Day One

A day in Portland simply must begin with coffee. Stumptown Coffee Roasters, Portland’s most famous coffee export, has four beautiful, bustling locations around the city, with two right downtown, at the Ace Hotel and on Third Avenue. Courier Coffee Roasters, located in downtown Portland, is another excellent option.

Once you’ve secured your caffeine fix, make your way to the Portland Farmers Market, the pride and joy of this food-obsessed city. Portland’s seriously next-level farmers market (every Saturday, rain or shine) fills the Portland State University campus with 200 rotating vendors that sell the region’s best produce, pastured eggs, grass-fed meat, freshly baked goods, artisan cheese and charcuterie, craft chocolate, and beyond. If you believe in shopping locally and sustainably and supporting small business owners, it doesn’t get any closer to the source than this.

If you’ve been bit by the shopping bug, walk up West Burnside Street to Powell’s City of Books.

Powell’s City of Books. Founded by the Powells in 1971, this family-owned iconic bookstore now occupies an entire city block. It’s also the world’s largest new and used bookstore, with nearly a million books in stock!

Like most landmarks, Powell’s flagship Burnside store offers free behind-the-scenes tours; they’re first come, first served, 45 minutes long, and held every Sunday at 10 a.m. and 4 p.m. The shop also hosts some of the world’s most renowned authors in the Pearl Room’s Basil Hallward Gallery; check the events calendar to see who’s reading during your stay. Be prepared to get lost in Powells for longer than you probably anticipate—the store is also home to a coffee shop and is chock-full of comfy reading nooks.

By now you’ve likely worked up an appetite. One highly-recommended lunch spot is Tusk, a stylish, modern restaurant that focuses on Mediterranean flavours, expressed through the Northwest’s most beautiful produce. Tusk is best enjoyed during the day, because of the abundance of natural light that floods into the modern dining room through large windows on two sides.

After lunch, spend some time in one of the city’s art galleries—whether you’re into galleries, public art or avant-garde institutions, Portland’s visual arts scene has it all.

For dinner, your options are endless, as Portland is truly a foodie’s dream.  Treat yourself to a unique experience at Ringside Steakhouse, serving slabs of beef and James Beard’s beloved onion rings since 1944. Its cozy dining room — full of fireplaces, burgundy booths, and white tablecloths. Beyond the dry-ages steaks and  decadent lobster mashed potatoes, the real draw of Ringside is likely its roster of career servers; the restaurant is home to the city’s finest service, from the first Old Fashioned to the last glass of pinot.

After dinner, head for a nightcap at Scotch Lodge, a speakeasy opened by one of the best bartenders in the city, Tommy Klus. Klus travels the world personally collecting Scotch-style whisky for his bar, and you can have classic cocktails made with your choice of cheaper or very, very rare Scotch.

Finally, rest your weary head at one of Portland’s more famous hotels, The Heathman.

Built in 1927, this much-loved Portland landmark that catapulted to international stardom when it cameoed in 50 Shades of Grey, and got a fashionable face lift. The 10-story hotel features opulently costumed doormen, a prime downtown location (next door to the popular Arlene Schnitzer Concert Hall), and luxe downstairs tea court. The hotel’s gym even features a mini rock-climbing wall, punching bag, and live-streaming Peloton bikes for those who can muster the energy after strolling Portland all day.

Day Two

Atfer breakfast, head to Washington Park, a 410-acre urban park with 40-plus miles of hiking trails designed by John Charles Olmsted, the son of Frederick Law Olmsted, who designed New York’s Central Park.

Washington Park is home to the Oregon Zoo, the Portland Japanese Garden, and the International Rose Test Garden, which are all well worth a visit.

Hop on the park’s free shuttle and make your way to the International Rose Test Garden, because a visit to the Rose City without a stop at the Rose Garden is sacrilege. If your timing’s off to catch the more than 10,000 bushes in their full glory (they bloom April through October and peak in June), the expansive views and general splendour of the nearly-five-acre garden are still worth a visit, even in the dead of winter.

Founded in 1917 to help preserve European hybrid roses people feared would be lost to persistent World War I bombing raids, the garden flourished, and is now the oldest official continuously operated public rose test garden in the United States. The garden also offers spectacular views of downtown and Mount Hood.

When you’re finished admiring the flowers, head just uphill to the majestic Portland Japanese Garden for more fabulous flora.

After enjoying the garden’s leafy trees or leafing through books, head back to the bricks to explore the Pearl District. A former industrial area, this chic neighbourhood is now home to boutiques, galleries, restaurants and cocktail lounges. Make your way north and enjoy the people watching at Jamison Square.

If you’re ready to tap into Portland’s famed microbrew scene, head to Deschutes Brewery & Public House. The state’s largest craft beer producer, Deschutes has been a Pearl District staple since 2008. Order the sampler tray to taste a variety of beers, some available only at this location.

Compared with cities like New York and Los Angeles, Portland is relatively small—which only makes its sheer density of destination-worthy attractions all the more impressive. However you spend your time in Portland, don’t be afraid to step just outside your comfort zone and do your part to Keep Portland Weird!