The Great Outdoors: A winter walk through history on Portland's Congress Street

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PORTLAND — In the interest of being efficient over this busy time of year we recently combined a walk with shopping duties and in-town appointments.

We decided a three-hour stroll down Congress Street was in order, fortified by many stops for muffins, hot chocolate, and various other munchies along the way.

We parked at the parking area adjacent to the East End Beach, scrambled up over the frozen tundra of the Eastern Prom to the George Cleaves monument at the head of Congress Street and headed from there two miles down to Longfellow Square on State Street.

It became readily apparent that as many times as we had driven Congress Street over the years – hundreds of times – we really had uncovered only the tip of the iceberg. Walking allowed us to see and experience so much more.

We immediately connected with Portland’s Freedom Trail near the Portland Observatory. The Freedom Trail was dedicated in 2007 to recognize the city’s significant role in the Underground Railroad. Sixteen interpretive markers dot the city landscape, many along Congress Street. Near Colucci’s Market the barber shop of Charles Eastman once stood. Barber shops were key outposts for freedom seekers, places where hair and beards were altered, wigs created, and information passed.

Many Portland abolitionists are buried in the nine-acre Eastern Cemetery, the city’s oldest cemetery. A few yards beyond the cemetery, at the intersection of India and Congress, a marker notes the site of the Thomas house, a key station house of the Underground Railroad. The home was destroyed by the July 4 fire of 1866. Five years before the Great Chicago Fire, it was the most destructive urban fire in American history to that point, and left 10,000 people homeless.

Set back from Congress Street at the head of India Street sits the Etz Chaim Synagogue, the only immigrant-era European-style synagogue remaining in Maine. In the early 1900s Portland was often called the “Jerusalem of the North,” due to a large influx of Jewish migrants.

We hardly knew where to look next, or what side of Congress Street to walk on. There was so much we had never realized was here. We walked through a small park near the Federal Courthouse complex. On the southwestern end of the park stood the remains of a millstone that came from a windmill operating on a nearby bluff in 1745.

Music lovers scurried across Congress Street for the matinee performance of “The Magic of Christmas” by the Portland Symphony Orchestra at Merrill Auditorium. We stepped into the lobby of City Hall to look around. A circular marble staircase led up to the second floor. A perfect pitch and rise made us feel as if we were floating up the stairs – it was effortless. The firm that designed City Hall in 1912, Carrere and Hastings, also designed New York Public Library.

Next door the First Parish Church Memorial Garden welcomed us in for a brief rest on the stone benches. Here in the old meetinghouse the state Constitution was drafted in October 1819. Thomas Jefferson, third president and founder of the University of Virginia, authored the education component of the document.

At Monument Square we stopped to marvel at the beauty of the newly renovated Portland Public Library, its giant turquoise windows radiant in the mid afternoon sunlight, while the iconic Civil War Memorial stood resolute in the chilling winter shadows.

Of all the Congress Street must-sees probably the most popular is the Wadsworth Longfellow House. Built in 1786, and the boyhood home of poet Henry Wadsworth Longfellow, it remained in the family until 1901, when it was given by Longfellow’s sister, Anne, to the Maine Historical Society. The Historical Society Museum Store is delightful, and if you need any book about Maine it probably is here.

The Maine College of Art sports festive holiday globes above its front entrance. This building used to be home to the Porteous department store. Remember those old elevators with the friendly elevator operators and scary safety gates? And of course where did grandma shop for Christmas gift clothe? Either here or over at Benoit’s. On Christmas morning we always put on a happy face despite knowing that the hoped-for train set was not emerging out of a rectangular Porteous box.

All too soon we were at Longfellow Square, staring up at the great poet dapperly clad in a red holiday scarf, holding a large gift wrapped in gold paper and red bow, with three more gifts piled under his regal chair.

It had been a wonderful stroll down the city’s “Main Street,” with many new discoveries and fond memories rekindled, once again reaffirming that Portland is truly one of the great American cities.

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Michael Perry is the former director of the L.L. Bean Outdoor Discovery Schools and founder of Dreams Unlimited, specializing in inspiring outdoor slide programs for civic groups, businesses and schools. Contact him at