I created this guide for the Airbnb "Hillside Getaway" (link below) with food and outdoor enthusiasts in mind and those wanting to experience the cultural side of Portland.
Although my childhood hometown has changed a lot over the years, Portland is still the vibrant, artsy, cultured city I've always known. The "Rose City" has so much to offer—a great food and music scene, the outdoors, and an independent spirit—surrounded by forests and set between two rivers, the peaks of the Cascades, and the Pacific Ocean. This environmentally conscious city has a good rail system with miles of bike paths and walking trails.
Virtual explorers and trip planners alike, explore Portland with this interactive guide. Check out what to SEE + DO, places to DRIVE + RIDE, and where to EAT + DRINK around this river city in the northwestern corner of Oregon.
This list is far from exhausted and will continue to expand. Click places and links to learn more.
Note: When you click and buy through links in this guide, we may earn an affiliate commission at no extra cost to you. To help fund production of these guides, tips are highly appreciated.
Tilicum means 'Bridge of the People' in the local Native Chinook language. The span offers a pair of wide paths for both pedestrians and cyclists with only bus- and lightrail-access to link the city’s South Waterfront at OHSU and the Aerial Tram with the burgeoning Central Eastside at OMSI and the Oregon Rail Heritage Center.
Cruise and dine for lunch or dinner with a scenic view of downtown and up the Willamette River on the Portland Spirit while you learn about the city's landmarks.
A Portland institution, this outdoor weekend arts-and-crafts market is the largest continually operating in the US that offers tons of food choices and gives visitors a unique opportunity to meet the artists.
Located in Old Town Chinatown, 'the mission of Lan Su Chinese Garden is to cultivate an oasis of tranquil beauty and harmony to inspire, engage, and educate our global community in the appreciation of a richly authentic Chinese culture.'
This Restoration Hardware Concept Store is an experience in itself but is also located in the heart of Northwest Portland's shopping and food district.
Among Portland's signature park are gardens, memorials, the iconic World Forestry Center, Oregon Zoo (see 4T trail below), Rose Test Gardens, the Hoyt Arboretum and the Forest Park wilderness. The Wildwood Trails starts here and stretches for 30 miles.
Touted as the most authentic Japanese garden outside of Japan, the 5-1/2 acres includes 8 unique gardenscapes, an authentic Japanese tea house, meandering streams, intimate walkways, and a exquisite view of Mount Hood.
The museum is dedicated to educating people about the importance of trees and forests worldwide with a first-floor focus on forests of the Pacific Northwest.
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4T Trail
Pick up a required all-day TriMet pass to complete the trail loop of 4Ts: Train, Trail, Tram, Trolley.
'Known locally as Portland’s “living room,” this public space hosts hundreds of events every year. The square features a waterfall fountain, two brick amphitheaters, two iconic statues and popular food carts at lunchtime.'
Just minutes from downtown, it's the oldest zoo west of the Mississippi with a nostalgic train and over 2600 animals in exhibits of the Great Northwest, Pacific Shores, Polar Passage, Discovery Zone (with butterflies), Primate Forest, (Asian) Elephant Lands, and Africa.
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Trail
Hike to Council Crest on the well-maintained Marquam Trail.
'At 1,073 feet above sea level, Council Crest is the highest point in Portland. From the top of the hill visitors can see five mountains in the Cascade Range: Mount Hood, Mount St. Helens, Mount Adams, Mount Jefferson and Mount Rainier.'
'The Portland Aerial Tram’s cabins rise 500 feet at 22 miles per hour for the three-minute trip from the South Waterfront to Oregon Health & Science University’s main campus, offering views of downtown, the Willamette River and the mountains.'
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Trolley
Board the Portland Streetcar back to the beginning at Pioneer Square or stop off for some enrichment at the Portland Art Museum and Oregon Historical Society.
