Downtown

This year, trick-or-treaters are invited to trade in their candy for cash and prizes for both them and their school at Aspire Dental’s Halloween Candy Buy Back! Kids will earn $1 per pound of candy, receive a prize bag, and have a chance to win...

Join Urban Art Network for a special holiday edition of First Thursday inside Portland’s iconic McMenamins Crystal Ballroom! For two festive nights, we’re bringing together an incredible lineup of local artists, makers, and small businesses for a...

Holiday Wine + Makers Market at Hi-Lo Hotel Kick off the holiday season at the Hi-Lo Hotel with a festive evening of wine, small bites, local makers, holiday shopping, coffee, self-care—and dogs! On Friday, November 13, from 5–7 PM, we’re transforming the Hi-Lo into a holiday marketplace featuring some of our favorite local and regional partners. Grab your friends, raise a glass, discover something new, and get a head start on your holiday shopping. Your ticket includes wine samples and small bites from CraftPDX, with an exciting lineup of wine partners: King Estate Winery • Del Rio Vineyard Estate • Columbia Distributing • Delicato Family Wines Taste your way through the evening, discover a new favorite, and get into the holiday spirit. Find something special for your holiday list—or yourself—with our growing lineup of makers and partners: Pools of Light: Discover Calley’s jewelry, including necklaces and beaded earrings, perfect for gifting or adding a little sparkle to your own collection. Good Wolf: Join us in welcoming Good Wolf to the market! Stop by their table, meet the team, and explore what they’ve brought for your holiday shopping. The Paper Bag Coffee Roaster: Enjoy locally roasted coffee samples and shop whole-bean coffee to take home. Be sure to visit the Hi-Lo Merchant for even more locally inspired gifts and Portland finds. More makers and partners are still to come! Oregon Dog Rescue will be onsite—with dogs! Take a break from sipping and shopping to meet some four-legged friends and learn more about the rescue’s work. A little holiday shopping, a little puppy love. What could be better? ️ Yes, you read that right. Jake from Vitality PDX will be joining the party, offering special event pricing on Botox and select wellness treatments throughout the evening. Because sometimes your holiday shopping list should include you. You’ve shopped. You’ve snacked. You’ve enjoyed a beverage or two. Make a night of it with a stay at the Hi-Lo Hotel! Holiday Market guests can take advantage of a special overnight offer: Discounted Hi-Lo room rate 50% off overnight valet parking Waived destination fee Use code N5731 when booking. Shop, snack, sip, treat yourself, and when you’re ready to call it a night, just take the elevator home. ️ Bring your friends, your holiday shopping list, and your appetite. Spend the evening tasting wine, enjoying small bites, meeting local makers—and a few dogs—while celebrating our Portland community. Sip. ️ Shop. Discover. Meet the dogs. Celebrate local. Friday, November 13, 2026 | 5–7 PM Tickets: $30 on Eventbrite — search “Hi-Lo Hotel” Hi-Lo Hotel, Autograph Collection 320 SW Harvey Milk Street Downtown Portland Wine samples and small bites are included with your ticket. Additional food, beverages, retail purchases, and Vitality PDX services are available separately. 21+ for wine tasting.

With four floors packed with festive fun, this holly, jolly brewfest might just be your new favorite holiday tradition! Put on your best (or worst!) ugly holiday sweater and join us for plenty of beer, cider, cocktails and other delicious beverages to taste, plus local...

Twelve vacant storefronts at eleven locations in downtown Portland have become windows of light-based art. Creative Storefronts features 12 installations by 18 artists, from interactive pieces that respond to passersby to detailed miniature...

Pass the gravy and bring on the glamour. Serving up a fabulous helping of bingo, laughs, and Thanksgiving fun at the Hi-Lo Hotel. Join the one and only Poison Waters as your host, with two fabulous queens performing and plenty of sparkle to kick...

The Library is pleased to announce the return of our wreath making event, complete with festive drinks and hors d’oeuvres to kick off the holiday season. A collaborative event with Jennifer Wilcoxon of FloraWood Curatorial Florals, guests will...

Sip, snack, and shop unique finds at the Holiday Wine, Food, and Makers Market at Hi-Lo Hotel. Kick off the holiday season at the Hi-Lo Hotel for a festive evening of wine, small bites, local makers, holiday shopping, coffee, and a little...