Portland, Maine Holidays

With its heady mixture of artistic and outdoor adventures, our region is stylish and sophisticated, yet remains genuine and unpretentious, a place where grey flannel and plaid flannel coexist companionably. And underlying the latest tech, fashion, and culinary scene is a deep sense of continuity. We invite you to experience the character of a region that blends the present with a very special past.

Lighthouses and lobsters and surf crashing on the rocky shore - these are the enduring images that come to mind when people think of the classic Maine seacoast. Here, in Greater Portland, you’ll absolutely experience the quintessential Maine coast, as well as an urban sophistication that’s creating quite a stir. TripAdvisor named Portland one of the Top 10 Destinations, based on positive feedback and interest shown by their well-travelled community.

History buffs will want to visit Henry Wadsworth Longfellow’s childhood home and see the room where he penned "Into each life some rain must fall”. Next door, the Maine Historical Society houses permanent collections and changing exhibitions. You’ll also want to tour the West End’s opulent Victoria Mansion and Colonial-era Tate House in the historic Stroudwater district.

Patrons of the arts will want to see the Arts District along Congress Street, anchored by the Portland Museum of Art in Congress Square. The Museum of Art began in the McLellan-Sweat house, currently a museum wing glorifying the architectural grandeur of the Spring Street mansion. The museum entrance was moved to Free Street in 1986 when the Payson Wing opened. Designed by the I. M. Pei firm, architectural genius behind Paris’s Louvre expansion, the contemporary addition brought Joan Whitney Payson’s vision (that helped make New York’s Metropolitan Museum of Art a world-class destination) to Portland.

Along Congress Street, galleries surround the Maine College of Art that features talented artists of tomorrow and houses the Institute of Contemporary Art displaying the gifted artists of today.

Regardless of personal interests, everyone’s time frame seems to include Portland Head Light and its museum. Commissioned by President George Washington, Portland Harbour’s 1791 sentry is the United States’ first lighthouse and purported to be the most photographed in the world.

Surrounded by crashing waves, a picturesque cliff walk meanders along the edge of Fort Williams Park leading to markers of Longfellow’s visits, base history, and famed shipwreck of the Annie C. Maguire. The white tower glows against the sparkling blues of ocean and sky, but experiencing the historic light during inclement weather forces anyone to appreciate the necessity for these elegant icons