Join us for a uniquely enchanting holiday shopping experience in downtown Portland.

Blue June Outfitters will be hosting a gathering of mystical vendors offering tarot and oracle readings, astrology insights, Introvert Tarot readings to-go in wax-sealed envelopes, live on-demand character drawings/paintings, and more! Enjoy browsing whimsical goods, connecting with intuitive readers, and soaking in the festive energy. Family-friendly and open to all, this is the perfect way to add a little wonder to your holiday season!  

⚲ 922 SW Yamhill St

Join us for a special holiday event with designer, Rene Escobar.

Discover an exclusive selection of handcrafted jewelry pairing rich textures with luminous metals and endless sparkle, the perfect gift just in time for the holidays.

Designer @escobarjewelry will be making an in-store appearance!

⚲ Mercantile Portland

Join us for a special holiday event with designer, Rene Escobar.

Discover an exclusive selection of handcrafted jewelry pairing rich textures with luminous metals and endless sparkle, the perfect gift just in time for the holidays.

Designer @escobarjewelry will be making an in-store appearance!

⚲ Mercantile Portland

Celebrate the season with a festive evening of sipping and shopping in the heart of Downtown Portland! Presented in partnership with the Portland Rose Festival, the Sip & Sleigh Wine Walk invites you to explore local shops and restaurants while enjoying tastings from top regional wineries, distilleries, and breweries.

Buy tickets here!

⚲ Registration is located at Director Park

Celebrate Hanukkah with Chabad of Oregon at the annual Public Menorah lighting, featuring live music, traditional foods, dignitaries, and family festivities.

Sunday, December 14 – Sunday, December 21, 2025.

For more information about Hanukkah and a local schedule of events, visit Chabad.org.

Chabad of Oregon offers Jewish education, outreach, and social service programming for families and individuals of all ages, backgrounds, and affiliations.

⚲ The Square

Nearly 300 tubas from cross Oregon fill the Square with festive brass and sing-along cheer in one of the nation’s largest (and free!) holiday performances.

⚲ The Square

Celebrate the joy of the season at Posadas Navideñas, a traditional Mexican holiday celebration filled with festive music, delicious food, singing, and children’s activities!

In partnership with Lara Media, the organizers behind Portland’s beloved El Grito, this vibrant gathering honors community, culture, and connection. Experience the warmth of shared traditions, the beauty of ancestral heritage, and the spirit of togetherness that makes the holidays shine in the heart of downtown.

⚲ Director Park

Hosted by KGW’s Drew Carney, this free competition brings hundreds of carolers downtown, with performances outside shops and a lively “carol-off” finale at The Square.

It’s the first official Menopunks Meetup!

Wednesday December 10, 6-9:30 pm (All Ages/FREE)

Come hang with your fellow Menopunks and the creative team behind the Menopunks movie and podcast while sipping wine and shopping a specially curated selection of peri/meno-focused comics and gifts at the Books With Pictures downtown Portland Holiday Pop-up!  We’ll talk about all things Menopunks and have a few menopause specialists and support providers on hand for an informal Q&A.  Menopunks merch will be on hand for holiday gifting and you will be able to make a tax deductible donation to our current fundraiser on site!  

Menopunks is a myth shattering feature documentary and podcast about peri/menopause and the creative process seen through the lens of defiant GenX musicians, trailblazing doctors and opinonate celebrity culture bearers.

Get on the list: www.menopunks.com

⚲ 333 SW Taylor St

Refreshments, prizes, tarot readings and a store wide 20% off sale!

The Fossil Cartel offers crystals, minerals, jewelry, fossils and meteorites from around the world. We specialize in local gems like Oregon Sunstone, Oregon Opal and Emerald Obsidianite from Mt. St. Helens.

⚲ 333 SW Taylor St #150

Join us for a lively evening in Portland for our Sparkling Soirée! We'll toast to the holiday season, enjoy in festive vibes, and sip through a selection of Divio sparkling! Chef Dustin Joseph with Biscuit and Pickles will be curating bites that compliment our sparkling offerings. Come dressed to impress in your best cocktail attire, and maybe, even add a touch of sparkle to your outfit! We will have select wines available by-the-glass and by-the-bottle throughout the event to enjoy in addition to your experience. Buy tickets here!

⚲ Domaine Divio Pop-Up 401 SW Morrison St.

Holiday brews will be served downtown at a multi-day festival under the sparkling lights of the Tree at The Square. The Portland Holiday Brew Fest will feature more than 30 holiday and winter beers, ciders, and delicious eats from around the Northwest. Festival goers will enjoy spacious heated tents, food, and live music all while enjoying tasty and frosty brews. Buy tickets here!

⚲ The Square

A festive holiday market brimming with a medieval flair, artisan treasures, and a touch of magic.

Step into The Pixie Bazaar, a whimsical holiday market where medieval charm meets Portland creativity. In collaboration with Pixie Panic Market, this magical pop-up features artisan treasures, local vendors, cozy hot cocoa, storytelling, D&D adventures, and a lineup of enchanting all-ages activities. Discover strange delights and festive fun in the heart of downtown PDX.

⚲ Director Park

Holiday brews will be served downtown at a multi-day festival under the sparkling lights of the Tree at The Square. The Portland Holiday Brew Fest will feature more than 30 holiday and winter beers, ciders, and delicious eats from around the Northwest. Festival goers will enjoy spacious heated tents, food, and live music all while enjoying tasty and frosty brews. Buy tickets here!

⚲ The Square

This beloved annual event features one-of-a-kind, handcrafted items created by p:ear youth alongside work from local community artists. Proceeds from the event directly support p:ear’s art, skate, and music programs—initiatives that empower young people through creativity, self-expression, and mentorship.

⚲ p:ear | 338 NW 6th Ave, Portland, OR

Complimentary "Sip and Shop" with coffee provided by Sinister Coffee and live music by talented musician friend, Jackson Warner.  It officially runs from 2-4 pm, but may run longer as long as coffee and tea lasts!

⚲ 922 SW Yamhill St

A joyful community sing-along led by Thomas Lauderdale of Pink Martini with local artists and chorale singers, culminating in Santa lighting nearly 10,000 colorful holiday lights downtown.

⚲ The Square

Explore cozy gifts and treats made by local artists hosted inside the snack shop and go home with something amazing for yourself or loved ones- all while supporting local. Art, stationary, desserts, beauty, home goods and more ...

The shop's shelves are stocked with exciting seasonal goods ready for holiday gifting. Come see what's new !

⚲ Goodies 139 NW 2nd Ave

This holiday season Director Park will turn back into a true winter wonderland with the return of Snow Day Village!

Warm up by a fire pit, grab some smore’s, and do your holiday shopping at Mike Bennet’s Ornament Gift Shop. Central City Concern will be hosting a Giving Tree in the gift shop for those wanting to spread holiday cheer to other families. And don’t miss our snowfall surprise! Thanks to a snow machine, snow will drift down three times daily.

Snowfall Schedule: 12pm/2pm/4pm

Santa's Mailbox: Come craft your letter to Santa and drop it off in our magical North Pole mailbox! Kids who send their letters by December 14 (and include a return address) will receive a special reply from Santa before the holidays!

Holiday goats will make their appearance at the park on November 21, 22, 29 & December 6, 20! From 11:30am - 2:00pm

⚲ Director Park