Shop Small Win Big

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.)

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.

Portland Holiday Events

Like an Advent calendar loaded with sugary treats, the days leading up to Christmas in Portland hold an abundance of sweet memories.

Near Me Now App

Learn more about Near Me Now, a map-based guide that lets you explore like a local. Carefully curated by professional Portland fans, the official Portland app will help you find events, food carts, restaurants, bars, attractions, stores and more.