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Shop Small Win Big is a holiday sweepstakes that lets you support local businesses, find awesome buys and earn raffle entries for more than 100 exciting prizes.

Shop Small Win Big

Elevate your shopping experience (and support Portland's best small businesses) this holiday season.

Download the App
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Editor's Pick
This is a recurring event and we’re showing the details from its most recent past occurrence. We’ll update this page with future event info as soon as we get it. Please check back!
When
Nov. 16–Dec. 10, 2024
Daily
Free
Where
Shops Citywide

Want to be more intentional with your holiday shopping while finding great only-in-Portland buys? The Shop Small Win Big holiday sweepstakes helps you do just that, rewarding you with raffle entries for awesome prizes just for shopping at Portland’s best small businesses.

Start by downloading the app, which will let you get registered and peruse participating businesses. Then play and shop from November 16–December 10, earning digital raffle entries each time you visit and make purchases at participating small businesses. (New this year, you can also collect small business trading cards, then share them on social media for weekly chances to win great prizes.)

Download the App

Explore just a few of the many local businesses taking part in Shop Small Win Big.

Find More Businesses

  • Tender Loving Empire – Downtown

    Since 2007, this indie record label has released albums from celebrated local artists. Their shops also offer a wide selection of made-in-Portland goods. Drop by to browse, or order curated boxes in bulk for event, team, or client gifting.

  • All Burn Wax

    Located in the hip Union Way shopping arcade, this local gift shop specializes in hand-poured soy candles and sprays. They also offer house plants, jewelry, artwork and more.

  • Straightaway Cocktails

    Straightaway Cocktails serves up timeless drinks and unique spins on the classics. Stop by their Southeast Portland tasting room — which can also be rented for private events — for meticulously crafted cocktails and tempting small plates.

  • Wildfang – Downtown

    This tomboy-chic boutique is all about (wo)menswear. Founded by two Nike alums, the local shop seeks “to liberate menswear one bow tie at a time” with stylish blazers, button-downs, cardigans, tees, wingtips and more for women.

  • Woonwinkel

    Woonwinkel (meaning “home shop” in Dutch) specializes in well-made, hand-crafted home furnishings. A departure from the hard, slick modern aesthetic of the past, Woonwinkel offers a new sort of modern: warm, inviting, tactile and quirky.

  • Orox Leather Co.

    Following in the footsteps of the proprietor’s great-grandfather, all Orox Leather creations are made by hand by a practiced craftsman. Their products are made with domestically sourced leather and sustainable (often even recycled) trappings.

You’ll get one raffle entry for checking in at a participating business. Making a purchase earns you three entries. To really start racking up the entries, visit as many shops as possible: Your raffle entries will double after three purchases, triple after six and quadruple after nine. The prizes on offer include roundtrip airfare, tickets to Portland Trail Blazers and Thorns games, stays at top Portland hotels, gift cards to local businesses and much more.

Shop Small Win Big gives you an opportunity to support local businesses, find awesome buys and earn chances to win more than 100 exciting prizes, making it a great way to elevate your shopping experience this holiday season.

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