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Best of Portland, Maine | Editors' Choice Awards

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Best of Portland, Maine | Editors’ Choice Awards
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Portland is the largest city in Maine and its historic Old Port has never looked better. Here’s a list of some of our favorite things to do in Portland, Maine plus our picks for where to eat, shop, and stay in the area. Read on, then let us know your favorites!

Portland Head Light
Photo/Art by Stephen A. Clarke
Sunset at Portland Head Light

BEST THINGS TO DO IN PORTLAND, MAINE

BEST STUDIO TOUR
WINSLOW HOMER STUDIO, Prouts Neck
After a major restoration, the Portland Museum of Art has opened this American master’s studio to the public for small-group tours departing from the museum’s campus.

Museum location: 7 Congress Square, Portland. 207-775-6148; portlandmuseum.org

BEST BAY TOUR
LUCKY CATCH LOBSTER TOUR
Cruise Casco Bay aboard the Lucky Catch, and in addition to learning all about lobsters, participants can help haul, bait, and set traps and perhaps even catch dinner.

170 Commercial St. 207-761-0941; luckycatch.com

BEST SHOPPING ADVENTURE
RENY’S
Whether you’re shopping for souvenirs, school supplies, brand-name clothing, housewares, food, toys, or personal necessities, find them at Reny’s, a Maine-grown department store with wallet-friendly prices.

540 Congress St. 207-553-9061; renys.com

BEST HISTORIC-HOUSE MUSEUM
VICTORIA MANSION
Widely considered the most magnificently ornamented dwelling of its period remaining in the country, the mid-19th-century Victoria Mansion retains about 90 percent of designer Gustave Herter’s original furnishings. Jaw-droppers include a 6-by-25-foot stained-glass ceiling window, mind-boggling trompe l’oeil wall and ceiling flourishes, and the dizzying colors and patterns of the Turkish Smoking Room.

109 Danforth St. 207-772-4841; victoriamansion.org

BEST HISTORIC LIGHTHOUSE
PORTLAND HEAD LIGHT, Cape Elizabeth
In Fort Williams Park, just 4 miles from downtown Portland, Maine’s oldest lighthouse, commissioned by George Washington, guards the harbor. Visit the museum in the keeper’s house and picnic in the park.

1000 Shore Road. 207-799-2661; portlandheadlight.com

BEST EASY ISLAND WALK
MACKWORTH ISLAND TRAIL, Falmouth
Tethered to the mainland by a causeway, 100-acre Mackworth was deeded to the state by Governor Percival Baxter. Borrow a map from the gatehouse and follow the easy 1.5-mile perimeter trail for great views of Casco Bay. Kids love Baxter’s pet cemetery.

Andrews Ave. Causeway (off Route 1). 207-775-2411; trails.org/our-trails/mackworth-island-trail

BEST CASCO BAY SUNSET SAIL
PORTLAND SCHOONER COMPANY, Portland
Let daylight fade to night while cruising by lighthouses, forts, and islands on a two-hour sail aboard the historic windjammers Bagheera and Wendameen, both elegant ocean schooners built in East Boothbay.

Maine State Pier, 56 Commercial St. 207-766-2500; portlandschooner.com

Lucky Catch Cruises in Portland, Maine
Photo/Art by Aimee Seavey
Best Bay Tour | Lucky Catch Lobster Tour

BEST PLACES TO EAT IN PORTLAND, ME

BEST BREAKFAST:
HOT SUPPA
Scratch-made breakfast specialties—such as rave-worthy corned-beef hash, biscuits and sausage gravy, French-style omelets, and burritos—draw the faithful to this venerable brick Victorian in the city’s West End. Breakfasts: from $5.

703 Congress St. 207-871-5005; hotsuppa.com

BEST FINE DINING: 
BACK BAY GRILL
It’s not the trendiest restaurant in town, but white-tablecloth elegance combined with professional service makes Back Bay Grill a perennial favorite for a special evening. The nightly changing menu might include grilled filet mignon or lavender-marinated duck breast. Entrées: from $18.

