When the holidays roll into Portland, the city goes full-on sparkle mode! Lights sparkle across neighborhoods, choirs fill the air, and the scent of pine and hot cocoa seems to follow you everywhere. Our team is excited to share some of their top holiday picks, and here’s where we’re getting all the festive feels this season.

A Little Day Trip Magic: Silverton Christmas Market

Looking for Hallmark movie vibes? Silverton Christmas Market is your place. Imagine millions of sparkling lights weaving through the beautiful Oregon Garden, cozy market full of handmade gifts, mulled wine, and pretzels of the size your head. And live music, festive food, and maybe even a surprise snow flurry, and you’ve got yourself a holiday wonderland.

Pro tip: Bundle up, grab some hot cocoa, and don’t skip the light tunnel – perfect for the ‘Gram or just max cozy energy.

When to go: November 21 – December 31, 2025. Open evenings from 5 – 9pm.

The Grotto – Christmas Festival of Lights

Want to feel all warm and fuzzy and maybe a little awe-struck? The Grotto’s Festival of Lights in Northeast Portland is a breathtaking mix of music, spirituality, and holiday magic. Thousands of lights illuminate the gardens, and the choirs fill the air with carols. It’s beautiful, peaceful, and the perfect place to slow down and soak in the season.

Pro tip: Sip hot cocoa while watching the lights reflect off the sanctuary walls – pure magic.

When to go: November 28 – December 30, 2025 (closed Christmas Day).

Pioneer Courthouse Square – Portland’s Living Room Lights Up

Downtown Portland’s Pioneer Courthouse Square shines extra bright during the holidays. Known as Portland’s living room, the square becomes the heart of the city’s celebrations with its towering Christmas tree, twinkling lights, and the annual tree-lighting ceremony that draws a crowd of every year. It is a great time to see the community come together at a common meeting space.

Pro tip: Grab a coffee, take in the sparkle surrounded by local cheer – it’s the quintessential Portland holiday moment.

When to go: The annual Tree Lighting Ceremony is Friday, November 28, 2025 at 5:30pm. Lights stay up through early January.

Peacock Lane – Portland’s OG Holiday Street

This one’s Portland’s iconic –the OG holiday street. Since the 1920’s this charming Southeast Portland neighborhood has been turning its street into a glowing wonderland of twinkling lights, nativity scenes, and even a few pop culture cameos (yes, there’s usually a Grinch or two). The walk is short and sweet, and full of nostalgia.

Pro tip: Visit on one of the pedestrian-only nights for the full festive experience.

When to go: December 15 – 31, 2025. Lights are on nightly from 6 – 11pm.

Whether it’s a peaceful night under twinkling lights or a cocoa-fueled adventure through the zoo, the holidays in Oregon remind us of what really matters – joy, connections, and maybe just one more gingerbread cookie. So pull on your cozy scarf, grab your favorite people, and go make some great holiday memories.