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Postcard-perfect county downtowns: some quaint and quirky, others bustling and bohemian, with a few urban oases added for good measure.
By Nancy L. Claus & Dave Zucker with Carol Caffin. W. Dyer Halpern, Marisa Iallonardo, and Laurie Yarnell
Urban with a small-town feel
Bronxville, a bucolic village of 6,543 residents that sits west of Yonkers and east of New Rochelle, was almost single-handedly laid out by William Van Duzer Lawrence, a prominent drug manufacturer who moved to the village in the 1890s.
Today, all of the downtown area — from the train station to the high school and all the shops in between — is in walking distance of each other. “The area is designed so you can walk to the train station, which is probably one of the most wonderful pulls,” explains Evelyn Besser, a real estate agent in the village. “Between that and the school district — the children are all able to walk to the schools — it gives it a very homey, family feel.”
Today, with an eclectic mix of mommies with baby carriages, groups of teens, commuting professionals, and funky Sarah Lawrence college students (who give off an artsy vibe), this original haven for artists has become a haven for post-Manhattanites looking to raise families in a close-knit sophisticated village.
Read More: How to Spend the Perfect Day in Bronxville
The Vibe: Understated wealth; the village feels more like an intimate small town than a sprawling suburb.
What We Love: With a spa, movie theater, hospital, supermarket, and scores of cute shops and restaurants all within walking distance, it’s no wonder Bronxville’s barely-one-square-mile downtown is the perfect place to find anything (and everything) you’re looking for. During the warmer months, the downtown evokes an almost European feel with lots of people strolling down the street, coffee or ice cream in hand, dining at outdoor tables, chatting on street benches, and overall, enjoying the weather and the small-town atmosphere.
What You Should Know: Although there is sufficient parking on the streets and in various municipal lots, before 6 p.m. most meters only last three hours, so, if you’re planning to spend the day, bring some extra quarters.
A trademark-free zone
Sure, it’s a little sleepy here (the sidewalks roll up at 9 p.m.), but you’ve got to admire a town with spunk. When the townspeople were told to vamoose 100 years ago to make room for the Croton Reservoir, they picked up their houses and businesses — literally — and moved a mile away.
When Starbucks sought entry into the no-chain community, the citizens stood their ground; Tazza Café now offers up the daily java. And when Martha Stewart decided to trademark the name Katonah for her line of furniture and home goods, the town girded for battle. Namesake Chief Katonah (who we just can’t envision perched on a Martha Stewart cabriole-leg settee) would be proud. Members of the Ramapoug Lenape tribe caught wind of Stewart’s plans and contacted Katonah officials offering support.
The Vibe: Artsy, casual (jodhpurs and riding boots are not out of place here). Good people-watching opportunities near the train station from tables at The Whitlock and the KR Café.
What We Love: This perfect little downtown didn’t get this way by accident. According to Lydia Landesberg, president of the Katonah Village Improvement Society, Katonah is one of the very first planned communities in the country. “When the town moved, the villagers got together and decided where the commercial district and residential districts should be,” she says. “They put deed restrictions on what kinds of businesses were allowed in town—unheard of in those days. I think those original town planners did a great job.”
What You Should Know: Katonah is a feel-good kind of place and it’s no wonder. The town is a veritable vortex of the healing arts; find doctors, therapists, and counselors of all kinds, specializing in everything from marriage to massage, podiatry to past-life regression.
A suburb for city people
Larchmont has not one but two distinct downtowns, both imminently walkable, filled mostly with individually owned stores and restaurants (the only chains are CVS, Starbucks, and Ann Taylor). “What I like about Larchmont is that it’s truly an urban suburb with a somewhat sophisticated city feel,” says Leslie Long, a 16-year resident. “It has fabulous downtown areas, which includes several terrific clothing shops, lots of fresh foods, the wonderful food market, Meateria, free parking, and friendly shopkeepers.”
The Vibe: School playgrounds, town parks, and beaches are always filled with children, parents, nannies, joggers, dog walkers, and more.
What We Love: Manor Park is one of the town’s nicest spots to walk along the water, sit on rock benches carved out of boulders or in the gazebos, and look out over Long Island Sound. Other spots where one can enjoy the water view is Red Bridge for fishing and Dog Beach, famous for sea-glass hunting.
What You Should Know: The French American School has attracted a large French population in town. There’s even a five-kilometer Tour de Larchmont every fall.
A mini-metropolis in the heart of horse country
Mount Kisco is Northern Westchester’s shopping and dining Mecca. Retail giants like Target, Gap, and Chico’s coexist with one-of-a-kind boutiques and specialty shops including Elephant’s Trunk and New York Dolls (where your teen will find her dresses for the year’s Bar and Bat Mitzvahs). There are dozens of restaurants in town, so take your pick of cuisine: Indian, Mexican, Spanish, Italian, Greek, Chinese, and lots of New American. And a tiny multiplex shows first-run movies. Plus there’s a popular farmers’ market open summer to early fall by the train station.
The Vibe: A mix of moms with strollers, couples and families, shoppers and diners, and business folk.
