Based on Wallowa County Chamber of Commerce Calendar – Updated 2026 April is quiet… but May is when things start waking up in Wallowa County. You’ll begin to see live music, cultural events, food experiences, and spring activities return.

⭐ Top Events Visitors Will Enjoy

🎉 Friday, May 1, 2026

🎟️ Joseph FFA Alumni Dinner & Auction

📍 Joseph Charter School
401 N Main St, Joseph, OR 97846
📞 (541) 432-7311
👉 https://business.wallowacountychamber.com/events/details/2026-joseph-ffa-alumni-dinner-auction

🕕 Time: Typically evening (around 5:30–8:30 PM)
💲 Cost: Usually $15–$25 (varies yearly)

• Dinner, raffle, and auction

• Open to the public

🎬 Friday–Saturday, May 1–2, 2026

🎥 Movie Night at OK Theatre

📍 OK Theatre
208 W Main St, Enterprise, OR 97828
📞 (541) 426-3044
👉 https://business.wallowacountychamber.com/events/details/nacho-libre-at-ok

🕖 Time: Typically 7:00 PM
💲 Cost: $5–$10

• Historic small-town theater

• Fun, relaxed evening

🎶 Saturday, May 2, 2026

🎸 Live Music – Cale Moon

📍 Stubborn Mule Saloon & Steakhouse
104 N Main St, Joseph, OR 97846
📞 (541) 432-6853
👉 https://business.wallowacountychamber.com/events/details/cale-moon-live

🕗 Time: Around 7:00–9:00 PM
💲 Cost: Free (food/drinks extra)

• Lively western bar setting

• Great nightlife option

💃 Sunday, May 3, 2026

🎶 Ecstatic Freestyle Dance

📍 Josephy Center for Arts & Culture
403 N Main St, Joseph, OR 97846
📞 (541) 432-0505
👉 https://business.wallowacountychamber.com/events/details/ecstatic-freestyle-dance

🕓 Time: ~4:00–6:00 PM
💲 Cost: $10–$15 suggested donation

• Music + movement experience

• Beginner-friendly

✍️ Wednesday, May 6, 2026

📝 Writing the Journey Workshop

📍 Josephy Center / Fishtrap
403 N Main St, Joseph, OR 97846
📞 (541) 432-0505
👉 https://business.wallowacountychamber.com/events/details/writing-the-journey

Date and Time

Wednesday May 6, 2026
5:00 PM - 7:00 PM PDT

Wednesdays, May 6, 13, 20, 2026
5-7 PM 

Location

Attend In-Person or Online

Fees/Admission

Registration $120 or $110 for Fishtrappers

Website

https://fishtrap.org/emerick/

Annual Spring Artisan Market:

"The Spring Artisan Market will take place in the parking lot of Stein distillery in Joseph.  This event will serve as an opportunity to celebrate Mother's Day weekend with local women artisans.  There will be Pottery, Jewelry, Fine Art Prints, Candles, Leather Work, Soap and Body Care, Knitting, Kettle Corn and much more." (Oregon's Wallowa County Chamber of Commerce)

Click Here

Date and Time

Saturday May 9, 2026
10:00 AM - 4:00 PM PDT

Location

Stein Distillery, 604 N. Main St., Joseph

Two Rivers Train Ride:

"The rushing rivers, wild flowers and dramatic landscape are highlights when the train departs from the Elgin Depot and follows the banks of the Grande Ronde River to Rondowa, where it is joined by the Wild & Scenic Wallowa River. The ride continues a couple of miles up the Wallowa, then reverses direction for the return to Elgin." "Departs from Elgin 10 a.m. / returns at about 1:30 p.m. 38 miles, round trip."(Oregon's Wallowa County Chamber of Commerce)

Date and Time

Saturday May 23, 2026
10:00 AM - 1:30 PM PDT

Location

 Oregon 300 Depot Street, Elgin, OR, United States, 97827

Fees/Admission

Adults = $85 / Seniors 60+ = $80 / Youth, 3 to 16 = $40 (kids under 3 ride for free!)

