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Located on the southwestern edge of Penobscot Bay, Rockland has long been proud of its blue-collar waterfront roots. Built around the fishing industry, the city long historically dabbled in tourism but never really waded. With the recent decline of local fisheries and the rise of Maine’s tourist economy, though, that balance has shifted.

Rockland is swiftly being colonized by restaurateurs, innkeepers, artisans, and other folks who are transforming the place from fish-processing center to arts-and-crafts mecca.

The waterfront has a small park from which windjammers come and go, but even more appealing is Rockland’s downtown—basically, one long street lined with historic brick architecture. If you’re seeking picturesque harbor towns, however, head instead for Camden, Rockport, Port Clyde, or Stonington. Rockland is best as a sensible local base for exploring a beautiful coastal region, especially if you like your towns to be a bit rough and salty around the edges.