Greater Portland & Casco Bay

Portland, Maine’s largest city, with a population of about 65,000, is considered the commercial and cultural center for Southern Maine. With its many fine restaurants, galleries, entertainment and harbor cruises, there are few dull moments in the city that was first developed as a seaport in the 1700s.

Henry Wadsworth Longfellow wouldn’t recognize his hometown these days, although high-rise office buildings blend nicely with historic landmarks and Victorian era architecture. The poet spent his childhood in Portland’s first brick structure that has been maintained as a museum by the Center for Maine History.

The Portland Museum of Art features many American artists such as Winslow Homer, Edward Hopper, Andrew and N.C. Wyeth, Rockwell Kent, as well as popular European artists like Degas, Renoir, Picasso, Matisse and Prendergast.

In 1776, after the Revolutionary War, Portland was established as a commercial port and began rapid growth as a shipping center. In 1820, Portland became the first capital of Maine, but that distinction was transferred to Augusta in 1832. A huge fire that started at a Fourth of July celebration in 1866, destroyed most of the public buildings, half of the churches and hundreds of houses in Portland. The city was then rebuilt primarily with brick and in the Victorian style.

The Old Port section of downtown Portland is filled with boutiques, galleries and wonderful restaurants. Just across town is the Portland Public Market with, an indoor, airy marketplace offering the freshest of local foods and other specialty items. A few minutes away, in South Portland, the Maine Mall has more than 140 stores.

In Portland Harbor is a retired car ferry that has been turned into a floating restaurant. DiMillo’s welcomes groups in their restaurant where all seats have a water view.

Portland is the second-busiest oil port on the East Coast and a growing port-of-call for cruise ships.

Amtrak now runs four trains per day between Boston’s North Station and Portland, Maine. Consider taking The Downeaster as part of your next tour.

If you’re interested in gaming, a visit to Scarborough Downs may be just the ticket. It is the largest harness race track in the state and one of the largest in New England. Visitors can play the ponies or relax in the Downs Club Restaurant and watch the races right from their tables.

You’ve heard of chocolate mousse, but have you ever seen a chocolate moose? Len Libby’s Handmade Candies in Scarborough and a 1,700-pound life-size chocolate moose named Lenny. Come watch a video about how Lenny was made and pick up some delicious chocolates to take home.

And speaking of large objects, the DeLorme Map Store in Yarmouth has Eartha the largest rotating globe in the world. Housed in a three-story glass atrium, it took two years to build.

A bit farther north is the shopping mecca of Freeport, home to L.L. Bean. L.L. Bean’s flagship store on Main Street is open 24 hours a day, seven days a week, including holidays. In addition to L.L. Bean, the village of Freeport has more than 100 retail stores and outlets.

A few miles south of Portland, in Cape Elizabeth, visit the Portland Head Light. Get an up-close-and-personal look at this lighthouse that was originally commissioned by George Washington in 1791. There is an exceptional lighthouse museum and remains of old Fort Williams that you can explore.