It’s time to put your money where your heart is, Portland! Small business owners city-wide have teamed up to create holiday magic with dazzling lights, towering trees, wonderful window displays, and special deals and discounts to make the season merry and bright. Shop small and win BIG with Small Shops, Big Hearts and venture out to your favorite business districts for a heaping helping of holiday cheer. We have compiled a list of the best events by business district to help you plan your shop local adventure today.
City-Wide: Head over to the Shop Small Win Big event page to discover 100+ small businesses with amazing gifts that will brighten your holidays! On 11/17-12/11, enter to win prizes including vacations and hotel stays, dining experiences, concert and performing arts tickets, iPads, and so much more!
Beaumont: Fremont Holiday Fest returns on 12/2 from 4-7pm. Activities include photos with Santa and Mrs. Claus, snacks, crafts, and wreaths for sale. Visit beaumontvillagepdx.com for more info.
Central Eastside: The Portland Night Market happens on 12/1-12/4 and is a blend of food, culture, music, drinks, and retail in the Industrial District.
Foster: Starting 12/1, find the Foster Holiday Tree at various businesses for your chance to win prizes. Clues will be given on Facebook and Instagram about the tree’s daily location. Find the tree, make a purchase, and take a picture with the tree. Post the picture on FB/IG and tag @fosterareapdx to be entered into their holiday giveaway.
Gateway: Gateway Winter Festival heads indoors with a special community event on 12/6 at the Nick Fish Building. Enjoy cookies, cider, free books for kids, music, an ornament making station, and a community tree lighting.
Hawthorne: Enjoy ornament making, entertainment, and a holiday tree-lighting from 2-5:30pm on Sunday, 12/4 at Dairy Hill Ice Cream.
Lents: The East Portland Collective and Larkspur are hosting a wreath making event on 12/11 and there will be a Holiday Shopping Bazaar on 12/17 and 12/18. Follow Lents Grown Business Association on Instagram for more info!
Lloyd: Join Lloyd Center as they kick off the Holiday Season with their Mrs. Claus Holiday Tree Lighting Event, on 11/19 from 1-3pm at the Lloyd Center Ice Rink. My People’s Market returns on 11/19 and 11/20 and it is bigger than ever! Visit the Oregon Convention Center for a gathering of Portland’s diverse and vibrant entrepreneurs, makers, artists, and culinary pros.
Midway: Division Midway Alliance and Midway Business Association have teamed up and will be distributing food, gifts, and winter supplies to community members on 12/9 from 12-2pm.
Mississippi Ave: Local businesses are lighting up Mississippi Ave this holiday season with bright and colorful lights throughout the street. On Giving Tuesday (11/29) shop owners will donate a percentage of that day’s sales to Boise Eliot Elementary School.
Montavilla: Montavilla Winterfest kicks off with a holiday tree lighting on 12/3, and then continues with Santa Saturday on 12/10, and the Merry Montavilla Soiree & Pub Crawl on 12/17! Go see the lights and window decorations in shops and follow #montavillawinterfest on Instagram for up-to-date events and promotions.
Multnomah Village/Hillsdale: Golden Ticket launches on 11/25. Receive a Golden Ticket when you shop at local, participating businesses. The Golden Ticket can then be redeemed at a neighboring participating business to receive a discount or a gift with purchase. On 12/3, things get even merrier with the district’s annual Holiday Gala, which includes hot chocolate, holiday window displays and decorations, and SANTA!
Old Town: Find the perfect gifts at the Old Town Holiday Market, happening at the Old Town Gallery on 11/26 from 4-9pm. Following that, Nuestro Navidad will take place on 12/17 and will feature vendors, food and music.
Sellwood Moreland: On 12/3, Sellwood’s Decemberville will be an all-day shopping experience complete with games and activities, sales, discounts, and family fun
St. Johns: Light Up St. Johns continues with the month-long Ugly Sweater Shopping Extravaganza and a Bar Crawl on 12/9-12/11! Look for posters at participating bars/restaurants, take a photo, post to Instagram with #lightupstjohns, and tag the business for a chance to win prizes! Fox 12 recently visited St. Johns and produced a few fun segments on the upcoming events. Check it out here, here, and here.
Williams District: On 11/26 from 2-5pm, BYOC (bring your own camera) to the DIY Bar and take a fun holiday photo with Prince the Llama while you enjoy jolly drink specials and gift certificate giveaways! The Community Warehouse will also be onsite to collect gently-used blankets for those in need.
This list is non-exhaustive so follow us on Instagram for updates. Pledge to keep your hard-earned money ‘home for the holidays’ by shopping locally and supporting the small businesses that help make Portland a wonderful place to live, work, and shop.