🌲 Northern Oregon
- 🎭 Rose City Comic Con – September 5–7 | Oregon Convention Center (Portland)
Pop-culture fun for all ages—comics, cosplay, gaming, and celebrity guests under one roof.
https://rosecitycomiccon.com/ - 🚣 Portland Dragon Boat Festival – September 6–7 | Tom McCall Waterfront Park (Portland)
Paddle into excitement beside the Willamette River—spectacular races with cultural flair.
https://www.travelportland.com/event/68543dac0eda5e10b63c9a3c/ - 🎶 El Grito – September 14–15 | Moda Center / Rose Quarter Commons (Portland)
Celebrate with mariachi, folkloric dancers, tasty food booths, and a joyful “Grito” ceremony.
https://elgritoportland.com/index.php/en/home/ - 🌽 The Corn Maize on Sauvie Island – Through October 31 | Sauvie Island (north of Portland)
Get (gloriously!) lost in twists and turns across acres of corn, with epic views atop the bridges.
https://www.travelportland.com/events/corn-maize-sauvie-island/ - 🍎 Farmer’s Market at Shemanski Park – Every Wednesday, 10 AM–2 PM | Downtown Portland
Midweek fresh finds—local produce, crafts, and community vibes in the heart of the city.
https://www.travelportland.com/event/6839b09782a3881357d89431/ - 🥕 Kenton Farmer’s Market – Every Wednesday, 3 PM–7 PM | Kenton neighborhood, Portland
A lively evening market with fresh picks, friendly faces, and a neighborhood buzz.
https://www.travelportland.com/event/6839b08f82a3881357d8942c/ - 🍓 South Waterfront Farmer’s Market – Every Thursday, 2 PM–7 PM | South Waterfront District, Portland
Sunset strolls with seasonal goodies and a beautiful riverbank backdrop.
https://www.travelportland.com/event/6839b0aa82a3881357d8943e/
🏞 Central Oregon
- 🌸 Swan Island Dahlia Festival – Through September | Swan Island Dahlias, Canby
A sea of blooms awaits—bright dahlia gardens, local treats, and peaceful plant therapy.
https://www.dahlias.com/ - 🧘 Drake Park Yoga – September 2 | Drake Park, Bend
Stretch into serenity—outdoor yoga surrounded by parkside calm.
https://visitcentraloregon.com/event/do-yoga-outside-12/ - 🥬 Bend Farmers Market – Every Wednesday through October 8 | Bend
A weekly spread of farm-fresh produce, handmade goods, and small-town smiles.
https://www.bendfarmersmarket.com/ - 🐶 Sunriver Dog Fest – September 6 | Sunriver
Paws, play, and tail-wagging fun—this is one doggy day out you won’t want to miss.
https://visitcentraloregon.com/event/sunriver-dog-fest-%F0%9F%90%BE/ - 🍀 Halfway to St. Patrick’s Day – September 13 | Halfway
Shamrocks in September? You bet—halfway fun with green cheer and community flair.
https://visitcentraloregon.com/event/halfway-to-st-patricks-day-4/ - 🍺 Sunriver Oktoberfest – September 26 | Sunriver
Prost! Celebrate fall with brews, music, and that unmistakable German goodwill spirit.
https://visitcentraloregon.com/event/sunriver-oktoberfest/
🌄 Southern Oregon
- ⚾ Eugene Emeralds – September 2–6 & 7 | PK Park, Eugene
Swing by for America’s favorite pastime—fun, family, and baseball under September skies.
https://www.milb.com/eugene/schedule/2025-09 - 🚴 Bike Show – August 11–September 19 | Southern Oregon
Gears, glides, and two-wheeled pride—whether you ride or just admire, it’s bike-tastic.
https://tockify.com/whattodoinsouthernoregon/detail/3587/1754928000000?startms=1756710000000 - 🍻 Klamath Basin Oktoberfest – September 20 | Klamath Falls
Fall vibes, Bavarian bites, and music in southern Oregon style.
