Portland events calendar for September 2016. Best festivals, fun things to do, free kids activities, street fairs, and Labor Day weekend events in Portland, Oregon.

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Best events for 12 months
September 2016
September 2016

Enjoy the best Portland events, festivals, and things to do with this calendar of events.

Mileage is from Pioneer Courthouse Square in downtown Portland, Oregon.

Oregon State Fair

September 1 -5, 2016 (begins Aug. 26)

49 miles south

See farm animals and craft displays, try fair food and fine wine, take carnival rides, and be entertained at the Oregon State Fair in Salem.

Fairy festival

September 2 - 4, 2016

25 miles NW

Faerieworlds is billed as the world’s largest faerie festival and features costumed faeries, music, entertainment, a food court, and 150 vendors of art, literature, and crafts at Horning’s Hideout in North Plains.

Pirate festival

September 2 - 5, 2016

81 miles south

Tortuga Pirate Festival offers outrageous activities and games for adults in pirate attire at Cheadle Lake Park in Lebanon.

Zoo concerts

September 2 - 11, 2016 (begins June 19)

3 miles west

Oregon Zoo Summer Concerts feature world-class performers and include a same-day zoo pass.

Pearl District art festival

September 3 - 5, 2016

0.5 mile north

Art in The Pearl features 100 booths of fine art as well as music, food, and hands-on art activities along NW 8th Ave in North Park Blocks. Free.

Dahlia Festival

September 3 - 5, 2016 (begins Aug. 27)

26 miles south

View 400 floral arrangements of dahlias indoors, 40 acres of dahlias outdoors, and dahlia growing and arranging demos at the Dahlia Festival at Swan Island Dahlias in Canby. See schedule. Free.

Dog-themed bike tour

September 4, 2016

1.5 miles SE

Dress like a dog or bring a stuffed pooch to the Tour de Lab, which is a 19-or-40-mile urban bike ride that begins at Lucky Labrador on SE Hawthorne and ends there with a costume contest, beer, and hot dogs.

Movies in the Park

September 4 & 10, 2016 (begins July 7)

Portland parks

Movies in the Park begin with entertainment at 6:30 followed by movies at dusk. Bring coats. Free.

Swim across the Columbia

September 5, 2016 (5:30 a.m.)

63 miles east

Join 500 hearty souls who jump from a paddleboat and swim 1.1 miles across the Columbia River, or cheer them on from the finish line, at the Roy Webster Cross-Channel Swim in Hood River.

Concerts on Main Street

September 7, 2016 (Wednesdays from July 6)

0.2 mile SW

Hear local musicians play funky soul to old-school country Wednesdays at Music on Main Street next to Arlene Schnitzer Concert Hall. Free.

Escape game

September 7 & 14, 2016 (also Aug.)

6 miles west

British Redcoats lock you and 9 others in a room in the game American Revolution, which requires you to solve clues and escape within 60 minutes or face the firing squad, in Cedar Hills. Discount tickets $15 (Wednesdays).

Volunteer Expo

September 8, 2016

0 miles

Connect with local non-profit organizations that need volunteers, and hear live music at Volunteer Expo in Pioneer Courthouse Square. Free.

Modern art festival

September 8 - 18, 2016

Portland locations

Artists from around the world display contemporary performance and visual art at the Time-Based Art Festival, which includes workshops & evening shows.

Folk music festival

September 9 - 11, 2016

154 miles SE

Hear roots music from blues to bluegrass at Sisters Folk Festival on 10 stages in downtown Sisters.

AIDS walk

September 10, 2016

1.1 miles north

The 2.4-mile AIDS Walk Portland includes music, entertainment, a kids’ corner, and a beer garden, with the start and finish at Fields Neighborhood Park.

Meet romance authors

September 10, 2016

1.7 miles NE

Passion in Portland is a book signing and optional dinner with 60 romance-novel authors at the Crowne Plaza Downtown.

Belmont Street Fair

September 10, 2016

2.5 miles east

Belmont Street Fair is a family-friendly event with live music, art, entertainment, shopping, kids’ activities, food vendors, and beer gardens on SE Belmont Street from 33rd to 39th. Free.

Beaverton Celebration Day

September 10, 2016 (9 a.m. to noon)

9 miles SW

Beaverton Celebration Day includes a 5K at 9 a.m. and a parade at 10 a.m., which begins with pets and goes from Allen Blvd. & Watson Ave. to Griffith Park. City Park has activities across from the library.

Street fair in Tigard

September 10, 2016

10.5 miles SW

Street Fair features 130 vendors, food booths, music stages, and kids activities on Main Street in Tigard.

Farm festival

September 10, 2016

12 miles south

Festival at the Farm offers a craft fair, farm stands, barbecue, live music, kids’ activities, and corn & hay mazes at Fiala Farms in West Linn. Free entry.

