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The Five-Point Weekend Escape Plan

Enjoy Fall in Litchfield County


5. Oddball Day

The Morrison Gallery is among numerous art spaces in Kent.  

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.

Published on Aug 11, 2011 as a web exclusive.

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