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by Heather Huey, CMP, Senior Program & Event Manager

Stumptown. City of Roses. Bridge City. Beervana.

Portland, OR has many nicknames, each eclectic and reflective of its diverse residents and landscape. It’s ideal location is situated right between the Cascade Mountains and Pacific Ocean, along the banks of the Columbia River at the top of the fertile Willamette Valley. With its vibrant food and drink scene, endless outdoor activities, and weird and wonderful museums and shops, and NO sales tax, there’s something for everyone in Rip City.

And because at SHW we love to plan, we’ve put together a perfect three-day itinerary to cover Portland’s best of the best!

Where to Stay

Staying in central Portland is the way to go. For those looking to treat themselves, Portland just welcomed The Ritz-Carlton, Portland, the first Five Diamond Hotel in the Pacific Northwest, to its downtown core. The hotel features nature-inspired interior (including Meadowrue – the fun wilderness-inspired Lobby Bar) and Flock Food Hall, a collection of BIPOC-owned businesses that occupy the ground floor and pay homage to the site of one of the city’s earliest food truck pods, which is where the Ritz-Carlton, Portland now stands. For something a little more budget-friendly but equally fun – check out Jupiter NEXT Hotel across the river in Portland’s uber-hip Central Eastside. The rooms features floor-ceiling windows and luxe accommodations with the chic and herbaceous Hey Love cocktail lounge and restaurant in the lobby. The sister Jupiter Original Hotel across the street features renovated rooms with a mid-century furnishings and wall-sized music murals and chalkboard doors (with real chalk!) in the rooms.

Day 1

Spend your first day in Portland’s Central Eastside District – Home of the Oregon Convention Center and a multitude of diverse eateries, including an insane amount of plant-based restaurants (by latest count Portland has at least 50-fully vegan restaurants). Start your day by grabbing a green tea matcha and avocado toast at Fairlane Coffee in the uber-cute Sellwood neighborhood. On a nice day, it’s a must to walk through verdant Oak’s Bottom Wildlife Refuge – Portland’s 163-acre park home to 185 bird species and a protected endangered tadpole/frog pond.

The Oregon Museum of Science and Industry (OMSI) is fun for adults and children alike and a good next stop. Go underwater for a tour of the USS Blueback Submarine or head to the stars and watch a movie in the Kendall Planetarium. After you’ve worked up an appetite with your museum visit, head to the Hawthorne Asylum Food Carts  where you can have your pick among 21 diverse food carts and 16 beers on tap, with food options ranging from waffle-themed or specializing in Korean Fried Chicken.

After lunch, head to one the Southeast’s many major streets primed for window shopping and snacking. First check out the up-and-coming and stylish Division Street for a visit to the independent Third Eye Books and pick up a good read and some African roots and teas. Hawthorne Boulevard is a few blocks north and is chock full of eclectic thrift and vintage shops and an artsy population. If you’ve seen the show Portlandia, there’s a good chance you have a sense for some of the quirkiness you can expect visiting this neighborhood. Catch an afternoon flick with a local beer at the iconic Bagdad Theater and Pub or grab an Egyptian Rose Mocha at Tōv Coffee. Lastly, hit up the Belmont neighborhood for dinner visiting the vegan Sri Lankan Mirisata for some Hot Chili Pol Roti and Pol Sambol or head to the playfully pink-hued Rukdiew Café for some soft shell crab Pad Thai. End the day at the 70s-themed speakeasy Sugar Hill for an out-of-this-world Espresso Martini.

Day 2

Spend your second day exploring Portland’s City Center. For a sweet start, hit up the iconic Voodoo Donuts and try their famous Maple Bacon Bar or my personal favorite, the Vegan ODB, a delectable raised ring with chocolate frosting, chocolate cream-filled cookies, and peanut butter drizzle. The Portland Saturday Market is a must visit and it’s celebrating its 50th anniversary this year. Located in Waterfront Park and Ankeny Plaza, the Market is the largest continuously operating weekly open-air craft market in the United States. Spend some time here soaking up the unique local craftmanship (and yes, there’s plenty of tie-dye and goat milk soaps). Afterwards, don’t miss out on seeing the smallest park in the world (really), about a ten-minute walk away. Mill Ends Park is just 452 square inches and only two feet wide. Locals will sometimes hang ornaments on the tiny tree in the park during the holidays. Gotta go for the ‘gram, at the very least!

