September Events
Enjoy some of Portland's largest festivals and seasonal events every September.
Every September, Portland’s calendar overflows with events and things to do. Catch the seasonal migration of thousands of Vaux swifts as they nest for the month at a local elementary school, dig into one of the nation’s largest foodie festivals (where you can taste dishes by culinary stars from around the world), and choose from multiple arts festivals and cultural offerings. Read on for some of our favorite September events, or check out our full events calendar to see everything on offer.
Art in the Pearl
More than 100 artists offer up their creations, from painting and photography to jewelry and hand-crafted furniture, for Art in the Pearl over Labor Day Weekend in the North Park Blocks, with food vendors, musicians, and family activities rounding out the offerings.
Rose City Comic Con
Every year fans of all stripes descend on Portland for one of the biggest pop culture events in the city, Rose City Comic Con. Held at the Oregon Convention Center, you can catch panels with your favorite celebrities, get access to artists, writers and creators and witness next-level cosplay – or craft a costume of your own!
Chapman Swift Watch
Every September, the towering smokestack of Chapman Elementary School in Northwest Portland attracts as many as 16,000 swifts looking for a place to hunker down for the evening. The Chapman Swift Watch attracts hundreds of onlookers who flock to a nearby grassy bank at sunset and watch in awe as the shadowy clouds of birds fly acrobatically to roost inside the craggy chimney for the night.
Fall in Portland
Enjoy the magical transition from summer to fall in Portland with these beloved activities.
Fall Hikes Near Portland
These fall hikes near Portland prove that autumn is an ideal time to explore Oregon wilderness, admire seasonal flora and fauna, and visit nearby farms.
Portland’s Best Spots for Fall Color
Autumnal beauty abounds in Portland, and there are plenty of prime places to revel in leaf-crunching relaxation.
Bird-Watching in Portland
Catch sight of 200+ types of birds at the Portland area’s dozens of prime bird watching destinations, including sanctuaries, refuges and urban parks.
Dahlia Festival
Swan Island Dahlias open their fields every year for the annual Dahlia Festival. Stroll through almost 40 acres (16 hectares) and a beautiful display garden of stunning dahlias featuring over 370 varieties. You can also shop for locally handmade items at the Sunday Market while enjoying a delicious treat from a food cart, take a flower arranging class or relax and enjoy some live music.
Portland Retro Gaming Expo
The Portland Retro Gaming Expo is a locally produced event celebrating the colorful history of console, computer and arcade gaming. The arcade is massive, and all coin-operated games are set to free play for the weekend.
Time-Based Art (TBA) Festival
During the Time-Based Art Festival, presented by the Portland Institute for Contemporary Art (PICA) visual artists, musicians, dancers and other creatives from all over the world push boundaries with installations, performances and interactive art experiences.
Dragon Boat Festival
Enjoy Portland’s annual Dragon Boat Festival, featuring dragon boat racing along with food vendors, a beer garden and more. The event features as many as 96 dragon boat teams from all over the world who race in Hong Kong-style dragon boats along Tom McCall Waterfront Park.
El Grito Fiestas Patrias
Hosted by the Mexican consulate in Portland, El Grito is a celebration of Mexican independence at the Moda Center. With mariachi bands, Aztec dancers, traditional food, drink, and more, Portland’s fiesta is one of many celebrated at Mexican embassies worldwide.
More September Events 2025
Check out our picks for top things to do in September in Portland.
First Thursday in the Pearl District
Starting in 1986, First Thursday in the Pearl is a district-wide celebration on the first Thursday of each month. Originally a gathering of art collectors and dealers, the celebration has grown to a monthly event of over ten thousand people, including art enthusiasts, wine aficionados, and scenesters looking to see and be seen. Art galleries in...
Slamlandia
Poetry Open Mic and Slam in Portland, Oregon. It is the mission of Slamlandia to provide an open mic and poetry slam that is creative, fun, and welcoming to all literary communities in Portland. They strive towards a safer space for poets to share work, witness others, and participate in the community.
