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This town is considered the gateway to Penobscot Bay and is the first stop on U.S. 1 offering a glimpse of the often-sparkling and island-dotted blue bay. Though once merely a place to pass through on the way to tonier ports like Camden, Rockland now gets attention on its own, thanks to a trio of attractions: the renowned Farnsworth Art Museum, the increasingly popular summer Lobster Festival, and the lively North Atlantic Blues Festival. Specialty shops and galleries line the main street, yet the town is still a large fishing port and the commercial hub of this coastal area.

Rockland Harbor bests Camden (by one) as home to the largest fleet of Maine windjammers. The best place in Rockland to view these handsome vessels as they sail in and out of the harbor is the mile-long granite breakwater, which bisects the outer portion of Rockland Harbor. To get there, from U.S. 1, head east on Waldo Avenue and then right on Samoset Road; follow this short road to its end.

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