Portland events May 2019. Things to do in Portland, Oregon.

Best events for 12 months

Portland events May 2019

Queer documentaries

May 2 - 5, 2019
3.5 miles east
QDoc is billed as the only U.S. festival devoted exclusively to Lesbian Gay Bisexual Transgender (LGBT) documentaries, at Hollywood Theatre.

Cinco de Mayo Fiesta

May 3 - 5, 2019
0.5 miles east
Enjoy live entertainment, authentic food, carnival rides, an artisan village, and family fun at Cinco de Mayo Fiesta at Tom McCall Waterfront Park.

Kentucky Derby party

May 4, 2019
20.7 miles SW
A ticket to Derby Day Grand Adventure includes a catered lunch buffet, a mint julep, a live broadcast of the race, fashion prizes, and a bottle of wine to take home at Blakeslee Vineyard Estate.

Garden fair

May 4 - 5, 2019
25.8 miles south
Shop for plants and garden decor, eat at the food court, ask a master gardener questions, and choose from 10-minute classes at the Spring Garden Fair at Clackamas County Fairgrounds in Canby. No pets.

Run along the river

May 5, 2019
1.1 miles north
Cinco de Mayo Run/Walk includes a half marathon, 10K, 5K, and half miler that begin and end at Fields Neighborhood Park, followed by a party with prizes.

Mother’s Day race

May 11, 2019
13 miles SW, or 5 miles east
Run Mama Run! is a 10K, 5K, and kids’ run in the hilly forest of Mt. Tabor Park.

Street fair & parade

May 11, 2019
8 miles NW
Kick off the summer street fair season at St. Johns Bizarre, with local music, 90 juried craft vendors, food, a beer garden, and kids’ activities the same day as the noon St. Johns Parade in North Portland.

Seaside wine tasting

May 11, 2019
78 miles NW
Taste wines in local shops with your ticket to Spring Downtown Wine Walk in Seaside. Repeats in Nov.

Mother’s Day cruise

May 12, 2019
two locations
Portland Spirit offers brunch and dinner river cruises boarding in Portland or Cascade Locks in the Gorge.

Mother’s Day restaurants

May 12, 2019
Portland area
OpenTable lists restaurants that offer special brunch, lunch, and dinner menus on Mother’s Day.

Mother’s Day walk

May 12, 2019
1.5 miles NW
Attend a reception at Castaway at 10 a.m., take the 5K Reigning Roses Walk through NW Portland at 11 a.m., and join the closing reception at 12:30 p.m. to honor women and support charity.

Mother’s Day zoo brunch

May 12, 2019
3 miles west
Take Mom to the Portland Zoo for a sweet and savory Mother’s Day Brunch, which does not include or require a zoo ticket.

UFO Festival

May 16 - 18, 2019
38 miles SW
The UFO Festival honors two locals who spotted UFOs, with a costume parade Saturday at 2 p.m., speakers, a movie, live music, a 5K, and kids’ fun at McMenamins Hotel Oregon in McMinnville. Schedule.

Rocks & minerals show

May 17 - 19, 2019
7.7 miles NE
Mt. Hood Rock Club Show features demonstrations, kids’ activities, and vendors selling rocks, minerals, fossils, and jewelry at Jackson Armory. Free.

Skin cancer screening

May 18, 2019
1.4 miles south
PDX Skincare Festival includes free skin checks, a chance to meet cosmetologists and aestheticians, a 5K run/walk, presentations, exhibits, music, and dancers at OHSU, 2730 SW Moody Avenue. Free.

Wear a red dress

May 18, 2019
1.4 miles NE
Men and women wear red dresses, drink red cocktails, and dance at the Red Dress Party for charity in the basement of Veterans Memorial Coliseum.

Armed Forces Day

May 18, 2019
12 miles SE
See historic and current military vehicles, uniforms, and equipment, and meet historians at Living History Day at Camp Withycombe. Adults require ID. Free.

Obstacle race

May 18, 2019
22.4 miles south
Overcome mud, fire, ropes, and barricades to complete the 3.12 mile Warrior Dash for a medal and T-shirt at Pat’s Acres in Canby.

Art walk

May 18 - 19, 2019
5 miles east
Visit local artists at two dozen locations on Mt. Tabor Art Walk, following the map on their website. Free.

