The Many Delights of Pleasantville

The Many Delights of Pleasantville

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A state-of-the-art film center, new shops and restaurants, and world-renowned architectural gems: a visitor’s guide to one of Westchester’s most charming—and rapidly changing—villages. 

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By Carol Caffin    Photography by Iko


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After years of denial and neon-and-concrete withdrawal, I’ve finally come to terms with suburban living. And you know what? It’s not so bad. This from a girl who once knew—and fearlessly rode—every bus and subway route in Philadelphia, who used to think dandelions were little sunflowers and sparrows were baby pigeons, whose only real glimpse of greenery was the tangle of weeds that occasionally broke through the cracks in the sidewalk.


Blame it on Pleasantville. Like most people who come here, whether deliberately or, as I did, inadvertently, I was hooked after just one visit. Living here has helped ease my transformation from city girl to suburbanite because, despite its name, Pleasantville is an unpretentious, funky little town that’s a far cry from the cookie-cutter suburbia of my nightmares. Remember that commercial for 7-Up, the “un-cola?” Well, think of Pleasantville as the “un-suburb.”


With its rustic terrain, winding roads, lush landscape, and hidden nooks and crannies, Pleasantville, like Marie Osmond, is “a little bit country.” (The operative words here are “little bit.” With three supermarkets and a smattering of convenience stores in or near town, it’s hardly what we city folk refer to so eloquently as “the boonies.”)

Despite its quasi-bucolic veneer, Pleasantville, with its lively nightlife, cultural amenities and newfound bustling retail community, has an indelible air of bohemian hipness that gives it a downtown, urban feel. Still, with so much going for it, it has yet to develop an “attitude.”


“Pleasantville is not about status,” says realtor and Pleasantville resident Daniel Tuck of Coldwell Banker Residential Real Estate. “It’s about family.”


Nestled snugly between Chappaqua and Briarcliff in that elusive part of the county known as Central Westchester, this 300-plus-year-old village sits halfway between White Plains and Mt. Kisco in the town of Mt. Pleasant. (For those of you in the southern part of the county, it’s just 10 to 12 minutes away from civilization, a.k.a.

Central Avenue

.) Though its location is convenient (it’s one of the few areas that has both north-south and east-west access from virtually every road), that can sometimes be a double-edged sword. Invariably, we’re the cutoff between “the Bronx border and the northern valleys” in News 12 Westchester weatherman Joe Rao’s forecasts—which means that, in winter, it’s really anyone’s guess whether we get three inches of snow, like Yonkers, or 12 inches, like Yorktown. 


Unlike a Scarsdale or a Greenwich, Pleasantville’s business district has, in the past, always looked like a business district, generic and rife with nondescript storefronts. But that’s rapidly changing, thanks to a number of entrepreneurs with vision—like Jeff and Cindy Lupica (owners of the enormously popular Keeping Room), Barry and Linda Schwartz of Try & Buy Toy  Stores, Jean-Jacques and Jens Gabrillargues of Jean-Jacques’ Culinary Creations, Len Bernstein of Jackson & Wheeler, and Stephen Apkon (founder of the Jacob Burns Film Center and perhaps the most visionary of all)—who were able to see past the stodgy facade of an area that, until fairly recently, was in danger of becoming what Barbara Clemmens, former Pleasantville Chamber of Commerce president, calls “another nail salon-pizzeria-dry cleaners downtown.”


Instead, Pleasantville has found itself in the midst of a downtown renaissance. “It’s evolving so much and so quickly,” says former New York Times critic (and current Times book reviewer) Janet Maslin, a longtime resident who has been involved with the Burns Center from the beginning and is on its board of directors. Maslin, who has lived with her husband, author Ben Cheever, and their two children in Pleasantville for 16 years, loves the friendly, laid-back sense of community. “I feel a real climate change when I cross over into Chappaqua,” she says. “We’ve got something really precious here.” New shops and restaurants continue to crop up regularly, transforming the town into a bona fide shopping and dining destination—not just a stopover on the way to somewhere else. 


So, bring your appetite, your wallet and your walking shoes, and get ready to discover Pleasantville.


A Walking Tour of Pleasantville           


I’m not one for saving the best for last, so I strongly suggest starting your Pleasantville excursion (or shopping spree, depending on whether your better half is with you) at The Keeping Room (29 Washington Avenue, 914-747-5017). Next to Richard Gere, this little gem may be Westchester’s hottest commodity. When the shop opened its doors in August 2001, my husband’s first words were, “Oh no.” Browsing here is like going on a treasure hunt, and I must say that owner Cindy Lupica’s vision—“Anthropologie meets Restoration Hardware”—doesn’t begin to do it justice. The Keeping Room’s wares range from rustic, primitive and folksy to French provincial, shabby chic and retro/kitsch. You’ll find a fantastic selection of pottery, furniture (mostly chunky, European antique pine and reproductions), housewares, kitchen linens, accessories, jewelry, crafts and seasonal items, as well as the most deliciously aromatic, homemade candles around. (My favorite is “Aunt Kook’s Apple Cider.”) A word to the wise: If you see something you like, better grab it fast—many items are one-of-a-kind, and all the good stuff gets snapped up quickly.