Website

https://eaglecaptrainrides.com/book-online/

Contact Information

541.437.3652

Jammin in the Canyon Music Festival:

Music Festival in the Heart of the Canyon!

Date and Time

Saturday May 30, 2026

Location

Imnaha, Oregon

Fees/Admission

Adults 26+ $45

Seniors 62+ $35

Student 3-12 $15
2 & Under Free

R.V. or tent camping will be $20 a night and $5 for parking for the day

Contact Information

Heather at 830-719-5141 https://www.jammininthecanyon.com/

Seeking Bigfoot Two Rivers Train Ride: 

"This trip promises excitement and fun, as we’ve heard Bigfoot has been spotted in the area! Are you a naysayer or a believer? Ride the train and join in the fun. A delicious, boxed lunch is included and served along the way. Departs from Elgin at 10 a.m. / returns at about 1:30 p.m. 38 miles, round trip."(Oregon's Wallowa County Chamber of Commerce)

Date and Time

Saturday May 30, 2026
10:00 AM - 1:30 PM PDT

Location

Elgin Train Depot, Elgin Oregon 300 Depot Street, Elgin, OR, United States, 97827 

Fees/Admission

Adults = $85 / Seniors 60+ = $80 / Youth, 3 to 16 = $40 (kids under 3 ride for free!)

Website

https://eaglecaptrainrides.com/book-online/

Contact Information

541.437.3652

🎶 Ongoing Weekend Activities

🎤 Live Music & Open Mic Nights

📍 Multiple locations (Joseph & Enterprise)

Popular spots:

• Terminal Gravity Brewing - click here
  📍 803 SE School St, Enterprise
  🕕 Evenings (varies)
  💲 Free

• Stubborn Mule Saloon - click here
  📍 104 N Main St, Joseph
  🕖 Evenings
  💲 Free

🌿 Spring Experiences (Highly Recommended in May)

(These are HUGE for tourists—even more than events)

🌼 Wildflower Viewing – Zumwalt Prairie

📍 Zumwalt Prairie Preserve

🕗 Time: Daylight hours
💲 Cost: Free

• Peak early wildflower season

• Wildlife viewing

🚴 Hiking & Scenic Drives

📍 Wallowa Lake State Park - click here
72214 Marina Ln, Joseph, OR
📞 (541) 432-4185

🕗 Time: Sunrise–Sunset
💲 Cost: Free day-use / small parking fee

🛶 Wallowa Lake Marina Opening - click here

📍 60060 Wallowa Lake Hwy, Joseph
📞 (541) 432-9115

🕘 Time: ~9:00 AM–5:00 PM
💲 Cost:

• Kayaks: ~$20–$40

• Boats: ~$60+

• Rentals begin reopening in May

📅 Where to Find Updated Events

👉 https://business.wallowacountychamber.com/events/calendar

📞 Helpful Visitor Contacts

Joseph Visitor Center
📍 Joseph Visitor Information Area

Downtown Main Street (across from Slack Drinks & Dining, 108 N Main St)
📞 (541) 432-1015, (541) 263-8497

Wallowa County Chamber of Commerce
📍 309 S River St, Enterprise
📞 (541) 426-4622

⚠️ Important Notes

• Times and prices may change yearly

• Always confirm before attending

• Late May (Memorial Day) = busier

✅ Final Tip

If you're visiting in May, aim for:

• Weekend evenings (music + events)

• Daytime outdoor exploring

👉 This combo gives you the best experience

🔥 Planning your trip?

Check out our favorite travel essentials, gear, and local recommendations:

What to Bring to Joseph Oregon: Packing List

Best Gear for Wallowa Lake (Boating, Hiking & Camping)

What to Bring to Chief Joseph Days Rodeo & Festivals