First Friday PDX
Located in Portland’s vibrant East Side Arts District, the First Friday Art Walk takes place on the first Friday evening of every month year-round. Offering a gateway into Portland’s thriving arts culture, First Friday PDX includes more than 23 independent galleries, shops, and studios and a street exhibition from April to October. The self-guided tour...
Hollywood Farmers Market
Year-round on Saturdays, the Hollywood Farmers Markets hosts 50+ vendors, bringing you the best of the region’s agricultural bounty. In addition to amazingly fresh, local food, you’ll find live music, children’s activities, and fun events throughout the season. April through September, every Saturday 8 AM to 1 PM,, October and November, every Saturday 9 AM...
Woodlawn Farmers Market
The Woodlawn Neighborhood Farmers Market was born out of a neighborhood’s desire to connect residents with small, local farms, making fresh, affordable, and healthy food more accessible. Farmers markets provide a gathering place for the community to celebrate the season’s harvest, connect with neighbors, friends, and farmers, and enjoy local music and educational opportunities. The...
Mt. Hood Loop Tour including Multnomah Falls
Buckle up for an epic journey as you are whisked away from Portland to the spellbinding Mt. Hood. With passionate and well-informed guides leading the way, you’ll have plenty of chances to snap up some breathtaking shots of the majestic landscape and soak up the mesmerizing history of this iconic mountain. Enjoy a full day...
Multnomah Falls & Gorge Waterfalls Tour
Prepare to journey back to the birth of the Cascade Mountain Range, where lava and pyroclastic matter oozed and flowed, creating a solid layer of basalt rock that coated Western Oregon. Fast-forward to the Pleistocene Ice Age and witness the epic Lake Missoula Flood, which carved out the majestic Columbia River Gorge, leaving behind sheer...
Oregon Coastal Tour
Get ready to soak up some serious sun and sand along Oregon’s stunning coastline. With towering cliffs, playful sea lions, and golden beaches for days, it’s no wonder this place is a beach bum’s paradise. The adventure will take you to some of the most jaw-dropping spots, like the iconic Cannon Beach, home to majestic...
Oregon Wine Tasting Tour
Sip your way through Oregon’s finest wines on an extraordinary tasting tour, only a day trip away from Portland. Discover the stunning Willamette Valley, and be guided through the best wine experiences it has to offer. Soak up the breathtaking views, visit three amazing vineyards, and unveil the secrets behind the perfect Oregon Pinot Noir....
Portland City Tour
Get ready to explore the heart and soul of Portland with a half-day City Tour. This isn’t your average tour; you'll be taken on a journey through the city’s charming streets, which will reveal its laid-back atmosphere. Brace yourself for an amazing tour of Portland’s must-see spots like the International Rose Garden (seasonally), the...
Portland City Tour & Gorge Waterfalls Combo
Ready for an adventure? Join the ultimate tour of Portland and the Columbia River Gorge. You'll see the must-see sights in Portland and the surrounding area and then whisk away to the stunning Columbia Gorge National Scenic Area. Discover the magic of the waterfalls, soak in breathtaking views, and dive into the history of the...
It's Gonna Be Okay
It's Gonna Be Okay is a free WEEKLY stand-up comedy show EVERY Monday. The show showcases the best comedians in Portland, along with national acts. Every Monday at 8 pm in the Tap Room 21 and up only
Live Music and Open Mic
Free live music at the Hostel Cafe every Monday. This fun event draws tons of people each week and features a local artist, as well as two open mic sessions. Come and check out the singer-songwriter sets and enjoy some Portland-made brews and locally sourced foods while you do it. Indoor and outdoor seating is...
Trivia With Sam
Get ready for TRIVIA WITH SAM. Sam is a trivia pro with three years of experience, starting in 2019 after one too many ciders at Mayfly Taproom, where he somehow volunteered to run a trivia night. (He stuck around until life sent him packing to DC in August 2021.) Now he’s back, and trivia’s coming with...
