Shop Local, Park Smart - Downtown Portland Holiday Shopping Guide

It’s the most wonderful time of the year - welcome to the holiday (shopping) season in Portland! December transforms the city into a winter wonderland of twinkling lights and festive storefronts. In this guide, we’ll cover the shop local movement, best places to shop, and holiday parking tips.

At The Hotel Zags, we're perfectly positioned to be your home base for Portland holiday shopping adventures. The hotel is ideally located within walking distance of the city's local boutiques, artisan markets, and unique retailers.

Why Shop Local?

As the heart of downtown Portland comes alive with seasonal cheer, there's no better time to discover the city’s shop local movement. Shop local isn't just a trend, it's a way of life that creates authentic connections, supports our community, and delivers gifts that can't be found anywhere else. From handmade goods at neighborhood boutiques to festive holiday markets, shop local not only supports our community, but also ensures you’ll bring home gifts with heart.

Portland is well known for its creative makers and independent spirit. This shines brightest during the holidays, when small businesses showcase unique, handcrafted, and locally sourced goods. Whether you’re browsing a curated boutique or a pop-up holiday market, shopping local means you’re helping artists, makers, and family-owned shops thrive. It is also the best way to find one-of-a-kind gifts that can’t be ordered by everyone with a single click. One more bonus of shopping in Portland - no sales tax. Tax-free savings across all your holiday shopping really adds up!

Holiday Shopping Hotspots in Downtown Portland

Portland Saturday Market Holiday Edition - Though famous in warmer months, Portland Saturday Market also hosts festive holiday shopping weekends. It’s a great place to meet artists and buy locally made jewelry, art, and home goods.

Union Way - Just a short walk from The Hotel Zags, Union Way is a beautifully designed shopping arcade featuring small Portland-based shops. From artisan leather goods to natural skincare, this hidden gem feels like stepping into a stylish urban market.

Crafty Wonderland Holiday Art + Craft Market - This annual December event is a must-shop for those who love creative, handmade gifts. You’ll find hundreds of local makers under one roof, offering everything from quirky stationery to handmade jewelry. Explore the market on December 12th-14th 2025.

Independent Bookstores & Vinyl Shops - Downtown is home to Powell’s City of Books, the world’s largest independent bookstore. Pair this with a visit to record shops like 2nd Avenue Records, and you’ve got gifts that carry a little piece of Portland’s culture.

Shopping Breaks

After a few hours of shopping, you’ll likely want to take a break and recharge your holiday shopping batteries. Fortunately, downtown Portland offers plenty of cozy spots to retreat.

Cozy Cafes - Take a break at Stumptown Coffee Roasters or Courier Coffee for a warm latte and a moment to regroup.

Festive Breweries - Breweries like Deschutes and Von Ebert often roll out seasonal winter ales worth sampling.

Holiday Parking Tips

While downtown parking during the holidays can sometimes feel tricky, below are some insider tips to make your visit stress-free.

Use SmartPark Garages - Portland’s SmartPark system offers affordable, centrally located garages throughout downtown. They’re well-marked and a reliable option for holiday shopping trips.

Park Once, Shop Many - Instead of hopping around by car, park once in a central garage and explore on foot. Downtown’s compact layout makes it easy to hit multiple shopping spots in a single stroll.

Street Parking - Metered street parking is available, but can fill up quickly during peak shopping times. Pay attention to posted hours and time limits to avoid surprises.

Park at The Hotel Zags - Offering convenient hourly parking at $4/hour or a full day rate of $40/day. The hotel’s secure parking garage is within easy walking distance of downtown shopping and public transit options.

Holiday Parking Promotions - In recent years, Portland has offered reduced (or even free) parking on certain days to encourage shopping local. Check the city’s website for announcements. These perks can save you both money and stress.

Skip the Car - Consider using Portland’s excellent public transit system. MAX light rail and TriMet buses stop all throughout downtown, making it easy to shop without worrying about parking. And if you’re staying at The Hotel Zags, many of the city’s best shopping spots are just a short walk away.

Your Holiday Shopping HQ at The Hotel Zags

After a full day of holiday shopping, you’ll be excited to return to your base at The Hotel Zags. When it’s time to take a break from all the shopping, stop by our Gear Shed and enjoy access to complimentary bikes, boards, cameras, Nintendo Switch, classic board games, and more. 

At the end of the day drop by our restaurant, PLS on Sixth and enjoy a meal and a nightcap from the bar. Ready to book your holiday trip to Portland? View the latest offers at The Hotel Zags and book your stay.