Portland, Oregon vs. Portland, Maine: A Tale of Two Cities

Historic Ties

These two cities share a name for one little-known reason. Portland, Oregon's founders were two settlers from New England: Asa Lovejoy of Massachusetts and Francis Pettygrove of Maine. Both men wanted to name the new port city after their respective home cities—Lovejoy for Boston and Pettygrove for Portland, Maine. The men flipped a coin to decide, and the rest is history. The 1835 penny that decided the city's name is on display at Portland, Oregon's Historical Society, along with plenty of other Oregon Trail-era artifacts.

But the parallels between these two hip cities don’t stop there.

Portland and Portland may be on opposite coasts, but they're like-minded in their dedication to keeping their outdoor spaces green. Adventure activities like biking and hiking are some of the main attractions in both cities.

Portland, Oregon, is a nature-lover's paradise, but its outdoor sites aren't exactly well-kept secrets. Oregon's sprawling national scenic area, the Columbia River Gorge, is rife with hiking trails and waterfalls. Don't miss the Gorge's tallest waterfall—Multnomah Falls, which can be seen up-close from a foot bridge about halfway up the rushing falls. But be ready to navigate crowds—Multnomah Falls may as well be a theme park with the number of tourists it attracts.

If you want unplugged outdoor relaxation, however, Maine has your back. The East Coast's Portland boasts remote mountains, secret Casco Bay islands, and remote waterways perfect for undisturbed kayaking, hiking, and swimming. Walk along Spring Point Shoreway's rocky coastline or venture to Mackworth Island for a far-off view of Portland.

Both Portlands are home to bustling downtowns with renowned arts scenes, which is why they also have some incredible museums and street art. You'll find big-name pieces at both Oregon's Portland Art Museum and Maine's Portland Museum of Art. Andy Warhol works can be found at both, though Oregon's institution has more Asian, Native American, and modern and contemporary pieces. Its Maine counterpart boasts the works of famous European artists like Matisse and Monet. You're likely to stumble upon street art in both cities as well, from colorful graffiti to whimsical sculptures and sidewalk installations.

Portland, Maine, is about two centuries older than Portland, Oregon—and it shows in its art and architecture. The colonial buildings and narrow roads of Maine's hippest city strike a stark contrast to its Oregonian counterpart's Art Deco vibe and funky public art displays. For historical art lessons that coexist with colorful street art, head to Maine; for newer and edgier exhibits with a more diverse and contemporary feel, head to Oregon.

Oregon's biggest city is famous for an inventive food scene that also delivers on sustainability. Perhaps the biggest reason to visit Portland, Oregon, is to sample quirky food-cart fare like vegan cupcakes, Korean fusion—plus fancier spots like tasting-counter amuse bouches, and creative tapas. Oregon's Portland is considered one of the best food cities in the world, and is so packed with award-winning restaurants that it's hard to find one that's not raved about. Expect fare featuring locally and seasonally sourced ingredients that support nearby growers, farmers, and businesses that employ sustainable and ethical practices. Don't miss brunch at Tasty & Alder, Voodoo Donuts’ famed confections, Olympia Provisions’ curated charcuterie boards, Pine Street Market's eclectic food court stalls, and local coffee roasters that have artistically mastered their craft.

Maine's Portland, meanwhile, is something of a leader in sustainable food practices and local specialties—but it's very no-frills in comparison to Oregon's sea of high-end eateries. Portland, Maine's farm practices, like goat mowing and public orchards, echo its West Coast counterpart's sustainability. Still, the restaurant scene is a lot less saturated and is far simpler—with shipyard seafood shops and vintage-feeling speakeasies that make it especially Maine. That's not to say you won't find famed food trucks, James Beard-nominated spots, and cozy farm-to-table dining with seasonal menus. Lobster and other succulent seafood are in no short supply, plus there are plenty of beloved vegan options—like the famous potato donuts at Holy Donut (pictured at left).

Perhaps the biggest tie between these two Portlands is their beer snobs. Sleepy Maine has its highest concentration of breweries in Portland, which is home to big-name brewing companies like Shipyard, Allagash (pictured at right), Rising Tide, Bunker Brewing, Fore River, Sebago Brewing, and many more. Portland's famed Maine Brew Bus totes beer drinkers from brewery to brewery for tours and tastings. Wineries and distilleries, on the other hand, are far and few—though Maine Mead Works and Maine Craft Distilling are certainly worth a stop.

Portland, Oregon, is home to plenty of beer as well, with brewing behemoths like Hair of the Dog, Hopworks, and Deschutes at the forefront. Wine snobs also love Portland, Oregon's sustainable urban wineries, and the city's booming spirits scene is tied to the Oregon city's dark history.

About a century ago, Portland, Oregon, was one of the most dangerous port cities in the nation. The "Forbidden City of the West" was home to a little-known kidnapping epidemic fueled by Prohibition. Inebriated drinkers in underground speakeasies would find themselves trapped in the now tourist-frequented Shanghai tunnels beneath Portland, from which they would be sold into sea labor. Abducted men were loaded onto China-bound ships and women were forced into prostitution in the tunnels right up until the 1940s. Now a much rosier city, Portland's Forbidden City legacy is alive in gin, whiskey, and rum tastings at historic Distillery Row's cocktail crawls.

Aesthetics aside, both Portlands know how to have a good time. Oregonian Portlanders imbibe at inventive downtown bars like Teardrop Lounge and the massive Multnomah Whiskey Library (pictured at right), enjoy live music and fire pits at Mississippi Avenue's stages and patios, flock to late-night food carts and beer gardens when the weather permits, and show up in droves to the city's many culinary, cultural, and art festivals. You're sure to stumble upon a light-strung outdoor space filled with revelers on any given night.

Across the country, Maine's biggest city has more secretive nightlife spots that deliver just as much fun. Slip in to speakeasy style taprooms like Novare Res Bier Café and Bramhall, bar hop on hidden cobblestoned Exchange Street, follow the sound of live music to the piers or Old Port, or sign up for a Latin dance class and salsa the night away. For a more relaxed evening, take a horse-drawn carriage ride down Fore Street, or plan your getaway around one of the summer seafood or winter holiday festivals. In the summer, there are plenty of waterfront patios, clam bakes, and cruises to enjoy, while winter weather simply means refuge in museums, breweries, concert halls, and candle-lit restaurants.

Both Portlands are postcard picturesque, but, like the opposing coasts they represent, they're beautiful in very different ways. Oregon's biggest city paints a picture of the great American West during the times of the Oregon Trail and Manifest Destiny that mingles with modern Art-Deco architecture. Meanwhile, Maine's vibrant port city has held onto its Brahmin roots in the form of colonial homes and cobblestone alleyways that now give way to both vintage theaters and modern sky scrapers.

In Oregon's Portland, you're sure to see as many retro neon signs and industrial-era bridges as you are green spaces and bike lanes. The mountainous landscape makes for plenty of hill-nestled neighborhoods and hike-worthy parks, and an extensive street car network marks downtown's wide, walkable grid of avenues and parks.