Cinco de Mayo at the Tom McCall Waterfront Park (May 1 â€“ 5), which will include live music, dancing, carnival rides, artisans, and food. It normally costs $8 for adults and $2 for kids but it's free entry if you go before 4 pm on Friday and Saturday. the Indie Wine Festival is also one of the coolest events in Oregon in May. It'll be held on NW 30th Ave. and Industrial Street between 1st and 2nd of May. You'll be able to taste local homemade wines and sample foods from local chefs. the general admission for this one is $80.