Moving To Bend

🎶 Music Bingo is back at Pinky G’s!

Grab your friends, order some pizza, and put your music knowledge to the test for a night of songs, laughs, and prizes.

📅 Wednesday nights, October 7–January 27
🕡 Starts at 6:30 PM
📍 Pinky G’s
719 SE 3rd Street, Bend

Plan to arrive by 6:00 PM to grab a table before the games begin.

Learn more:

🔗 https://visitcentraloregon.com/event/music-bingo-night-at-pinky-gs/

🍂 Fall takes over Downtown Bend for three full days!

The Bend Fall Festival returns with the Harvest Market, live music and entertainment, arts and crafts, a Family Fun Zone, the Harvest Bake-Off, food, and plenty more to explore throughout downtown.

📅 October 2–4
📍 Downtown Bend

Festival hours:

Friday: 5:00–10:00 PM
Saturday: 11:00 AM–10:00 PM
Sunday: 11:00 AM–5:00 PM

This is a free community festival presented by Ember Saunas and organized by Lay It Out Events.

Learn more:

🔗https://visitcentraloregon.com/event/bend-fall-festival-where-fall-comes-to-life/

🍻 Fresh-hop season is here!

Fresh Hops on the Pond returns to Bend Brewing Company—and this year, it’s a two-day celebration. Taste your way through more than 30 fresh-hop b**rs from breweries across the West Coast while enjoying live music throughout both days.

📅 October 2 & 3
🕚 11:00 AM–3:00 PM
📍 Bend Brewing Company
1019 NW Brooks Street, Bend, Oregon

Grab a tasting package, collect your glass and tokens, and explore fresh-hop season one half-pour at a time.

Learn more:

🔗https://visitcentraloregon.com/event/fresh-hops-on-the-pond-at-bend-brewing-co/

🛍️ Spend Thursday evening in Downtown Madras!

Madras First Thursdays brings local vendors, music, food, and neighbors together for a relaxed community evening. Browse locally made goods, stop by your favorite downtown restaurants, and see what Madras has to offer.

📅 Thursday, October 1
🕔 5:00–7:00 PM
📍 Downtown Madras

First Thursdays takes place monthly in the heart of downtown.

Learn more:

🔗 https://visitcentraloregon.com/event/madras-first-thursdays/

🍷 A five-w**e flight and four chef-created dishes are coming together for one special evening in downtown Bend.

The Harvest Chef’s Pairing Experience at Willamette Valley Vineyards will be hosted by Winery Ambassador Ashley and Chef Cuin. The tasting is designed as a communal experience, giving guests time to enjoy each pairing and connect with other food and w**e lovers.

📅 Wednesday, September 30
🕓 4:00–6:00 PM
📍 Willamette Valley Vineyards — Bend
916 NW Wall Street, Bend
🎟️ $80–$95 per person

Tickets include gratuity and a $40 bottle credit with the purchase of two or more bottles.

Learn more and reserve your seat:

🔗 https://visitcentraloregon.com/event/harvest-chefs-pairing-experience/

🎶 Tuesday night plans?

Enjoy dinner, drinks, and live music at Greg’s Grill along the Deschutes River. Local artists provide the soundtrack for a relaxed evening with good food and great company.

📅 Tuesday, September 29
🕕 6:00–8:00 PM
📍 Greg’s Grill
395 SW Powerhouse Drive, Bend, Oregon

September 29 is the final listed date in this month’s Live Music Tuesdays series.

Learn more:

🔗https://visitcentraloregon.com/event/gregs-grill-live-music-tuesdays/

🚵 Ready for a full day on Central Oregon singletrack?

Cog Wild’s next Adventure Ride heads to Round and Lookout Mountains in the Ochoco National Forest. Expect around five hours on the trail, followed by cold drinks with the group.

📅 Saturday, September 26
📍 Ochoco National Forest
🚐 $95 with transportation from Bend
🚵 $50 when meeting at the trailhead

These rides are designed for very fit intermediate and expert mountain bikers. Bring plenty of water and food, a charged phone, first-aid supplies, and tools for trailside repairs.

The 2026 Adventure Ride series continues through October 10.

Learn more and register:

🔗 https://visitcentraloregon.com/event/cog-wild-adventure-ride/

🍺 Oktoberfest is underway in downtown Bend!

McMenamins Old St. Francis School is celebrating the season with German-inspired food specials, plenty of b**r, and live music on select dates.

📅 September 18–October 3, 2026
📍 McMenamins Old St. Francis School
700 NW Bond Street, Bend, Oregon

Stop by for a seasonal meal, raise a glass, and enjoy a little Oktoberfest spirit without leaving Central Oregon.

Specific menu pricing and live-music times are not listed on the event page, so check with McMenamins before visiting.

Event details:
🔗 https://visitcentraloregon.com/event/oktoberfest-sept-18th-oct-3rd/

Follow MovingToBend for more food, music, and community events around Central Oregon!

✨ Ready to turn your goals into a plan you can actually follow?

Create Your Next Chapter is an interactive workshop from Happy Well Coaching that combines movement, creativity, and guided reflection. Participants will identify realistic next steps, create a personalized action plan, and make a vision board to take home.

📅 Thursday, September 24, 2026
🕤 9:30 AM–12:30 PM
📍 Bend Tea + Art Lounge
1024 NW Bond Street, Suite 101, Bend
🎟️ $99, plus a $2.48 service fee

Come ready to move, laugh, create, and gain a little more clarity about what comes next.

Event details and tickets:
🔗 https://visitcentraloregon.com/event/create-your-next-chapter/

Follow MovingToBend for more workshops, community events, and things to do around Central Oregon!

🎸 Three Texas guitar powerhouses. One night at the Tower Theatre.

Texas Headhunters brings Ian Moore, Jesse Dayton, and Johnny Moeller together for a high-energy mix of blues, roots rock, funk, and outlaw country.

📅 Wednesday, September 23, 2026
🚪 Doors open at 6:30 PM
🎶 Show starts at 7:30 PM
📍 Tower Theatre
835 NW Wall Street, Bend, Oregon

🎟️ Tickets: $17–$27, plus an $8 Historic Preservation fee.

If you like loud guitars, raw musicianship, and the energy of an Austin club show, this one belongs on your calendar.

Event details and tickets:
🔗 https://visitcentraloregon.com/event/texas-headhunters-featuring-ian-moore-jesse-dayton-johnny-moeller/

Follow MovingToBend for more concerts, events, and things to do around Central Oregon!