Portland events calendar for May 2018. Best festivals, fun things to do, weekend street fairs, kids activities, and free entertainment in Portland, Oregon.

Best events for 12 months

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

Miles are from Pioneer Courthouse Square.

Cinco de Mayo

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.

Craft show

May 5, 2018

1 mile NW

Shop from 200 artists and craft makers at the Crafty Wonderland Spring Art + Craft Market at the Oregon Convention Center. Repeats in Dec. Free.

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.
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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.

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.

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, food carts, and canine contests.

Street fair & parade

May 12, 2018

8 miles NW

Kick off the summer street fair season at St. Johns Bizarre, with local music, 70 juried craft vendors, food, a beer garden, and kids’ activities the same day as the noon St. Johns Parade in North Portland.

Women’s run in Hillsboro

May 12, 2018

13.7 miles NW

Hippie Chick Quarter Marathon, 15K & Half Marathon at Ron Tonkin Field is preceded by a kids’ race and followed by a breakfast.

Plant fair

May 12, 2018

21 miles NE

Camas Mother’s Day Plant & Garden Fair features plants, trees, garden art, kids’ activities, live music, and food vendors in pretty downtown Camas, WA. Free.

Seaside wine tasting

May 12, 2018

78 miles NW

Taste wines in local shops with your ticket to Spring Downtown Wine Walk in Seaside. Repeats in Nov.

Mother’s Day flower show

May 12 - 13, 2018

5 miles SE

Mother’s Day Show and Sale is a rhododendron show and sale at Crystal Springs Rhododendron Garden.

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., and then take the 5K Reigning Roses Walk through NW Portland at 11 a.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.

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.

UFO Festival

May 17 - 20, 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.

Wear a red dress

May 19, 2018

Location uncertain

Men and women wear red dresses, drink red cocktails, and dance at the Red Dress Party for charity.

Armed Forces Day

May 19, 2018

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.

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.

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.

Wine country weekend

May 26 - 28, 2018

34 miles SW

More than 150 wineries in the Willamette Valley are open for tastings and tours on Memorial Weekend in the Wine Country.

Comedy festival

May 2018 (undated)

multiple location

Bridgetown Comedy Festival showcases hilarious local and nationally known comedians in bars and theaters.

Czech film festival

May 2018 (undated)

0.3 miles SW

See five innovative films from the Czech Republic at New Czech Cinema at the Portland Art Museum.

Vampire’s Masquerade Ball

May 2018 (undated)

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.

Train day

May 2018 (undated)

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 2018 (undated)

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.

Bicycle film festival

May 2018 (undated)

3.3 miles NE

See short films about bicycling at Filmed by Bike at the Hollywood Theatre, which on opening night has both films and a free street party.

Silent-film festival

May 2018 (undated)

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.)

Bakery sale for depression

May 2018 (undated)

5 miles NE

Just like people sometimes, cakes, cupcakes, and cookies at the one-day Depressed Cake Shop Portland are gray on the outside but great inside. Sales at The Little Church support Baby Blues Connection.

Tour historic homes

May 2018 (undated)

8.5 miles south

The Lake Oswego Historic Home Tour features four historic homes within walking distance, starting at Oswego Heritage House.

Oregon City festival

May 2018 (undated)

12 miles south

Pioneer Family Festival has a carnival, food vendors, entertainment, a police K-9 demonstration, and a Saturday teddy bear parade in Oregon City. Free.

Rum Run

May 2018 (undated)

13 miles SW

The Rum Run includes a 10K, 5K, and kids’ run with awards and a tropical party at Big Al’s in Beaverton.

Mother’s Day race

May 2018 (undated)

13 miles SW, or 5 miles east

Run Mama Run! is a 10K, 5K, and kids’ run in forested Mt. Tabor Park, which is preceded by a light breakfast.

CityFair & fireworks

May 2018 (undated)

0.5 mile east

CityFair has fireworks on May 26, carnival rides, exhibits, beer, a food fair, and live music on the second weekend at Tom McCall Waterfront Park. No pets. Dates: May 26 - 29, June 2 - 4 and 9 - 11.

Meteorite festival

May 2018 (undated)

16 miles NW

Meteorite and Family Fun Day includes seeing and touching meteorites from outerspace, kids’ games, scavenger hunts, and talks by a meteorite expert at the Rice Northwest Museum of Rocks and Minerals in Hillsboro.
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© May 2018 calendar of events in Portland, OR. Best events, fairs, festivals, and things to do in Portland, Oregon. pdx-05