It’s the most wonderful time of the year! This season is about singing in unison, sharing comforting meals, and savoring special moments with special people. We all have our own outlooks on the holidays — we all have our own traditions and our own ways of moving through the season. No matter how you choose to recognize the season, one of the many great things about Portland is that there is always something to do for everyone!

NAYA Native Made Winter Marketplace – Dec 10th -11th

Looking for original holiday gifts this year? Come out to the NAYA Native Made Winter Marketplace and support local Native artists! You’ll find beautiful jewelry, clothing, crafts, prints and much more. Enjoy delicious Sisters’ Frybread with your family, get those unique gifts and make a day of it. NAYA provides Native entrepreneurs with the knowledge, tools, and skills to build a business from an idea or scale their existing business to their personal bar of success. 

The Great Figgy Pudding Caroling Competition – Dec 9th

Pioneer Courthouse Square is excited to host the Great Figgy Pudding Caroling Competition – a fun, festive, and joyful competition that will bring caroling groups to Portland’s Living Room and extend to a ten-block radius downtown. The top three caroling groups will hold a “carol-off” at the Square hosted by KGW’s Drew Carney, and the grand prize winner will be selected by crowd applause and awarded $1,000. Second and third-place prizes and the coveted People’s Choice designation will also be awarded. Sign up here.

Crafty Wonderland – Dec 9th-11th

Founded in 2006, Crafty Wonderland is now the city’s biggest arts and crafts market, drawing hundreds of vendors and tens of thousands of visitors to the (nice and dry) Oregon Convention Center in Northeast Portland. The twice-yearly market returns in early December and May (just in time for holiday shopping and Mother’s Day, respectively!) What began as a “pure DIY” production with 40 vendors and a couple hundred shoppers, Crafty Wonderland has grown into extravaganza of creativity. You can find portraits of punk rock cats and hipster triceratopses, pins, patches, prints, geodes and gemstones, food, craft spirits, natural soaps, terrariums and so much more!

Trailblazers vs. Nuggets Basketball Game – Dec 9th

Watch the Portland Trail Blazers take on the Denver Nuggets. Cheer along with Rip City at the Moda Center and become part of a Portland tradition. Get your tickets here!