Only got a couple of days to get to know a new city? Our Big Five City Guides can help. We break each destination down into culture, history, dining, shopping and relaxation must-sees and dos. Roslyn Jolly checks in from Portland, Oregon in the USA...
Indie; alternative; hipster; green — Portland’s reputation precedes it, and the reality of the largest city in Oregon doesn’t disappoint.
Yet while ‘Keep Portland Weird’ remains a city mantra, that hasn’t stopped the emergence of a sophisticated shopping and dining scene. Graced with America’s best airport, a brilliant public transportation system and beautiful civic parks, Portland is easy to navigate and full of surprises. On top of all that, it’s the gateway to the breathtaking scenery of the Pacific Northwest.
Enjoy this Portland travel guide.
Top cultural experiences in Portland
There’s no better way to explore Portland’s art and cultural scene than by visiting its diverse neighbourhoods.
The northwestern Pearl District is home to the historic Armory building, where Portland Center Stage produces classic plays, musicals and innovative modern drama. Nearby, Old Town/Chinatown is Portland’s late night entertainment hub. Come here for live music, dance clubs and a street-party atmosphere on Friday and Saturday nights.
Portland hosts a packed calendar of events. Music dominates with at least eight major festivals annually, including July’s famous Waterfront Blues Festival. Films, beer, bikes, books, flowers, food and gardens also have their own, often multiple, annual celebrations.
Portland for history lovers
This former frontier town wears its past proudly, weaving it into the fabric of modern urban life.
The iconic neon sign that greets visitors as they approach the city centre from the airport — a white stag leaping over the words ‘Portland, Oregon’ — is a fabulous piece of 1940s advertising reimagined as a symbol of the old town’s retro vibe.
Downtown, beautiful historic brass drinking fountains punctuate the sidewalks. These hundred-year-old ‘Benson bubblers’ lend charm to the city streets and tell a story of local philanthropy. They were gifts to Portland from one of its first millionaires — timber king Simon Benson.
When built in 1875, Portland’s Italianate-style Pioneer Courthouse expressed confidence in the fledgling city, then little more than 20 years old. Now the gracious structure presides over an urban park known as ‘Portland’s living room’. At the heart of the CBD, Pioneer Courthouse Square is a place for people to gather, dine, shop, and enjoy community events.
Portland’s most notable historic landmark is the Pittock Mansion. This stately home, built for the publisher of the Oregonian newspaper in the early 1900s, is a time capsule of upper-class luxury in the early twentieth century. From its hilltop position it offers great views, along with wonderful opportunities for rambling through the extensive grounds.
Where to shop in Portland
Tax-free retail, famous local brands and unique independent stores make Portland a paradise for holiday shoppers.
Homegrown companies Nike and Columbia Sportswear maintain glossy flagship stores in downtown Portland. Less well-known but highly esteemed footwear brand Danner (home of the boot featured on the cover of Cheryl Strayed’s adventure classic, Wild) has both a downtown retail presence and a factory outlet on the way to the airport.
Powell’s City of Books, the world’s largest independent bookstore, occupies an entire city block in the Pearl District. Heaven for bibliophiles, its mazes of shelves hold millions of new and secondhand books. Computer catalogues help shoppers navigate the huge space.
Standouts among Portland’s many innovative clothing stores are Wildfang, for tomboy-chic women’s workwear and suiting, and Frances May, a grandmother and granddaughter joint venture where strong design meets vintage influences.
The southeastern Hawthorne district epitomises Portland’s handmade/homegrown, retro/recycle ethos. Browse the plethora of small boutiques and craft shops, shop the huge vinyl collection at Jackpot Records, admire retrieved mid-century furnishings at Lounge Lizard, or pick up a fabulous fashion find at Red Light Clothing Exchange. Independent record label and handmade goods/fair trade retailer Tender Loving Empire also has a store here.
Great places to eat in Portland
Portland takes its food very, very seriously — and so should you, as this is one of America’s best dining destinations.
Vegan cuisine is huge here. Top picks for meat-free meals include the sumptuous Middle Eastern flavours at Aviv and elegant Asian small plates at Ichiza Kitchen. Little Chickpea serves incredible plant-based ‘ice cream’, while Sweetpea Baking Co. has delightful cakes and pastries. For a real vegan food adventure, try the eight-course all-plant tasting menu at Farm Spirit — a work of culinary art that takes several hours to appreciate.
Non-vegans aren’t overlooked in Portland’s rich restaurant scene. The hearty meals at Bullard showcase meat and seafood from handpicked local suppliers. For finer dining, sit down to a French-influenced meal at Le Pigeon. Omnivores will enjoy the mix of meat and vegetarian options at brunch mecca, Tasty n Alder.
Finally, what would Portland be without its hipster staples — craft beer, coffee and donuts? Get your flat whites (Australian-made) at Proud Mary, choose from an amazing array of donut flavours at Blue Star Donuts, and sample local brews in the convivial atmosphere of late night drinking establishment, Shift Drinks.
Ways to relax in Portland
Portland is a fantastic base for enjoying the natural beauty of the Pacific Northwest.
However, you don’t have to leave town to get back to nature. Washington Park on the city’s northwest side contains an arboretum, an acclaimed Japanese Garden and Portland’s famous International Rose Test Garden, along with the Oregon Zoo. Dozens of walking paths criss-cross the park, and the more challenging Wildwood Trail (encompassing nearly 50 kilometres of wilderness hiking) begins here.
For a rainy day option, visit Escape Games PDX to test your wits against one of five brilliantly designed puzzle rooms. ‘Portlandia’ is an affectionate tribute to the city’s history, geography and culture.
Where to stay in Portland
Kimpton Hotel Monaco Portland
Portland’s quirky but chic vibe is captured perfectly at the Hotel Monaco. From the animal-print bathrobes to the yoga mats in every room, the hotel has plenty of sass and heart. The refurbished 1912 building is full of eccentric and eclectic design touches — especially in the gloriously red lounge/library, where a hosted wine hour with live music is held each evening.
Hotel Monaco’s central location provides a great base for exploring Portland. Everything in the Downtown, Cultural and Pearl Districts can be easily reached on foot, and there are light rail connections within a minute’s walk if you decide to explore further afield. Alternatively, borrow one of the hotel’s free bikes!
Do you have any tips to add to our Portland travel guide? We would love to hear from you. Please leave a comment below.
Additional images: Bigstock
About the writer
Roslyn Jolly is a freelance travel writer whose work has appeared in Luxury Travel, Get Up & Go, The Sunday Telegraph and The Australian. In her former career as an English Literature academic, Roslyn studied and taught the work of great travel writers, such as Henry James, Herman Melville and Robert Louis Stevenson, and became fascinated by the history of travel and tourism. Two years at school in Wales and three years at university in England allowed her to travel extensively in Europe and North America, which she continues to do.