Prior to the walk, drive to the Eastern Promenade, a row of Victorian houses opposite the waters of Casco Bay. Check out Fort Allen Park and its Cleve Tucker Memorial, at the eastern tip of the area.
From here, proceed in a southerly direction along the waterfront, looking on Commercial Street for a place to park, to begin your walk.
My walk begins at the Information Center, at the intersection of Commercial and Center Streets. Pick up a map here and get some basic information about the city. Now, walk in a northeasterly direction along Commercial Street, admiring the renovated Old Port Exchange Buildings, on your left, opposite the piers, and the busy harbor to your right. When you reach Pearl Street, turn left and then right on Fore Street to see the US Customs House (#312). Return to Commercial Street and turn left to find the Whaling Wall, a large mural, at the Maine State Pier, near the corner of Franklin Street.
Next, turn left and head westward on Franklin as far as Lincoln Park. Stroll diagonally through the park to reach Congress Street. Turn left on Congress and look for City Hall on your right, at #389. Beyond City Hall is the First Parish Church (#425 Congress) which dates to 1825. Further ahead, near the corner of Elm Street is Monument Square. The Lady of Victories Monument commemorates men from the city who served in the Civil War. Turn right on Elm Street and then left on Cumberland Avenue to reach the Public Market, an indoor collection of stalls selling all types of food and flowers.
After your visit, continue south on Cumberland and then turn left on Preble Street to return to Congress. If you turn right, you will find the Wadsworth-Longfellow House, boyhood home of the famous American poet, on your right (#489). The house was built in 1785.
Now, continue west on Congress Street, through the Portland Arts District, with its many galleries. On the way to State Street you will pass Congress Square, on your right. At State Street is Longfellow Square, with a statue of the city’s famous native son. (Beyond State Street, at #714 Congress is the Neal Dow Memorial, a Federal-style mansion belonging to a prominent Maine politician.) Turn left on State Street and then left again on Danforth Street to reach the Victoria Mansion, a luxurious Italian-style villa which was built in the 1850s for hotel-owner Ruggles Sylvester Morse. From here, turn right on High Street and left on Commercial Street to return to your starting point.
After the walk, be sure to drive through the Western Promenade, a well-preserved neighborhood of restored Victorian homes, and also visit the Portland Head Light, one of the east coast’s most prominent lighthouses, across the Casco Bay Bridge, on Cottage Road.