For lunch, tempt your tastebuds at one many delicious food carts dotting the downtown core. The “Pods” are a Portland institution with over 1,000 food carts spread across the greater Portland area in various pods. For those wanting to sample Portland’s microbrew scene, check out Deschutes Brewery & Public House, the state’s largest craft beer producer first started in Bend, in the Pearl District. Their famous Black Butte Porter and Mirror Pond Pale Ale are must-trys.

After lunch, get lost in the aisles of Powell’s City of Books, a full city block and the world’s largest independent bookstore. Thank goodness for all the directional signs in the store, as getting lost is easy amongst the all the new, used, and hard-to-find books that encircle you inside.

After picking out a few new reads, spend some time in nature. Walk to the tranquil Lan Su Chinese Garden in Old Town Chinatown, or drive or take a quick Lyft ride eight minutes away to the Portland Japanese Garden. When the former Ambassador of Japan to the United States His Excellency Nobuo Matsunaga visited the garden, he proclaimed it to be “the most beautiful and authentic Japanese garden in the world outside of Japan.” Truly a great place to visit in any season, as the garden and its colors are always changing. Afterwards, explore the famous International Rose Test Garden (this is the City of Roses, after all) if you’re visiting in late May through October, where you can see more than 10,000 rose bushes bloom representing over 610 varieties. End your nature time at Hoyt Arboretum, a “living museum of trees” founded in 1928 home to over 2,300 species of trees and shrubs and 12 miles of hiking trails.

For a fun dinner back in downtown, enjoy breathtaking views, Pan-Asian cuisine and 15th-floor rooftop dining at Departure in The Nines Hotel. With an amazing à la carte or tasting menu and cocktail list, there is something for everyone here. Have final nightcap at Fortune, a buzzy plant-based bar with plenty of Instagram-worthy photo spots, Friday-night fortune tellers, and DJ’s spinning tunes to dance your heart out to on Saturdays.

Day 3

Wow – you’ve done a lot so far! Time to get outside the city on your third day and take in some of the local nature and bounty just steps outside of Portland. Depending on your preference, here are three fun options for how you can explore beyond Portland.

Option 1: Coast Day Trip – Cannon Beach

For those looking to dip their toes in the Pacific Ocean, look no further than the adorable town of Cannon Beach. A 90-minute drive from Portland, the crowning jewel of the beach at Cannon Beach is Haystack Rock. Named one of the world’s 100 most beautiful places by National Geographic, this is a do not miss if you decide to visit the coast. The town of Cannon Beach is quaint and lovely, with upscale eateries and cute cafes, less touristy than its sister city Seaside.

Option 2: Willamette Valley – Wine Tasting 

If wine tasting is your jam, look no further than the verdant Willamette Valley! The Valley, which follows the Willamette River starting in Portland to just south of Eugene, is home to more than 500 wineries and recognized as one of the premier Pinot noir-producing areas in the world. Pinot Gris, Chardonnay, Riesling and other varietals also do well in the area. Just one hour outside of Portland, start in the quaint McMinnville – their historic downtown is home to 20 tasting rooms, farm-to-table restaurants, and a good home base to explore the vineyards. Check out the helpful Willamette Valley Wine Map to filter by location, varietal, family-friendliness, etc.

Option 3: Columbia Gorge – Waterfalls and Windsurfing

Heading east from Portland you’ll snake along the Columbia River through the Columbia River Gorge. This is the land of stunning vistas and dozens of waterfalls, including Oregon’s tallest waterfall Multnomah Falls, just 40 minutes outside of Portland. This popular site requires a timed use permit from Memorial Day through Labor Day but is wonderful to visit any time of the year. For something less crowded, check out Bridal Veil or Latourell Falls. Continuing on to the town of Hood River, you’ll enter the “windsurfing capital of the world,” where the Columbia River cuts a canyon up to 4,000 feet high above water through the Cascade mountains, creating an excellent wind tunnel great for those looking to partake. Book a lesson, then grab dinner at pFriem Family Brewers and enjoy stunning views of the river.

This just scratches the surface of all the amazing things to do in Portland and the greater area. We love this city – and encourage you to come enjoy all the quirky, yummy and beautiful that Portland has to offer.