When The Keeping Room’s current expansion and renovation (it will be taking over an adjacent property or one nearby) is completed, there will be an additional 1,000 square feet of goodies, including an expanded bath and body section, more linens, rugs, lamps, home décor and kitchen items. My husband is seriously considering a restraining order to keep me 300 feet—okay, miles—away from the premises.


If you have little ones in tow (or at home), you’ll definitely want to visit Try & Buy Toy Stores (

45 Washington Avenue

, 914-769-2997), the flagship store of Barry and Linda Schwartz’s three-store chain (the others are in Katonah and Bronxville). Try & Buy is stocked to the rafters with all the hot brands—Corolle, Playmobil, Lego, Leap Frog—plus many hard-to-find items you won’t see anywhere else. Little girls will revel in the huge selection of dolls—from the popular Groovy Girls to the high-end ($50—$200-plus) Madame Alexander line—as well as wooden doll houses, craft kits, games, dress-up clothes and accessories, and more. Boys will find all the popular stuff—Rescue Heroes, Tech Deck Dudes, Thomas trains, Bey Blades—plus building blocks, sports equipment, dinosaurs, puppets, science kits, museum-quality toy animals, and a slew of new and classic games. Don’t be afraid to ask questions—if there were academic degrees in toys, these friendly, patient and knowledgeable gals would all have PhDs.  


Precious Papers (

71 Wheeler Avenue

, 914-747-6850) is the place to go for fine stationery and invitations, which can be personalized in-store and picked up before you head home and often, within an hour or so.


The Village Bookstore (2 Washington Avenue, 914-769-8322), a fixture for nearly three decades, has a great selection of tomes, including titles of local interest, selections by Hudson Valley authors, and other rare finds you won’t see at Borders.


Hungry yet? When it comes to dining, Pleasantville offers some of the best restaurants, pubs, grills and eateries in the county. In addition to the requisite bagel shops and pizzerias, every town needs a diner, and the recently renovated Pleasantville Diner (10 Memorial Plaza, 914-769-8585), just across from the train station, is a bright, cheerful, spotlessly clean choice for breakfast, lunch or dinner. Plus, the diner has some of the best “regular” coffee (piping-hot and always fresh) in town, and service is always with a smile.


Starbucks fans may jump ship once they’ve tried the creamy, sublime café au laits and lattes at the Dragonfly Caffé (

7 Wheeler Avenue

, 914-747-7477), an ethereal little coffeehouse just around the corner from the Jacob Burns Film Center. When I’m not in the mood for Dunkin’ Donuts, I head for the Zen-like tranquility of the Dragonfly. Around the huge, old wood Indonesian table, you’ll find (and smell) a large selection of imported coffees and teas. The Dragonfly also has an assortment of baked goodies, soups, wraps, salads and fresh-fruit smoothies. In the warm weather, you can take a table outside and pretend you’re in Paris. Or, you can have a seat at one of a handful of tiny tables indoors and imagine you’re in Tibet—until the strains of Shania Twain’s “You’re Still the One” coming through on WHUD kill the moment for you. But still, bad music is a small price to pay for near-perfect java and, if it’s good enough for the mayor, it’s good enough for me.            


Just a stone’s throw from the Dragonfly is the one-year-old Jackson & Wheeler (

25 Wheeler Avenue

, 914-741-2000), a 108-seat restaurant that’s become one of the town’s hottest and hippest spots for wining, dining and live music. You simply cannot leave town without trying one of J&W’s delicious, boxing glove-sized muffins. And, now that they’ve recruited a French-trained pastry chef, the baked goods have been kicked up a notch to heavenly. Lunch and dinner selections are reasonably priced, there’s a raw bar and brick-oven pizza, plus dry-aged meats, cioppino, and possibly the best New England clam chowder this side of Boston. Heads up: J&W’s monthly wine-tasting dinners are beginning to generate a buzz.


Another great choice for a quick meal or snack—and especially for dessert—is Jean-Jacques’ Culinary Creations (

468 Bedford Road


Marble Avenue

, 914-747-8191), the only shop in Jean-Jacques Gabrillargues’s three-store chain (the others are in Croton and Millwood) that has a full café and bar. Forget that it’s a chain: This place is bustling morning, noon and night (it’s open Sunday to Thursday from 6 a.m. until 11 p.m.; Friday and Saturday until midnight), and for good reason. In addition to its full breakfast menu, which includes brioche French toast; quiche Lorraine; croque madame and fresh-baked goods like the mouthwatering chausson aux pommes (apple turnover), Jean-Jacques’ offers a huge selection of homemade lunch and dinner entrées (reasonably priced for the quality) from simple sandwiches like Brie with tomato and basil vinaigrette to gourmet dinners (available only for 10 or more) like shimp Provençal, lobster Thermidor and beef Wellington bordelaise. There’s live music (mostly blues and jazz) in the lounge three nights a week.  


