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Portland, Maine: The Jewel By The Sea

Portland, the largest city in Maine, is on a small peninsula that juts into Casco Bay. It draws visitors for its seaside setting, succulent seafood, picturesque lighthouses, flourishing performing and visual arts scene, and exhilarating outdoor adventures.

The scents, sounds, sights and savories of a major seaport city are all found in a compact and charming area within a few blocks of the waterfront. This downtown area is a fusion of the cultural diversity, attractions, and nightlife of a major metropolitan area with the charm of a small town and the scent of salt air.

You can stroll past Victorian architecture on tree-lined cobblestone streets or dine or browse galleries and boutiques in Old Port’s restored former warehouses.

Enjoy a toasted lobster roll with a local brew on the working waterfront while watching fishermen unloading their catch.

Harbor Fish Market, Portland, Maine
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Harbor Fish Market, Portland, Maine

Tour museums and historic homes, go deep sea fishing or whale watching, or pick up some gourmet foods in the Public Market for an island excursion. Evenings, enjoy the symphony, theater, a sunset cruise, or live local music by night.

fishing boat, Casco Bay, Portland, Maine
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fishing boat, Casco Bay, Portland, Maine

When you explore the bay and islands on a tour boat or ferry, you will pass fishermen and fishing villages and reel in a little history along the way. Back on land, enjoy a scenic stroll along this pedestrian-friendly city’s Eastern or Western Promenades.

U.S. News and World Reports named Portland one of the best places to retire, and the University of Southern Maine’s Osher Lifelong Learning Institute offers popular low-cost courses for senior citizens.

A Little History

The protected harbor and easy access to the Atlantic made this an ideal 17th century British fishing and trading settlement. The Pine Tree State’s vast supply of inland timber for ship building and masts provided the raw material for what became a flourishing industry. The prosperity from shipping and trade created a new wealthy class and grand homes, some of which may be toured today.

Portland’s city seal, a phoenix rising from the ashes, and motto Resurgam, I will rise again, represent its survival after devastating fires, disasters, and economic reversals. In 1675, townspeople fled to Massachusetts when what was then known as Falmouth was completely destroyed by Indian raids in the King Philip’s War. A century later, during the Revolutionary War, the city was again destroyed when citizens refused to surrender to the British.

The economy was devastated when the Embargo Act of 1807 banned trade with the English and by the War of 1812. It did not recover until worldwide trade resumed in 1820.

When Maine became a state that same year, Portland was named its first capital. In 1823, the first steamships began passenger service from Boston, and three decades later, Commercial Street opened, which expanded the waterfront and connected rail and water transportation.

The Great Fire of July 4, 1866, the most devastating fire in our nation, began on Commercial Street during the Independence Day celebration—the first since the end of the Civil War. (The Great Chicago Fire was five years later.) Much of the Victorian charm of today’s city is a result of the rebuilding with red brick.

Victoria Mansion, Portland, Maine
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Victoria Mansion, Portland, Maine

A preservation movement began in the 1960s, and by the 1970s artists’ galleries and studios began popping up in the Old Port. In 2003 the National Trust for Historic Preservation named Portland one of America’s Dozen Distinctive Destinations.

Arts and Architecture

From classical to cutting-edge, Portland’s professional performing arts organizations present an exciting array of dance, theatre and musical events. A top-notch symphony, opera, and two theaters create a vibrant cultural hub, and in the summer, the eclectic local music scene moves outdoors.

A self-guided First Friday Art Walk through the Arts District is offered August through December. The hub of the Arts District is the Portland Museum of Art, Maine’s largest public art institution.

The Portland Museum of Art showcases three centuries of fine and decorative art in three architecturally unique buildings built between 1800 and 1983. The post-Modern Charles Shipman Payson wing (1979-83) was designed by Henry N. Cobb of I.M. Pei and named for the donor of the Winslow Homer paintings and watercolors. The Beaux-Arts Sweat Memorial Galleries (1911) were named for the family who gave the McLellan House, its third structure, to the museum.

McLellan-Sweat House, Portland, Maine
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McLellan-Sweat House, Portland, Maine

The McLellan House (1801) was built in the booming economy following the Revolutionary War for Portland’s most prominent citizen. Major Hugh McLellan was the founder of Maine’s first bank and insurance company and owner of Maine’s largest fleet. This luxurious Federal era mansion with Palladian windows and a flying staircase was built for the grand sum of $20,000 in the fashionable neoclassical style inspired by excavations of Pompeii and Herculaneum.

It was sold in 1817 during the economic downturn to the Clapp family for $4050, and again in 1880 to its final residents, U.S. Congressman and Colonel Lorenzo de Medici Sweat and his wife, writer and preservationist Margaret Jane Mussey Sweat, who donated the property to what is now the Portland Museum of Art.

Wadsworth-Longfellow House, Portland, Maine
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Wadsworth-Longfellow House, Portland, Maine

Portland was the childhood home of Henry Wadsworth Longfellow, who called it his “Jewel by the Sea”. He lived on Congress Street in the city’s first all brick home, built by his grandfather in 1785-1786. The Wadsworth-Longfellow House, with its three generations of family furnishings, was willed to the Maine Historical Society by Henry’s younger sister and is the oldest remaining residence in the city.

