Find Family-Oriented, Walkable Villages in the Valley

A glimpse of Hudson Valley small-town family life can be seen in the Veterans Day parades, harvest festivals, and weeknight committee meetings that keep it going.

A glimpse of Hudson Valley small-town family life can be seen in the Veterans Day parades, harvest festivals, and weeknight committee meetings that keep it going. Parents make their voices heard on school boards, neighbors offer recommendations on trustworthy contractors, and kids on bikes fly up and down main streets, blissful and secure throughout their childhoods.


Bethlehem High School. Photo provided by Bethlehem Central School District

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Starting upstream, the Albany suburb of Bethlehem (and its hamlet Delmar) is most well known for Bethlehem Central School District’s position near the top of every school ranking. For the second year in a row, Buffalo Business First has ranked it 5th of upstate NY’s 431 districts. Niche gives the school a rare A+ grade overall. Bethlehem looks very much like the suburb it is; cul-de-sacs, raised ranches, and well-kept lawns dot the landscape, but it also features a charming village center in Delmar with local favorites where regulars bump elbows and school kids congregate on lunch hour.

A recent college graduate tells us, “McCarroll’s Village Butcher is the place to go for the absolute best breakfast sandwiches.” Like other Capital Region locales, it is only a few hours from Boston, Montreal, and NYC for longer city getaways, and is close to both the Catskills and Adirondacks for outdoor adventuring. Homes in Bethlehem are among the most affordable in the area, ranging from $150,000–$400,000.


Photo by Daniel Case

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Down river, in northern Dutchess County, Red Hook (above) offers a mix of the beauty and solitude that weekenders look for, along with the jobs, in-town cultural offerings, strong community, relative affordability, and high-performing public schools (they get an A- rating on Niche), making it attractive to families year-round. Town supervisor Robert McKeon lists a range of employment options including jobs in education at Bard College and Red Hook Central School District, healthcare at Northern Dutchess and Columbia Memorial hospitals, and small business — “The Red Hook Chocolate Factory now serves as the premiere HV incubator, with over 30 small businesses under one historic brick building.” The main streets are in many ways defined by those businesses, and the village stands to get an additional boost in 2020, when a new commercial district will be underway, McKeon tells us.


Old Rhinebeck Aerodome. Photo by Phil (Ghost) Makanna


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Bard College also brings cultural capital with architecture from Frank Gehry, the gallery at CCS Hessel Museum of Contemporary Art, and events at Richard B. Fisher Center for the Performing Arts. There’s also plenty of old-fashioned fun, including farm visits, classic airshows at the Old Rhinebeck Aerodrome, and sweet-tooth delights — like their regionally famous Holy Cow Ice Cream Shop, the annual Chocolate Festival, or the cinnamon buns at the Historic Village Diner (also the best place for local gossip among the whole cross-section of residents) — to keep them buzzing. Two- to four-bedroom homes in the town are affordable, ranging between $200,000–$350,000.


Warwick Center for the Performing Arts. Photo by John Desanto


In the case of Warwick — most known for its massive annual apple festival — many of the newcomers are actually just returning home. Melissa Padham grew up there before following a dance career to NYC, London, and then finally back home, where she took over operations at the Warwick Center for the Performing Arts. She tells us, “I see people who moved away coming through the doors of my dance studio with their kids now all the time. I couldn’t imagine starting a family anywhere else.” Padham explains that it has “maintained a small-town feel, even through all of its cultural, economic, and population growth. There’s still a sense of comfort in allowing your children to run around without worrying.” A quick stroll down Warwick’s sweet-as-apple-pie Main Street reveals a lack of national chains, a signal of the community’s values. The school district gets an A grade on the Niche rating site; houses range from $250,000 for a small village cottage to $650,000 for a five-bedroom farmhouse tastefully restored with every rustic detail.


The view of Storm King Mountain from Cold Spring. Photo by AHODGES7


While many of our favorite Valley towns maintain a vibrant local economy through keeping big business out, this may be truer than anywhere in Cold Spring, which has a Main Street that slopes down continuously towards the water, opening up to a town plaza on the river across from the hulking Storm King Mountain.

Cold Spring’s Haldane High School was recently profiled by this magazine as one of the most outstanding public high schools in the area, not just because of its local and national rankings but because of the familial culture and creative academic approaches they are taking.

Cold Spring Apothecary. Photo by Chris Wesselman


When school lets out in the summer, the town takes on a new life with days spent hiking Breakneck Ridge or kayaking through the Cold Spring marshes, followed by evening movies on the waterfront with Moo Moo’s ice cream and pizza from Cold Spring Pizzeria in hand. This kind of living comes at a cost, however; even the smallest houses in the central village usually cost well over $400,000.

First Village Coffee in Ossining. Photo by Ana Maria


Where the family-focused small towns on our list leave slim options for those seeking diversity, Ossining provides a welcome reprieve. More than 56 percent of the village’s residents are minorities, and the village and school embrace that change. Assemblywoman Sandy Galef, who has been there since 1969 and has seen her children and grandchildren grow up in Ossining’s public schools, tells us, “Ossining is a real-life place and reflective of the world we live in today. There are so many community organizations here that can satisfy and stimulate one’s need for local involvement. A new resident can be just as involved in those things as those who have lived here a long time. Community participation and diversity is Ossining’s strength.”


Ossining Waterfront. Photo by Gregory Perry


With this comes a great array of eateries like First Village Coffee, Cravin’ Jamaican Cuisine, and Aji Limo Peruvian Cuisine; well-protected outdoor resources like the Old Croton Aqueduct and Teatown Lake Reservation; and exciting events like the annual village fair in June and concerts at the waterfront park. The schools play to their strength through bilingual education, and the high school is strong in academics and sports. In 2018, four students were named Regeneron Science Talent Search Scholars, and one of those students won 8th place in the nation.

The largest employer is Sing Sing Correctional Facility; but with under an hour’s Metro-North ride to Manhattan, employment options are endless. In fact, it has been the nightly landing spot for generations of commuters — as seen in Don Draper’s character in Mad Men, which was based here. Houses in town are available across a wide price range. An online search shows 3-bedroom, 2-bath houses around $300,000 that require some TLC up to 5-bedroom newer houses at $500,000.


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