What to do in Portland Jan. 21–27, 2026: Beer festival, seafood-and-wine weekend, and live music

A midwinter week with neighborhood events and a packed weekend calendar

Portland’s calendar for Jan. 21–27, 2026, is anchored by a cluster of ticketed tasting events and multi-day gatherings that concentrate activity into the weekend of Jan. 23–25. The schedule also reflects a familiar winter pattern in the region: indoor festivals, food-and-drink programming tied to seasonal products, and music events designed around venues that can operate regardless of weather.

St. Johns Winter Beer Fest returns with three sessions

One of the most defined dates in the week is the St. Johns Winter Beer Fest at StormBreaker Brewing’s St. Johns location. Organizers have structured the event across three separate sessions: Friday, Jan. 23 (5–8 p.m.), and Saturday, Jan. 24 (1–4 p.m. and 5–8 p.m.). Entry is organized as a pass-based experience that includes a branded festival glass and a fixed number of tasting tickets, positioning the event as a controlled-capacity tasting rather than open-ended service.

Seafood and wine festival expands the Expo Center weekend lineup

At the Portland Expo Center, the Portland Seafood & Wine Festival is scheduled for Saturday, Jan. 24 (noon–9 p.m.) and Sunday, Jan. 25 (noon–5 p.m.). The event is built around Oregon seafood and regional wine, with additional beer and spirits vendors listed as part of the program. Organizers have also indicated live entertainment and a market-style component featuring small businesses and makers.

Ticketing is structured by day, with discounted categories for students and seniors and free admission for children 12 and under. A VIP tier is offered for both days, with benefits centered on designated seating and included food-and-beverage service within the VIP area.

Old-time music gathering wraps up just before the week’s midpoint

While it concludes before the Jan. 21–27 window fully unfolds, the Portland Old-Time Music Gathering runs Jan. 14–18, 2026, and shapes the broader month’s live-music landscape. The festival is organized around concerts, dances, workshops, and informal jamming sessions, emphasizing participatory programming rather than a single-stage format. Its placement in mid-January also sets up a transition from community-based, multi-venue events into the more tasting-focused weekend programming that follows later in the month.

Planning notes for attendees

• Expect the highest demand on Saturday, Jan. 24, when multiple festivals operate in parallel across different parts of the city.

• Many tasting events are session-based or have defined hours; arriving early can matter more than staying late.

• For Expo Center events, allow extra time for parking and entry during weekend peak periods.

Across Jan. 21–27, Portland’s most time-sensitive plans concentrate on Jan. 23–25, when winter tasting events dominate the metro calendar.