Rockland’s walkable Main Street, close enough to the harbor that you can catch a whiff at low tide, is lined with restaurants, boutiques, art galleries, and two of Maine’s most impressive museums in the Center for Maine Contemporary Art and the Farnsworth Museum. You may also want to check out the contemporary art at the Dowling Walsh Gallery, 365 Main Street.

Not so long ago, a lot of these storefronts were empty, but comparatively cheap real estate has attracted creative types, entrepreneurs, and younger folks and families who can afford this still-rough-around-the-edges harbor town better than Camden and Rockport. When the CMCA opened in 2016, it seemed like confirmation of Rockland’s new direction, and a handful of sleek new Main Street restaurants opened on its heels.

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Artists have long been drawn to Rockland’s coastal surroundings (and the islands nearby). A trip to nearby Cushing, 12 miles southwest of Rockland, shows off scenery that’s been captured on canvas by the likes of Edward Hopper and Andrew Wyeth (including the farmhouse made famous in Christina’s World).

It’s worth a call to the Georges River Land Trust at tel. 207/594-5166 to ask about the Langlais Sculpture Preserve at 576 River Road; as of this writing, it is slated to open in fall 2017. When it’s open, the pastoral property will feature a self-guided walk among the site-specific sculptures of the late Bernard Langlais, a much-admired, somewhat whimsical sculptor whose preferred medium was scrap wood. Highlights include his geometric, 13-foot Horse and a model of Richard Nixon standing in a pond.

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Crafting a Vacation

The Maine coast has been a haven for visual artists, jewelers, sculptors, photographers, potters, and other creative types for as long as I can remember. Studios, galleries, arts centers, and museums of surprising quality crop up nearly everywhere, even in the tiniest coastal villages.

While cruising the coast, you’d do well to drop in to some of these crafts studios—and the best way to find them quickly is to contact the Maine Crafts Association (tel. 207/205-0791; www.mainecrafts.org), which publishes a comprehensive annual guidebook to its member artists, which maintains a database of its members online, searchable both by media and region. 

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You’ll find everything from glassblowers to sculptors to fiber artists to basketmakers.

It’s recommended you call ahead to get studio hours before making the trek to an out-of-the-way crafts studio or gallery. They are artists, after all—hours are likely to be a little whimsical.

Windjammers on the Water

During the transition from sail to steam, captains of fancy new steamships belittled old-fashioned sailing ships as “windjammers.” The term stuck; through a curious metamorphosis, the name evolved into one of adventure and romance.

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Maine is the windjammer cruising capital of the U.S., and the two most active Maine harbors are Rockland and Camden on Penobscot Bay.

Cruises last from 3 days to a week, during which these handsome, creaky vessels poke around tidal inlets and small coves that ring the beautiful bay. It’s a superb way to explore the coast the way it’s historically always been explored—from out on the water, looking in. Rates run between about $110 and $180 per day per person (which is $300–$1,200 per person for an entire trip); the best rates are offered early and late in the season.

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Maine boasts a sizable fleet of sailing ships both vintage and modern that offer private cabins, meals, entertainment, and adventure. The ships range in size from 50 to 130 feet, and accommodations range from cramped and rustic to reasonably spacious and well appointed. Most are berthed in the region between Boothbay Harbor and Belfast—they cruise the Penobscot Bay region during summer, and some migrate south to the Caribbean for the winter.

Cruise schedules and amenities vary widely from ship to ship, even from week to week, depending on the inclinations of captains and the vagaries of Maine weather.

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You choose your adventure: An array of excursions is available, from simple overnights to weeklong expeditions gunkholing among Maine’s thousands of scenic islands and coves. A “standard” cruise often features a stop at one or more of the myriad spruce-studded Maine islands (perhaps with a lobster bake on shore). Breakfasts are served at tables below decks (or perched cross-legged on the deck), and you absorb a palpable sense of maritime history as the ships scud through frothy waters.

Ideally, you’ll have a chance to look at a couple of ships to find one that suits you before signing up. Several windjammer festivals and races are held along the Maine coast throughout the summer; these are perfect events to shop for a ship on which to spend a few days. Among the more notable events are Windjammer Days in Boothbay Harbor and the Camden Windjammer Weekend in early September.

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If you can’t do that, contact the Maine Windjammer Association (tel. 800/807-9463; www.sailmainecoast.com) for a packet of brochures or simply check its good website of member ships and comparison-shop. If you’re trying to book a last-minute windjammer cruise on a whim, stop by the chamber of commerce office on the Rockland waterfront (see above) and inquire about open berths.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.