Festival of cider, beer, wine, and pickles

September 10, 2016

12.2 miles NW

Oregon Fermentation Festival has fermented foods, food trucks, a beverage garden, workshops, and family-friendly entertainment at a Sauvie Island farm.

Outdoor dance

September 10, 2016 (3 to 8 p.m.)

14.6 miles west

Care to Dance? is a family-friendly event with dance lessons, food vendors, a DJ, and a big band (6 to 8 p.m.) outside Orenco Station in Hillsboro.


September 10, 2016

28.2 miles south

The Oregon Fall Half Marathon and 10K is located at St. Josef’s Winery in Canby.

Harvest festival

September 10, 2016

36 miles SW

Carlton Crush has a grape-stomping competition, barrel-rolling race, kids’ watermelon-eating contest, artists’ market, entertainment, live music, festival food, wine, beer, and cider in Carlton. Free entry.

Corvallis beer festival

September 10, 2016

85 miles south

Septembeerfest offers dozens of beers, ciders, and meads under the trees of Avery Park in Corvallis.

Comics convention

September 10 - 11, 2016

1.5 miles NE

Fans of comic books, games, sci-fi, and pop culture can meet artists, celebrities, and publishers at Rose City Comic Con in the Oregon Convention Center.

Renaissance fair

September 10 - 11, 2016

79 miles SW

Watch knights joust on noble steeds, mingle with costumed minstrels and troubadours, shop 125 artisan and food-purveyor stalls, and see children delight in games and adventures at Shrewsbury Renaissance Faire in Kings Valley.

Clackamas River cleanup

September 11, 2016

multiple locations

Register online to join a flotilla of volunteers who assemble at five parks and raft, kayak, canoe, inner tube, scuba, or walk down the Clackamas to remove trash at Down the River Clean Up on the Clackamas.

Women’s soccer

September 11, 2016

0.7 miles west

Watch the Portland Thorns play at Providence Park.

Discount tickets $13.

9-11 memorial

September 11, 2016

6.5 miles SE

Recognize our heroes on the anniversary of that fateful day in 2011 at Commemoration and Honoring of First Responders and Veterans at Milwaukie City Hall. Free.

Small-town celebration

September 11, 2016 (10 a.m. to 3 p.m.)

24 miles SE

The Celebration in Boring offers live music, pony and wagon rides, a classic-car show, games, firefighter waterball, and food booths. Free.

Food and drink festival

September 15 - 18, 2016

Portland locations

Taste Oregon’s bounty of wine, beer, cheese, and fine cooking; hear culinary stars speak on stage; and take cooking classes at Feast Portland.

RV and van show

September 15 - 18, 2016

7 miles north

Meet RV dealers and makers, and see new models of 5th wheels, campers, travel trailers, park models, conversion vans, and Class-A motor homes, at Portland Fall RV & Van Show, Portland Expo Center.

Swing dancing

September 15 - 18, 2016

15 miles NE

BridgeTown Swing features competitions, lessons, workshops, and social dances at the Hilton Vancouver Washington.

Oktoberfest in Mt. Angel

September 15 - 18, 2016

38 miles south

Mount Angel Oktoberfest has beer and wine gardens, live music, singing, dancing, arts and crafts, and a car show in Mount Angel.

Mexican Independence Day

September 16, 2016

1.4 miles NE

Celebrate the independence of Mexico and its neighbors from Spain at El Grito y Fiestas Patrias, which includes folkloric and Aztec dancers and live mariachi, salsa, cumbia, and pop music, plus food & craft vendors at Moda Center. Free.

Car show

September 17, 2016

13 miles south

Cruise to Historic Downtown Oregon City fills Main Street with 400 classic cars, hot rods, trucks, and motorcycles from the 1950s to 1970s. Free.

History night

September 17, 2016

20 miles south

Bring a flashlight for the evening Willamette Living History Tour, which features a one-hour walk and carriage ride in a recreated 1913 town, with actors in costume and a barbershop quartet in West Linn.

Sidewalk chalk art

September 17, 2016

26 miles west

Create your masterpiece on a sidewalk in downtown Forest Grove, or admire hundreds of others’ works at Sidewalk Chalk Art Festival.

Bigfoot festival

September 17, 2016

52 miles east

Bigfoot Bash & Bounty is a small-town carnival, beer garden, evening band, and speakers in the heart of Sasquatch country at Home Valley Park, WA.

Polish Festival

September 17 - 18, 2016

4.2 miles NE

Enjoy Polish food, beer, dance, music, and polka at the Polish Festival at 3900 N Interstate Ave. Free.

Festival of Serbia

September 17 - 18, 2016

7.2 miles SE

Enjoy authentic food, wine, dance, music, and kids’ activities at the Serbian Festival in Milwaukie. Free.

Vegan week and prom

September 17 - 24, 2016

Greater Portland area

Try Vegan Week includes free workshops, speakers, dine-outs, and mentoring. It ends in a vegan prom night of dancing, raffles, food, and costumes.

