Portland and Area Activities Planner - Aug 29-Sept 5, 2025

PACIFIC OFFICE AUTOMATION 147
Aug. 29-30
The 2025 Pacific Office Automation 147 (Aug. 29-30, 2025) marks the fourth annual NASCAR Xfinity Series event at Portland International Raceway (PIR). PIR is a 1.97-mile, 12-turn permanent road course owned by the City of Portland and operated under Portland Parks and Recreation. The two-day event features an ARCA Menards Series West race on Friday, August 29, and a NASCAR Xfinity Series race on Saturday, August 30. The inaugural Pacific Office Automation 147 in 2022 featured the first visit to the Pacific Northwest by a NASCAR national racing series since 2000. 

Kids 12 and under receive free general admission.

MONTAVILLA JAZZ FESTIVAL
Aug.  29–31
The 12th Annual Montavilla Jazz Festival, presented by Accelerator Design Studios, celebrates the vibrant voices of Portland’s music scene in an outpouring of original, boundary-pushing jazz by local artists. The three-day MJF includes 26 featured concerts in 5 venues in and around East Portland’s historic Montavilla neighborhood with its boldest and most musically diverse lineup ever.

SIPPING FOR SCIENCE: STAR PARTY WITYH THE CARLTON OBSERVATORY
Aug. 30
Join Carlton Observatory for an unforgettable evening of wine, wonder, and stargazing. The team from Carlton Observatory will guide guests on a tour of the night sky, complete with telescope viewings of the sun, stars, and more. A portion of each ticket supports Carlton Observatory and their mission to bring a public observatory and planetarium to life.

Ticket Includes:

• Welcome pour of our estate wine
• Artisan cheese & charcuterie platter
• Guided stargazing + telescope access

CRABBING EXPLORIENCE
Aug. 30
Enjoy the bounty of Siletz Bay with Explore Lincoln City's Crabbing Explorience. Hit the sand and catch your own dinner. Before heading out to the shoreline to toss a line, meet a local expert for an overview of Oregon's crabbing regulations, harvesting methods, identification, cleaning, and cooking techniques. Each crabber can use up to three devices; we recommend a folding crab trap for Siletz Bay crabbing, which can be done right from the shore. The adventure will last approximately one to two hours, is free, and requires no registration.

DAHLIA FESTIVAL
Aug. 1–Sept. 30
You are invited to celebrate the season of Dahlias. Stroll through almost 50 acres of breathtaking fields and a beautiful display garden of stunning dahlias featuring over 375 varieties. Treat yourself to a rainbow of colors by taking photos, shopping in our gift shop, and purchasing fresh-cut dahlias to take home. Select and order your favorite dahlias for spring delivery to enjoy the beauty in your garden the following year. Fill your belly with yummy treats from the food carts, relax and enjoy the live music on the weekend, or take one of the classes throughout the festival dates.

SALEM CONSPIRACY GAME: THE OUTDOOR ESCAPE
Ongoing
Try this outdoor escape game where your city transforms into a thrilling web of clues, puzzles, and hidden messages! You will play as a detective caught in a high-stakes conspiracy game. Guided only by your phone and your instincts, you’ll gather clues and uncover the truth behind a powerful secret organization planning their boldest move yet: to annihilate or recruit all the world leaders. This is the perfect blend of mystery thriller, urban adventure, and “holy sh*t, I can’t believe that was part of the game.” If you're into escape rooms, scavenger hunts, or just want to do something different outside that isn't another rooftop bar or the same brunch spot — this is your move.

HELVETIA FARM FAIR
Aug. 29
The Helvetia Farm Fair is Helvetia Farm Market's way of honoring the rich farming heritage of Washington County and celebrating the community here in Helvetia. Nestled in the rolling countryside, the fair is a lively gathering where neighbors and visitors come together just as folks have for generations—sharing good food, great music, and friendly competition. Enjoy live performances, tempting bites from three local food vendors, and hands-on activities like face painting, candle making, and a charming photo booth. There's even a corn shucking contest! At its heart, the fair celebrates the farmers, families, and traditions that built this community, offering a taste of the old country way—where summer evenings were for coming together, swapping stories, and taking part in contests for the pure fun of it.

COLUMBIA RIVER  CROSS CHANNEL SWIM
Aug. 30
For 81 years, swimmers have boarded the famous Sternwheeler paddleboat on the south shore of the Columbia River at the dock in Cascade Locks and are ferried to the Washington side of the river. When signaled, swimmers jump off the Sternwheeler into the Columbia and swim an approximately 1.1-mile stretch across to Cascade Locks. To help them find their way, a special swim lane lined with volunteers in sailboats, kayaks, and paddle boards are there to guide, encourage, and protect swimmers as they cross the channel.

Join in on the banks of the Columbia River this Labor Day weekend for an exhilarating open-water swim.

ORIGINAL PRACTICE SHAKESPEARE FESTIVAL
June 20–Aug 31
OPS Fest brings no-cost repertory Shakespeare to parks and venues all over the Portland Metro area. The company uses the original practice techniques of Elizabethan England: limited rehearsal, scrolls in hand, audience interaction, and an onstage prompter.

In Shakespeare’s Era, the audience knew the actors had not rehearsed and that the only context each had of the play was their own role on a scroll. The play was as fresh to the actors as it was to the audience.

In the Original Practice Shakespeare Company, you’ll NEVER see the same cast do the same play in the same way. Because Shakespeare should be a little dangerous.

