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How to Spend 24 Hours in Portland, Maine

In the Old Port | © Phillip Capper/Flickr
In the Old Port | © Phillip Capper/Flickr
Picture of Christopher Crosby
Updated: 16 September 2017
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At its heart Portland is the urban imagination of a bucolic state better known for its rural pursuits. Residents here sail and paddle in the harbor; restaurants take that cue and bring in fresh fish and fowl; and the local music always seems to have a banjo.
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Resizing Portland into a single day is no easy feat. The city of locavore restaurants, indie arts scene, cobblestone streets and burgeoning beer choices yields spacious parks, harbor views and Victorian architecture to those who step out from the Old Port. Not that you need to: downtown Portland can happily occupy most of your day, whether it’s the arts district on Congress Street, rows of renowned restaurants set just back from the water, or a lively indie and folk music scene feet from it all. There’s a lot to do, so here are a few ways to organize your day.

Eastern Prom

Beloved, if not the biggest park in Portland, the Eastern Prom offers stunning vistas of Casco Bay. Start your day by parking the car along this stretch of green and walking along the hilltop, admiring sprawling Victorian mansions and watching ferries carrying year-round commuters to islands just offshore. The boisterous should rent a bike at CycleMania in East Bayside and complete the 3.6-mile Back Cove Trail. The Front Room will revitalize the famished with one of the city’s best breakfasts, while those merely peckish can grab a coffee and muffin at Hilltop Coffee Shop.

Old Port

Hop in the car and drive down Munjoy Hill, stopping briefly if time allows at the Portland Observatory, a signal tower built in 1807 and the only one of its type surviving in the US. Head for the Old Port—a loose grid of cobblestone streets teaming with indie shops and restaurants and bars. There are a number of tacky gift shops, so take some time to explore the area, stopping at shops like Portland Trading Company, which sells Maine-oriented clothing (including axes) and women’s designer Judith.

After witnessing what passes for a crowd in Maine, backtrack slightly to Middle Street for lunch at Eventide Oyster Co., which will shuck oysters caught that morning right before your eyes while you’re waiting for a lobster roll. If seafood isn’t your thing, across the street Duckfat serves European-style sandwiches and frittes fried in—you guessed it—duck fat with a selection of fancy mayos.

Winslow Homer “Weatherbeaten”
Winslow Homer “Weatherbeaten”

Artists, poets and fleas

Leave the car for a stroll up Congress Street, where you’ll see suits, panhandlers and artists headed to work. This is Portland’s creative hub, a stretch of galleries and gastropubs that fill with punters and the well-heeled come night fall. Head past Monument Square and the lovely Portland Public Library, lingering only slightly as you make your way to the historic home of poet Henry Wadsworth Longfellow, a three-story brick landmark and the oldest building on the peninsula. Step back into the daily life of the most famous author of the day and check out his garden, which likely helped feed the family. After, turn your attention to the Portland Museum of Art, which houses significant works from painters Winslow Homer, Jasper Johns, Degas, Renoir and local artist Andrew Wyeth.

Around the corner you can try your best to stay abreast Portland’s indie fashion scene at Flea-For-All (only open Friday through Sunday), which houses vendors featuring Maine artisans.

Seafood Paella at Local 188
©Courtesy of Local 188.
Seafood Paella at Local 188

Farm to Table

Hungry yet? You have two choices for dinner, both showcasing Maine’s best farm-to-table restaurants. Around the corner is Local 188, a veritable old man (it opened in 1999) of Portland’s hectic dining scene, an open-air tapas bar with a Maine spin. Local art lines the walls, and more than 100 wine bottles are stocked in the cellar. Ask for the special—made from produce the chefs bought that day—or dig into the seafood paella, sufficient for two.

If your legs can still master the pavement, head to Fore Street, regularly in the running for accolades, which features food gathered, foraged, farmed and fished in an intimate open-air kitchen. Get the mussels, which showcase the best of the state’s coast. If you’re spoiled for choice let the experienced servers take control of the main course.

Fore Street Kitchen
© Courtesy of Fore Street
Fore Street Kitchen

Fermented follies

No trip to Maine would be complete without trying the hometown brews, so head to Novare Res Bier Care, one of the country’s best bars for connoisseurs. Grab a spot at one of the long tables and wait for a server, who is likely a brewer, is planning a brewery, or has worked at the bar for years. If dozens of tap handles and a voluminous, 400-line bottle list with aged, rare and barreled suds present a dilemma, take your server’s advice—they’ll let you sample—or simply choose from the local selection (they also have wine). If cocktails are more your thing, The Portland Hunt & Alpine Club has a small, modern bar featuring small plates and creative cocktails inspired by Scandinavia.

Lights out

Head back to the hotel and sleep. You’ve earned it. And if the morning allows, breakfast at the comfortable Becky’s Diner, a Portland institution that’s made its name refueling night prowlers, will fortify you for the trek home.

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