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Destination – Castine, Maine

With the boat on the hard and winter just around the corner in northern climes, many boaters start dreaming of next summer’s cruising plans. Those who prefer a peaceful, friendly New England village should consider Castine, on the eastern shore of upper Penobscot Bay, in the midst of Maine’s prime cruising grounds.

On the approach, boaters enter the Bagaduce River (Castine Harbor) at Dyce’s Head, following the same course sailing ships have for more than 400 years. The town, home to 500 residents and 800-plus Maine Maritime Academy students, lies to port on the high, wooded peninsula separating the Bagaduce and Penobscot rivers.

One of the oldest towns in the United States, Castine has been continuously occupied by Europeans since the early 1600s and for prior centuries by American Indians. Its harbor once held hundreds of sailing ships loading and unloading cargo from the West Indian, European and salt trades. Now it bustles with yachts, especially during the Classic Yacht Race from Castine to Camden, the Retired Skippers’ Race, and many smaller competitions and sailing events. When the academy’s 500-foot training ship, State of Maine, is in port, it dominates the downtown waterfront. You can tour the ship for free.

The historic town radiates outward and upward from the harbor (and Maine Maritime Academy docks). The retail district is only steps from the Town Dock, Dennett’s Wharf, Eaton’s Boatyard and the Castine Yacht Club, all of which welcome transients.

“This is a lovely town with lots to see, and it’s safe for kids to walk around,” says Kenny Eaton who, with his daughter, runs the boatyard his grandfather established in 1939. “I always tell visitors to first go up to Castine Variety Store for a lobster roll and an ice cream cone,” he says. Then they can explore the town by following the walking tour map.

If too many customers are waiting at Castine Variety, you can pick up a quick meal or snack at The Breeze takeout on the dock, then watch the yachts slip by. Or take a waterfront table at Dennett’s Wharf Restaurant and Oyster Bar, specializing in seafood, microbrews, nautical décor and harbor views — not to mention rental kayaks and bicycles. The building, like most of downtown, has had several previous lives — sail and rigging loft, steamboat dock, boatbuilding shop, bowling alley. The dollar bill you attach to the ceiling will eventually go to charity. (Around $30,000 was taken down and donated to Sept. 11 victims, another $12,000-plus to Hurricane Katrina victims.)

Main Street leads up the hill from the town dock, its first block housing Castine’s retail businesses, some in buildings dating to the late 1700s. Most cruisers’ needs and wants can be found downtown: banks, a post office, Four Flags (NOAA charts and accessories with a nautical flair), Castine Historical Handworks (traditional handcrafts), T&C Grocery (extensive wine and liquor selection), and the aforementioned Castine Variety (snacks, meals, newspapers). Places to eat include Bah’s Bakehouse, Stella’s Restaurant, Compass Rose Bookstore and Café, and the 1894 Pentagoet Inn (lodging and fine dining). Stella’s and Dennett’s have live entertainment.

Stately American elms shade Main and surrounding streets, giving the mix of 18th- and 19th-century houses a quiet, refined air. Many impeccably maintained sea captains’ homes date to the mid-1800s, when Castine — a port of entry, county seat, shipping port and shipbuilding center — ranked among America’s wealthiest towns per capita. Some 120 vessels slid down the ways here.

When you stroll to the town green, you’ll feel you’ve stepped back 150 years. The 1790 Unitarian Church steeple houses a Paul Revere bell. The classic Italianate 1859 Abbott School is occupied by the Castine Historical Society. The public library, Adams School and several elegant classic homes also surround the green, site of summer evening concerts.

Castine’s tranquility, however, hides a tumultuous past, exhibited at the historical society and described on 100 markers around town. The peninsula commands the narrows of the Penobscot River, a major colonial-era highway to the interior. A century after European fishermen camped here, French explorer Samuel de Champlain sailed these waters. The Castine peninsula appears on his 1612 map. In 1614, Capt. John Smith charted the coast for Britain, and conflict began.

The town changed hands dozens of times before 1814, as four nations — France, Britain, Holland and the Untied States — fought for control. During the Revolutionary War, an attempt by Americans to retake Castine from the British resulted in what many historians consider this country’s greatest naval defeat.

Of Castine’s 16 European fortifications, no visible trace remains of Fort Pentagoet. Built by French traders and then enlarged by Baron Castin around 1667, it lies beneath the present Catholic Chapel on Water Street. Fort Madison, built in 1804 on the harbor and garrisoned during the Civil War, is a town park. Some earthworks remain at Fort Griffin and Battery Gosslin. Fort George, Britain’s largest colonial fort in North America, stood at the top of present-day Main Street. Its sprawling ruins are a state park.

Three blocks south of the docks stands Wilson Museum. Most artifacts were collected in the early 1900s by Dr. J. Howard Wilson, a geologist and anthropologist. The eclectic exhibits range from minerals and prehistoric fossils to displays of foreign cultures and 19th-century woodworking tools. Workshops, lectures and demonstrations of weaving, blacksmithing and other traditional crafts are conducted in-season. The Wilson Museum runs tours of the 1763 John Perkins House, the oldest in town, which illustrates the lifestyle of early British settlers.

Elaborate waterfront “cottages” built by summer visitors in the 1890s stand farther down Parker Street. Several of these palatial homes are inns and/or gourmet restaurants. Until the 1920s, Castine was a popular steamboat port with eight summer hotels.

Dyce’s, or Dice, Head Lighthouse stands at the end of Perkins Street, where the Bagaduce flows into the Penobscot. The 1829 lighthouse, discontinued in 1935, and keeper’s house are private, but you can see the tower as you follow the path to the present beacon, a skeletal tower on the waterfront rocks. The panorama encompasses Camden Hills across Penobscot Bay.

Along Battle Street, Witherle Woods offers hiking trails, and the Castine Golf Club, founded in 1897, has a nine-hole course and tennis courts. Nearby is Maine Maritime Academy’s main campus, which you can tour. You can walk west over the ridge to the free town beach on the Penobscot River and adjacent tidal saltwater swimming pool. Both abut the 1814 canal dug by the British to sever the peninsula and deter desertions.

Now artists, writers and wealthy retirees are changing Castine from a year-round working maritime community to a summer resort. Eaton, the boatyard proprietor, likens Castine to a “miniature Camden,” without the “madding crowds.” Unnoticed by most tourists streaming past on U.S. 1 some 20 miles to the north, Castine is best visited by boat. And those cruisers who do will enjoy its friendly residents, amenities and charming nautical setting.