A population of about 67,000 has earned it the title of Maine's largest city, but at 21 walkable square miles, Portland feels delightfully town-like.
With terrific, forward-thinking restaurants, stylish independent boutiques, a vibrant arts and culture scene, and cobblestoned streets, Portland is the perfect New England destination for a long weekend. The area is particularly magical in summer when the weather's clear and dry, and when delicious eats in the Old Port abound.
The only problem? You'll never want to leave.
There are lots of old-timey B&Bs in Portland. Mercury Inn, named for the Roman god of travelers, is not one of them. The chic, urbane little gem fills exactly the niche Tim Karu and Jacob Krueger hoped it would when they set about modernizing a historic Victorian inn in the leafy, residential Parkside neighborhood a few years ago. Sourcing from local makers, vendors, and vintage stores, the husband-and-husband duo dressed the common spaces and seven guest rooms with low-slung furnishings, high-impact art, and multicolored textiles. It's as if Design Within Reach and Anthropologie had the coolest kid, ever—one who happens to love gray and yellow, and one who's committed to using LEDs, non-toxic paints, and compost bins. Mercury's house-made breakfast, which takes over the elegant front room of the parlor floor, changes daily based on what's available at Karu and Krueger's favorite farms and purveyors.
273 State Street, mercuryinn.com
Print may be dead in some places, but the history of newspapers is still very much alive at the 110-room Press Hotel, which occupies the brick-and-stone building that was home to the Portland Press Herald until 2010 when the paper moved offices. Today, the hotel finds clever ways to play up its storied past. Inkwell, the lobby bar, calls its happy hour "Off the Record"; typographical murals spell out Press Herald headlines of yore; and leather desk chairs are embroidered with "The quick brown fox jumps over the lazy dog," a phrase once used to test typewriters because it has every letter in the alphabet. Beyond these throwbacks, the Press Hotel is stocked with plenty of contemporary creature comforts, including a gallery featuring works by local artists and marble baths with C.O. Bigelow toiletries.
119 Exchange Street, thepresshotel.com
Fresh on the heels of a renovation, the Danforth Inn is ready to strut its stuff. When the nine-room B&B changed hands in 2014, its new owners added a much-raved-about Southeast Asian restaurant, yet still managed to preserve the splendor and grace of the 1823 house. Guest rooms are all plushly decorated and named for local neighborhoods and attractions; Casco Bay is bedecked with olives and plums, Eastern Promenade is bright white with gray accents. Public spaces recall the history of the building: relax in the wood-paneled billiard room, which served as a hideout during Prohibition, or soak in views of the harbor from the benches lining the original rooftop cupola.
163 Danforth Street, danforthinn.com
Eventide Oyster Co.
It's likely you'll have to wait for a table—or, even better, a seat at the concrete oyster bar—at Andrew Taylor and Mike Wiley's hugely popular seafood spot. No worries, though: just use the downtime to slurp back a couple of oyster shooters, dig into the nicely curated list of local and international beers, and mull over your order. Thankfully, it's very hard to make the wrong choice at Eventide, where the lobster roll—a sweet steamed bun stuffed with lobster meat that's been tossed in brown butter, lemon juice and salt—the tangy crudos, and the local oysters (accompanied by creative alternatives to mignonette, including Tabasco ice and kimchi ice) are all top-notch. And should you find yourself eating at Eventide more than once on your trip to Portland—well, you certainly wouldn't be the first to do so.
86 Middle Street, eventideoysterco.com
The Federal-style brick building at the corner of Fore and Central streets has worn many hats over the course of its 200-plus-year history: it's been various shops (wine, burlap bags, blacksmith supplies) and once served as a storage facility for the East India Trading Company. In 2014, the space became a restaurant for the very first time, with husband-and-wife team Chris and Paige Gould at the helm. He's the chef, she's the GM, and their menu, driven by seasonality and local produce, changes daily. That said, the outstanding crudos (like scallop with tarragon, pistachio, lemon, and bottarga), inventive veggies (like fried cauliflower with ras el hanout, a Moroccan spice blend), and pristinely prepared proteins are all a constant. And whatever you do, don't overlook the bread and butter—crusty sourdough with fresh butter and lemon sabayon. Yes, it costs $7, but it'll rock your world.
414 Fore Street, central-provisions.com
J's, the no-frills seafood joint on a pier off Commercial Street, is diner-like and dark, with a large, U-shaped wooden bar taking up most of the interior space. It's the kind of place where ordering a well Martini in the middle of the day feels like the right call. (In 1977, the year J's opened, craft cocktails hadn't yet become trendy.) While there are plenty of places in town for lobster rolls, J's version does right by minimalists: it's a hot dog bun with a heaping pile of lobster meat. That's it. Even the mayo comes in an individual-size packet on the side. Be sure to order a bucket of steamers, as well—if you're unsure how to eat them, one of the hilarious straight-shooters behind the bar will gaily lend a hand.