Portland Food Cart Tour
Discover what the food cart hype is all about in the city that invented food cart pods. With over 600 food carts throughout the city, you'll explore some of the best and taste the delicious foods that make Portland a true foodie destination. On this small-group walking tour you’ll discover global foods, quench your thirst...
Sit Down, Shut Up, and Write
No more procrastination. Bring your work in progress and join other writers for some dedicated time to get your words down. Every Wednesday 5:30–5:45 Arrive, get comfortable, meet your fellow writers, and chat about your projects 5:45–6:45 Time to shut up and write
Trivia Night at The Hostel Cafe
Join every Wednesday night for free trivia night. Whether you're flying solo or bringing a team, everyone's welcome — show up, no sign-up required. The Hostel Cafe is all about bringing locals and travelers together over great food and local brews. It's one of the most popular events, with chances to win appetizers and gift...
Weird Portland Pub Tour
This tour is a must-do for anyone who likes beer and is interested in Portland’s artistic flair. Skip those boring tours about the Founding Fathers; hear stories of Bigfoot sightings, exploding whales, a bagpipe-playing unicyclist, wacky-themed bike rides, hipsters, the world’s smallest park, aliens, and more. The tour takes place in the vibrant Hawthorne neighborhood...
BOLD Children’s Storytime
Join Saturday mornings for children’s storytime. Whether an author is here to read their book or the staff is reading a favorite, the stories featured will spread compassion, awareness, and positivity. Children will get a coloring page or sticker to take home, too. The shop carries juice, snacks, and other items for kids and adults. While...
Sleaze Pleaze Video Dance Party
Indie classic and current music videos dance party every Saturday at Swan Dive. Swan Dive is a vintage craft cocktail bar with nightly events and dance parties downstairs and a speakeasy-style live music venue upstairs. Located in a historic building overlooking the Morrison Bridge, offering a unique blend of vintage charm and New Age entertainment....
Bridge Tour
This downtown Portland walking tour will take participants around, across, under, and inside the unique and storied spans that shape the experience of those living and visiting Portland. The route will include several bridges (with specific spans TBA), and on one of those, the tour will plan to meet a Multnomah County bridge operator to...
Linkin Park
Rooted at the crossroads of aggressive metal and beat-driven hip-hop, Linkin Park became one of the most successful acts of the early 21st-century by incorporating elements from across genres, injecting hardcore rap, raucous punk, atmospheric electronic, and even polished pop stylings into their music. Despite being burdened with the oft-derided nu-metal and rap-rock genre designations,...
Karaoke Cabaret at Portland Wine Company
What use is sitting alone in your room on a Sunday night? Come to the Karaoke Cabaret at Portland Wine Company. You can channel your inner Sally Bowles, show off your Sondheim chops, or just sit back and sing along to Golden Age classics while sipping on handcrafted Oregon pinot noirs, rieslings, orange wines, and...
Megan Moroney
Megan Moroney's sunny demeanor belies her cleverness as a songwriter, an aesthetic showcased on her 2022 breakthrough single "Tennessee Orange" and its accompanying album Lucky. On that 2023 debut, Moroney's embrace of classic country songwriting tropes -- she is at ease with a boot-scooting boogie as she is with plaintive storytelling— intertwined with a pop...
Forest Crafts
Once a month, explore your creative nature at World Forestry Center’s Discovery Museum with friends at RAD Creative. From Forests in a Bottle to paper snails, seed shares, and fairy houses — tap into your creative side and make something memorable. This event is family-friendly and geared toward children aged two and up (though younger are allowed)....
More September Events
Explore more things to do and see in September in Portland.
Celebrate Negroni Week in Portland
You can do good while sipping delicious twists on a classic cocktail during Portland’s Negroni Week, when proceeds benefit dozens of charities.
The Corn Maize on Sauvie Island
The Corn Maize, located on Sauvie Island north of Portland, offers visitors eight acres of physical and mental challenges in a cornfield.
Grand Prix of Portland
Every fall since 2018, Portland International Raceway has hosted the celebrated open-wheel racing with the Grand Prix of Portland.
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