Food & Drink❯Wine❯Wine Tastings

🍷 Your Favorite Downtown Tradition Is Back and Better Than Ever 🛍️ On Saturday, November 7 from 3:00PM to 7:00PM, Historic Downtown Hillsboro comes alive for Sip & Shop 2026, a festive self-guided stroll through the heart of the district featuring over a dozen local wineries, cideries, breweries, and mocktail makers, live music, carolers, holiday shopping, and a dining guide packed with specials

Join us for Harvest Celebration, a one-of-a-kind evening where the worlds of art and wine come together in the heart of Portland. Presented by the Portland Art Museum and the Willamette Valley Wineries Association, this immersive tasting...

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.

Sunday, November 15 | 4:30 PM – 7:30 PM Good food, great wine, live music, and friends — that’s what Friendsgiving is all about! Grab your friends and join us at Lady Hill Winery for a fun and festive evening celebrating the season.

Need some fresh inspiration for your holiday entertaining? Join us for our Holiday Appetizer and Wine Pairing event! We’ll be pouring a flight of 6 wines, with 4 of them perfectly paired with delicious holiday bites. Discover new flavor...

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...

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...

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...