oregon Community College for both community members and degree seeking students.

Brooklyn Del & The Revelators deliver a Portland, Oregon take on Americana, led by Brooklyn Del at the front of the group. Their music blends dust-kissed country grit with widescreen storytelling, matching vivid lyrics to seasoned players for a sound that feels both unvarnished and spacious. Their debut EP, Lights and Last Resorts, introduced a restless, roots-forward approach, and their energetic live set reflects growing momentum throughout the Northwest. Expect evocative songs, tight interplay, and a cinematic sense of place from a band hitting its stride.

Experience the Italian edition of the FivePine Destinations Dinner Series, where Central Oregon’s freshest ingredients from local farms and ranches are transformed by the in-house chef and served creekside at the Elda Teresa Event Center. Enjoy an evening of warm company in a beautiful setting while benefiting Seed To Table, with ingredients and provisions sourced locally from Seed to Table, Mahonia Gardens, and Cascade Mountain Pastures. Make it a luxury weekend at FivePine with a stay of two or more nights that includes the night of the dinner, and the ticket cost will be credited back to the final lodging bill.

Only Yesterday pays tribute to the mellow hits of the 1970s, spotlighting songs made famous by the Carpenters, Anne Murray, and Linda Ronstadt. Vocalist Amy Daves interprets these classics with heartfelt clarity rather than imitation, and with support from an experienced band the show is crafted to feel more like rediscovering a time capsule than a typical concert. The performance takes place at the Tower Theatre. Guests are encouraged to embrace the era with bell bottoms, fringe, platform shoes, macrame accents, and vintage concert tees, and to be ready for sing-along moments. Tickets are limited. VIPs receive an up-close photo opportunity with Amy Daves, a band-signed set list, and a meet and greet.

Saturday nights bring an adults-only open skate with music pumping and the lights turned low for a nostalgic rink experience. Skaters must be 18 or older. Admission is $10 for ages 18 to 64 and $9 for ages 65 and up. Skate rentals are available for $4 per person. Please bring your own helmet. On the fourth Saturday, a live DJ plays favorites.

At Hayden Homes Amphitheater, the Bend stop brings a calm yet intent energy that lets every note breathe in the open air. The performance feels open and grounded, inviting listeners to tune into the subtle details as the music settles into a summer evening. Keep On Growing unfolds slowly, echoing the unhurried mood. Susan Tedeschi’s vocals are warm and expressive, while Derek Trucks shapes graceful guitar lines that favor melody and tone over speed. With Lukas Nelson adding a roots-infused color that blends naturally into the band’s sound, the night centers on patience, musical trust, and a quiet strength that has become a hallmark of this tour.

The Flying Kayak Open is celebrating its fourth edition and returns to central Oregon’s Davis Lake, known for amazing scenery, lava flows, clear water, tall reeds, and big largemouth bass. Organizers are working on payout boosts, and kayak fishing gear giveaways are planned, including a brand new G. Loomis’ IMX-PRO V2 8810-4 8-weight, 8-foot-10-inch fly rod valued at $595, along with more prizes. This event follows the KFNW Summer Open on nearby Crane Prairie Reservoir. KFNW membership is not required for either event, and for the Crane Prairie competition, flies and fly rods are not required but are allowed.

Join Heart of Oregon Corps for Not'cho Grandma's Bingo at Silver Moon Brewing. Tickets include reservable tables and seats. Doors open at 9:30 AM, bingo cards are available for purchase from the nonprofit, and the morning includes a series of bingo games with a nonprofit shoutout during the rounds.

The Sisters Farmers Market brings fresh foods, local farms, handcrafted art, and a welcoming sense of community to the heart of Sisters, Oregon. Browse offerings from more than 45 Central Oregon farmers, ranchers, food producers, and makers, including seasonal fruits and vegetables, meats, eggs, baked goods, honey, and a variety of handmade items. Weekly activities are planned for children and adults. The market accepts SNAP/EBT and also offers Double Up Food Bucks to help stretch food budgets and increase access to locally grown food.

