Lay of the land: Ossining is a town in transition. Stroll down historic Hamilton Avenue and you’ll find lovingly restored Victorian homes next door to sagging porches in need of more than a little TLC. And while new restaurants like Danny’s and Guida’s Italian are revitalizing downtown, there are still plenty of dilapidated façades like the old Ossining National Bank Building, which was bought but never restored. Although many of the Victorian and Colonial homes downtown date from the late 1800s, the past ten years have brought an explosion of new construction in surrounding suburbs—especially the Croton-Harmon area—and prices have steadily risen. “It’s got a real small-town feel,” says one resident who left a Chelsea loft for a three-bedroom colonial when he moved here ten years ago with his wife. “At the same time, it’s a very diverse community.” the big house: Towering over the village like a medieval castle is the Ossining correctional facility—a.k.a. Sing Sing. With an eye on the tourism dollars generated by San Francisco’s Alcatraz, village officials would like to transform sections of the prison into a museum.
Meet the neighbors: “The funky atmosphere reminds me of the East Village,” says Dan Di Paola, whose restaurant, Danny’s Café.com on Main Street, is one of many new businesses cropping up downtown. A look at Ossining’s demographics shows an almost equal mix of blacks, whites, Asians, and Hispanics. Famous Ossining alums include Peter Falk, John Cheever, and marathon world-record holder Khalid Khannouchi.
Needful things: You won’t find a Starbucks—but there’s no shortage of lattes. “The big companies got beat out by the locals because they protested,” explains village manager Paul Shew. “So we have lots of little espresso and cappuccino shops.” There’s also the Arcadian Shopping Center, a mini-mall that houses a Stop & Shop—functional but hardly comparable to gourmet-food shops in Manhattan—several pharmacies, and a few small gift shops. There’s no movie theater in the town center, but a megaplex is fifteen minutes away. “We’re still a good three years away from having a viable nightlife scene,” says Di Paola.
School report: Ossining High offers extracurricular programs, including one of the most comprehensive instrumental-music facilities in the country. The average SAT score is 1031; 64 percent of the class of 2001 went on to a four-year college. “Basically, we’ve got a much larger tax base than the other schools, which translates to better facilities,” says Roy Temkin, a twelve-year resident whose two children are products of the Ossining school system. The school district spends $15,638 per pupil.
Commute: Ossining is 36 miles from midtown Manhattan. It takes from 48 minutes on the express train to about an hour on the local to reach Grand Central Terminal, with trains departing about every half hour.
See also: Ossining Web Guide