Plan Around Local Events & Make it a Staycation

What's happening in the city?

(SPOTLIGHT) Portland Sunday Parkway – September 12–14

This year’s Downtown Portland Sunday Parkways transforms the streets into a 2.3-mile car-free celebration of music, families, food, art, and community spirit. From SW Broadway to SW Park Avenue, enjoy live entertainment, vendor marketplaces, and family-friendly activities at every turn. The route winds through the Halprin Sequence, connecting Pettygrove Park and Lovejoy Fountain Park before looping back toward Broadway.

Bring your bike, your friends, and your curiosity. When it’s time to unwind, return to Sentinel, store your bike safely on us, and savor the quiet glow of downtown from your refined retreat.

Portland Rose City Comic Con – September 19–21
The city’s biggest pop culture convention featuring celebrity guests, artist showcases, cosplay contests, and fan meet-ups.

Feast Portland Food Festival – September 26–28
A multi-day celebration of Pacific Northwest flavors with chef-led dinners, tastings, and culinary workshops.

Portland Marathon – October 5
One of the city’s most scenic races, winding through iconic neighborhoods and along the Willamette River.

Portland Open Studios – October weekends
A unique chance to step inside local artists’ studios, watch them work, and purchase original pieces directly.

Halloween at the Oregon Zoo – October 25–26
A family-friendly Halloween experience with trick-or-treat stations, themed activities, and animal encounters.

Portland Book Festival – November 8
A full day of author talks, readings, and literary events in venues across downtown.

Holiday Tree Lighting in Pioneer Courthouse Square – November 28

Kick off the festive season with live music, hot drinks, and the lighting of Portland’s iconic downtown tree.

make it a staycation