Portland, Maine vs Portland, Oregon: which Portland is best?

Depending on which US coastline you find yourself closest to, Portland could mean something completely different. There's the Maine version, known for its classic coastal New England vibe and maritime history. On the West Coast, Portland, OR, is laid-back, indie-spirited and as outdoorsy as they come. Both cities have elite food scenes and celebrate the natural beauty of their surrounding regions, but that's about where their similarities end. (Though legend has it Oregon's Portland takes its name from Maine's – after two men tossed a coin to bring their East Coast city names of Boston or Portland west.)

So, which city comes out on top? We asked two expert contributors to vouch for their preferred Portland.

Why Portland, Maine, is the best place to go

A huge fan of all things New England, Lonely Planet Senior Social Media Manager Rachel Lewis has a special love of Maine: it’s one of her grandmother’s favorite places, and it’s quickly become one of hers.

You feel it the second you land: New England envelops you in quiet, with even the buzziest towns feeling quaint but welcoming. I live in Wilmington, NC, a place known for its beaches and eats, yes, but also for its traffic and ever-increasing population, so visiting places like Portland, ME, feels like stepping into a slower version of the world (but with no less to do).

Maine’s most populated city, Portland is still under 70,000 people – where I live has double that amount – and yet it buzzes with creativity and all things maritime. Massive hydrangeas curl up alongside beautiful old houses. Live music plays throughout the Old Port. Chic shops like Soleil – a gift shop that’s blown up on the likes of Reddit and TikTok because of its adorable $1 art prints from local artist Ana Inciardi – prove that in Portland, ME, whimsy is everywhere.

Perhaps the best part of Portland, ME, is that it’s delightful no matter when you go. In spring, pop on a sweater and wander cobblestone streets. Take advantage of near-perfect weather and day trip to Acadia National Park. Come summer, it’s all about the water, and you simply have no choice but to make your way down to Casco Bay by boat. A morning sail along the coast? Breathtaking. A sunset cruise? Magical. Even a trolley city tour is worth your while, especially if you’ve got your eye on all those dreamy lighthouses. Winter is for brewery and museum hopping: add the Portland Museum of Art, Maine Historical Society, Wadsworth-Longfellow House and Victoria Mansion to your itinerary.

And fall. Oh, glorious fall.

If, like me, you live for all things fall foliage, it’s hard to beat the stunner that is Portland, ME, in autumn. Yes, Oregon has its own beauty in its endless greenery, but Maine knows how to really do it up. Wander the Old Port district and shop downtown, take a day trip to Freeport and Bar Harbor (my New Englander grandmother’s favorite part of Maine, if you’re curious) or road trip to beautiful orchards like McDougal Orchards, Hansel’s Orchard and Orchard Ridge Farm, where you can sip apple cider, eat apple cider doughnuts, walk the trails and pluck berries. If a quintessential fall is what you’re after, Portland, ME, is the clear winner.

Speaking of apple cider doughnuts (which, by the way, yum), we need to discuss the food. I’m an outlier here in that I’m a vegetarian, so I’ve never sunk my teeth into Maine’s most beloved dish: a lobster roll. But I’m told by other travel lovers that the best lobster rolls in Maine are easily accessible and indeed delicious. (One of our travel writer’s favorites is from Luke’s Lobster at the end of the Portland Pier.) Still, on a recent visit, I found my palate very pleased by the many vegetarian eats that Portland, ME, had to offer – as well as the lack of crowds. Despite not making a single reservation, I was able to eat, and do it well, which is a rare thing in even medium-sized cities these days. 

I happily ate overnight oats – mixed berries, oat milk and chia seeds – at Twinflower Café, the breakfast spot inside the Longfellow Hotel in the West End. For lunch, I had mushroom tempura at Green Elephant, a vegetarian bistro. A simple cheese pizza will serve you well after dark at Brickyard Hollow Brewing Company, a local chain that makes gourmet pizza from Freeport to Yarmouth (the original) and beyond. (Or be bolder than I am and give pizza topped with Maine blueberries a try.) After a long day of walking, a mushroom lentil patty at the burger joint Black Cow will fill you up nicely. All that is to say: Portland, ME, has you covered in more ways than just its famous seafood. 