https://klamathoktoberfest.org/event/klamath-basin-oktoberfest-2025/ - 🌍 Medford Multicultural Fair – September 27 | Medford
A festival of flavors, traditions, and stories—discover the rich mosaic of our community.
https://www.facebook.com/events/702601119114934/?acontext=%7B%22event_action_history%22%3A[]%7D - 🛒 Grants Pass Growers’ Market – Every Saturday | Grants Pass
Fresh from the farm each weekend—local produce, plants, and neighborly chats.
http://www.growersmarket.org/ - 🌅 Applegate Evening Market – Every Wednesday through October | Applegate Valley
Twilight browsing with wine tastes, artisanal goods, and a relaxed valley vibe.
https://agreaterapplegate.org/1596-2/
🤠 Eastern Oregon
- 🎡 Baker County Fair & Rodeo – September 1 | Halfway
Boots, barns, and rodeo thrills—classic fair fun with big heart in small-town Eastern Oregon.
http://www.halfwayfairandrodeo.com/ - 🐴 Hells Canyon Mule Days – September 5–7 | Hells Canyon area
Mules, music, and canyon views—it’s outdoorsy, historical, and oh-so-Oregon.
https://www.hellscanyonmuledays.com/ - 🤠 Pendleton Round-Up – September 6–13 | Pendleton
Where the West still wins—the grand rodeo tradition that’s a statewide favorite.
https://www.pendletonroundup.com/
🌊 Coastal Oregon
- 🚗 Annual Cruz the Coos – September 20 | Coos Bay Area
Car show lovers, rev your engines—local rides and friendly car-enthusiast culture by the coast.
https://visittheoregoncoast.com/cities/annual-cruz-the-coos-2/ - 🔮 Lincoln City’s Finders Keepers Glass Floats – Various special drops | Lincoln City
Hunt for hidden treasures on the beach—keep your eyes peeled for these sparkling surprises.
https://www.explorelincolncity.com/things-to-do/glass-floats/special-drops/ - 🏛 Coos History Museum: First Tuesday Talk – September 2 | Coos Bay
Dive into local lore with museum talks that make history feel like a friend.
https://visittheoregoncoast.com/cities/coos-history-museum-first-tuesday-talk-5/ - 🛶 Conservation Kayak Excursion – September 3 | Coastal Waterways
Paddle with purpose—wildlife, waves, and ocean awareness on the water.
https://visittheoregoncoast.com/cities/conservation-kayak-excursion/ - 🎪 Mahaffy Ranch Home & Harvest Vendor Fair – September 5–6 | Mahaffy Ranch
Handcrafted treasures, home décor, and harvest-inspired finds await at this rustic fair.
https://visittheoregoncoast.com/cities/mahaffy-ranch-home-harvest-vendor-fair/ - 🌎 Biosphere Beach Ambassador – September 7 | Oregon Coast Beaches
Make a difference while strolling the sand—learn eco-beach stewardship with a friendly guide.
https://visittheoregoncoast.com/cities/biosphere-beach-ambassador-5/ - 🎸 Beach, Bike & Blues Festival – September 13 | Coast
Sun, tunes, and a bike-friendly beat—this is beachside rhythm at its best.
https://visittheoregoncoast.com/cities/beach-bike-blues-festival/ - 🍒 Bandon Cranberry Festival – September 13–14 | Bandon
Cranberries galore—celebrate the tart little berries with food, crafts, and fun coastal flair.
https://visittheoregoncoast.com/cities/bandon-cranberry-festival/ - 🪁 Fall Kite Festival: Night Flight – September 19 | Oregon Coast Beach
Glow-in-the-dark kites dancing over dunes—magical family night vibes on the beach.
https://visittheoregoncoast.com/cities/fall-kite-festival-night-flight/ - 🎉 Annual Bay Area Fun Festival – September 20–21 | Bay Area Coast (Coos Bay)
Family-friendly fun by the bay—music, crafts, and that relaxed seaside feeling.
https://visittheoregoncoast.com/cities/annual-bay-area-fun-festival/
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