River's Place Taproom in Bend hosts a live trivia session presented by UKB Trivia. Teams play for free and compete for house gift cards. The taproom pours cold brews and ciders and features a house mimosa menu, while the beer garden offers food from Nik's Snacks, Bai Tong on Wheels, The Zone, and Fresco & Fryed. Bringing a pen is recommended. UKB Trivia highlights a commitment to human intelligence and creativity and states that no AI is used in the creation, marketing, production, or presentation of its shows.

This family art camp at FREAK'N ART invites ages 7 and up to create colorful dessert-themed paintings with teaching artist Anastasia Zielinski. Inspired by Wayne Thiebaud’s iconic confections, participants use acrylics and thick texture while exploring palette knife techniques, playful color mixing, and composition to craft a frosted-looking piece to take home. All materials are provided, and a sweet treat is included for inspiration. Please share any food allergies at checkout so treats can be planned accordingly. Families registering two or more can use code SWEETTREAT10 for 10% off. Space is limited to 10 artists per session.

A family-friendly open skate invites participants to roll for $8 per person, with skate rental included. Access to The Pavilion’s skatepark features is part of the session, and a variety of wheels are welcome, including roller skates, roller blades, skateboards, and scooters. Children under 3 are free with a paying adult, and all children must be accompanied by a parent or guardian. Please bring your own helmet, as helmets are required in the skatepark.

Designed for those who have completed a jewelry class at DIYcave, this open studio provides time to practice techniques, work on personal pieces, and create gifts in a friendly, shared workspace. It is not a class, and techniques are not taught, but someone will be available to answer questions and assist with tools. Participants are expected to have the basic knowledge and skills required to complete their projects. Tools are provided. Jewelry-making supplies can be purchased on site or you can bring your own. Materials are not included. DIYcave Members receive a 20% discount.

Bring a team for a free trivia event at Initiative Brewing with UKB Trivia. Play for prizes while you put your knowledge to the test, enjoy food and brews, and have some fun. If possible, bring a pen and your best vibes. UKB Trivia highlights human intelligence and creativity and states it does not voluntarily use AI in the creation, marketing, production, or presentation of its shows.

This open mic offers a welcoming, encouraging space to refine your craft and share your work. Enthusiastic hosts create a comfortable setting for open sharing.

The River Ramblers perform as a Missoula-based bluegrass quintet, pairing fast picking with close harmonies for a powerful live presence. Emerging from the University of Montana music scene, they blend traditional bluegrass with high-energy, toe-tapping numbers that keep audiences engaged throughout the show.

Presented by Volcanic Theatre and 1988 Entertainment, Nick Shoulders brings the Apocalypse, Never! Tour to Volcanic Theatre Pub for an outdoor show in the Volcanic Courtyard. The performance highlights outlaw country and folk influences. Tickets cost $20 in advance and $30 at the door.

Gavin Adcock brings The Day I Hang It Up Tour 2026 to Hayden Homes Amphitheater. The concert takes place rain or shine at a grassy venue with no permanent seating. Reserved seating may be available at select shows, and low profile chair rentals vary by concert, so check the venue website for details specific to this performance. Outside food and beverages are not permitted, and professional grade cameras or recording devices are not allowed. The venue is cashless. Only clear bags up to 12 inches by 12 inches by 6 inches are allowed, with small clutches up to 6 inches by 9 inches as the only exception. This summer, the amphitheater is partnering with Commute Options to encourage walking, biking, carpooling, transit, or other alternatives to ease traffic and parking. Concertgoers can take part in the Commute Options Summer Commute Challenge for chances to win prizes and concert tickets throughout the season. For venue maps, directions, parking information, permitted and prohibited items, accessibility details, and other FAQs, visit the venue website.

McMenamins presents a Great Northwest Author Tour conversation featuring Gabi Moskowitz and Jim Newton, focusing on Jerry Garcia and Deadhead culture. Moskowitz is the author of Dead in the Kitchen: The Official Grateful Dead Cookbook, and Newton wrote Here Beside the Rising Tide: Jerry Garcia, the Grateful Dead, and an American Awakening. The event will be held at McMenamins Old St. Francis School in Father Luke’s Room. It is part of the McMenamins Days Between Celebration. Signed books will be available for purchase courtesy of Roundabout Books. Admission is $15, or $20 at the door.