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.
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.
Autumnal beauty abounds in Portland, and there are plenty of prime places to revel in leaf-crunching relaxation.
Experience nature not far from the city's hustle and bustle at these wildlife preserves.
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.
The Biggest Clothing Swap in The Northwest
Whether you’re looking for a great costume idea or need a new fall wardrobe, The Biggest Clothing Swap in The Northwest will have something to catch your eye. Bring a bag of clean, wearable clothes to share or buy an empty bag to fill with your newfound treasures.
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.
Grand Prix of Portland
Portland International Raceway hosts the celebrated open-wheel racing every fall at the Grand Prix of Portland. Portland’s 1.967-mile (3.166 km) course boasts 12 turns and several exciting passing opportunities and is the only Verizon IndyCar Series race in the Pacific Northwest.
Kharisma brings the heat with Kaliente, the newest Drag Brunch at your Stag PDX. Start your month with a bit of spice every 1st Sunday, with a show that has that extra kick that only Kharisma and her special guest performers can bring. Enjoy all-you-can-eat brunch options served from the buffet with mimosas available -…
Roll out with your friends and loved ones to the monthly Gay Skate Session, held the 1st and 3rd Monday night of the month. Everyone is welcome at this all-ages event at this all-ages event. Admission tickets allow the Oaks Park Roller Rink access for the selected Gay Skate Session date/time. Includes standard skate rental.
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 to…
Prepare to journey back in time 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,…
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 takn on a journey through the city’s charming streets and reveal its laid-back atmosphere. Brace yourself for an amazing tour of Portland’s must-see spots like the International Rose Garden (seasonally), the World Forestry…
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…
Maximize your beach time while at the Oregon Coast Oregon’s coastline is graced with unforgettable vistas: dramatic cliffs, offshore rocks and sea lions, wide sandy beaches, majestic capes, historic lighthouses, enchanted forests and lovely small beach towns which artists and artisans make their home. Locations we may visit include: Cannon Beach, Haystack Rock, Short Sand…
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 then be whisked 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 area’s top attractions….
Experience the eccentricity of Portland, Oregon and visit one of its quirkiest neighborhoods on this walking pub tour. This tour is a must-do for anyone who wants to immerse themselves in the fascinating history of the city, including stories of UFO sightings, Bigfoot sightings, exploding whales, wacky bike rides, strange locals, hijackings, hipsters, artists, and…
Uncover Portland’s dark side on this spine-tingling walking pub tour. In the early 1900s, unsuspecting sailors were often ruthlessly abducted and whisked away through the notorious Shanghai Tunnels. Tour guides will tell you how notorious criminals kidnapped thousands of people and why their ghosts still haunt Portland today. This is Portland’s longest-running ghost tour with…
Beginning in the Cascades and moving upriver through the eastern stretch of the Columbia River Gorge is the relatively young but rapidly growing wine-making region known as the Columbia River American Viticulture Area (AVA). Often referred to as “A World of Wine in 40 Miles,” the Columbia River AVA consists of a combination of climates,…
Oregon is home to some of the most beautiful vineyards in the world, not only known for its distinctive pinot noir but many other varietals such as pinot gris, chardonnay, riesling and more. Your experience will take place in the heart of the Willamette Valley, home to renowned, award-winning wineries. Oregon's Willamette Valley has elevated…
Comedy Open Mic for every skill level. Beginners are welcome. Weekly mic every Monday night with 8:30 p.m. sign-ups. Hosted by Sam Bass and Milo Loza. The Cheerful Tortoise is an iconic Portland bar that has been around for more than 60 years and provides a cheerful environment for everyone to enjoy.
Jump into a day-long adventure and discover what makes the Columbia River Gorge National Scenic Area a true gem. Be awed by the majesty of the USA's second tallest waterfall, witness the incredible salmon journey at the Bonneville Dam Complex, catch some windsurfing thrills in the windsurfing capital of the USA, and explore the official…
Hop aboard a ride from your swanky Portland hotel and savor the stunning views of Columbia River's bustling ship traffic. The first stop? Two of Astoria's coolest breweries, where you can sip on the finest brews and grab a bite to eat. Fort George BreweryAstoria Brewing CompanyReach Break BrewingBuoy Beer CompanyRogue AlesGeek out with the…
Get ready to be swept off your feet by your guides as they take you on a journey of a lifetime through the stunning Columbia River Gorge and the Hood River Valley. Brace yourself for a riveting tale of this breathtaking terrain and its awe-inspiring past. And just when you thought it couldn’t get any…
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 comics Bjorn RG and Eliza Butler host this weekly show at Neighbors Taproom with curated lineups of local and nationally touring comedians. 21+
Goodness is a show that brings the best stand-up comedy in Portland to the incredible Laurelhurst Club! Tickets are only $10, with even more affordable drinks! (21+)
Join hostess Devlin Lynn Phoenixx and her cast of talented queens for a Sunday brunch experience you won’t soon forget. Your ticket includes admission to the show, your meal, AND your first mimosa. Vegetarian, vegan, and gluten-free options are available. So grab your friends and get down to The Pharmacy for a spectacularly fun time.
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, located on Sauvie Island north of Portland, offers visitors eight acres of physical and mental challenges in a cornfield.
Every fall since 2018, Portland International Raceway has hosted the celebrated open-wheel racing with the Grand Prix of Portland.
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