A century ago, 300 individual communities dotted the islands of Penobscot Bay, Maine, each independently thriving off the land and sea. Today, the town of Rockland is one of 15 remaining communities, and it takes its role of culture-preserver seriously. Sail into Rockland on a warm September afternoon, grab a guest mooring for $30, and stroll down Main Street, where you’ll be within striking distance of culture, food and adventure.
Downtown Rockland is both hip and historic, having earned its place on the National Register of Historic Places for the popular Strand, a cinema built in 1923 and refurbished in 2005. A 20-minute walk from the harbormaster’s office on Mechanic Street takes you to the Sail, Power and Steam Museum, which was founded by Capt. Jim Sharp who made his living in Camden’s windjammer trade. Upon retirement, Sharp moved to Rockland where his many contacts—arctic explorers, divers, shipbuilders and seafaring folks—donated their heirlooms to help him kick-start the museum.
Back in town, culture abounds at the Farnsworth Art Museum, with its extensive Andrew Wyeth collection; the Puffin Visitor Center; the Island Institute, which works to preserve the remaining year-round Maine communities; and the Apprentice Shop, where students learn the traditional craft of Maine boatbuilding.
Rockland is equally appealing to foodies, whether it’s a hearty breakfast at Brass Compass Café, lunch at the Brown Bag or coffee at Rock City Café.
“There is so much to see and do on the waterfront and along Main Street,” says Robin McIntosh of the Rockland Chamber of Commerce. “The only thing sailors can’t find within walking distance of the town landing is a big grocery store. So, for stocking up on food supplies, we suggest you pay $5 for a cab to the grocery stores.”
Perhaps the most alluring aspect of Rockland is its location as a jumping-off point to other islands. Leaving Rockland, you will pass between the picturesque Owl’s Head and Breakwater lighthouses guarding Penobscot Bay then head south toward the Mussel Ridge Channel and more than a dozen islands worth exploring.
The north shore of Dix Island, one of my favorites, features a pretty beach and a protected anchorage. The island is technically private, but public walking trails wind around one of the country’s only “granite graveyards,” where an abandoned granite quarry serves as a reminder of the days when the Island shipped granite to the mainland; New York City and Philadelphia’s post offices were both built with Dix granite.
A more vital working harbor can be found on the nearby island of Vinalhaven, which you can reach within an easy day’s sail. There, Carver’s Harbor features great lobstering as well as numerous gorgeous, secluded residences. The picturesque island is an artists’ hotspot, home to many working studios and galleries, and also includes Lane’s Island nature preserve, perfect for bird watching.
Heading east from Rockland, Rockport is another great destination. Located a day’s sail from Rockland, this small remote village sports a gorgeous little harbor, an art colony and Rockport Marine—an internationally renowned wooden-boat yard, where some of Maine’s finest yachts are built. The boatyard is owned and operated by Taylor Allen, whose father-in-law was famed boat designer Joel White—son of E.B. White, the author of Charlotte’s Web and Stuart Little, whose title character also happens to be a passionate sailor.
The months of July, August and September are arguably the best time to visit Rockland, with July and August, in particular, boasting four stand-out festivals: the North Atlantic Blues Festival which draws nearly 10,000 people; the Lobster Festival; the Maine Boats and Harbors show; and the Friendship Sloop Days. Bottom line: if you’re craving to know the Maine coast, from coastal living to island culture, Rockland is the place to do it.
Photo courtesy of Schooner Stephen Taber; map by Christa Madrid