Film festival

September 19 - 28, 2016

Eugene & Portland

Oregon Independent Film Festival (OIFF) [sound] screens roughly 75 independent films from 14 countries and is particularly known for its documentary programming.

Senior zoo day

September 20, 2016

3 miles west

If you’re 65 years old, you and a guest get free admission and a train ride plus a lunch special during Senior Safari at the Oregon Zoo.

Quilting expo

September 22 - 24, 2016

7 miles north

See creative quilts on display, shop for quilts and supplies, and attend seminars at Northwest Quilting Expo at Portland Expo Center.

Bavarian festival

September 22 - 25, 2016

330 miles east

Alpenfest [sound] celebrates Swiss and Bavarian culture with polka music, folk dancing, yodeling, a craft show, bratwurst, and beer near Wallowa Lake in NE Oregon.

American Indian day

September 23, 2016

0 miles

Watch traditional dance in native regalia, hear drums, and shop vendors at American Indian Day Celebration at Pioneer Courthouse Square. Free.

German Film Festival

September 23 - 27, 2016

1 mile NW

See thought-provoking German films with English subtitles at the German Film Festival at Cinema 21.

Free museum day

September 24, 2016


Get a free ticket for two people to visit one of 20 Oregon museums on Museum Day Live.

Saxophone concert

September 24, 2016 (8 p.m.)

0.2 miles south

Grammy-winning saxophonist Chris Mitchell plays a combination of romantic Latin jazz, bassa nova, and R&B at Portland’5 Centers for the Arts. Discount tickets $28.

Obstacle race

September 24, 2016

25 miles NW

Overcome mud, fire, ropes, and barricades to complete the 3.3 mile Warrior Dash for a medal and T-shirt at Horning’s Hideout in North Plains.

Cider Squeeze

September 24, 2016

29 miles SE

Cider Squeeze features cider pressing, food, music, blacksmith demonstrations, and tours of Philip Foster Farm from the 1860s in Eagle Creek.

Hops festival

September 24, 2016

62 miles east

Enjoy beer from microbreweries, local cuisine, arts and crafts vendors, and live music at Hops Fest in Hood River. Kids OK until 5 p.m. No dogs.

Hemp festival

September 24 - 25, 2016

0.5 miles SW

Hempstalk has food vendors, live music, speakers, and info booths about hemp products and marijuana decriminalization at Waterfront Park.

Natural fiber festival

September 24 - 25, 2016

26 miles south

Oregon Flock & Fiber Festival is about natural fibers from beginning to end, from animal or plant fiber to finished product. Find rabbits, goats, classes, kids’ activities, and food at the fairgrounds in Canby.

Beer festival

September 30 - Oct. 1, 2016

6 miles SE

Portland Fresh Hops Fest features hoppy beer for adults, plus root beer and lemonade for kids at Oaks Amusement Park.

Greek festival

September 30 - Oct. 2, 2016

2.8 miles east

Portland Greek Festival has Greek food, crafts, music, and dance at NE 32nd Ave. & NE Glisan St. Free.

Juggling festival

September 30 - Oct. 2, 2016

5 miles SE

Portland Juggling Festival offers shows, workshops, vendors, and a juggling & vaudeville extravaganza Saturday night at Reed College.

Pumpkin festival

September 30 - Oct. 30, 2016

35 miles south

See pumpkins shot from a cannon, take a hayride, navigate a corn maze (haunted some evenings), try archery & paintball, and choose a pumpkin during Pumpkin Fest at Wooden Shoe Tulip Farm in Woodburn on Fridays, Saturdays, and Sundays.

Haunted house: 4 Horsemen

September 30 - Oct. 31, 2016

18 miles north

Four Horsemen Haunted Attractions promises a live cinema experience, complete with Hollywood-grade set and costume design at Clark County Event Center in Ridgefield WA. See schedule.

Oktoberfest at Widmer

September 2016 (undated)

2 miles north

Enjoy Munich-style ales, German food, and music at Widmer Oktoberfest at Widmer Brothers Brewing for age 21+.

Police & fire fighter tribute

September 2016 (undated)

7.7 miles east

First Responder’s Tribute features entertainment, drone demonstrations, a flag ceremony, a gun salute, and food & business vendors at NE Halsey & 111th. Free.

Oktoberfest at McMenamins

September 2016 (undated)

15 miles NE

Enjoy beer, food, singing to live music, and entertainment during Oktoberfest at McMenamins Edgefield. Free for all ages.

Yoga on the farm

September 2016 (undated)

23 miles SE

Farm to Yoga includes a tour of Wheeler Tree Farm, adult & kids’ yoga classes, meditation, dinner of local food, live music, and dancing in Oregon City.
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© September 2016 calendar of events in Portland, OR. Best events, fairs, festivals, and things to do in Portland, Oregon.