Portland Maine for First-Timers

Photo by Kim Grant

Your best bets for day trips and weekend visits

Save to my Account

History is kept alive in the Greater Portland Region, where historical homes and maritime museums chronicle the emergence of the area from a trading and fishing settlement into one of the nation’s most active seaports. Long known for lobster and seafood, Portland’s contemporary cuisine has created a buzz with its award-winning chefs and burgeoning farm-to-table movement. In the city’s downtown, a live music scene thrives, where the Old Port provides the nightlife with music, dancing and waterfront pubs, as well as a chance to visit the state’s famed microbreweries and sample fine ales brewed on site.

Food and Drink Tours

Foodies will no doubt wish to explore the culinary offerings of many of the city’s renowned eateries, too numerous to list.  On a tasty Maine Foodie Tour, you will  interact with culinary artists and taste their creations, learn about Portland’s culinary history and current scene with fun-loving guides on a walking tour about town. For wine and food pairing education at its best, contact Wine Wise for an enlightening wine education experience. Taste delicious wines with paired fresh fare at a series of great local restaurants and on a 74-foot sailboat in Casco Bay while taking in scenic views of Maine lighthouses, waterways and islands. Don’t forget about seeing all the local breweries in Portland. The Maine Brew Bus is a tour company dedicated to promoting these local breweries by offering a unique and personal beer tour experience.

History, Art and Architecture

History buffs will want to visit the Wadsworth-Longfellow House, 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 art museum 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, the 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.

Go Play Outside

Outdoor enthusiasts will be delighted with options. For the cyclist of any level, try Summer Feet Cycling Adventures for a leisurely ride to several area lighthouses. Water lovers can take a guided tour of Casco Bay or rent kayaks and paddle boards from Portland Paddle, Maine Island Kayak or L.L. Bean Outdoor Discovery. True Maine Tours and Forest City Adventure Tours specialize in private and custom tours designed to fit your interests and activity level.

Maritime Landmarks

Nautical buffs should head straight to Munjoy Hill to see the Portland Observatory, built in 1807, the last wooden signal tower in North America, and one of the only structures to survive the Great Fire of 1866. Head up the hill to Fort Allen Park to soak in the harbor’s many fortifications. Across the harbor in South Portland, Bug Light Park, located on the site of one of the former World War II shipyards that gave the world Rosie the Riveter, memorializes the Liberty Ships with a monumental bow seemingly ready to launch.

Regardless of personal interests, everyone’s time frame seems to include Portland Head Light and its museum. Commissioned by President George Washington, Portland Harbor’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 the 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.

This itinerary is compliments of the Greater Portland Convention + Visitors Bureau.

At A Glance

Price Range:

Comments, Tips & Hints


You need to login to favorite a post.

Need to sign up? Create an account here.

Forgot your password? Reset your password here.