Surrounding a scenic lake with a picnic area, playground, off-leash dog space, horseshoe pit, and basketball, tennis and volleyball courts, Laurelhurst Park was the first city park named to the National Register of Historic Places.
Firstly, the views from here on a clear day are spectacular: panoramic views of Mount Jefferson and the Three Sisters to the south (Mount Adams and Mount St Helen's to the north). As the name denotes, it's at the timberline with a view to the peak of Mount Hood above.
We also recommend skiing or snowboarding the resort's slopes with dinner at the restaurant and an overnight stay in the lodge.
Travel just 30 miles east of Portland to this deep canyon forged by the Columbia River that’s home to gorgeous waterfalls, epic vistas and seemingly endless options for outdoor recreation.
Crown Point offers jaw-dropping views from this 100-year-old observatory. Hood River is known for microbrews and served as a jump-off point to the Columbia River, one of the most famous kiteboarding and windsurfing locations in the US.
This iconic resort, built by lumber magnate and philanthropist Simon Benson in 1921 on the original site of a small, successful 1904 summer resort, is perched on a cliff overlooking the Columbia River within the Gorge near Hood River.
Well worth a short day trip to hike the highest waterfall in Oregon, the second-tallest year-round waterfall in the nation, with a combined cascade drop of 620 feet.
The crown jewel of the Columbia River Gorge, this century-old observatory, rest stop and museum, only 25 miles from downtown Portland, offers epic views as a beacon for Oregon’s founding history.
With 80 miles of forest trails, fire lanes, and roads, 5200 acres stretch 7 miles through the Tualatin Mountains along the eastern slope that overlooks Northwest Portland at the convergence of the Willamette and the Columbia Rivers.
The imported Milanese wood-burning oven 'unites tradition and creativity' in Neapolitan pizza and Italian street food, while the bar serves memorable beverages with 'only the finest spirits, daily-pressed juices, and large format ice cubes' along with local beers and acclaimed old world wines.
Modern gourmet Cretan cuisine — that's from the Greek island of Crete — a healthy Mediterranean cooking heritage favoring organic vegetables and all-natural meats.
Some may call this sophisticated city to the south a bit bougie, known for fabulous high-end retailers and lake-side estates, though you'll also find some hidden haunts and places to chill by the lake.
Enjoy a modern dining experience from the creative French-inspired tasting menus at the bar or communal tables in a cozy atmosphere from James Beard Award-winning chef Gabriel Rucker.
Cocktails in a tropical modern setting in the Jupiter NEXT Hotel, this restaurant and bar is open every afternoon into the night and brunch is served here on the weekends.
Cozy German pub with some "serious German food" as deemed by Lonely Planet that also recommends the meat-filled dumplings called Schwäbische Maultaschen from southwestern Germany. Also try the Jägerschnitzel topped with mushroom gravy and served with red cabbage.
Ciao, I'm Ali Giaudrone, the creator of AMG Inspired (see website link), crafting Inspired Guides. Tap into my insight. As an avid traveler, I dive deeply into places of the world, valuing experiences over checking boxes.
My Inspired Guides are informative interactive digital guidebooks offering you traveler tips gained through my hours of research, travel experiences, and talking with locals.
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As a designer, I've traveled throughout Europe and the Western world to learn about architectural products and methods. Now as an expert luxury traveler, I share culturally enriching experiences that aren't necessarily opulent or expensive but are focused on quality and authenticity. The best way to understand the world is to experience the unique aspects of places with an open mind and heart.
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Architectural Designer | Writer | Photographer | Travel Creator
My travel and work experience in architectural design and hospitality have deepened my appreciation for detail and quality. I built AMG Inspired to create quality architecture and support sustainable tourism defined as “tourism that respects both local people and the traveler, cultural heritage and the environment.”
Join me as I find cool places, great food, and interesting features. Check out my library. Let me know if you'd like me to create a custom guide for you with recommendations and/or itineraries focused on your needs, desires, and length of trip.