That Portland Life

September Events

The weather is changing, nights are getting cooler, and the summer festivals are coming to an end. We are still holding on to the last bits of summer and we have some fun things for you to do while you take in the last of the warm sunny days.

Grand Prix of Portland

Every fall since 2018, Portland International Raceway has hosted the celebrated open-wheel racing with the Grand Prix of Portland.Held from 1984–2007 under various names, the race is back at Portland International Raceway as the only Verizon IndyCar Series race in the Pacific Northwest.

Portland International Raceway

From $40 – TICKETS

September 1st-3rd

Montavilla Jazz Festival

This year, the festival highlights some of Portland’s jazz scene-makers, with internationally-acclaimed drummer Alan Jones headlining the festival Sunday evening with his quartet featuring Grammy Award-winners Tivon Pennicott and Kevin Hays, joined by NYC bassist Joe Martin.

Various Locations

Pricing Varies by EventTICKETS

September 1st – 3rd

Dahlia Festival

Celebrate the season of DAHLIAS. A Rainbow of Color. Stroll through almost 40 acres and a beautiful display garden of stunning dahlias featuring over 370 varieties. The beautiful fields are open from August to September each year, closed on Wednesdays. 

Swan Island Dahlias

Free

August 2nd – Sept 30th, 9am – 5:30pm

Chapman Swift Watch

To catch all the avian action, plan to arrive at least half an hour before sunset — that’s about 8 p.m. near the start of September and 7 p.m. by the month’s end. Bring your binoculars, snacks, jackets and something comfy to sit on, and settle in for one of the city’s best free spectator events.

Chapman Elementary

Free

All Month at Sunset

Art in the Pearl

Portland’s Art In The Pearl Fine Arts and Craft Festival celebrates 26 years of bringing art to the community. The distinctly artist-run event has long been a favorite in Portland, and it’s the perfect Labor Day destination to gather and celebrate the end of summer.

North Park Blocks

Free

September 2nd – 4th, 10am – 5pm

First Thursday

Stroll through the art galleries in the pearl for an evening of art, music, and wine! Parking is difficult so public transit is recommended

The Pearl District

Free

September 7th, 5pm – 10pm

Belmont Street Fair

The Belmont Street Fair is one of the largest-attended street fairs in Portland. With food and retail vendors of all kinds, show-stopping performances, and activities for all ages, the Belmont Street Fair is fun for everyone.

SE Belmont st from 31st -39th

Free

September 9th, 10am – 5pm

Dragon Boat Festival

Enjoy Portland’s annual Dragon Boat Festival, featuring dragon boat racing along with food vendors, a beer garden and more. DragonSports USA Portland Dragon Boat Festival features over 40 Oregon, Washington, and California teams.

Tom McCall Waterfront Park

Free

September 9th-10th, starting at 9am

Mt Angel Oktoberfest

Go and enjoy the largest folk festival in the NW and wander the streets of Mt Angel which are filled with celebration! Join in our German/Swiss festival and see why Mt Angel Oktoberfest is a Touch of Bavaria.

Mt. Angel Oregon

Free to attend

September 14th – 17th

NW Clothing Swap

The BIGGEST Clothing Swap in the Northwest. Two full floors of swapping fun. The Ballroom on the 3rd Floor: The main swap area with tons of clothing sorted into non-binary categories as well as a plethora of shoes and accessories.Plus, a bar. $10 and a bag of clothes get you a WHOLE NEW WARDROBE. 

Crystal Ballroom

$10 – TICKETS

September 17th, 12pm – 3pm

Oaks Park Oktoberfest

Head to Oaks Amusement Park for their annual Oktoberfest, where you can expect several beers on tap, delicious German food, live bands and performances by dance groups.

Oaks Park

Starting at $22 – TICKETS

September 22nd – 24th

The Wedge

The Wedge is a Farmers Market-style festival celebrating cheese and everything with it. Sample and purchase local artisan cheese, specialty foods, beer, wine, and cider. This is a family-friendly event that’s open to all cheese lovers.

Alder Block

Starting at $25 – Tickets on sale soon

September 30th

We hope to see you at some of these awesome events!

Looking for something else to do? Check out our best of lists!

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