5 Portland Pier, jsoysterportland.com
If you're looking for a healthy meal, you're not going to get it at Duckfat. But if you're looking for one last hurrah—say, an indulgent snack before you pack up and head to the airport—there's really no place better. As its name implies, Duckfat specializes in cooking things in duck fat; best among them, the Belgian-style fries, which come with standard (Heinz, malt vinegar) or more inventive (truffle ketchup, garlic mayo) condiments. Wash it down with a milkshake made from local gelato, like the to-die-for wild Maine blueberry.
43 Middle Street, duckfat.com
THINGS TO DO
Portland Museum of Art
The Winslow Homer Studio
The Portland Museum of Art is small and mighty; it's packed with many wonderful pieces, but it won't consume an entire day. Recent exhibitions have highlighted Georges Braque; Georgia O'Keeffe, Florine Stettheimer, and other women modernists; and Henri Matisse. The museum's permanent collection is studded with works by Warhol, Monet, and Winslow Homer, arguably the most famous artist to come from Maine. In spring, summer, and fall, PMA offers round-trip excursions to and from Homer's former home and studio, located 12 miles north on the peninsula of Prouts Neck.
7 Congress Square, portlandmuseum.org
Peaks Island is one of the more than 200 islands in Casco Bay, and the simple act of getting there will check another item off any good Portland bucket list; that is, taking a boat ride. One 20-minute ferry later, Peaks is best explored on foot or by bike—there's a rental shop right near the dock. Toodle around for an hour and whiz past charming Shingle-style cottages; then, be sure to swing by the Umbrella Cover Museum—a shoebox-size storefront filled with the world's largest collection of umbrella sleeves, according to Guinness World Records—before making the return trip.
Portland Sea Dogs
At Hadlock Field, a quick cab ride from downtown, aspiring Boston Red Sox players hone their chops as Portland Sea Dogs. It's worth catching a game here if you're visiting Portland during the season, if only for the sheer sense of Americana: Tickets are cheap and easy to come by; dining options are proudly non-gourmet; the mascot keeps the crowd entertained; and local kids participate in inter-inning competitions and games, right on the field. There's even a microbrew stand by the first base line—it may be Double-A baseball, but this is still Portland.
271 Park Avenue, milb.com
Aside from a Lululemon, the Old Port remains nearly free of retail chains, making it easy to support Portland's myriad independent businesses. Standouts include the Salt Cellar, with dozens of finishing and cooking salts from across the globe; K Colette, with so many beautifully arranged soaps, pottery, linens, and other trinkets that you'll wish you had more wedding presents to buy; Portland Dry Goods, a hipper, more outdoorsy version of J.Crew; Furniturea, an Arts District shop with modern, Maine-made furniture and decor; and Vena's Fizz House, with barware, mixology books, tonics, and syrups, plus a bar serving up fizzes and other post-shopping cocktails.
Portland Hunt + Alpine Club
With sparse decor and a wall of windows overlooking Market Street, Portland Hunt + Alpine Club practically begs you to Instagram your drink. And whatever you order—whether it's a classic Old Fashioned or something from the "Adventurous" category—will be beautiful enough to brag about. That's because husband-and-wife owners Andrew and Briana Volk are meticulous through and through, right down to the folklorish Irish toast ("And if you're going to drink, drink with me") printed inside the leather-bound menu. There's food, too, including a house smörgåsbord and other Scandinavian fares. But if you're just looking for a snack, go for the house popcorn, which is dusted with green chile powder, butter, and parmesan.
75 Market Street, huntandalpineclub.com
Portland consistently reigns supreme on lists of destinations for beer lovers, and it's not hard to see why. According to Forbes, the city has the highest rate of microbreweries per capita of any city in the country—including its brewery-rich sibling in Oregon. In the East End alone, small-batch makers like Rising Tide and Oxbow—plus a cluster of food trucks—promise to fill a weekend afternoon with leisurely tastings and tours.
With exposed brick, thick wood beams, and an open kitchen, Fore Street, the patriarch of farm-to-table dining in Maine, is rustic glamor at its best. And even if you don't leave time for a full meal here—a revelatory experience, if you can swing it—at least carve out time to grab a drink in the spacious, elegant bar, which offers one of Portland's best wine lists. Kick back and watch Fore Street's servers and cooks man the massive hearth, grills, and rotisserie in the dining room just beyond. Who knows—you might just find yourself putting in your name for a table.
288 Fore Street, forestreet.biz
This story originally appeared on Townandcountrymag.com.
* Minor edits have been made by the Townandcountry.ph editors.