PEDALPALOOZA BIKE FESTIVAL
Ongoing
Whether you’re a cycling fanatic, an occasional cruiser or just a lover of fun events, Pedalpalooza  — aka Bike Summer — has something for you. Held all over Portland, this bike- and fun-focused festival celebrates summer’s arrival with over 100 rides throughout town.

Inspired by the success of Bikesummer, a traveling event Portland hosted in 2002, Pedalpalooza (also known as Bike Summer) has entertained bike enthusiasts since 2003. While local bike-fun organization Shift runs the festival’s site and helps with planning, anyone can create and lead a ride.  

Named after the Japanese word for fireworks, hanabi festivals are common throughout Japan as a way to invite tourists and locals to celebrate the summer season. Customs include wearing yukata—a lightweight cotton kimono to beat the heat, street food such as yakitori, takoyaki, and shaved ice, and live music.

LABOR DAY WEEKEND: WINE AND BBQ
Aug 29–31
Celebrate Labor Day Weekend with a deliciously fun and flavorful event at Hip Chicks Do Wine. They’re pouring five favorite wines alongside a seasonal, refreshing Sangria—perfect for sipping on a warm summer day.
What to Expect:

• Winetasting: Taste five incredible wines plus seasonal Sangria for just $25
• BBQ-Themed Small Plates: Enjoy mouth-watering small plates with a BBQ twist, available for purchase throughout the weekend.
• Special Discounts: Take advantage of exclusive multi-bottle discounts and stock up on your favorites.
• Take the Sangria Home: Bring your growler and fill it with delicious Sangria to enjoy at home.

Join a weekend of great wine, tasty bites, and good company. Whether you’re a wine enthusiast or just looking to unwind with friends, this event is not to be missed!

AMERICANA HARVEST FEST
July 8–Sept 7
Topaz Farm is excited to announce the 2025 Americana Harvest Fest series. The festival features a mix of nationally and internationally known folk, country, and bluegrass artists. Bring a blanket or lawn chair to enjoy live music on the farm, surrounded by farm animals, U-pick fields, and the market bar and grill. Come early to enjoy the farm, including the cow train, fresh grilled farm food, craft beer, cider, and more.

JURASSIC WORLD BY BRICKMAN
Mar. 15–Sep. 31
Get ready for an immersive adventure like no other as Ryan ‘Brickman’ McNaught re-imagines Jurassic World, the blockbuster franchise from Universal Pictures and Amblin Entertainment, through 6 million LEGO bricks.

It features large-scale LEGO brick dinosaurs, props, scenes, and activities, as well as the newest Jurassic World by Brickman® dinosaur, made from over 100 thousand LEGO bricks, the Baryonyx. Walk through the iconic Jurassic World gates and relive the magic of beloved stories and characters from the Jurassic World franchise, as you embark on a thrilling journey across the Isla Nublar.

Get hands-on with LEGO brick paleontology, mystery mosaics, island-building, hybrid dinosaur creations, and much more. There will be 2.5 million LEGO bricks for you to show off your own building skills.

LINCOLN CITY'S FINDERS KEEPERS GLASS FLOATS 2025
Year-Round
Finders Keepers is Celebrating its 25th Anniversary in 2025. Be on the lookout for the colorful twinkle of a hand-blown glass float when you’re exploring the beaches of Lincoln City. As the name says, Finders Keepers.

Discover “random acts of findness” in Lincoln City, with —Finders Keepers. Over 3,000 glass treasures are hidden along the town’s seven miles of sandy beach, made by local artisans. If you find a float, it’s all yours. Let your treasure hunt begin. Discover glass treasures every day of the year from Roads End on the north to Siletz Bay on the south.

PORTLAND SATURDAY MARKET
Mar. 1–Dec. 20
Combining the vibes of an art show, a live street concert and an open-air bazaar, the Portland Saturday Market has been a beloved Rose City tradition since 1974, earning it the “Oregon Heritage Tradition” title in 2024. In fact, the market is considered the largest continually operating arts-and-crafts fair in the United States, drawing up to one million visitors during its annual season.

On any given weekend from the beginning of March to the day before Christmas, shoppers can wend their way through the rows of tents of this large outdoor market featuring local makers, artisans, and chefs. A full sensory experience, the sights, and sounds will have shoppers and on-lookers tapping their heels to bluegrass pickers and jazz trios with weekly sets of local musicians performing for market-goers and passersby in Tom McCall Waterfront Park

FARMERS MARKET AT PORTLAND STATE UNIVERSITY
Year-Round
The Portland Farmers Market at Portland State University will be open every Saturday, year-round. April through October hours are 8:30 a.m. to 2 p.m. November through March hours are 9 a.m. to 2 p.m.

The Market at PSU is located in Downtown Portland in the South Park Blocks between SW College & Montgomery Streets.

HOLLYWOOD FARMER'S MARKET
Year-Round
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 1 PM,, and
• December through March: 9 AM to 1PM on the 1st and 3rd Saturdays of each month

ST. JOHN'S BAZAAR AND PARADE
May 10
The St. Johns Bizarre is a uniquely crafted celebration that kicks off Portland's summer street fair season. Held annually on the second Saturday in May, the Bizarre brings music, crafts, and food to the crowds who traditionally attended the St. Johns Parade. After the parade, a portion of the business district in St. Johns is closed to traffic and filled with over 135 juried craft vendors, several stages for music, great food, and tons of games and activities.
It’s a fantastic community event with something for everyone.
The event is free.