Wildflower Festival

May 19, 2019
115 miles south
Wildflower and Music Festival has flowers on display, plants for sale, experts to answer questions, food, arts and crafts, music, guided walks, and kids’ activities at Mount Pisgah Arboretum in Eugene. No dogs.

Festival of Flowers

May 22 - June 4, 2019
0 miles
See a giant design made from 20,000 flowers during Festival of Flowers in Pioneer Courthouse Square, with live music at noon on some days, followed by a flower sale.

CityFair & fireworks

May 24 - June 9, 2019
0.5 mile east
CityFair has fireworks on opening night (May 24), carnival rides, exhibits, beer, a food fair, and music concerts at Tom McCall Waterfront Park. No pets. (Closed May 28 to 30, and June 3 to 6, 2019.)

Fruit beer festival

May 31 - June 2, 2019
1.3 miles NE
Buy a ticket to try two dozen fantastically fruity beers and ciders outdoors at Portland Fruit Beer Festival, which also has food vendors at 7th Avenue & E. Burnside Street.

Taste of Canby

May 31 - June 2, 2019
25 miles south
Buy samples of wine, beer, and food; hear live music; and shop from vendors at Canby Wine, Food & Brew. Children age 15 and younger are free.

Architecture tour

May 2019
multiple locations
The Mid-Century Modern Tour includes a lecture (Friday 7 p.m.) about the Pacific Northwest Modernism of architect John Storrs, plus a self-driving tour (Saturday) of the inside and outside of five homes he designed, plus an after-party (Saturday 6 p.m.).

Marijuana rally

May 2019
0 miles
Oregon Cannabis Festival promises speakers, bands, and vendors at Pioneer Courthouse Square, plus a march at 4 p.m. Free.

Charity dessert tasting

May 2019
0.3 miles SW
“Taste the finest cakes, savories, cocktails, and more” at Bake to End Hunger at the Portland Art Museum.

Move with the dogs

May 2019
0.5 miles east
Doggie Dash is a 1.5 or 2.5 mile untimed walk/run that begins and ends at Tom McCall Waterfront Park, including breakfast, a beverage, a pet festival, vendor booths, and canine contests.

Adult brunch at OMSI

May 2019
1.2 miles SE
A ticket to Marys & Mimosas includes 6 drink tokens for bloody Mary’s and mimosas, plus 4 food tokens for brunch bites, and a chance to explore the Oregon Museum of Science and Industry (OMSI) for age 21+.

Train day

May 2019
1.4 miles SE
Portland Train Day includes games, live music, a free museum visit, steam trains on display, train rides, and food carts at Oregon Rail Heritage Center. Free.

People in the street

May 2019
Located 1.7 miles SE
Walk, bike, or roller-skate on 7 miles of streets when most cars are banned for Southeast Portland Sunday Parkways. Nearby parks offer activities & music. Free.

Used book sale

May 2019
2.7 miles NE
Browse thousands of books and movies at Spring Used Book Sale at the DoubleTree near Lloyd Center. Repeats in October. Free.

Bicycle film festival

May 2019
3.3 miles NE
See short films about bicycling at Filmed by Bike at the Hollywood Theatre. Opening night includes films and a free street party.

Animated film festival

May 2019
4 miles NE
NW Animation Fest celebrates the best work from independent animators in many countries by screening nearly 200 hilarious, dramatic, strange, and inspiring films at Hollywood Theatre. Repeats later in Eugene.

Silent-film festival

May 2019
4 miles NE
Watch silent films recently made by Northwest kids under age 21 and accompanied by live music at the International Youth Silent Film Festival at Hollywood Theatre. (See June 7 for global awards.)

Music festival with beer & tacos

May 2019
6.4 miles north
Sabroso Craft Beer, Taco & Music Festival “is a day filled with craft beer, tasty gourmet tacos, Lucha Libre style wrestling, and live music” at Portland Meadows. Children are OK after 4 p.m.

Obstacle race

May 2019
8 miles north
Feel like a kid again at The Great Inflatable Race, which includes at least eight blow-up obstacles you must get over, under, around, or through at Portland International Raceway.

Vampire’s Masquerade Ball

May 2019
1 miles east
Vampire’s Masquerade Ball is a formal gala at Melody Ballroom with gothic and industrial music, a classic midnight waltz, an included buffet, and a no-host bar for age 21+.

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