Maybe you want to eat lobster in its many forms all season long. Maybe you want to see the bay by sailboat at all hours of the day. Maybe you want to fill your carry-on with art and adorable lobster-shaped goodies. In Portland, ME, it’s almost too easy.

Why Portland, Oregon, is the best place to go

Lonely Planet writer Erin Gifford knows the magnetic pull of Oregon – whether gazing into the depths of deep blue Crater Lake, paddling the Deschutes River in Bend or sampling wines in the Tualatin Valley. But it’s Portland’s laid-back vibes and pedestrian-friendly landscape that keep her coming back to the Rose City.

As someone who’s checked off half-marathons in both Portlands, I’ve enjoyed a runner’s-eye view of what makes each city hum. But it’s the one in Oregon that keeps calling me back (sorry, Maine). Maybe it’s the doughnuts. Maybe the waterfalls. Or the nationally top-ranked airport. Probably the food carts. Whatever it is, Portland, OR, just speaks my language.

This city rolls with a casual rhythm and a come-as-you-are vibe. Yes, it rains – 36in per year on average – but somehow, you don’t mind. Portlanders walk, bike or hop on the MAX Light Rail in both showers and sunshine. Just don’t bring an umbrella. Seriously. No local would. Portland is all about authenticity, and I’m 100% on board with that.

Portland, OR, is a place where city energy blends seamlessly with nature immersion. You can sip single-origin espresso in a minimalist café, bike across the car-free Tilikum Crossing and hike moss-covered trails at Forest Park – all before lunch. Forest Park is a sprawling 5200-acre urban forest with more than 80 miles of trails, including the 30-mile Wildwood Trail that winds through towering firs and lush ferns. But that’s just the beginning. Hoyt Arboretum shelters a grove of redwoods, and Washington Park boasts panoramic views of Mt Hood, Oregon’s tallest peak. All this within city limits.

Multnomah Falls, the state’s tallest, is only 30 minutes from downtown, tucked into the Columbia River Gorge National Scenic Area. The region is home to around 80 named waterfalls, earning it the nickname “Waterfall Alley.” Add in hiking, mountain biking, windsurfing and even kiteboarding, and you’ll see why Portland’s not just a city. It’s a base camp. You can even stop and smell the roses at the International Rose Test Garden.

Portland also leans way into its quirks. This is the land of cereal-covered doughnuts, vegan strip clubs and people who move house entirely by bicycle. There's even a World Naked Bike Ride. And every summer, Mt Tabor Park hosts an adult soapbox derby that’s part race, part costume parade. Yet beneath the eccentricity lies a soulful, creative core. The city thrives on independence, imagination and community. Wander the mural-covered Alberta Arts District, then find peace at the Portland Japanese Garden or the Lan Su Chinese Garden.

Maine has lobster. Portland, OR, has everything else. Let’s start with the food carts – more than 500 of them citywide, serving up a diversity of flavors. For a proper intro, head to Cartopia on SE Hawthorne Blvd for wood-fired pizza, Thai street food and Belgian-style fries with all the house-made dipping sauces. Craft beer? Portland’s got it covered. Dozens of breweries pour everything from crisp pilsners to juicy IPAs to tart sours. The wine scene is equally bold, especially at Pairings Portland, a quirky wine shop that pairs bottles with zodiac signs, movie characters and even couples on Love Island. Seriously. You may never look at a cabernet the same way again.

Portland helped pioneer third-wave coffee culture, so naturally, the coffee is on point. Then there’s the doughnut scene. Start at Pip’s Original – named Oregon’s best doughnut shop by Yelp (accurate) – for mini honey-and-sea-salt doughnuts and a chai flight. Then make the rounds: Blue Star, Mikiko Mochi, Doe Donuts (all vegan, don’t skip the Portland Fog) and of course, Voodoo Doughnut, the offbeat original with fans nationwide.

Portland is effortlessly explorable. You don’t need a car. Grab a bike, hop on the MAX or simply follow your feet. The city’s walkability makes wandering part of the adventure. More than anything, Portland gives you space to be yourself. No dress codes. No pretense. Just parks, food carts, trails, espresso and murals inviting you to explore, taste and chill.

Portland is wild and weird, green and gritty, laid-back and full of life. If you’re deciding between the two Portlands, I say head west. This one never disappoints. Just leave the umbrella at home.