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Portland, Oregon is the second largest city in the Pacific Northwest and a major vacation destination for those interested in the artsy, educated, progressive vibe for which it has become famous. It’s a bit of a tricky city for visitors, though. It can be tough to crack through the façade in a town where it seems like everyone knows everyone. And with the massive array of breweries, coffee shops, bookstores, funky boutiques, and even live music performances, it can be genuinely difficult to figure out which ones are actually worth checking out. While in a lot of cities, guided tours have a reputation (often deserved) of being a bit dorky, Portland’s guided tour scene, like the city itself, is pretty cool. There are a whole bunch of options available, both by theme and preferred method of transportation, and all of them will give you a local’s take on what’s actually happening in this always-changing city. Check out these excellent options.
Best Walking Tour: Downtown Portland Walking Tour
Get yourself oriented in charming downtown Portland on this informative walking tour. You’ll start your morning at the massive historic Multnomah County Central Library, where you’ll meet your local expert guide and begin your 2.5-hour exploration of the city’s heart. You’ll visit the famous Powell’s Bookstore, consistently rated as one of the top independent booksellers in the country; admire the Portlandia statue, the second-largest figural statue in the USA (second only to the Statue of Liberty); see Mills End Park, the world’s smallest park; and visit Pioneer Square, among others.
Your guide will both explain Portland’s history and point out the ways that this famously progressive city is moving into the future, with its LEED-certified buildings and accessible public green spaces galore. Your tour wraps up just in time for lunch, and your guide will happily offer you any number of recommendations just a stone’s throw away, or you can head to the nearby Alder Street food cart pod and see what strikes your fancy.
Best Bike Tour: Essential Portland Bike Tour
Portland is a famously bike-friendly city, with a web of planned bike paths and a generally bike-aware road culture that makes it both safe and comfortable to ride on the roads. Conveniently, bikes are also an ideal vehicle for sightseeing, as you can both cover ground efficiently and get uninterrupted views in every direction. This two-hour guided tour begins in downtown Portland and rolls through some of the city’s most interesting neighborhoods, including Chinatown and the Pearl District, as well as parks and green spaces, like Tom McCall Waterfront Park and the South Park Blocks.
The tour will also visit some of Portland’s newest parks, to help give participants a sense of how city planners are reinterpreting the future of public green spaces. The tour includes a fitted bike (advise the company of your height when booking) and a bike helmet and is limited to participants over 10 years of age and 4’11” in height.
Best Hop-On/Hop-Off Tour: Portland Hop-On/Hop-Off Tour
Forget those giant red double-decker buses that make up the hop-on/hop-off network in other cities. This is Portland, you know it’s going to be a little bit quirkier. Here, the premier hop-on/hop-off company runs a network of wooden open-air trolleys, painted bubblegum pink. Buy a one- or two-day pass and enjoy open access to the trolleys, which arrive every hour or so at a network of 14 different stops.
On the docket: Pioneer Courthouse Square, Hoyt Arboretum, Powell’s Books, Caruthers Park, Tilikum Crossing, and many more, from which you can plan your own itinerary. Drivers provide colorful commentary as you roll through the city from stop to stop, so simply getting comfy and riding the full route is also a great option.
Best Beer Tour: Portland Brewery Bike Tour
Portland is well-known as a hophead’s paradise, with over 40 microbreweries and brewpubs within the city limits and some of the world’s most innovative brewers cookin’ up everything from brutally hoppy IPAs to fruity, fizzy lambics and weird, funky sours. Hop on a bike (provided), strap on a helmet (probably needed), and get to tasting. Your tour guide will lead you through several of the city’s finest brewing establishments, from icons of the local beer scene to quirky young start-ups, tasting all the way.
As you roll, they’ll also point out local landmarks and points of interest along the five-mile route of the city’s west side. The tour takes place in the afternoon and finishes up just in time for happy hour, so you can put your newfound knowledge to immediate good use. All tastings plus a bike and helmet rental are included.
Best Food Tour: Portland Foodie Fieldtrip by Bike
Calories consumed while on a bike tour don’t count, so hop on and get to munching. This 2.5-hour tour takes food-lovers through a hearty handful of Portland’s most iconic and interesting food and beverage crafters to sample, sip, and nibble their offerings. The tour includes stops at Cup & Bar, for a taste of small-batch coffee from Trailhead Coffee Roasters; a hefty sampling of some of the city’s most iconic food trucks at the Cartopia Food Cart Pod; and a dessert stop at either local creamery Fifty Licks for ice cream or Alma Chocolates for hand-dipped single-origin chocolate bonbons. The tour is vegan- and gluten-free-friendly, though celiac or severe allergy options might be limited. All tastings and bike and helmet rental are included, as is a knowledgeable local guide.
Best Portlandia Tour: ‘Portlandia’ Tour of Portland
Fans of the popular sketch comedy series Portlandia can get an insider’s look into filming locations and inspirations, plus a heavy dose of the same self-effacing progressive humor on which the show is focused, with this driving tour of downtown Portland. The three-hour tour starts with a hotel pickup and then heads straight to Voodoo Doughnuts, where you’ll sample the delicious, slightly weird wares (maple bacon, anyone?). You’ll follow that up with a coffee tasting at a local artisanal cafe and then a combined drive and stroll along several of the city’s most interesting shopping streets, stopping at Land (where “Put a bird on it!” was born), and In Other Words Feminist Community Center, the inspiration for the show’s Feminist Bookstore, among others.
Along the way, you’ll also hit up the Mississippi food cart pod, where “Stu’s Stews” was filmed, and the Vera Katz Esplanade, where the show’s opening “Dream of the ‘90s” scene was filmed, as well as the actual Portlandia statue and other iconic locations you’ve seen time and time again in the show. It’s a colorful, tongue-in-cheek tour that illuminates both some of the filming processes for the show and the history and culture of the town itself.
Best Nature Tour: Guided Hike in Portland’s Forest Park
True to form, Portland is home to the only urban wilderness park in the U.S. This five-mile guided hike is ideal for nature lovers who’d like some deeper understanding of the forestry and natural history of the Pacific Northwest, along with tidbits about the city itself and how it intentionally incorporates nature into its urban planning and design. Your guide will take you through some of the park’s most beautiful trails at your own pace, with plenty of photo stops and a healthy snack included.
You’ll spot flora and fauna, learn about the history of the indigenous people who lived here, get some understanding of how the Lewis and Clark expedition and the Oregon Trail factored into the region, and get a bit of moderate exercise while you’re at it. This tour is really ideal for anyone who likes to get outside, but particularly for those whose travel plans don’t involve leaving Portland but who’d like to see some of the Pacific Northwest’s legendary old-growth forests while they’re in the region.
Best Ghost Tour: Haunted Pub Tour
Though it’s better-known for third wave coffee and food trucks, Portland, like any city that’s been around for a while, is chockablock with stories of hauntings, possessions, and dastardly deeds. This tour lets you enjoy this eerie history alongside a curated selection of the city’s finest craft brews. The 2.5-hour tour includes guided introductions to the sites many of Old Town’s historic dens of iniquity (brothels, opium dens, speakeasies, and more) plus a 20-minute visit into the underground Shanghai tunnels, once used to move goods from the port into the basement storehouses of businesses around the city, but also used to kidnap (or, not coincidentally, “shanghai”) sailors into forced servitude. Of course, it also includes plenty of beer tastings, and the price includes tastes of six of the city’s most delicious microbrews at two different haunted pub stops.