65 Portland St. 207-772-8833; backbaygrill.com

BEST PATISSERIE: 
PORTLAND PATISSERIE & GRAND CAFE
Find Paris in Portland at Steve and Michelle Corry’s classic pâtisserie, serving pastries, cakes, and tarts, of course, but also crêpes, croissants, quiche, sandwiches, salads, and other light fare in a bright and airy, order-at-the-counter spot in Old Port. Baked goods: from $5.

46 Market St. 207-553-2555; portlandpatisserie.com

BEST ICE CREAM:
MOUNT DESERT ISLAND ICE CREAM
Oh my! Crazy rich, crazy good, crazy flavors. Try “Bay of Figs,” “Cinnamon 7 Layer,” lavender–white chocolate, blackstrap–banana, and other small batches of deliciousness. Ice cream: from $4.50.

51 Exchange St. 207-210-3432; mdiic.com

BEST FARM-TO-TABLE DINING
THE WELL AT JORDAN’S FARM, Cape Elizabeth
Gaze over the Spurwink River and Marsh while dining al fresco. Chef Jason Williams offers a four-item menu drawn from the farm’s bounty. Cash only.

21 Wells Road. 207-831-9350; jordansfarm.wix.com/thewell

BEST EVENING IN PARIS
PETITE JACQUELINE
Traditional French bistro fare–Nicoise salad, onion soup, cassoulet, dessert crêpes–plus daily cheese and charcuterie plates and a raw bar are the draws at this unpretentious Arts District restaurant.

190 State St. 207-553-7044; bistropj.com

BEST NEIGHBORHOOD RESTAURANT
CAIOLA’s
Chef/co-owner Abby Harmon elevates traditional comfort foods, drawing from local sources to create the daily Mediterranean-accented menu at this cozy West End restaurant.

58 Pine St. 207-772-1110; caiolas.com

Best of Portland, Maine Best Downtown Hotel | The Press Hotel

BEST PLACES TO STAY IN PORTLAND, ME

BEST B&B: 
THE DANFORTH INN
New owners have revitalized this 1823 Federal mansion, updating it with a mix of period and contemporary Asian-accented art and antiques. The inn’s justly acclaimed fine-dining restaurant serves authentic Southeast Asian cuisine. Rates: from $210.

163 Danforth St. 207-879-8755; danforthinn.com

BEST DOWNTOWN HOTEL:
THE PRESS HOTEL
The full-service Press Hotel’s décor takes its cue from its home in the former headquarters of the state’s largest newspaper. Fronting on Congress at the head of Exchange and Market streets, the location is ideal for exploring the city. The hotel’s Union restaurant earns raves. Rates: from $175.

119 Exchange St. 207-808-8800; thepresshotel.com

BEST ISLAND INN:
INN ON PEAKS
Walk off the ferry, and it’s just steps to the Inn on Peaks on Peaks Island, where each suite has a water view, a gas fireplace, a Jacuzzi, and a private deck for taking in sunset views of Portland’s skyline across the harbor. Rates: from $135.

33 Island Ave. 207-766-5100; innonpeaks.com

BEST BEACHFRONT FAMILY ESCAPE
INN BY THE SEA, Cape Elizabeth
A pool, boardwalk, onsite butterfly and bunny preserves, kids’ programs, lawn games, and a dog-friendly policy make family vacations easy at this seaside inn.

40 Bowery Beach Road. 800-888-4287; innbythesea.com

BEST BOUTIQUE HOTEL
PORTLAND HARBOR HOTEL
Built around a courtyard in an enviable Old Port location one block off the waterfront, the hotel pampers guests with handsome updated rooms and suites, a cozy lounge and restaurant, and concierge and spa services.

468 Fore St. 888-798-9090, 207-775-9090; portlandharborhotel.com

BEST ISLAND ESCAPE
CHEBEAGUE ISLAND INN, Chebeague Island
Only 15 minutes by ferry from the mainland but a world away, this meticulously renovated seaside inn blends simple charm with contemporary style and a topnotch dining room.

61 South Road. 207-846-5155; chebeagueinn.com

Selections originally appeared in print in 2013 and 2016.

Please Note: This information was accurate at the time of publication. When planning a trip, please confirm details by directly contacting any company or establishment you intend to visit.

Updated Monday, May 9th, 2016
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