Our Monthly Picks Around Town: October 2025

Oct 1

Crisp mornings, golden leaves, and weekends that beg for adventure, it’s peak fall in Portland. From giant gourds taking to the water at the West Coast Pumpkin Regatta to spanakopita and baklava at Greek Fest, pups in costume at Dogtoberfest to endless caffeine buzz at Portland Coffee Fest, this month is packed with cozy, quirky, only-in-Portland happenings you won’t want to miss.

GREEK FESTIVAL
October 3rd-5th | Holy Trinity Church

The countdown is on for the 72nd annual Greek Festival! Feast on baklava, dance to traditional music, and soak up Greek culture in full color. This iconic Portland festival features traditional food, music, dance, pastries, and church tours.

PORTLAND COFFEE FESTIVAL
October 4th | The Redd on Salmon St

Wake up and smell the beans! Explore Portland’s coffee scene with local roasters, hands-on workshops, guided tastings, live roasting demos, and food pairings from pastries to sandwiches. From seed to cup, it’s a must for coffee lovers!

DOGTOBERFEST
October 4th | Lucky Lab Brew Pub

Bring your fur babies and your thirst! This family-friendly event features dog washes, exclusive brews, adorable pups, and take-home pint glasses—all while supporting Portland’s own DoveLewis Blood Bank.

DOZER DAY
October 4th-5th | Clark County Event Center

At Dozer Day, kids climb into real bulldozers, diggers, and dump trucks with safe, hands-on guidance. Add in games, activities, and big machines to explore—it’s the ultimate family adventure where construction dreams come true.

WEST COAST PUMPKIN REGATTA
October 19th | Lake of the Commons

When pumpkins become boats, you get a festival like no other! Cheer on costumed racers paddling giant gourds, plus enjoy weigh-offs, games, face painting, pumpkin bowling, pumpkin golf, and more.

DIA DE LOS MUERTOS FESTIVAL
October 16th-Novevmber 9th | Milagro

A blend of memory, art, and community: experience vibrant altars, live theater, and traditions rooted in Indigenous Mexican culture. This festival invites all to celebrate life, remembrance, and the connections that unite us.