The giant bronze-and-granite eyeballs peer out from the lawn on the Williams College Museum of Art campus like a newly awakened monster in a children's storybook—or a group of undergrads pulling an all-nighter (15 Lawrence Hall Dr., wcma.williams.edu, free).

However you look at it, there's clearly a message behind Eyes, by the celebrated contemporary artist Louise Bourgeois. The liberal-arts school in rural Williamstown, Mass., 150 miles west of Boston near the intersection of Vermont and New York State, commissioned this surreal sculpture 10 years ago and placed it right in front of the school's art museum, as if to announce: This place isn't some staid cloister of old masterworks.

In the past few years, colleges across the country have been shaking up their museums with new acquisitions. But only in the Northeast will you find so many contemporary outposts in a relatively small area.

With that in mind, I chose a golden autumn weekend for an art—forward, backcountry college tour.

Day 1: Williamstown, Mass. to Burlington, Vt. (139 miles) The museum at Williams doesn't just cater to undergraduates; it designs year-round programs for primary and secondary students, too. On the day I arrive, a visiting class of elementary-school kids is climbing all over the Bourgeois eyes and running wild with loaner cameras. I'm also hypnotized by Pepón Osorio's Drowned in a Glass of Water, a pile of kitsch (toy cars, a deer head, a mannequin wearing a red macramé gown) that takes up a whole room and rotates on an 18-foot carousel.

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    It's like someone walked into a Norman Rockwell painting and ransacked the place. That said, it's hard for the art to outshine the one-woman show Mother Nature is mounting outside. From Williamstown, rural Route 7 leads north through the Green Mountains, where the leaves lining either side of the road meet in the middle to create a tunnel of brilliant red and orange. (I'd been keeping an eye on the color forecast at foliage-vermont.com to catch the peak.)

    The thing about Vermont—empty, beautiful, single-area-code Vermont—is that even its highways offer Ralph Lauren-worthy views of horses in wool saddle blankets and cabins with thin plumes of smoke swirling up from their chimneys. I wouldn't want to rush, and I don't have to, because a private, docent-led tour at my next destination—the Middlebury College Museum of Art, two and a half hours north—starts whenever you get there (Porter Field Rd., museum.middlebury.edu, free).

    The museum made art-history professor John Hunisak's popular walking tour of the 20 (mostly outdoor) public works into a series of two- to three-minute, bite-size YouTube clips you can access-ta-da!-right from your phone. Middlebury devotes 1 percent of its annual construction budget—the amount varies each year—to art. The college created the fund and its supervisory committee in 1994, after a group of alumni torched a controversial installation.

    "Some works are experienced in unintended ways," says Douglas Perkins, the museum's administrative operations manager, citing Frisbee Dog, a bronze sculpture of a dog mid-catch that has become an unofficial target on the campus Frisbee course.

    I've lived in college towns for 15 years, sucked in by the combination of high-and-low culture (and the cheap eats). Middlebury falls on the tame side of the spectrum, but even here there's the potential for serendipity, such as Neat Repeats, a vintage store crammed with silk kimonos, things that sparkle, and a mother-of-pearl box that I wish didn't cost $80 (3 Bakery Lane, 802/388-4488, vintage scarves from $6).

    I stop for a bite at the artisanal American Flatbread, where pizzas are baked in a beehive-shaped earthenware oven, and then hop back on the road (137 Maple St., americanflatbread.com, pizzas from $7.50). After the sleepy postcard quality of my first two stops, I'm struck by the energy of Burlington—a buzzing city with traffic, glassy condos, and kids on skateboards downtown.

    It's dark when I arrive, but the University of Vermont's Fleming Museum is lit up, Gatsby-style, for an opening, complete with a buffet table of crudités, a jaunty string quartet, and ladies milling about the marble staircase in Vermont couture: sequins and snow boots (61 Colchester Ave., uvm.edu/~fleming, admission $5). After paying the $5 admission, I stroll through a temporary Christo and Jeanne-Claude gallery featuring sketches of unfinished projects.

    But the star for me is Barn Ball by UVM grad Lars-Erik Fisk, who once worked as the artistic director for the band Phish. The piece takes the elements of a barn—a red wooden clapboard exterior, white window frames, hay piled high and lit by the yellow glow of a utility light—and shapes them into an 18-foot sphere parked in the lobby like a child's playhouse.

    It's pure state pride molded into a surprising package. I break for a late-night snack of international tapas at ¡Duino! (Duende), whose name is a mashup of Rilke and Lorca book titles (10 N. Winooski Ave., duinoduende.com, small plates from $6). All the dishes "are from places we've been to or want to visit," says my waitress, Kat Wright (the owner's wife). When the folks at the next table hear where I'm staying—cross chat is encouraged here—they give my choice a thumbs-up. In a land of $200-a-night B&Bs, I consider the $59-a-night G.G.T. Tibet Inn a triumph in more ways than one (1860 Shelburne Rd., ggttibetinn.com, doubles from $59).

    Opened 18 years ago by Kalsang G.G.T.-a Tibetan Buddhist refugee who hiked across the Himalayas to escape his occupied homeland-the inn has an uplifting quality that belies its standard-issue motel decor, starting with a photo in the lobby of a beaming Kalsang kneeling before the Dalai Lama. When he checks me in, Kalsang is wearing a "Peace on Earth" T-shirt.

    Day 2: Burlington, Vt. to Claremont, N.H. (113 Miles) With less museum ground to cover today, there's time for impulsive detours, so I exit Vermont's I-89 to pop into the Simon Pearce glassblowing studio, which is situated next to a waterfall in Quechee, Vt (1760 Quechee Main St., simonpearce.com, glass vases from $65).

    Upstairs, there are well-lit displays of handmade bowls and pitchers, but the real action is downstairs: 1,650-degree flame-filled ovens with open doors and the fluid athleticism of men rolling molten glass with steel rods reminiscent of javelins. From there, it's an easy jaunt across the state line to Dartmouth's Hood Museum in Hanover, N.H., where I park alongside a quad filled with preppy students in sweaters tossing around a football (hoodmuseum.dartmouth.edu, free). Inside Hood, a narrow vestibule has been turned into a pop-up gallery curated by students, drawing from the museum's 65,000-piece permanent collection.

    The exhibit—Representations of the Glove as Fetish Object—has a weirdness that might have been squelched by a professional curator, but I love the idea of students pushing the envelope just around the corner from a Perugino Virgin and Child. The joyful surprise of that stop casts a glow on the last half hour of my drive, past wholesome New England colonials with Halloween ghosts dotting their lawns.

    Then I reach my home away from home, the two-year-old Common Man Inn in Claremont, a riverside mill that's been converted into a hotel and restaurant (21 Water St., thecmaninn.com, doubles from $99). The exposed stone walls and roaring fires manage to be both cozy and chic, and the library-like lobby is unimprovably charming, from the scattered mystery novels and chess sets to the resident black Labrador retriever swinging his tail back and forth like a happy metronome. I flop into a leather sofa at the bar, order a martini, and lift up a red gingham cloth to help myself to the complimentary hors d'oeuvres: crackers and an enormous block of Vermont cheddar—itself a perfectly unstudied New England still life.


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