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Great Quirky Places to Retire

10 funky and artsy cities that free spirits will love

AARP list of quirky places where you can retire- a man paddles a canoe in New Paltz New York in Ulster County

Ulster County villages are spread out along the Hudson River. — Photo by J. Dennis Thomas/Corbis

Ulster County, N.Y.

Ulster County, N.Y. (population 182,493) is a funky string of artist-haven villages edged by vast swaths of bear-haven mountains. Residents occupy villages and the bears roam the 287,500-acre Catskill Mountains Forest Preserve.

Ulster’s villages are strung prettily along the Hudson River. The biggest city is Kingston (population 24,000); the second-biggest is New Paltz, about 13 miles southwest of Kingston, where the 7,000 permanent residents are outnumbered by SUNY-New Paltz’s 7,754 students. The tourism-based economy helped keep Ulster County’s unemployment rate below the national average for much of the recent recession, but at 9.1 percent it’s now slightly higher than the national average.

Of special note to retirees: Residents age 59 1/2 and older can take $20,000 a year from qualified pensions free of state income taxes, and all pensions are tax-free for retired military and government workers.

Kingston’s historic core is the waterfront Rondout neighborhood, which features brick buildings from the 1800s and a slew of restaurants, galleries and avant-garde venues like the Kingston Museum of Contemporary Arts and Deep Listening Institute, a center for poets and experimental musicians. Kingston is home to the Ulster Performing Arts Center, a restored 1927 movie palace now lit for touring acts and community productions. The area is also a foodie haven, with many small farms and artisan food makers having settled in the Hudson Valley.

The Kingston Farmers’ Market draws thousands downtown on Saturdays between May and Thanksgiving and from December to April. Off season, locals also hit the indoor Adams Fairacre Farms, which is like a farmer’s market on steroids.

Student-artists from the SUNY-New Paltz School of Fine and Performing Arts draw enthusiastic crowds, but the big ticket in town is often the Midnight Ramble concerts, four-hour parties in a barn that doubles as the Woodstock recording studio of Levon Helm, the former drummer for The Band.

For outdoor recreation, the area boasts fine golf courses, the Belleayre Mountain Ski Center, and extensive options for hiking, camping, canoeing and cross-country skiing on and around Slide Mountain. Shawangunk Ridge is world-famous for both rock climbing and the deluxe accommodations at Mohonk Mountain House. 

Crime rates here are very low. The number of doctors and hospital beds per resident is below average but big medical centers are 50 miles away in Albany. The number of smokers is above average, and so is the death rate from cancer. But many people here say that they eat healthy and get regular exercise. No word on how often that exercise involves fleeing from bears.

Next Page: Live among free thinkers and liberal edginess. »

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