Our Monthly Picks Around Town: January 2026

Monthly Picks

Dec 19

January may be chilly, but Portland is off to a fun, community-filled start to the year. From cultural celebrations, and live music to dog shows, bike rides, and cozy winter beer festivals, there’s plenty happening to get you out of the house and into the mix. Whether you’re easing into the new year or jumping right in, these local events are a great way to connect, explore, and enjoy the season.

FAMILY-FRIENDLY BIKE RIDE
January 10th | PSU Farmer’s Market

Pedal into the new year with a family-friendly bike ride to the PSU Farmers Market! This relaxed, all-ages group ride celebrates local makers and farmers while making it easy to explore the market together as a community..

O-SHOGATSU FESTIVAL
January 11th | Portland Japanese Garden

Celebrating Japanese New Year (the Year of the Horse), this family-friendly event brings traditional customs to life with performances, cultural activities, and beautiful seasonal decorations within one of Portland’s most peaceful winter landscapes.

ROSE CITY CLASSIC DOG SHOW
January 15th - 18th | Portland Expo Center

Dog lovers, this one’s for you! Enjoy one of the Northwest’s premier dog show weekends. From breed judging and agility courses to meet-the-breeds and fun canine competitions, it’s a must see for pups and people alike.

OLD-TIME MUSIC GATHERING
January 15th-18th | Various Locations in Portland

Enjoy a weekend of toe-tapping tunes and community spirit with the Portland Old-Time Music Gathering. This grassroots festival features concerts, square dances, jamming sessions, workshops, and performances across multiple venues.

AUTORETRATO DE FRIDITA
January 20th-23rd | Milagro

Experience a creative, family-friendly performance inspired by young Frida Kahlo’s early life. With music, dance, puppetry, and storytelling, it’s a vibrant theatrical pick for kids and adults alike.

ST. JOHNS WINTER BEER FEST
January 23rd & 24th | StormBreaker Brewing

Warm up your January at the St. Johns Winter Beer Fest! Enjoy tastings featuring 20+ local beers, ciders, and creative beverages across three sessions. A cozy (and delicious!) way to celebrate winter brews with friends.