A few doors down, the Yellow Tomato Restaurant & Bar (formerly Harrington’s; same owner, new name; 472 Bedford Road, 914-773-7640) is a small, dimly lit casual American restaurant/bar with a small menu featuring specialties like soy and ginger-marinated sesame seed crusted tuna.


If you’re a meat-and-potatoes kind of guy (or gal), McArthur’s American Grill (

14 Washington Avenue

, 914-773-4282) is a good—but rather pricey—choice. It offers standard American fare in a cozy (if a bit dark), pub-like atmosphere. From what I hear, Stephen King seemed to like the onion rings when he stopped by for dinner after an evening at the Burns center. Try the stick-to-your-ribs shepherd’s pie—but have a forklift handy to remove you from the booth afterward.


If you don’t mind a view of Key Food Marketplace (and its loyal legion of fans couldn’t care less), you might like Mediterraneo (

75 Cooley Street

, 914-773-1020), where Italians go to eat Italian—always a good sign. There’s live jazz on Wednesdays.


The Iron Horse Grill (

20 Wheeler Avenue

, 914-741-0717) is an elegant, 60-seat dinner-only establishment that’s garnered rave reviews for its inspired contemporary American cuisine. Housed in the restored, historic train station building, the Iron Horse has an exquisite wine list and delicious fish, meat and poultry dishes, including Cremini-crusted filet of bass, thyme rubbed rack of lamb and timbale of peaky toe crab.


Got your heart set on Chinese? The Magic Wok (

43 Wheeler Avenue

, 914-769-5656) is the place to go for Cantonese, Hunan and Szechuan dishes. The egg rolls are sometimes a bit greasy, but the chicken, pork and beef entrées are usually right on the money.

If, unlike me, you’re a sushi lover, I hear Hanada Japanese Restaurant (

8 Pleasantville Road

, 914-769-0638) is great for cooked seafood and steak as well as sushi.

For a lil’ chocolate fix, check out the Lil’ Chocolate Shoppe (15 Washington Avenue, 914-769-0771), or head on down to the brand new Fanda’s Pop Shop (11 Wheeler Avenue, 914-747-9797), a retro joint with black and white checkered floors, an ice cream counter (20 flavors), and an assortment of more than 100 different candies, many (like Mary Janes and Candy Buttons) from days gone by.


If you do come by car, you might want to take a short but scenic drive through town and up through winding Bear Ridge Road past Usonia, an historic and significant enclave of post WWII Frank Lloyd Wright-designed and inspired houses (see sidebar on page 45), two of which are still standing in their original form.


The Jacob Burns Film Center (

364 Manville Road

, 914-747-5555) is a must-see, and a great place to wind down your tour of Pleasantville. Opened in 2001 in what was once the old Rome Theater, the Burns Film Center has become perhaps the pre-eminent cultural center in the county. Founded by Pleasantville resident Stephen Apkon, the Center was named in honor of the not-for-profit Jacob Burns Foundation, which helped fund it. Hundreds of films from more than 40 countries have been shown at the Center since its inception, and scores of filmmakers, writers and actors have shared their work with its patrons. The Burns Center has three screens, shows independent and documentary films on a regular basis, and features educational programs, seminars and guest lectures. For those of you who are unabashed star gazers, this is the place in Pleasantville to be for frequent celeb sightings—recent visitors include Clint Eastwood, Stephen King, Jonathan Demme, Omar Sharif, Meryl Streep, Mike Nichols and Vanessa Williams.


“I do lots of interviews,” says the New York Times’s Maslin, “and I try to get everyone I know from the movie industry to come.” Obviously, she has clout. Plans are in the works for the Burns Center’s latest—and perhaps most wide-reaching—endeavor: a full-fledged educational center for burgeoning filmmakers and others interested in movies, which will operate at

405 Manville Road

under the auspices of Burns. “We’re about to close on the property,” says Maslin, “and the whole project should take about three years. This,” she contends, “is big.”


Frank Lloyd Wright was definitely onto something when he chose Pleasantville as the site of his ideal American community. I’m not saying it’s Utopia—but it ain’t Mayberry, either. And one thing’s certain: Once you’re here, you won’t want to leave because, whether you’re a little bit country (like Marie) or a little bit rock ’n’ roll (like me), you’re bound to feel at home in Pleasantville.


Carol Caffin is a freelance writer who lives in Pleasantville with her husband, Michael, and their son, Alex.




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