Travel Guides

A Tale of Two Portlands

America’s Coolest Corner Cities

By Cele & Lynn Seldon

Even though they are located on opposite sides of the country, there are many similarities between Portland, Maine, and Portland, Oregon. Both are known for their eco-friendly outdoors, coffee and beer scenes, thriving art (and artisan) communities, uber-cool vibe, and, of course, the ever-changing weather. This is a tale of two Portlands.


Tours are a great way to get introduced to any city.

Portland, ME:

With water being such an important part of Portland’s history, Portland Discovery Land & Sea Tours provides a great introduction to the city. Combine a Harbor Lights and Sights, Lighthouse Lovers, or Sunset Lighthouse cruise with one of their trolley tours to double-duty your Portland exploration. Other city tour possibilities include: ghostly walks with Wicked Walking Tours or exploring Maine’s breweries, distilleries, and wineries on the Maine Brew Bus.

Portland, OR:

Walking is the best way to explore the “Rose City” and Portland Walking Tours offer lots of tour options, ranging from art and architecture on the “Best of Portland,” to the scandalous and sinister in “Underground Portland.” Other tour options include exploring Portland by bike with Pedal Bike Tours or waterfall, whitewater, and Willamette Valley tours (and more!) with Evergreen Escapes.



Both Portlands have garnered a reputation for an eclectic and noteworthy art scene.

Portland, ME:

Portland Museum of Art

The Portland Museum of Art is the largest and oldest art institution in the state of Maine and houses significant American, European, and contemporary art, as well as local works highlighting the rich tradition of Maine’s landscape and artist community. Another artsy option is First Friday Art Walk, Maine’s largest year-round (and free!) monthly cultural event celebrating Portland’s artistic awareness, education, and creative culture.

Portland, OR:

The Portland Art Museum is the seventh oldest museum in the United States and the oldest on the West Coast. It is internationally recognized for its permanent collection, and houses some of the world’s finest public and private collections. For something a bit trendier, head to PDX Contemporary Art in the Pearl District.



Both cities feature stunning parks and other green spaces to enjoy nature and natural surroundings.

Portland, ME:

Deering Oaks Park  is an urban oasis located just west of downtown. It’s listed on the National Register of Historic Places. Developed and designed in the late 1800s in part by Frederick Law Olmstead (of Central Park fame), the park features a rose garden, a pond, playgrounds, and is home to the weekly Portland Farmer’s Market. For other natural endeavors, visit the Tate House and Colonial Herb Garden or the garden at the Wadsworth-Longfellow House.

Portland, OR:

Strolling Pond Garden. Photo courtesy of Michael Drewry

The Portland Japanese Garden is proclaimed to be the most authentic Japanese gardens outside of Japan and is quintessential Portland. Situated in scenic Washington Park, there are eight garden spaces, including the Strolling Pond Garden, Sand and Stone Garden, Tea Garden, and more, along with changing exhibitions, cafés, and a gift shop. Also found in Washington Park is the International Rose Test Garden. Another option nearby is the adjacent 5,200-acre Forest Park and its’ 70 miles of hiking trails. Or head to Chinatown and the Lan Su Chinese Garden.



With a dedicated approach to “local” in terms of makers and artisans, shopping in both Portlands is a study of community creativity.  

Portland, ME:

The tastiest shopping in Portland is Stonewall Kitchen in the quaint Old Port on Middle Street. What started in 1991 with jars of jam being sold at the local farmers market—as an ode to a grandmother’s blueberry pie—has morphed into a specialty food giant selling jams, chutneys, jellies, sauces, cooking oils, mustards, home and kitchen accessories, and more. They often host cooking classes and always have jars open for tastings. Other shopping adventures can be found at Reny’s (“A Maine Adventure”), Edgecomb Potters, and Browne Trading Company.

Portland, OR:

MadeHere PDX

Dedicated to showcasing the Portland artisan mentality and community, MadeHere PDX pools the talents of designers, artists, and makers into one location. Or, in this case, three locations throughout the city selling art, apparel, accessories, food, jewelry, pet items, and home décor. Other local specialties can be found at Tender Loving Empire and Portland Made.



The coffee culture—and resulting java junkies—in both Portlands is undeniable (blame it on the weather). So much so that coffee shops and roasters are part of the daily fabric of each city.

Portland, ME:

With two locations in Portland, Tandem has brought the roasting process to the people at their roastery and café. Enjoy a hot and fresh cup o’ joe while you watch sample roasting and cupping of new coffees. Or settle in at the gas station-turned-laundromat-turned-Tandem Coffee + Bakery to sip coffee and eat delicious scratch-made baked goods. Other roasters and coffee shops brewing it up include Coffee by Design, Bard, and Speckled Ax.

