1. Where to Stay
The Portland Regency Hotel & Spa (from $149), in a beautiful red-brick armory in the heart of the hip Old Port shopping district, has 95 rooms decorated in traditional dark wood and brocade and updated with flat-screen TVs and Wi-Fi.
An Italianate mansion on Portland’s landmark-packed west end, the boutique Pomegranate Inn(from $140) has eight rooms with unique hand-painted floral wall murals (the hydrangeas in room six are especially stunning), original artwork and sculpture, and fine linens.
The Harraseeket Inn in Freeport, only a twenty-minute drive from downtown Portland, has 84 elegant, countrified rooms, toile bedding, and fireplaces. Book the spacious Thomas Moser Room ($350) to be surrounded by the Maine designer’s sleek, Shaker-influenced furniture as well as the requisite plasma-screen TV and Bose stereo.
2. Where to Eat
Former French Laundry chef Rob Evans of Hugo’s was nominated Best Chef in the Northeast by the James Beard Foundation in 2008 for innovative New England dishes like the Casco Bay cod in a chowder broth topped with celery-root brandade. Evans also cooks at Duck Fat, a hole-in-the-wall where you can dunk light and crispy duck-fat fries into Thai-chili or curry-mayo sauce.
Napa expat Steve Corry, named Best New Chef in 2007 by Food & Wine Magazine, prepares a popular and sophisticated Sunday-only brunch at Five-Fifty-Five. Order the sweet and savory “American toast” of sourdough bread with Maine blueberry-ginger jam and a pistachio crust. Doors open at 10:30 a.m.; delay and find a line.
Sam Hayward’s Fore Street started Portland’s foodie influx in the mid-nineties, and the seafood and meat dishes grilled over its soapstone and brick hearth are still some of the city’s best culinary offerings. Menu changes daily, but you’ll always find wood-oven-roasted mussels, turnspit-roasted pork loin and chicken, and grilled marinated hanger steak. On your way out, pick up breakfast in the Standard Baking Company downstairs (75 Commercial St.; 207-773-2112), which uses organic flour to make rich sticky buns and ethereal croissants.
Masa Miyake’s (formerly of Inagiku at the Waldorf-Astoria) eighteen-month-old Food Factory Miyake is a 25-seat Japanese restaurant (129 Spring St.; 207-871-9170) specializing in expertly crafted sushi and oversize shrimp shumai. The chef harvests his own clams at nearby Orchard Beach. Bring your own booze and drink it without a corkage fee.
3. What to Do
Discover Portland’s burgeoning design scene, starting with the cotton and wool rugs (also sold at Design Within Reach), modish tableware, handbags, and furniture by Sherwood Hamill at Angela Adams (273 Congress St.; 800-255-9454). A few blocks away, Field peddles furniture and the interior paint jobs customized for your home. Next door at More, peruse whimsical letterpress and photography by Maria Alexandra Vettese and seventies-inspired works by artist and graphic designer Christopher David Ryan.
The nonprofit alternative-arts venue Space anchors Portland’s underground arts scene with gallery shows, indie-rock concerts, and art-film screenings. New York photographer and Paper and Vice contributor Tod Seelie shows there through November 19.
Old Portland has several specialty stores worth visiting. Appraiser Don Lindgren and his wife, a former pastry chef, run the culinary bookstore Rabelais. Rogues Gallery sells edgy vintage T-shirts with old-timey typefaces, skulls, and nautical themes. Around the corner, sniff hand mixes, organic perfume oils, and sprays at 2 Note Botanical Perfumery. Sonata, a blend of French lavender, sandalwood, and black pepper, is the most intriguingly layered.
4. Insider’s Tip
Plan your trip around the first weekend of the month when the free, self-guided First Friday Art Walk takes place from 5 to 8 p.m. For a map and information about the more than 60 participating artist studios and galleries, visit the website.
5. Oddball Day
Travel about an hour northeast of Portland to visit Phippsburg, home of the secluded Seawall Beach. Follow a two-mile trail through woods and marshland within the 600-acre Bates-Morse Mountain conservation area. The mile-long beach is moody and deserted in autumn; bring along a flask and watch the fog creep over the water. After the excursion, head to nearby Bath, off Route 1, a pretty, old shipping city for a bite to eat. Solo Bistro Bistro serves dishes like pan-seared scallops and spring rolls with duck rillettes and sweet potato in an airy, modern dining room.
Design*Sponge breaks down Portland’s design shops and galleries by neighborhood.
Visit Slow Food Portland’s website for information about CSA fairs, farmer’s markets, and culinary author readings.
Organize your own walking tour of historic buildings on Greater Portland Landmarks’ Self-Guided Tours page.