September 2017 | view this story as a .pdf

Savor the last sips of September sun on Portland patios.

By Sarah Moore

Welcome to Patio Season in Maine–a rare, precious, slim spell of time. With our long winters, you may think Portland’s establishments would forgo the effort and money needed to create killer patios. Lucky for us, they know the juice is worth the squeeze–Portland’s patios come alive with revellers almost every evening throughout the long, golden evenings of September. Like fiddlehead season, it’s fleeting, vanishing, something to be savored, and for that, it’s all the more fun, especially when you know where the unforgettable patios are hiding.

A windy but sun-drenched Friday evening in Portland sees us making the ritual evening bike ride downtown in search of hedonism and happy hours. Instead of peeling left from Congress Street and gliding into the familiar web of the Old Port, we veer right on Elm Street, our bikes picking up speed on the steep incline that leads us swerving into the parking lot of Bayside Bowl (pictured above) on Alder Street. My aversion to sharing footwear with strangers means I’ve never visited the bowling alley and bar joint (please keep your rental bowling shoes at a safe distance.) However, rumors of a game-changing rooftop bar are enough to entice our group to venture into West Bayside for the night. We pass through the bowling hall and hop into the elevator. At the top, a walkway stretches between solar panels to reach a wide deck. The rooftop space is bordered by long benches on one side and on the other, a 1962 Airstream, partially sunken into the decking, that does duty as a taco truck. The scene whisks you to another dimension. Out of sight of Maine’s recognizable waterfront, with the sunlight glancing off the Intermed high-rise, potted palm plants, and crisscrossing string lights, you might have stepped through a portal to downtown LA. The bar staff, all with aviators and bright, white smiles, could be Hollywood hopefuls. The stiff, salty breeze is the only reminder that we’re still in Vacationland.

We order cans of beer and congregate around an old whiskey barrel-table. Beside us, as the taco truck shifts into high gear with rapid service, three burly guys somehow prepare plates of exotic-sounding cactus tacos from the confines of the aluminum trailer. The rooftop bar has a capacity of 200, and the space is soon teeming. Dresses and long hair stream in the wind. A large portion of the crowd seems mostly intent on capturing the scene on their iPhones. The seemingly foreign surroundings and blazing sunset have us all in giddy high spirits.

As the night lengthens, we reluctantly come back down to earth and meander our way back to the familiar buzz of Monument Square. It’s fun to step out of Portland for a night, but it feels even better to get back.

Hit the Deck

The lucky bonus of patios? They frequently allow canine companions. Good news if you’re a dog owner. Great news if you desperately want a dog but can’t keep one. The sprawling patio/garden behind Silly’s, below, has plenty of space for patrons and their pups. We go at dusk and take a seat on the lowest of the three-tiered patio next to a family of harried-looking parents who are more than happy to let us fuss over their golden labrador as they attempt to corral three children.

“I remember when that little deck was Silly’s only outdoor space,” says my boyfriend, pointing to a tiny purple patio above the large garden area. Nowadays it’s over 1,000 square feet of decking and gravel patio.

True to the colorful, maximalist aesthetic of Silly’s, the outdoor area is overgrown, with vines tumbling over the pergolas and assorted floral ornaments. As with everything at this establishment–decor, menu choices, serving sizes–more is more. We stick to drinks–a couple of beers served in the kind of dented tin cups you’d expect to see camping–and spend an hour sipping beer and people/dog-watching as the sky deepens to night.

Hidden in Plain Sight

When you think of Commercial Street’s longtime players, J’s Oyster or Three Dollar Deweys surely come to mind. But what about Dry Dock Tavern? It’s been part of the Commercial Street landscape for over 30 years, and yet it seems to slide beneath the radar. I’d only ever visited once at the behest of some relatives visiting from abroad. We’re sitting on the Dry Dock patio! they texted. Where? I replied, disgruntled not to be the one choosing our destination. My sulk faded once I’d climbed the two flights of stairs and emerged onto the upper balcony to see the view over Custom House Wharf.

Hey, good enough for Carole King, who’s performed here, good enough for me.

With this in mind, I head down on Saturday night, some reluctant friends in tow. “Why not The Porthole instead?” they demand. The Porthole might be a great destination for dancing, but if you’re in the mood for spying, the Dry Dock affords a lofty vantage point to watch Porthole’s raucous patio, Boone’s has a buzzy dining deck, and, if you time it right, you have front-row seats to watch the Casablanca “booze cruise” pulling into port. With scenes like these, who needs Netflix? We settle in and place an order of drinks with the server. The tavern’s drinks list is straightforward and not particularly memorable, much like the food menu, but the sights and sounds of the waterfront bars and the lights flashing off the ocean keep us enraptured. From this hardscrabble Mt. Olympus we observe the marauding crowd below. Do you see that couple fighting? What about the ones flirting by the bar? Which of those frat boys is going to fall over first? Who knows? Next week, the roles will probably be reversed and you’ll be the fodder for some other spectators’ Saturday night gossip at the Dry Dock Tavern.

From the outside, there’s little to suggest Timber Steakhouse prizes anything in the way of outdoor space. But if you slip through the restaurant and out the bar door, you emerge onto a peaceful patio walled off from a parking garage by large sycamore trees and a fence of stacked whiskey barrels. The largest part of the patio is filled with wooden tables and parasols. There’s an intimate corner filled with loveseats. This hidden corner of the world is busy, and the clientele is sharper-dressed and a little older than those we’ve seen on other patios around town. We choose a spot in the wicker armchairs surrounding the fire pit, where we’re immediately presented with a dish of fiery wasabi peas. The drinks are on the expensive side–you’ll pay $15 for a cocktail–but the service and space are welcoming. Barbecue smoke drifts from the kitchen, turning the night air a hazy blue. On nights like these, you almost believe winter will never arrive. 

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@PrtlndAfterDark.

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