The holiday season is upon us and business districts all around Portland have been buzzing with cheer! How are you supporting local businesses this season? Shop small and win BIG with Small Shops, Big Hearts and venture out to your favorite business districts for a heaping helping of holiday joy. Here are some more upcoming events by business district to help you plan your shop local adventure today! Check it out:

  • City-wide: November 16-December 10 – Shop Small, Win Big! 
    Win Big! makes holiday shopping fun and rewarding! Each visit or purchase to a small business earns customers raffle entries. Visit as many small businesses as possible November 16th through December 10th for a chance to win one of over 100 prizes. The more places you shop, the greater chance you have to Win Big! 
  • Foster: December 17 from 3-5pm – Cocoa, Cider and Caroling 
    Celebrate the holidays on Foster with free cocoa, cider, and caroling! Take in some festive cheer, do some last-minute shopping, and enjoy a warm drink with the Foster Area Business Association and local shops. Meet at 6406 SE Foster and see where the evening takes you. Don’t forget that the Foster Passport promo is happening until December 22nd.
  • Greater Brooklyn: The GBBA compiled a Gift Guide! Check it out here. Also, all throughout the month of December Hip Chicks Do Wine are hosting a variety of amazing events! See them here and attend one or all! 
  • Hillsdale / Multnomah Village: November 24-December 31 – Golden Ticket 
    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.
  • Lents: December 16 & 17 – Queer Holiday Market
    Get all of your holiday shopping done and support Queer makers in the heart of Lents Town Center at this cozy 2-evening winter night market.
  • Lloyd: December 9 from 11-6pm – Photos with Santa
    It’s not Christmas without your annual Santa Photo! Reserve your spot today to get your Santa picture at Lloyd Center, located next to the ice rink. 100% of your $10 donation supports the Salvation Army.
  • Mississippi: December 7 from 6-9pm
    Come Sip ‘n Shop on Mississippi Ave and enjoy complimentary ‘sips’ while you shop locally and support small businesses. Bonus! Get 10% off one drink or appetizer at participating restaurants/bars on the ave.
  • Montavilla: Winter Fest is on and there are a few upcoming events that you do not want to miss! Check out the line up of family-friendly events here.
  • Old Town: December 9 & 10 – The Labor Market
    This holiday flea market was established to help those affected by the Hollywood strikes. Stop in at Goldsmith Blocks and check out the unique gifts on offer!!
  • St. Johns:  December 9 from 6-11pm – Ugly Sweater Holiday Pub Crawl
    Don your best ugly sweater and come have a cheers with the St Johns community to celebrate the season! Collect stamps on your Ugly Sweater commemorative coaster for your chance to win a free Double Mountain Falalalala beer at The Park. Drink specials, scavenger hunt, and free pizza from Louie’s Pizza are in store!

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.