Bedford

There’s a white oak standing near the center of Bedford’s historic Village Green, a noble and venerable old tree that was already 200 years old when Puritans from Stamford, Connecticut established the settlement in 1680. These days, Bedford’s oldest citizen still casts a long shadow over the stone wall at the corner of Hook Road and Cantitoe Street, both a symbol of the town’s beauty and a testament to its strength. The Bedford Oak stands less than an hour outside midtown Manhattan, but with its small-town storefronts, horse farms, Revolution-era buildings and laid-back charm, Bedford feels worlds away. “It’s the first place you get to after leaving the city where you feel like you’re truly in the country,” says Lindsay Matthews with Houlihan Lawrence. “People from out of town will say, ‘When are they gonna pave this dirt road?’ But we’re proud of it. It’s a part of our character.”

Many of Bedford’s 2,000 residents are Manhattan transplants, wealthy families and retirees retreating from the bustle of the country’s largest city in search of a slower pace in a greener space. The neighborhood’s sprawling colonial estates also entices celebrities – Martha Stewart and Ralph Lauren call Bedford home – but the celestial stars attract far more attention from Bedford locals, spectacularly visible on clear nights from backyard fire pits. Even with these newer transplants and famous residents, the town has stayed true to its character. “It’s a place from back in time where everybody knows your name,” Matthew says. “I’ve been a resident since 1993, and it really hasn’t changed much.”

The village green at Historic Bedford serves as the cultural and commercial heart of the community, where locally owned wine shops, boutiques, delis and restaurants share real estate with historic buildings dating back to the 18th century, including a courthouse built in 1787 after the British burned the village. The homes surrounding the Village Green are modest, at least by Bedford’s standards. Brick ranches, classic colonials and Cape Cods feature charming rustic touches – white picket fences, woodburning stoves and tiered decks – that highlight Bedford’s historic village vibes. Home prices near the village green range from $700,000 to $900,000.

Drive past the stone walls and tall trees lining the county roads that fan out from Bedford’s village green, and you’ll quickly find yourself among a rustic landscape of pastoral horse farms, quiet woods and spring-fed streams flowing into the lakes that dot the hills. These hills are home to some of New York’s most sought-after hidden estates: classic country-house colonials with horse stables and hay barns, six-bedroom center-hall colonials with decks overlooking private forests, and newer mid-century moderns with private lake access. Most lots in rural Bedford are zoned for a minimum of four acres, providing plenty of privacy along with a price tag ranging from $1.5 to $10 million.

It’s easy to get involved and stay active in Bedford. Check out the outdoor galleries on the Katonah Art Walk, sign up for a pickleball tournament at the Bedford Village Memorial Park, support local theater or screen a classic film at the Bedford Playhouse, or volunteer with Bedford 2030, a local nonprofit aimed at finding creative ways to reduce the neighborhood’s carbon footprint. Birdwatchers wander the hiking trails of Indian Hill Park, a 110-acre natural sanctuary and wildlife refuge along New York’s primary bird migration corridor. Most residents are members at one of Bedford’s two most popular sporting clubs – Bedford Riding Association and Bedford Golf & Tennis – depending on whether they prefer to ride horses or golf carts. Even the local dogs have their own park at the Canine Commons.

The 3,700 students living in Bedford attend the Bedford Central School District, and begin their education at one of the district’s five K-5 elementary schools, all of which are rated among the top public schools in the state. Fox Lane Middle School has an A-minus grade from Niche and shares a campus with Fox Lane High School, where the average SAT score is 1260 and graduating seniors are regularly accepted into prestigious local universities such as Cornell, Syracuse and NYU. Bedford is also home to several prestigious day and boarding schools, including Rippowam Cisqua School and The Harvey School, 100-year-old private institutions where tuition for middle and high school students is over $50,000 annually.

Written By

Jack Hale

Photography Contributed By

Daniel Byrne

Video By

Drew Webster