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CONVENTION + VISITORS BUREAU /
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Photos Left to Right, Top to Bottom: Corey Templeton,
Robert Witkowski, Convention + Visitors Bureau,
Black Point Inn, file photo (2)
One of the few buildings to survive the
devastating fire of 1866 is the Portland
Observatory. Built in 1807 as a way for
commercial ship owners to know when
their vessels were entering the harbor,
this 86’ octagonal tower is one of the only
remaining wooden maritime signal tow-
ers in the country. Its unique profile is
one of the defining features of our coastal
city, and the views after climbing its spiral
staircase are spectacular and panoramic.
If you can’t get enough of historic archi-
tecture, you can stay at an historic bed
and breakfast decked out in antiques,
some with operating fireplaces in the par-
lors and rooms. The Inn at St. John (1897)
is the oldest continuously operating Vic-
torian hotel; comfortable rooms with pe-
riod details are a bargain find if you don’t
mind the lack of an elevator. Also on the
peninsula, the Portland Regency is a full-
service hotel housed in a late 19th century
armory, a marriage of historic sophistica-
tion with modern amenities.
Greater Portland is also steeped in his-
tory and oozing visual appeal. On a drive
along Shore Road in Cape Elizabeth,
you’ll see brick, stone, and wooden man-
sions that overlook the sea. Route 88 in
Falmouth and Cumberland Foreside is
also lined with stately homes. Yarmouth
and Gorham exemplify traditional New
England villages with distinct town
centers surrounded by lovely houses.
Freeport’s downtown has become a
world-renowned shopping destination
with many boutiques occupying historic
buildings; even the Freeport McDonalds
is a tourist destination, located as it is in
an historic village home.