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In 1845, Portland, Oregon was only a penny flip away from being called Boston. Two immigrants both wanted to name the new settlement after their hometown. But in two out of three coin flips, Francis Pettygrove from Portland, Maine won the honour.

Though the West Coast settlement has far outgrown its East Coast namesake, the two US cities remain oddly similar. If you are looking for a city with sustainably sourced food, local brews, a GLBT-friendly scene or a place to vacation with your pooch, either Portland would easily fit the bill.

For every feature they share, however, each city has attractions that outshine the other. Here’s how to see Portland, Maine and Portland, Oregon at their individual bests:

Seafood lovers: Maine
Portland, Maine is still a working port city, as you can tell by the industrial-looking seaside, so tonnes of fresh fish and shellfish come in daily. To experience the life of a fisherman yourself, hop aboard the Lucky Catch, a working lobster boat that takes guests out to buoys and lets them pull up real lobster traps. If you catch any, you can buy them straight off the boat at bargain prices and walk next door to the Portland Lobster Company to have them boiled up.

Not a lobster lover? Try the raw oysters at the Old Port Sea Grill and Raw Bar, the seared shrimp and green tea soba noodles at Walter’s or the Irish-inspired fish and chips at Bull Feeney’s.

Walkable parks and gardens: Oregon
Portland, Oregon has more than 200 parks within its city limits, including the world’s smallest park: Mill Ends, at only 2ft across. Get a panoramic view of the city and nearby Mt Hood at Council Crest Park, Portland’s highest point at 1,073 feet above sea level.

The city also claims some of the United States’ most beautiful public gardens. The International Rose Test Garden features 500 varieties across 7,000 bushes; to see them in bloom, visit June through early October. In the cooler months, visit the sprawling 5.5 acre Japanese Garden, once the city’s zoo, and the smaller, but expertly structured Lan Su Chinese Garden, where pine, flowering plum and bamboo, known as the Three Friends of Winter, are featured for their heartiness through the winter months.

Quiet isolation: Maine
With a population of only 60,000, Portland, Maine is much smaller and slower-paced than Portland, Oregon, which has a population of nearly 600,000. The largest city in Maine also has seven beaches within a 15-minute drive, making it easy to find relaxation by the sea (at least in the summer and autumn). Stay at Inn by the Sea on nearby Crescent Beach, four miles south of the country’s most painted and photographed lighthouse, Portland Head Light. If you are looking to completely avoid the tourists downtown, the property offers a little bit of everything that defines the city: a restaurant featuring only local produce and seafood, LEED certification, Maine blueberry martinis and even a Tuesday afternoon doggy happy hour, where pampered pooches are served soy ice cream and biscuits.

Wine aficionados: Oregon
Sitting atop the fertile Willamette Valley, Portland, Oregon has access to some of the region’s best pinot noir, pinot gris, chardonnay and pinot blanc — varietals that thrive in cooler growing conditions. With nearly 500 vineyards in the north Willamette Valley region alone, Portland visitors have easy access to plenty of wineries within a 30-minute drive of downtown. Inside Portland city-limits,  make reservations at Uptown Billiards to sample brilliant pairings from Oregon and abroad. The swanky upstairs space features a five-course meal highlighting a single seasonal ingredient across all five dishes (the menu changes every few weeks). The meal is a reasonable $25, with an additional $10 for wine pairings. It is well worth the price to highlight the subtle notes on each plate. 

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