What We Love: Of course we love the shopping and the dining here (do try Little Drunken Chef on Lexington for dishes made with fresh locally grown products), but we also adore the fact that Mount Kisco is a town with a lot of heart. Multiple major fires have hit the downtown over the past two decades or so and, each time, the town picks itself up, dusts itself off, and knocks itself out helping the burned-out businesses get up and running again.
What You Should Know: This town is thriving, so traffic on the main drag (Route 117, aka North Bedford Road) can be a real drag during rush hour and on Saturdays. Avoid the worst of it by hopping on the Saw Mill North off Kisco Street, then off at Green Street, north of town.
Bleecker Street meets Mayberry
Pleasantville is an unpretentious, funky little town with a bustling retail community, lots of quaint shops (many of those nondescript and unsightly storefronts have been replaced with charming and sophisticated boutiques), lively nightlife (there’s something for virtually every age group), and a wealth of cultural amenities.
The village of 7,172 residents has an indelible air of bohemian hipness that gives it a downtown, urban feel, minus the attitude. The Jacob Burns Center is the cultural hub of this walk-to-everything town, whose nearby residential “Old Village” is full of tree-lined streets and lovely colonials and Victorians, and has helped transform Pleasantville from dowdy to downright cool. It’s not just that the Center shows great indie flicks and documentaries; it draws noted producers, directors, and actors, and big names like Michael Moore, Jonathan Demme, and Woody Allen, to discuss their work. The influx of film patrons has been a boon for local restaurants like Playa Bowls, Wood & Fire, Tzatziki Greek Grill, Pub Street, Sal’s Pizza and more.
Don’t forget the trusty Pleasantville Diner which, even with a Starbucks next door, still serves the best coffee in town. On Pleasantville Day in May, the whole town turns out to eat hot dogs and mingle with neighbors and there is an annual outdoor music festival in July. New York Times crossword puzzle editor Will Shortz lives here and holds a crossword tournament to benefit a local scholarship fund. If you’re lucky, you may even run into Bill Clinton power-walking near the train station.
The Vibe: Laid-back, quasi-bohemian, friendly, hip, family oriented.
Read More: How to Spend a Saturday in Pleasantville
What We Love: It’s smack dab in the middle of the county and easily accessible by the Saw Mill Parkway, the Sprain Brook Parkway, the Taconic, Route 9A, and Routes 117 and 120. It’s also virtually equidistant from two of our favorite shopping hubs: downtown Mount Kisco and downtown White Plains.
What You Should Know: The downtown is a bit circuitous; though everything is adjacent to or close by the Metro- North station, you have to meander a bit to discover all the nooks and crannies.
The county’s international food capital
“Saw Pit,” as Port Chester was once known (thanks to the saw mill at the mouth of the Byram River where laborers would stand inside pits cutting gigantic logs), was once a bustling center of commerce where farmers would bring the fruits of their labor and ship them throughout the region. Nearly two centuries later, the mill, the logs, the factories are gone. And in their place? A thriving, ethnically-diverse city, that is turning into the ethnic food capital of Westchester.
Want a freshly made taco with your cerveza? You can get it at bartaco. Or perhaps you’re in the mood for steak and churros? Drop by Copacabana Steakhouse. A whopping 46 percent of the city’s population comes from Spanish-speaking countries — Ecuador, Colombia, Mexico, El Salvador, Uruguay.
Retailers and merchandisers have sensed that Port Chester is fast becoming an “in” place: a 14 screen state-of-the-art movie theater has rolled into town, as have a number of retail chains: PETCO, DSW, Costco, and Bed, Bath and Beyond.
The Vibe: International, revitalized, relaxed
What We Love: There are so many great restaurants and snacking places within a short stroll — The Kneaded Bread, Paleteria Fernandez, plus Saltaire right on the Byram.
What You Should Know: The parking lot inside the new theater complex is free, and you can even hop on the train at the nearby Metro-North station without paying a dime in parking fees. How’s that for a good deal?
A quaint New England-like shopping district oozing charm, Rye is so picture-perfect, a short-lived TV series, Hometown, filmed here in 1985. This darling city by the Long Island Sound is made for relaxed strolling and browsing; most of the shops, often in old house-like buildings, are located on its tree-lined main street (Purchase Street) and some smaller offshoots (Purdy Avenue, Elm Street, etc.)
And while in recent years its retail mix has been compromised somewhat by the addition of some chains and banks (enough already), Rye is still one of the loveliest shopping and dining destinations in the county and an ideal spot for a little day-tripping. Just don’t leave the credit cards at home; Rye shops don’t do discount.
The Vibe: Preppy, proper, swanky, and decidedly old-school; a little like Southampton-on-the-Sound. Think lots of Lilly P., khakis, and sock-less Docksiders.
What We Love: The quaint old-fashioned feel, the still-interesting mix of often one-of-a-kind shops, and a foodie’s fantasy selection of fabulous upscale eateries.