Victoria Mansion, Portland, Maine
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Victoria Mansion, Portland, Maine

The Morse-Libby House, an Italianate villa later named Victoria Mansion, was built as a stylish summer home for Ruggles Sylvester Morse, who amassed a fortune in New Orleans before the Civil War in the luxury hotel business. The brownstone’s magnificent interior is the earliest known Gustave Herter commission and the only one still intact. Morse incorporated amenities usually found only in fine hotels, including a master bedroom with adjoining bathroom and a Turkish smoking room. The home is one of the finest examples of both Victorian and Italian Villa design in America. It was subsequently sold to Joseph Libby, owner of a prominent Portland department store.

Also of architectural interest are Portland City Hall (1909-1912), built in a Second Renaissance Revival design, and the granite U.S. Customs House (1868-1871), with painted and gilded ceilings, finely crafted woodwork, and marble floors.

The Eastern Promenade, the last work of Frederick Law Olmstead, runs through Munjoy Hill, site of the Portland Observatory, the last remaining maritime signal tower in the United States. Grand Victorian homes were built for the view– 175 feet above sea level– from the Western Promenade neighborhood.

Casco Bay

A visit to this city by the sea is not complete without getting out into Casco Bay and the Calendar Islands—so named because it is said there is one for every day of the year.

Unique scenic tours are also offered by Casco Bay Lines, one of the oldest ferry systems in the world. A century and a half ago they ran summer visitors on wooden steamers with coal-fired engines to island cottages and hotels. With theaters and amusement parks, Peaks Island became known as the Coney Island of Maine. Summer theater included productions by George M. Cohan and performers included the Barrymores, who still maintain a family home in Casco Bay. Jean Stapleton, and Martin Landau made their stage debuts here.

Casco Bay Lines now operates a year-round commuter and delivery service. Pack a picnic or bring along a bicycle for exploring an island. See the bay come alive with sea birds, seals, lobstermen and fishing boats setting out for the day with the 2 1/2 hour when ferry service begins the day with its 5:45 am Sunrise on the Bay departure. Join other passengers on the morning or afternoon 3-hour Mailboat Run, the longest operating service of its kind, or sit back and enjoy the views on the 5:45 pm. Sunset Run. A variety of seasonal cruises are also offered.

For the most comprehensive Portland tour, Portland Discovery, a locally owned and operated company, offers entertaining and informative narrated bay cruises and city trolley tours. The Land & Sea Tour includes the inner harbor Lighthouse Lover’s Cruise past Maine’s oldest and best-known lighthouses and other landmarks combined with a trolley tour of Portland’s history and architecture. Their Eagle Island Cruise takes the back channel past quaint fishing villages for a stop at the island where Arctic explorer Admiral Robert E. Peary’s former summer estate of may be toured.

You can also opt for a dusk departure with the Sunset Lighthouse Cruise. Tours depart from the Maine State Pier, easily identified by the 450’ long Whale Wall by Robert Wyland.

Dining

Portland’s restaurant options range from pub grub to haute cuisine. It was named the “Foodiest Small Town in America” by Bon Appetit in 2009. Here are a few favorites.

You can start your day with a hearty breakfast with fishermen at the family-run Becky’s on Hobson’s Wharf. It’s diner comfort food at its best, like the light and sweet fried clam plate or the grilled crab sandwich that oozes with Swiss cheese.

The city’s 2010 winner for Best Lobster Roll is Portland Lobster Company on Commercial Street. Large chunks of lobster glistening with melted butter are served on a grilled and buttered roll with fries and cole slaw. Dine in or outdoors on the waterfront.

appetizer, Corner Room, Portland, Maine
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appetizer, Corner Room, Portland, Maine

If your taste runs more to dining on crab bisque with rouille, an arugula and goat cheese salad, and grilled hangar steak with Andouille sausage-cheddar grits and onion rings, head for the Grill Room. Chef Harding Lee Smith owns all the Rooms restaurants–serving wood-fired meats at The Grill Room, new American comfort food at the Front Room, and Italian-inspired affordable and casual dining at the lively Corner Room, which opened in 2009 and was voted a Best of Portland 2010. Favorites there are the Cioppino, an Italian seafood stew with crab, mussels, clams, and shrimp and strawberry sorbet to.

You can savor the best at Maine’s premier food experience, Harvest on the Harbor in October. Creative celebrity chefs offer savory samplings of the flavors of Maine, using fresh local ingredients from area farmers and fishermen. There will live music, a Grand Tasting on the Harbor, cooking demonstrations, food artisans, and Maine-made products. Attendees must be 21 or over. Ticket prices vary by event and tend to sell out early. Call (888)-795-4966 for more information.

Accommodations

Holiday Inn By The Bay, Spring Street, just up the hill from Becky’s and across from the McLellan-Sweat House, offers free parking and a variety of specials. It’s also an easy walk to the Arts District, Old Port and waterfront.

Trip Planner

Check with the Convention and Visitors Bureau of Greater Portland for discount coupons and information on attractions, festivals, and special events.

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