May 2015 | view this story as a .pdf

Multiple personalities, one love.

By Olivia Gunn

“There are so many bars here, and they’re all so different.” My friend Rachel is visiting from New York, and it’s her first night in Portland. Because it’s Thursday, we’ve decided to take things easy, avoiding the all-too-well-known set-up of “just one drink.” Instead we walk to Gorgeous Gelato on Fore Street, and because weekends start early in this part of town, Rachel gets to witness the pulse of the Old Port.

A recent graduate, she’s suffering from the restless panic of 22 and has decided to make her way to as many cities as possible in the hopes of finding her start. Her fears, concerns, and anxieties were my own two years ago as a recent transplant to Maine. Now, walking through the town I’ve come to call home, where I have favorite spots and my go-to watering holes, it’s rejuvenating to see this part of the city through a first-timer’s eyes.

What I first noticed about the Old Port were all the different facets of nightlife occurring within the same few blocks. Walking along Fore Street on any given Saturday night, you’ll spot a young, flirty couple, arm in arm, headed to Wharf Street to catch a live show at Oasis. Meanwhile, the same couple, only 20 years older, heads into Central Provisions for their long-awaited date night.

Music floods the streets. Depending on where you’re walking, you’ll hear a local cover band playing Mumford and Sons or Kenny Chesney blaring out of Bonfire. And as campy as it can be, it’s hard not to be swept up by it all. You know what I mean. We’re all guilty of taking on a shot or one more beer after hearing “American Girl” blaring out of Old Port Tavern.

Then there’s the live music you can find at Brian Boru, where you’ll surprise yourself, dancing the night away to a Maine country band called North of Nashville or kicking back at Sonny’s on a Thursday night with live jazz.

Because there is something to satisfy just about everyone in the Old Port, you’ll find there’s really no lack of personalities. From the Pabst drinkers at Rosie’s to the cocktail buffs at Portland Hunt + Alpine Club, there’s always a crowd with whatever vibe you’re looking for.

“You’ll go into the Old Port alone?” Rachel asks. Of course. And a lot of people do. If you’re not a fan of the obvious spots on the obvious nights, you can always head to a low-key joint like The North Point. Every Monday, The North Point celebrates the start of the week with half-price bottles of wine, and this time of year their outdoor seating is the perfect hideaway. If you’re a true wino, you already know about MJ’s Wine Bar, where you can end your weekend with a glass of red and Lady Zen’s Obbligato midtown jazz sessions.

Of course summertime brings a whole new level of energy: college students free of classes, the cruise ships, and the vacationers. The hot nights downtown also bring out the lovers. The ladies have kicked off the Bean boots, men have finally shaved their beards, and the heat is on. Sexy, low-lit spots like Vignola Cinque Terre; Zapoteca; or Street and Co., where you can keep it casual at the oyster bar, really do the trick.

Every night of the week there’s something worth doing in the Old Port. Stroll by Pearl on Thursday and you’ll find a sea of salsa dancers tearing up the floor until 1 a.m. Looking for a mid-week pick-me-up? Head to Bull Feeney’s with Portland Comedy Showcase on Wednesdays for some laughs, or play Picasso for the evening at Muse Paint Bar. However you get your kicks, you’ll find somewhere to do it.

While the Old Port does wear on you and eventually you may find yourself on Congress Street craving a little less action, it’s good to know there’s always something going on right down the road. And no matter how many times you’ve danced at RiRa’s on the crowded floor, stood in line at Bull Feeney’s, or ended a night at the Thirsty Pig, it never gets old experiencing it all over again with someone who never has.