Know Before You Go
Editor’s Note: Check back in November 2020 for information about this year’s holiday season.
If you want a big ol’ dose of the holidays, you’re in the right place. Every winter, Downtown Portland gets a 75-foot-tall (23 m) Christmas tree, a 12-foot-high (4 m) menorah, 63 blocks strung with twinkle lights and roughly 300 people tooting carols on tubas — but who’s counting?
After all, when it comes to holiday fun, quality wins out over quantity (though in all honesty, Downtown Portland has both). With brand-new shops, a beer festival featuring exclusive brews, a caroling competition throw-down and visits from Hipster Santa, there’s a festive flavor for everyone.
What’s more, all the special events, cultural happenings and free performances are filled with Portland’s unique take on all things celebratory. So whether you’ve called Rose City home your whole life or are just visiting, know that Downtown Portland has everything holly and jolly during the holiday season.
Here are just a handful of Portland’s holiday attractions we’re merry and bright about.
Uniquely Portland Holiday Shopping
If you’re looking for one-of-a-kind gifts (or goodies for yourself—no judgment!), Downtown Portland has oodles of opportunities for destination shopping.
More than 30 new retailers moved into Downtown Portland and celebrated their first holiday seasons in business in 2019. Baseballism turns America’s favorite pastime into beautifully designed t-shirts, caps and an entire line of accessories made from mitt and baseball leather. Compound Gallery sells new and collectible streetwear, so you can find your go-to brands and discover new ones. And Laundry PDX is Rip City’s go-to spot for vintage Blazers gear and paraphernalia.
And for everyone who waits until the 11th hour to finish their 12 days of Christmas shopping, the annual Portland Saturday Market’s Festival of the Last-Minute extends its hours just for you. In the days leading up to Dec. 24, find the Market’s signature goods — think art, organic beauty products, hoodies and delicious treats — in this open-air Portland landmark.
Holiday Lights in Downtown Portland
Portland celebrates the start of the holidays with its annual Tree Lighting Ceremony. Local celebrities lead a community-wide sing-along at Pioneer Courthouse Square, known as Portland’s “living room.” And amid much fanfare, Mayor Ted Wheeler flips the switch on 14,000 multicolored lights, turning a 75-foot-tall Douglas fir into the city’s largest Christmas tree.
Later in the season, Chabad of Oregon hosts a Menorah Lighting every night of Chanukah. The Festival of Lights starts out with a big celebration for the first night of Chanukah, with live music, kids’ crafts and traditional food. This Director Park tradition continues throughout the rest of Chanukah, bringing a little more light to the Pacific Northwest’s wintry nights.
And throughout the entire season, the core of Downtown Portland lights up with thousands of twinkling lights. More than 730 trees get a special festive treatment, lending a cheerful vibe to the city’s main retail streets. And keep an eye out for the snowflake installation around Pioneer Courthouse Square: it’s a perfect Instagram opportunity!
Downtown Portland Holiday Events
Portland’s own take on holiday cheer is refreshingly quirky—just like everything else in this city.
In early December, more than 50 breweries converge on Pioneer Courthouse Square to share their latest seasonal beers and ciders. The Holiday Ale Fest specializes in brews crafted especially for the event, so you won’t be able to find them at the supermarket. (If you miss the Holiday Ale Fest, know that the Portland Beer Museum — a shop that sells and pours your favorite brews, along with beer-themed gifts — is open year-round.)
The Great Figgy Pudding Caroling Competition returns every December. Caroling groups of all ages compete for a grand prize and bragging rights in the heart of Downtown Portland.
And you won’t be able to miss the annual Tuba Christmas Concert — just try to ignore the sound of 300 tubas tooting seasonal songs! This beloved outdoor performance is one of Portland’s most memorable holiday events.
Holiday Sips and Snacks in Downtown Portland
We know that holiday shopping and celebrating takes a lot of energy. If you need a sugary pick-me-up, 1927 S’mores sells traditional and avant-garde campfire sweets. (They also sell artisanal s’mores kits, perfect for stocking stuffers!)
For something a little stronger, Little Taco and Tequila features more than 100 different tequilas and seasonal drinks in their cozy neighborhood space. And Casa Tolteca is a mezcal bar that also serves up delicious artisanal Mexican food.
If you’re looking for family-friendly crowd-pleasers, new restaurants serve bites even the pickiest diners can get behind. Raising Cane’s southern-inspired chicken fingers and Texas toast round out its appealing menu. Find both vegetarian and meaty burgers at BurgerFi. And if you can’t decide between Italian and Mexican food, go for both: Zapapizza‘s fusion food blends Mexican flavors in pan pizzas.
With something fun and festive for everyone, you can’t go wrong heading to Downtown Portland — the city’s heart of the holidays.
Holiday Events at Pioneer Courthouse Square
Portland’s living room bustles with free, festive activities every holiday season.
Portland Winter Light Festival
Brighten your February with glowing sculptures and thousands of twinkling lights at the annual Winter Lights Festival.
Holiday Shopping Events
Do your holiday shopping for locally made gifts at hip parties, makers' fairs, sprawling sales and garden grounds filled with handcrafted items.
Portland’s Holiday Ale Festival
The Holiday Ale Festival, set beneath the region’s largest decorated holiday tree, returns every year with more than 50 big, bold beers designed to keep revelers warm on cold winter nights.
Ice Skating in and Around Portland
Here are your best bets for ice skating in Portland and the region, from year-round indoor rinks to winter-only outdoor options.