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20 Great American Drives

10 New York MILES 45. DRIVING TIME One day. Luminous vistas of New York's Hudson River inspired a 19th-century school of painting and drew the era's gilderati to build palatial estates. How long you spend on the 45-mile drive north from Beacon to Hudson, via U.S. 9 and local 9G, depends on how many sites you tour. Highlights include the 54-room Neoclassical Vanderbilt mansion, FDR's Georgian-style Springwood, and painter Frederic Edwin Church's Persian fantasy Olana. Treat yourself to lunch at American Bounty Restaurant in Hyde Park (845/471-6608; www.ciachef.edu; lunch for two from $50). Operated by the Culinary Institute of America, it specializes in local ingredients.

11 Maine: All by Myself

by David Handelman

After flying five hours and driving another five to get to Saco, Maine, I was more than ready for bed. But since that bed was in a B&B, I was obliged to take a chatty tour of the 1828 Greek Revival house with its gray-haired owner-host. I wanted to be polite, of course, since he had patiently guided me there, via my cell phone, through dark unmarked streets and had waited up for me till 11 with a now tepid glass of Chardonnay. And I'm sure he, too, was just trying to be polite, seeing in me a rumpled fortysomething solo traveler who had barely spoken to anyone all day. But being newly single, I kept wincing at his innocent spiel.

His property, the Crown 'n' Anchor Inn, was "quite popular for weddings," he told me. Then he asked me my seating preference for breakfast, adding that all the other guests were couples. Up in my room, he cheerfully demonstrated that the sconce above the private Jacuzzi was on a dimmer. "You're alone, so you don't need a romance light," he said, "but we've got one!" Then he shut the door, thus officially beginning my first solitary vacation in 20 years.

Solitude was in fact the point of my drive, more than the locale itself (mid-coast Maine and Penobscot Bay). Recently divorced, with two children, I hadn't been on a pleasure trip without offspring or a significant other since postcollege backpacking by Eurail. The idea was appealing. Anything I wanted to do. Nothing I didn't want to do. But suddenly left to my own devices, where would I go?What would I do?Who was I?

I wanted to treat myself to some real relaxation—not easy when the first question from every maître d' was "Will someone be joining you?" I chose Maine because it was familiar—I'd gone to camp and summered there for 15 years, but I intended to avoid certain old haunts and their ghosts.

My initial act of liberation was at the car-rental counter. After years of schlepping from New York in a toy-strewn station wagon, I indulged in a sleek Mitsubishi Spyder convertible. I asserted my new devil-may-care independence after breakfast by intentionally heading in the "wrong" direction for my itinerary—I backtracked to Wells to explore Wells Reserve at Laudholm Farm, a hidden wildlife estuary preserve that leads to a secluded beach, where I waded meditatively among snails and terns. Back in the Spyder, I hit Route 1 and found myself at the Maine Diner. I had eaten here before, but I was hankering for their "lobster pie"—fresh lobster meat baked in a dish with Ritz cracker crumbs and butter—which I devoured at the counter (one advantage to solo travel: not having to wait 20 minutes for a table).

I-95 is beautiful, in Maine, anyway: river crossings, forest, no fast food. By the time I reached the Bangor exit, dinner hour had arrived; I backtracked again, for lobster in the rough at Young's, a big, red no-frills barn in Belfast. It was already dark when I drove down Routes 175 and 166 to the peninsula that's home to the out-of-the-way Shangri-la of Castine. The town, which dates from 1604, was settled by the French and then held by the British, who reclaimed it from the United States briefly, in 1814, a testament to what a prime spot it is.

My lodging was at the sweet Castine Inn, which has been open since 1898 and has a reputation for serving the best food in town (though old-timey locals spurn the restaurant as too fancy-pants). The man behind the desk, Ray, informed me there was no space left the next night in the main dining room; I'd have to eat in the pub. Ray empathized about traveling solo. "The hardest time is dinner," he said, "when you want to tell someone about your day." And restaurants were always seating him at the worst table, he added. ("You mean, like the pub?" I remarked. He laughed.) My room was charming, but I hadn't anticipated the humblingly monastic impact of twin beds. At breakfast, I looked around the dining room—families, older couples, romantic pairs—and felt like a swimmer in a desert. People don't ordinarily allow themselves this kind of trip alone unless they're on business or recovering from something.

I found Castine to be the perfect walking-tour town, with well-maintained 18th- and 19th-century houses (and trees), dozens of quirky historical markers, and water everywhere—the Bagaduce and Penobscot rivers collide into the bay. (Castine's only flaw: the hulking Maine Maritime Academy training ship is sometimes docked downtown.) I got an ice cream from the Breeze, a shack on the downtown pier, then wandered the quaint, gently sloping Main Street to the McGrath-Dunham gallery, where a painting by Joshua Adam, depicting an empty boat cradle in a sun-dappled boathouse, spurred me to take a kayak expedition in the calm, nearly boat-free bay. Kayaking proved a satisfying mix of group and solitary venture. On our way back in, the sunset, at first muffled by clouds, exploded into a pink masterpiece, and the mosquitoes descended in celebration.

I returned to the Castine Inn too late for my pub reservation, which allowed me to get into the now emptying main dining room after all. As the waitress paraded out the chef’s delicious extravagances (spicy duck on anise zabaglione), with no one to share them with and nothing to do between courses but read or eavesdrop, I couldn't help feeling self-consciously indulgent. As a solo traveler, I ended up preferring my my less self-conscious lunch experience the next day: a lobster roll at the dingy, rental-video-cluttered Castine Variety shop—the best I'd ever eaten. (Prix fixe $9.50.)

On the ride out, on 175, 15, and 172, I sampled fried clams at the Bagaduce Lunch in Brooksville, a trailer-sized shack with picnic tables overlooking reversing falls; hiked up a mountain in Blue Hill for a stunning view of the bay; then picked up a few gifts for my daughters at a toy store in Ellsworth. But Acadia National Park, on Mount Desert Island, beckoned: 55 percent of all tourists who visit Maine go there, yet I'd never made it in two decades' worth of visits. I drove up Cadillac Mountain and took in the 360-degree view, then proceeded to the Jordan Pond House, with its great vista of the pond and the hills beyond (known as the Bubbles). For lunch, friends had recommended Thurston's Lobster Pound, in the tiny fishing hamlet of Bernard, but all the tables were inside, behind screens, because it's such a mosquitoey cove. It was dusk by the time I reached Bar Harbor, the commercial hub of the island, and checked into the Bar Harbor Inn. In summer, the town is almost like Disneyland's Main Street, U.S.A.—just as picture-perfect, just as thronged. I ran into acquaintances from New York, a couple and their 10-year-old, who'd been hiking all day, and felt sheepish explaining that I was alone. The next morning at breakfast, I spotted the sister of a friend. "I'm on my honeymoon!" she beamed.

I had some kind of breakthrough that day, finding my niche among the pairs and families. On my way to Southwest Harbor, one of the smaller, more charming towns on the island, I pulled away when I saw cars parked at the foot of the Acadia Mountain trail on Route 102. I was in a chattier mood than I had been, which was lucky; at the summit I was asked to snap a family picture, and the father told me that instead of swimming at the public area, south on Echo Lake, I could walk down a path to a much less crowded point of entry. I did and it was wonderful: a rock slab abutting the water, only about a dozen bathers. I dove in. This, at last, was my Maine—the leisurely, solitary lake swim.

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