If BRATTLEBORO, in the south-central section of the state, is your first taste of Vermont, it may come as a surprise. Not the quaint, 1950s-throwback village you might expect, its style owes more to the central and northern Massachusetts college towns, with numerous little stores catering to the youthful and vaguely "alternative" population that has moved into the surrounding hills over the last two decades. The town's one unlikely claim to fame is that this was where Rudyard Kipling wrote his two Jungle Books.

Trains follow the river into town and stop behind the Old Union Railroad Station, which, as the Brattleboro Museum & Art Center (mid-May through Oct Tues–Sun noon–6pm; $3), now displays locally made Estey organs and works of art. Buses, on the other hand, pick up and drop off next to exit 3 off the interstate, a couple of miles north. Much the best place to stay is in one of the lovely river-view rooms at the Art Deco Latchis Hotel, 50 Main St (tel 802/254-6300, www.brattleboro.com/latchis; $100–130). There's also a good restaurant, the Riverview Café, serving dishes made with local ingredients in a waterfront setting (tel 802/254-9841). The nearby Common Ground Community Restaurant at 25 Elliot St (tel 802/257-0855) is a long-established worker-owned vegetarian restaurant, serving dinner, lunch and Sunday brunch in a very pleasant glassed-in conservatory. Homemade baked goods and specialty coffee make Mocha Joe's at 82 Main St (tel 802/257-7794) a good place for a morning snack or evening dessert.

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