Unwrap The Magic Of Holiday Shopping On Mt. Hood Territory Main Streets
It's time to make your shopping list and check it twice! Mt. Hood Territory Main Streets are waiting to charm and delight you this holiday season. From the mountain to the valley and everything in between, our Main Streets have it all — whether you're on the hunt for local, unique gifts from boutique shops or items from larger retailers. When it's time to set the bags down to rest and refuel, you won't have to wander far to find a variety of delectable places to eat, drink and be merry.
Bonus: Shopping is tax-free in Mt. Hood Territory. With all these savings, perhaps you can get yourself a little something special as well. Better yet, grab some friends and make a whole weekend of it.
Whether you’re strolling historic blocks, browsing artisan boutiques or enjoying cozy cafés, the main streets of Mt. Hood Territory invite you to slow down, explore and celebrate the season.
Why Shop On Mt. Hood Territory Main Streets?
- Support Local: Locally owned boutiques and restaurants dominate our main streets. Shopping and eating at these places not only supports the local economy, but also scores you the best quality, unique flavors and personalized experiences.
- Amazing Photo-Ops: Need we say more? You'll find Instagram-worthy backdrops galore in the hearts of our bustling Oregon cities.
- Walk, Shop, Repeat: Since you can hit up each stop by foot, you're sure to cover more ground both in terms of your step count for the day AND the amount of treasures you can collect in one outing!
Every visit to the main streets of Mt. Hood Territory is a chance to connect with local culture, savor seasonal charm and create memories that will last well beyond the holidays.
Urban Main Streets
Downtown Lake Oswego is as convenient as it is scenic. Tucked in the heart of the city along the edge of Oswego Lake, you'll find storefronts of all types mixed in with public displays of art. Its European influenced architecture and brick sidewalks will transport you to another time and place. Find larger retailers such as Chico's alongside smaller shops like Mapel Boutique, as well as both upscale and casual eateries. The holiday ambiance is hard to beat!
For a truly unique experience, head to the lively historic downtown Milwaukie. Check out the world famous Dark Horse Comics and Made in Milwaukie for hand made treasures. The craft cocktails are matched only by the vibes at the hip bar Decibel Sound & Drink. Stop into the rebuilt Historic Milwaukie City Hall where pFriem and Keeper Coffee moved int earlier in 2025. Just steps away from downtown, Milwaukie Bay Park boasts a dazzling view of the Willamette River.
When you’re exploring urban Mt. Hood Territory main streets, you’ll discover a blend of tradition and modern flair, perfect for shoppers who love variety in a single stop.
Valley Main Streets
Canby is the place to go for a small town, authentic main street feel. Get lost in stories at the independent The Book Nook. (Pro tip: Treat yourself with a tour of Canby's bakeries.) While you're in the area, make sure to say "Cheese" at some great cheese based stops.
South of Portland make sure to stop into Wilsonville. Start your day with a warm drink and snack at Lux Sucre, featuring incredible pastries. Just a quick drive from downtown grab some fresh air, a Christmas tree and holiday gifts at Yesteryear Farms. Find more trip ideas at Explore Wilsonville.
These valley towns showcase the heart of Mt. Hood Territory, where local flavor and small town pride create unforgettable holiday shopping experiences.
Mountain Main Streets
The quaint and quirky downtown Estacada attracts visitors with its colorful murals, dining and of course, shops. The Mossy Rock is a gift and nature shop with locally made jewelry, bird houses and hummingbird feeders as well as a variety of rocks, minerals and crystals. If you're hunting for a gift for the art lover in your life, you'll want to stop by The Spiral Gallery for unique pieces created by local artists who also work the front counter. Not far from downtown are unique shopping experiences right on the farm, like Wade Creek Vintage Marketplace that sits on an old farm plot.
Government Camp is an alpine village nestled at the foot of Mt. Hood. While often thought of as the jumping off point for outdoor adventures, its inviting main strip entices visitors to stay and play. Browse previously used ski, snowboard and cross country gear for a discount at Valian’s Sports if you're shopping for an adventurer. While the Mt. Hood Cultural Center & Museum is known for its exhibits, there is also a gift shop stocked with jewelry, arts and crafts from local makers and books from local authors.
