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.
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.
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.
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.
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
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.)
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.
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.).
Oregon Cannabis Festival promises speakers, bands, and vendors at Pioneer Courthouse Square, plus a march at 4 p.m. Free.
Charity dessert tasting
0.3 miles SW
“Taste the finest cakes, savories, cocktails, and more” at Bake to End Hunger at the Portland Art Museum.
Cinco de Mayo Fiesta
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.
Move with the dogs
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
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+.
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
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.
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.