Portland, OR:

Open daily 363 days a year, Sterling Coffee Roasters serves up the classic cast of coffee characters, along with tasty pastries and sandwiches. For those who prefer to brew at home, they sell their world’s finest micro-and-batch-craft-roasted beans and grounds, as well custom flavors for special occasions. Other joltin’ joes include the “snob-free” coffee at Deadstock Coffee and farm-to-cup coffee at two locations from the folks at Nossa Familia Coffee.



Another undeniable similarity between the two Portlands is the craft beer culture. Some might even call it a cult.

Portland, ME:

Bissell Brothers was one of the earliest craft brewers to arrive on the scene. What was once a one-room taproom is now the largest in all of Maine. Serving up five- and 10-ounce pours of their rotating beers in the taproom, Bissell Brothers can also be found in bars and restaurants throughout Portland. Honorable mentions go to Rising Tide, Foundation, and Allagash Brewing Companies.

Portland, OR:

Tasting at Hair of the Dog. Photo courtesy of Jess Alworth

Boasting more craft breweries than any other city in the world (75 at last count), Bridgeport Brewing Co. is Portland’s oldest craft brewery and appropriately located in a century-old brick and timber building. One of the top specialty brewers in the state—and one of the oldest in the country, the brewpub features brewery-fresh ales, pilsners, and IPAs, as well as a mezzanine bar and cocktail lounge, a tasty menu of pub grub favorites, outdoor seating, private event rooms, and free brewery tours. Other brewtopia options include Hair of the Dog and Gigantic Brewing Company.



Exceptional dining can be found throughout both cities. But some neighborhoods reign supreme.

Portland, ME:

The Old Port district along Portland’s historic waterfront was originally known for its cobblestone streets, 19th-century brick buildings, and fishing piers. Today, it’s more known for its dining (and nightlife) with everything from fine dining to pub grub, seafood specialties to ethnic destinations, and coffee to breweries filling every nook and cranny. Honorable mentions go to Washington Avenue in the city’s East End, the Arts District, and along Congress Street.

Portland, OR:

With the West Coast Portland being about ten times larger, there are that many more neighborhoods to find a good meal. The 50-odd blocks of Division Street, however, has so much dining and nightlife going on that they even have their own website ( Other notable places where food and beverages rule are the West End and East Burnside.



Food trucks have become ubiquitous in many cities across the country and that’s certainly the case in both Portlands.

Portland, ME:

Food Trucks in Portland, Oregon

Featuring “Mexican Food from the Heart,” El Corazon serves up traditional Mexican using authentic local ingredients for dishes like tacos, taquitos, and burritos (not to mention the Sonoran Hot Dog, the house specialty) from Mexican Chef Joseph Urtuzuastegui. Other tasty food trucks include the lobster rolls at Bite Into Maine, Japanese street food at Mami, and bite-sized gourmet donuts at Urban Sugar.

Portland, OR:

Originally created as an economic development project and incubator for Latino businesses, Portland Mercado has become a hub for Latino culture. The outdoor plaza features nine rotating food carts representing the diverse flavors of Latin America, while the market contains various food and beverage shops and entrepreneurial kitchens. Other food truck options include more than 30 food carts under the big tent at Cartopia Food Cart Pod and the one dish wonder at Nong’s Khao Man Gai.



Anytime is a great time to head to either city and it seems like there’s a special event on the calendar every month.

Portland, ME:

Photo courtesy of Jamie Francis

Harvest on the Harbor is the motherlode of Portland events. The city’s annual food and drink festival highlight the local culinary and beverage scene with sustainable suppers, Flavors of Maine tasting events, happy hours, pub crawls, lobster competitions, and Market on the Harbor sampling and tasting tents. Other harbor events include Portland Schoonerfest and Old Port Festival.

Portland, OR:

It’s not surprising that one of the biggest parties of the year is the Portland Rose Festival. For more than a century, Portland has celebrated its diverse culture and heritage with more than 60 events, including parades, fairs, entertainment, great food, and more, starting in late-May and ending with the Rose Cup Races the second weekend in June. Other events that highlight the area’s bounty include the Portland Craft Beer Festival, the Oregon Brewers Festival, and Feast Portland, one of the country’s top food festivals.


To plan your next visit to either (or both!) of these Portlands, or many other locations across the nation, take a look at our website,

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