This handsome village is mostly known for Red's Eats (famous lobster rolls; see photo below) and as a traffic bottleneck. U.S. Route 1 snakes through town, down a hill, and across the Sheepscot River. Years ago, Wiscasset voted down a by-pass, figuring that it would hurt downtown business. So huge trucks grind gears going up a long hill in the town.
Wiscasset was cursed by having been chosen decades ago by photographer Samuel Chamberlain as the "prettiest village in Maine'' (see photo below), in a book that featured a town from each of the New England states. A constant battle to live up to that, especially as signs on the town borders serve as constant reminders. (Sort of like being voted the Most Likely to Succeed in high school. Where are you now, oh promising youth?)
That old houses that make Wiscasset so attractive (along with the beautiful natural setting) were built during her greatest age, around the turn of the 19th Century, when its ships traveled the globe. Such wealth got frozen by Thomas Jefferson's Embargo and by "Mr. (James) Madison’s War" (of 1812). Wiscasset fortunes never fully recovered.
Since the wide Sheepscot River does not freeze over, a scheme was floated in the 1920s to connect Wiscasset by rail with Montreal and transform it into that city's winter port. It came to naught.
Traffic, tourists and a flat off-season economy aside, the town is still fabulous.
William Morgan is a Providence-based architectural historian and columnist.