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Portland, Oregon, may get all of the attention for being the birthplace of the flannel-rocking, Warby-Parkers-and-beard-bedecked hipster, but there’s another Portland you need to have on your radar. This one’s a little less rainy, but every bit as awesome.

I spent a weekend there to cover the city’s Harvest on the Harbor food festival for Delish.com, and I immediately fell in love with its waterfront downtown area and unbelievable hospitality (seriously — Holiday Inn By the Bay serves complimentary hot cocoa and provides free shuttle service to/from the airport and the surrounding area! No need for a taxi or Uber here).

Though it was a quick trip, I ruthlessly chatted up everyone I met to get their must-see destinations and restaurant recommendations, then hit up as many as I could. Here are the ones I really loved.

FOOD:

The Holy Donut in Portland, ME (Photos: Candace Braun Davison)
Photos: Candace Braun Davison

The Holy Donut
7 Exchange Street
Who knew mashed potato donuts could be so light and fluffy (and taste nothing like po-tate-ohs)?! The chocolate glazed with sea salt is a must-order.

Vena's Fizz House in Portland, ME

Vena’s Fizz House
345 Fore Street
This place is a mixologist’s dream. It’s loaded with all kinds of surprising finds to stock your bar cart (including booze-infusing kits using mason jars), and serves its own creative mocktails and cocktails, like the Lumbersexual, a mix of gin, pine, lemon, spice tonic and bitters.

Carnitas tamale at Zapoteca - Best places to eat in Portland, ME

Zapoteca
505 Fore Street
Out of all of the food I sampled that weekend (and trust me, it was a LOT), Chef Shannon Bard’s Mexican-by-way-of-Oklahoma fare outshined ’em all. Seafood fans will love her beer-and-tequila-boiled lobster, which is served with fresh tortillas and mayo-and-cheese-coated elote, though my personal favorites were the carnitas tamales and chicken taquitos.

FUN:

Best Things to Do in Portland, ME - East End Cupcakes

Window shop along Fore Street
There are plenty of great boutiques and eateries to scope out, especially the seasonally inspired windows at East End Cupcakes.

Best Things to Do in Portland, ME - love locks fence

Show off your sentimental side at the Love Locks fence
Just before Valentine’s Day two years ago, people started putting padlocks on the chain-link fence on Commercial Street, overlooking the harbor. The tradition (which includes inscribing a love note on the lock and throwing the key away — or into the harbor), remains to this day.

Best Things to Do in Portland, ME - Card Works store

Pick up a souvenir they won’t throw away
Old Port Card Works, 3 Moulton Street
Warning: You must have a sense of humor to enter this store. The mix of kitschy and genuinely delightful cards, mugs and gag gifts is enough to make anyone smile — and completely over-stuff their carry-on for the trip home.

FULFILLMENT:

Best Things to Do in Portland, ME - cruise harbor

Cruise the harbor around sunset
The view alone is worth it; the perspective change that comes from stepping away from the day-to-day and spending a few hours on a boat is one heck of a refreshing bonus.

Visit the Portland Observatory
Why? Beyond being a cool photo opp, this is the only remaining wooden maritime signal tower in the U.S. It was built in 1807, so the building’s got plenty of stories to tell.

Explore the Portland Museum of Art
7 Congress Square
The museum features a painting that bears one uncanny resemblance to the “Mona Lisa,” prompting many to wonder if it is somehow tied to Da Vinci. See it for yourself, then ponder the meaning of life (or maybe something a little less existential-crisis-inducing, like whether M-Lisa’s smirking) while taking in the other pieces.

 

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