Portland events May 2018. Things to do in Portland, Oregon.

Best events for 12 months

Portland events May 2018

Music & fashion show

May 3, 2018
(9 p.m., VIP 8 p.m.)
1.2 miles east
Watch a showcase of local designers and models, hear “fresh” music, and see dancers and aerialists perform during Regenerate Portland at The Bossanova Ballroom for age 21+.

Button show

May 4 - 5, 2018
43.5 miles south
See antique and ornate buttons at Oregon Button Show and Sale at Quality Suites near Salem. Free.

Cinco de Mayo Fiesta

May 4 - 6, 2018
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.

Bicycle film festival

May 4 - 6, 2018
3.3 miles NE
See short films about bicycling at Filmed by Bike at the Hollywood Theatre. Opening night on May 4 includes films and a free street party.

Marijuana rally

May 5, 2018
(noon to 5 p.m.)
0 miles
Oregon Cannabis Festival promises speakers, bands, and vendors at Pioneer Courthouse Square, plus a march at 4 p.m. Free.

Obstacle race

May 5, 2018
(9 a.m.)
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.

Kentucky Derby party

May 5, 2018
(noon to 5 p.m.)
20.7 miles SW
A $100 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 5 - 6, 2018
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.

Used book sale

May 5 - 7, 2018
2.7 miles NE
Browse thousands of books and movies at Fall Used Book Sale at the DoubleTree near Lloyd Center. Repeats in October. Free.

Run along the river

May 6, 2018
1 mile SE
Cinco de Mayo Run/Walk includes a half marathon, 10K, 5K, and half miler that begin and end at OMSI, followed by a party with prizes.

Silent-film festival

May 9 - 10, 2018
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.)

Quilt show

May 11 - 12, 2018
7 miles north
Admire hundreds of quilts, see demonstrations, and shop at A Festival of Quilts in Portland Expo Center.

Czech film festival

May 11 - 13, 2018
0.3 miles SW
See five innovative films from the Czech Republic at New Czech Cinema at the Portland Art Museum.

Architecture tour

May 12, 2018
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.).

Move with the dogs

May 12, 2018
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.

Mother’s Day race

May 12, 2018
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 12, 2018
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.

Geeky art fair

May 12 - 13, 2018
1.5 miles NE
GeekCraft Expo is a curated market of handmade “things to complement your geeky lifestyle” at Oregon Convention Center. Free.

Mother’s Day cruise

May 13, 2018
two locations
Portland Spirit offers brunch and dinner river cruises boarding in Portland or Cascade Locks in the Gorge.

Mother’s Day restaurants

May 13, 2018
Portland area
OpenTable lists restaurants that offer special brunch, lunch, and dinner menus on Mother’s Day.

Mother’s Day walk

May 13, 2018
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 13, 2018
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.

Music festival with beer & tacos

May 13, 2018
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.

UFO Festival

May 17 - 19, 2018
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.

Queer documentaries

May 17 - 20, 2018
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.

Adult brunch at OMSI

May 18, 2018
(7 p.m., VIP 6 p.m.)
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+.

Adventure race

May 18 - 19, 2018
5 miles south
Questival is a 24-hour race that begins with a check-in party at Sellwood Riverfront Park. Your team of 2 to 6 people completes the challenges assigned by a smartphone app to win prizes. Video.

Skin cancer screening

May 19, 2018
(9 a.m. to 2 p.m.)
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.

Train day

May 19, 2018
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.

Wear a red dress

May 19, 2018
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 19, 2018
(9 a.m. to 4 p.m.)
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 19, 2018
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.

Seaside wine tasting

May 19, 2018
78 miles NW
Taste wines in local shops with your ticket to Spring Downtown Wine Walk in Seaside. Repeats in Nov.

Art walk

May 19 - 20, 2018
5 miles east
Visit local artists at two dozen locations on Mt. Tabor Art Walk, following the map on their website. Free.

People in the street

May 20, 2018
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.

Bakery sale for depression

May 20, 2018
(1 to 4 p.m.)
2.4 miles NE
Just like people sometimes, cakes, cupcakes, and cookies at the one-day Depressed Cake Shop Portland look gray on the outside but are great inside. Sales at Opal 28 support Baby Blues Connection.

Wildflower Festival

May 20, 2018
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.

Animated film festival

May 23 - 27, 2018
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.

CityFair & fireworks

May 25 - June 10, 2018
0.5 mile east
CityFair has fireworks on May 25 at 9:50 p.m., carnival rides, exhibits, beer, a food fair, and music concerts at Tom McCall Waterfront Park. No pets. Dates in 2018: May 25 - 28, June 1 - 3 and 8 - 10.

Vampire’s Masquerade Ball

May 26, 2018
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+.

Charity dessert tasting

May 30, 2018
(5:30 to 8 p.m.)
0.3 miles SW
“Taste the finest cakes, savories, cocktails, and more” at Bake to End Hunger at the Portland Art Museum.