Essential Portland

Tour Creator

Becky is a Portland-based travel writer and the author of Walking Portland,, a guidebook of quirky neighborhood walks in the City of Roses. She's been writing about Portland since she…Read More Bio »



Remote Tour Included



As you’ll find on our tour, Portland is a great town for walking. It’s mostly flat, with a compact, almost European-style layout and an abundance of parks and open spaces—thanks to the city’s unconventional approach to planning and transportation, especially during its formative years. Despite rapid growth in the last decade, Portland still has plenty of odd little nooks and crannies where you can hang out, relax, and explore ideas like “What if we used bicycles to transport our brewpub around the city,” or “How about we put a design hotel in that abandoned building?” And in case you’re worried about the city’s infamous rain, there’s an inviting café, brewpub, coffee shop or tea house on nearly every block.

The area generally considered Downtown Portland radiates out from the city’s “living room,” its civic heart, or at least its best vantage point for people-watching: Pioneer Courthouse Square, a public gathering space often filled with downtown workers scarfing lunches bought from nearby food carts. Our downtown tour also includes the South Park Blocks and surrounding area—basically the city’s museum district. This is where you’ll find the art museum and history center, along an invitingly wide, tree-lined walkway through the park blocks. Finally, we’ll stroll along Waterfront Park, for an appreciation of the river that gives the city so much of its character.

Avoid the Crowds

Allows you to explore without having to be shoulder-to-shoulder in a large tour group

Created by an exceptional travel writer

Written by a Portland-based travel writer, who enjoys her city's hidden treasures

GPS Directions

Easy-to-follow GPS directions to get you from one point to the next on your tour

Highlights include:

Portlandia, Mills End Park, Skidmore Fountain

Remote Tour Included

As with all our tours, a remote tour is included that can be enjoyed from home


Essential Portland

  1. Pioneer Courthouse Square – Known as Portland’s living room, this public square is home to all kinds of civic activity, from farmers’ markets and food festivals to political protest rallies and live music, it’s a great place to sit and people-watch; the street theater here is tops.
  2. Director Park – This relatively new plaza, built in 2009, disguises a much-needed underground parking garage. It features food carts and outdoor seating beneath an attractive glass canopy, and it’s the home of the Portland visitor center.
  3. Portland Art Museum – Founded in 1892, PAM consists of several building and galleries, including the Northwest Film Center; it was one of the stops on the 1913 tour of the New York Armory Show, which rocked the art world of the time. These days it’s especially known for its Native American collection.
  4. Oregon Historical Society museum – After a multimillion-dollar renovation, the OHS museum rewards history buffs with permanent exhibits like ‘Experience Oregon’ plus a history-themed bookshop and an extensive archive of photos, maps, and documents. Look for the giant trompe l’oeil on the building’s exterior.
  5. Arlene Schnitzer Concert Hall – “The Schnitz,” as it’s called, is the home of the Oregon Symphony and several other performing-arts groups. Originally a vaudeville hall, then a movie house (the Paramount), then a concert venue, it has a stunning interior and a famous neon sign out front.
  6. Portland Building & Portlandia – Looking like a giant Christmas present that’s slowly being unwrapped from the bottom, this Michael Graves-designed office building has been controversial from the get-go. Perched over the entrance is the iconic statue Portlandia, the city’s beloved 50-foot woman.
  7. Thompson Elk Fountain – As you cross Main Street, glance to your right for a glimpse of a large bronze elk standing in the middle of the street. A gift to Portland’s mayor in 1900, it was the city’s second major piece of public art – we’ll see the first piece later on the tour.
  8. The Quest – In front of the Standard Insurance building is a large marble sculpture installed in 1970 and known locally as 'Three Groins in a Fountain' or ‘Saturday Night at the Y,’ for reasons that become obvious when you see it.
  9. Mill Ends Park – Mill Ends is the city’s tiniest park; in classic Portland fashion, it is literally a planter in the middle of the road. It’s at the edge of Tom McCall Waterfront Park, which occupies the west bank of the Willamette River. Waterfront Park was a major traffic thoroughfare for years until the 1960s, when then-Gov. Tom McCall began planning to turn it into park space. It’s full of walkers, runners and cyclists, water fountains, maritime relics, and tons of geese. From here you can see pointy Mount Hood and the Eastbank Esplanade across the water.
  10. Oregon Maritime Museum – In the middle of Waterfront Park is the sternwheeler Portland, semiretired and now home to the Oregon Maritime Museum, a kid-friendly favorite among Portland’s tourist activities. It usually stays moored but recently has been taken out on occasional summertime exhibition trips.
  11. Portland Saturday Market / Old Town - A stop at Portland’s lively weekend market, a weekly outdoor arts and crafts and food bonanza that involves a satisfying amount of street theater, plus crafts and snacks. It runs every weekend (including Sundays, despite the name) from March until Christmas Eve.   Old Town – An introduction to the historic core of Portland, once upon a time a rough-and-tumble waterfront where sailors and loggers went carousing in the muddy streets. Like many urban cores, Old Town suffered from a few decades of neglect and was considered a pretty sketchy area until a decade or so ago, when the city’s focused attention helped revitalize the neighborhood. It’s now a hub of nightlife, which we’ll see on the final stop.
  12. Skidmore Fountain & Ankeny Arcade – Portland’s first major piece of public art, the fountain within Ankeny Arcade is from 1888. A sign says it was intended for “horses, men, and dogs,” but . . . drink at your own risk.
  13. Voodoo Donut & Ankeny Alley – The pedestrianized Ankeny Street has become an outdoor hangout shared by several restaurants and bars. At the far end of the alley is Voodoo Donuts, a mandatory stop for many visitors, who wait in epic lines to buy large pink boxes of donuts with weird shapes and even weirder toppings.

Check out a free sample of this tour!

Share this tour


Get the tour in our app today!