The old “ugly duckling” story comes to mind when sailing inbound past the impressive and much-loved breakwater protecting Rockland Harbor. But instead of turning into a mere swan, this Penobscot Bay city now soars well beyond an improved look and sensibility. Heck, even the rich and famous have discovered it.

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“The most surprising development lately is the number of really big boats that are visiting,” says harbormaster Ed Glaser. And exactly how big are these pleasure boats? “Oh, a 150 feet or more. They usually just anchor because we don’t have a mooring big enough for them.”

A City Transformed

The ten-year veteran of Rockland’s waterfront is a little cagey when asked exactly who these high rollers are. “We like to respect people’s privacy,” he says simply, noting most Rocklanders tend to leave even the biggest celebrities to themselves.

Photo by  Joe Devenney

Photo by Joe Devenney

Still, with boats that range from mega motoryachts to diminutive daysailers, visitors to Penobscot Bay’s acknowledged hub of boating make the trip for pretty much the same reasons. One is easy navigation in and out of the harbor, which boasts plenty of room for even the biggest flotilla, plus good protection from storms. Another is the array of shoreside attractions, including festivals, shops, galleries and museums. And then there’s the food.

Foodie Fantasy

Photo by  Joe Devenney

Photo by Joe Devenney

Wandering gourmands now flock to what was once a down-and-dirty fishing port, complete with the traditional sights and smells that come with processing the bounty of the sea. But that’s all in the rearview mirror. Today, the scents wafting along Main Street range from scrumptious to darn near irresistible.

Harbormaster Glaser is again diplomatic when it comes to recommending one particular restaurant. “There are just too many” to pin down to one, he says.

During our own investigations, my wife and I tried one of the top-rated, high-end eateries, Cafe Miranda, and found its award-winning menu as advertised. Even better, there are coffee bars, diners and all levels of expense and atmosphere throughout the town. And for those who prefer to cook onboard, a short walk from the harbormaster’s office on a Thursday morning puts you in the middle of an extensive Farmer’s Market, where you can pick up local produce, meats and fish for the galley.

If you’re on a diet, Rockland also offers plenty to see and do within reasonable walking distance of the Rockland Public Landing or one of the four marinas huddled around centrally located Crockett Point.

Art About Town

Photo by  Joe Devenney

Photo by Joe Devenney

If you’re on a diet, Rockland also offers plenty to see and do within reasonable walking distance of the Rockland Public Landing or one of the four marinas huddled around centrally located Crockett Point. Art aficionados will be drawn to the Farnsworth Museum on Main Street, where works by the Wyeth family (N.C., Andrew and James) seem to dominate the collection, although there are plenty of other sea-oriented masters, from Winslow Homer to Edward Hopper. This concentration of fine artistry has spawned a plethora of galleries, antiques boutiques and related businesses along Main Street or just off it, many featuring contemporary Maine artists who may be on the way up.

Many visiting sailors eventually wind up at the Maine Lighthouse Museum, which is a short walk just north of the public landing. Keep your sunglasses handy when visiting, as there is an abundance of bright, shiny, polished brass among the displays. The guided tours are also pretty informative, and admission is only $5.

For anyone interested in early-American autos, motorcycles and aircraft, the Owls Head Transportation Museum is well out of town, but worth the effort to visit. With one of the best collections of pre-World War II vehicles and “flying machines” in the nation, be prepared to spend a long day gazing at ancient Harleys, a Steffy motorcycle or perhaps a Prescott or Stanley “motor carriage.” If you’re lucky, your visit may coincide with a fly-in, bike-in or some other gathering of hundreds of golden-oldies from all over the country. Ironically, there is no public transportation to the Transportation Museum from downtown Rockland, but the local cabbies know the way and are happy to oblige.

Lobster and Blues

Those fly-ins, bike-ins and whatnot have to compete with a long line of festivals for which Rockland has become justifiably famous. Perhaps the best known is the annual tribute to the Pine Tree State’s most celebrated citizen: Homarus americanus. For nearly 70 years, the Maine Lobster Festival has served these popular crustaceans to throngs of visitors, recently topping more than 20,000 pounds of Mr. Redcoat to satisfy the four-day appetites on hand. Usually held during the first week in August, even the foodies show up to sample unusual lobster concoctions, which reportedly have included lobster ice cream.

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Rockland, Maine Chart

Rockland, Maine Chart

Rockland offers another alternative for waistline-watchers when the North Atlantic Blues Festival takes over the town in mid-July. This four-day event attracts thousands of music lovers, who descend on the area for an al fresco event that now includes a popular “pub crawl” well into the night. The local clubs, bars and restaurants sport every imaginable version of blues style, making one pause and marvel at just how far a backwater fishing town has come from its blue-collar roots.

Want more? Well, back on the waterfront there are all manner of schooners sailing out of Rockland these days on day trips, evening cruises or weeklong adventures all over Penobscot Bay. In fact, Rockland now lays claim to the title “Schooner City,” an accolade that miffs a few other Penobscot ports that also advertise the passenger boats in significant numbers.

Thus it’s easy to see how a small brick-and-mortar city has evolved pretty nicely into a destination that welcomes boats big and small. Rockland has always had its eyes on the sea. It’s just that, at least in recent decades, the casual visitor has become the focus of attention.