• 1. Where to Stay
• 2. Where to Eat
• 3. What to Do
• 4. Insider’s Tip
• 5. An Oddball Day

The Morrison Gallery is among numerous art spaces in Kent.   (Photo: Courtesy of The Morrison Gallery)

Experience culture clash in the town of Kent, home to a quirky mix of wealthy New Yorkers with second homes (Oscar de la Renta, Henry Kissinger), prep schools, art galleries, and scruffy backpackers. Fuel up with sweet potato pancakes ($5.49) at the Villager Restaurant before spending a few hours on the Appalachian Trail. The best option is the Bull's Bridge trail, which offers everything from a relatively easy walk across the namesake covered bridge past waterfalls and rapids along the Housatonic River, to a more strenuous uphill jaunt to a picture-postcard scenic overlook above the river. Reward yourself back in town with an espresso ($1) and Three Funkey Monkeys (a trio of white-, milk-, and dark-chocolate chimps; $7.95) at Kent Coffee & Chocolate Company. Spend the afternoon browsing the stacks at the pleasantly musty Richard Lindsey Bookseller (15 North Main Street, Kent; 860-927-3025), home to 7,000 titles. In the early evening, stroll Old Barn Road to view contemporary paintings at the Morrison Gallery and Ober Gallery. For dinner, try the roast half-duck flambé ($28), carved tableside, and a bottle of Silver Oak Cabernet ($130) at the old-school Continental dining haunt Fife ’n Drum.