Food & DrinkWineWine Tastings

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FRINOV 13
5:00 PM – 7:00 PM
💰 $29Holidays & SeasonalCraft FairsNight MarketsWine Tastings

Holiday Wine, Food, And Makers Market At The Hi-Lo Hotel

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.
SATNOV 28
NOV 28–NOV 29 · Hours not provided
Holidays & SeasonalAuthor TalksWine TastingsCraft Fairs

Words & Wine Holiday Book Pop-Up at Hip Chicks do Wine

Kick off your holiday shopping by supporting local authors, independent books, and small businesses at Words & Wine at Hip Chicks do Wine! Friday, November 28 | 12:00 PM – 5:00 PM Saturday, November 29 | 12:00 PM – 4:00 PM We're bringing together...
FRINOV 13
Hours not provided
+2 more
SpiritsWine TastingsCraft FairsHolidays & SeasonalArts & Media

Holiday Food and Gift Festival

The 37th Annual Holiday Food & Gift Festival is one of the largest holiday celebrations in the Northwest, welcoming thousands of shoppers each year who love to complete their holiday shopping early. Explore hundreds of exhibitors offering...

Multi-day events

FRINOV 13
5:00 PM – 7:00 PM
💰 $29+Holidays & SeasonalCraft FairsWine Tastings

Holiday Wine, Food, and Makers Market

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...
SUNNOV 15
12:00 PM – 3:00 PM
Craft FairsArts & MediaHolidays & SeasonalWine Tastings

Shop and Sip Makers Market at Colwood Golf Center

Join Portland Parks Golf for a festive Shop and Sip Makers Market celebrating local art, handmade goods, and the flavors of the season. Get a head start on holiday shopping while discovering unique, locally made treasures from talented artists...
FRINOV 27
3:00 PM – 7:00 PM
ChoralHolidays & SeasonalCraft FairsKids & FamilyArts & MediaPerforming ArtsWineStreet Festivals

62nd Annual Tree Lighting Festival

Presented by the City of Lake Oswego and Lake Oswego Chamber of Commerce ! Celebrate the holiday season at Lake Oswego’s 62nd Annual Holiday Tree Lighting Festival! Join family and friends for an evening of festive fun, community traditions, live...
SATNOV 14
12:00 PM – 6:00 PM
Craft FairsCeramicsHolidays & SeasonalWine Tastings

Holiday Artisan Market & Wine Tasting

Kick off your holiday shopping at Cathedral Ridge Winery in Hood River! Browse a festive collection of local artisans offering handcrafted candles, pottery, jewelry, clothing, original artwork, and unique gifts for everyone on your holiday list. Enjoy Cathedral Ridge Winery's award-winning wines as you explore one-of-a-kind creations, meet local makers, and support our creative community. Bring fr
SATNOV 21
6:00 PM – 9:00 PM
💰 $85+Singles & DatingPartiesDiningWine TastingsCultural Heritage

A Date for the Holidays: Singles SoirĂŠe, Wine Tasting and Buffet

Single and ready to mingle? Cupid has something special in store for you this holiday season! Join us for an exclusive Singles Soirée, winetasting and a Nigerian buffet. Designed for singles ages 35–50, this elegant evening brings together...
SATNOV 7
11:00 AM – 7:00 PM
Cultural HeritageSingles & DatingFood & DrinkArts & MediaStreet FestivalsMusicCraft Fairs

Frybread Fest

Frybread Fest is coming back to Downtown Portland, and it’s going to be bigger than ever. Help celebrate Native American Heritage Month through food, culture, art, and community. Enjoy delicious frybread from several Indigenous chefs and...
FRIDEC 4
5:00 PM – 10:00 PM
CeramicsMakersGalleriesCraft FairsNight MarketsHolidays & SeasonalWorkshopsToursBeerWine

Past Lives Holiday Bizarre

Shop hyper-local this year! Find one-of-a-kind creations by more than 35 artists and makers at our 2nd Annual Holiday Bizarre. Plus, do some hands-on art, watch art demos, eat and drink, and do our scavenger hunt for a chance to win prizes. It will be a night to remember!

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