What You Should Know: Parking is a pain. And while there are no meters on the main streets, those spots go fast. Even metered parking in the municipal lots is hard to come by during peak hours, so avoid lunchtime and just about all day Friday. Best time to find parking? Before 10 a.m. and around school pick-up time. And dinner reservations are a must just about everywhere, but definitely Ruby’s Oyster Bar & Bistro, Frankie & Johnnie’s Steakhouse, and Morgans Fish House, sometimes even during the week.
Ambiance, affluence, and attitude
Its very name conjures up images of mansions, manicured lawns, and Mercedes-Benzes. Not only is it Westchester’s wealthiest town (the median family income is more than $417,000), it’s also one of its best educated; nearly 80 percent of its residents have bachelor or graduate degrees. And their kids are smart, too (or at least good test takers) — Scarsdale students have some of the highest SAT scores in all of Westchester County.
So it stands to reason that its downtown would be packed with pricey boutiques and upscale shops (the natives can afford them), and pretty darn good restaurants (ditto). The downtown consists of about two square blocks of retail shops in quaint split-timber and brick Tudor-style buildings, connected by a couple of arcades and flanked by additional shopping strips. Zachys, a nationally recognized wine emporium, has been the site for oenophiles since 1944. Just across the tracks is Lulu’s Cake Boutique on Garth Road, a favorite of Hill and Martha. And the homes that surround the town? Let’s repeat: the natives can afford them.
Read More: How to Spend a Saturday in Scarsdale
The Vibe: The Beverly Hills of Westchester — where if you’ve got it, you really flaunt it. Lots of designer handbags and designer shoes can be seen about town.
What We Love: The lovely park and bike path that winds along the Bronx River Parkway and Bicycle Sundays when the Parkway is closed to cars from Bronxville to White Plains.
What You Should Know: Construction has eliminated lots of street parking which was already a nightmare, so many businesses deliver.
We like the nightlife, we like to boogie
My teenage daughter and I emerged from a show at the Tarrytown Music Hall on Main Street late one summer night to a wondrous Westchester sight: people, lots of them, sitting at outdoor cafes, walking the sidewalks, laughing, talking, making a night of it.
The gloriously restored Music Hall doesn’t limit itself to music — it also shows movies, hosts comedians, children’s theater, and dance troupes, bringing in lively crowds. Before and after a show there are lots of places to get nourishment (the ribs at Bridgeview Tavern are addicting, as is pretty much anything at the locally famous Twisted Oak).
Stop in at Coffee Labs Roasters for a cuppa. And people come from all over the county to pick up the succulent free-range chickens at Mint Premium Foods. There’s a lot of international diversity in Tarrytown — in both the population and dining options. For Greek, there’s Lefteris Gyro, for Portuguese, try Churrasqueira, and head to Equus for the best gnocchi you’ve ever had.
Main Street Sweets is an old-fashioned ice cream and dessert shop (the best flavor is Cookie Monster — naturally, it’s bright blue). There’s also a whole slew of antiques shops and boutiques selling everything from booties to handcrafted baubles.
The Vibe: Bustling and bohemian.
What We Love: Views of the Hudson River, of course. And Sunnyside and Lyndhurst Castle are must-sees, both particularly lovely during the holiday season. Twice a year, there is a fabulous craft show on the Lyndhurst grounds.
What You Should Know: On the third Friday of every month, retail stores stay open late as Main Street turns into one big party with music, artists, and entertainment such as face-painting and wine-tasting.
An urban oasis
In the 1950s and ’60s, Mamaroneck Avenue was known as the “Fifth Avenue of Westchester County.” Then urban renewal and indoor malls sucked the life out of the city, leaving a dreary landscape of dollar stores and sneaker outlets. All that has changed and White Plains today is humming with activity, around the clock, with wonderful places to dine and some of the best watering holes and singles hangouts in the county.
At night, a virtual river of revelers winds through the bars on Mamaroneck Avenue, Main Street, and East Post Road: Ron Black’s for college kids and recent grads; Brazen Fox for the 20s crowd; Lazy Boy Saloon for beer hounds (it carries nearly 500 varieties), and Vintage Lounge & Restaurant for cover bands and karaoke. There are loads of choices for restaurants too, including Morton’s Steakhouse, City Limits Diner, Mulino’s, and Sushi Nanase — a must!
As for shopping, now The Westchester really is the Fifth Avenue of Westchester County with 150-plus stores (heard of Neiman Marcus? Tiffany & Co.? Gucci?) And of course, Mary Jane Denzer is the last word on county couture.
The Vibe: Lots of hustle and bustle during the day, with business professionals jostling with construction workers, shoppers, and students. At night, the workers depart and 20- and 30-something revelers take over, filling bars and eateries.
What We Love: That wonderful fountain in Renaissance Square that choreographs the water jets to music. Downtown Music at Grace Church in the heart of White Plains and its free 30-minute concerts at noon every Wednesday from September through May. And the multiplex at City Center!
What You Should Know: The city is hyper-vigilant about issuing parking tickets and lots have the type of meter where you have to estimate how much time you need and pay at a kiosk instead of manned booths at exits.