The Hudson Valley’s Best Main Streets (And Why You Should Live There)

A bird’s eye view of New Paltz. Photo by Ian Poley

By Mike Diago, Robert Rubsam, and Deborah Skolnik

While you can’t fully explore the following locales with the current business shut downs, we encourage you to read about them below and continue your research online in the event you’d like to move to one of these areas. 

Photo by Hector A. Diaz


Beaconites used to play this game on the community Facebook page — “What else does Beacon need?” Suggestions included a dog park, a hardware store, and a butcher; some optimists even wished for the old theater on Main Street to be revived.

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A few years later, dogs are leaping through obstacles at their park, handyfolk are on a first-name basis with Brett’s Hardware clerks, home cooks get tips from Barb the butcher, and movie-goers are checking the marquee at Story Screen Beacon Theater for the first time in around 50 years.

Add those amenities to hiking trails up Mount Beacon and along the river, harvest festivals, free evening cruises held by the Beacon Sloop Club, not to mention nationally lauded breweries like Industrial Arts Brewing Company and Hudson Valley Brewery, and you see why it has been named the “Coolest Small Town in America.” Residents will be quick to remind you however: “It’s a city!”

Photo by Meghan Spiro

The Main Street 

“Your Main Street is your smile, and you don’t want it to have broken teeth,” according to George Mansfield, city councilman and owner of Beacon-based bar Dogwood (above; bottom right). “Broken teeth” are no longer a problem on Main, as each storefront is filled, some with businesses as new and niche as a Hudson Valley Marshmallow Company and others as seasoned and essential as BJ’s Soul Food.

Walking east on Main, the ever-changing silhouette of the buildings provides a frame for Mount Beacon at the other end. As you stroll, you’ll see naturally dyed garments hanging in the windows of Colorant; smell freshly brewed coffee from Big Mouth Coffee Roasters; hear jazz, classical, and folk music coming from the Towne Crier or the Howland Cultural Center; and feel the warmth of your community when you run into neighbors and friends.

Realtor Kimberlee Markarian of Berkshire Hathaway tells us, “I walked into Max’s on Main the other day and saw some friends who were struggling to eat while their baby cried, so I picked up the baby for the rest of the dinner. Things like this happen all the time.”

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Photo by Ian Poley

The Homes 

According to Markarian, over the past four months, single-family homes have ranged from $215,000 for two bedrooms and one bathroom to $995,000 for four beds, two baths, and two half-baths, with a view of the Hudson River.

The Schools 

Beacon City School District has close to 3,000 students across one high school, one middle school, and four elementary schools. “We are a diverse and thriving community that is very supportive of our public schools, ” says superintendent Matthew Landahl.

High school students can take advantage of up to seven AP courses; kids learn about gardening and nutrition through Hudson Valley Seed and Common Ground Farm; a newly formed computer science project, Project Lead the Way, keeps kids ahead of the technology curve; and teachers get professional development through programs on responsive classrooms, restorative practices, equity/diversity, and student engagement.

Photo by Ian Poley


Though Catskill is the seat for all of Greene County, it is the region’s coziest capital by far, with a shop-lined Main Street, local theater troupe, bustling community center, and the brand-new canning center for Crossroads Brewing Company — all easily accessible from the New York State Thruway. Farther afield, residents can take advantage of Dutchman’s Landing, a riverside park with boat launches; and the Audubon Society’s extensive RamsHorn-Livingston Sanctuary, a mix of forest and wetlands that is home to a squadron of birds, including eagles.

The town possesses its own unique mix of history, including a historical designation as one-time home of the real-life Uncle Sam, Samuel Wilson, who is said to have earned the name during the War of 1812 for the markings he would make on containers of packed meat. Also notable is the Thomas Cole National Historic Site, which preserves the home and studio of the father of the Hudson River School, and thus of American landscape painting.

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The Main Street

Catskill’s Main Street has seen a revival over the past five or so years, with a number of new shops, restaurants, cafés, and studios offering many options for both visitors and residents. Magpie Bookshop stocks good-quality used books for fair prices, while Spike’s Record Rack does the same for vinyl.

Gourmands will want to stop in at New York Restaurant for Americanized Polish dishes, with Wasana’s offering the same for Thai food. For those looking to cook at home, the Circle W Market sells gourmet and local groceries. Kirwan’s Game Store stocks many board and card games and hosts frequent card and tabletop tournaments, while those looking to take in a movie can do so at a discount at the local Community Theatre, a massive former vaudeville venue.

One of the most exciting additions has been HiLo, a hip coffee shop/performance space. According to Liam Singer, he and co-owner Laura Davidson “chose Catskill because we were looking for a place to open our business that we could afford, that didn’t yet have a central hub for coffee and casual drinks, and that had a creative community in need of an outlet.” Operating on Main Street, he says, “is a sometimes-exciting, sometimes-challenging, always-fulfilling process of trying to welcome and serve customers from a very wide variety of backgrounds.”

Photo by Leigh Campbell

The Homes

“We are seeing larger 19th century homes on some streets trading in the high $400,000s to $500,000, whereas smaller homes one street over may be trading in the $200,000s,” says David Ludwig, Catskill Office manager of Gary DiMauro Real Estate Inc. “Smaller and more modest, mostly 20th century homes, may be selling in the $150,000 to $200,000 range. First-time home buyers may be taking advantage of federally backed homeowner mortgages such as FHA or VA which require as little as 3 percent down making home ownership very attractive over renting.”

Ludwig adds that “those old brick Main Street commercial buildings are attracting investors looking for bargain prices, as most need updating and reconfiguring for new uses. Around mid $500,000 is the sweet spot. The takeaway is that in today’s strong economy and market, everything is selling. And since it’s a small village and limited real estate market, competitive and multiple offers are not unusual.”

The Schools

In 2019, Catskill residents approved a $40.8 million Capital Project to repair facilities and enhance learning spaces for students to engage with their peers and explore their own learning.

Highlights of the school district, according to Ronel Cook, EdD, superintendent of Catskill Central School District, include: Catskill Elementary School’s recognition as a School in Good Standing by the state education department; middle school students’ demonstrated double-digit growth on the New York State Grades 6-8 English Language Arts and Math assessments; the performing arts and Odyssey of the Mind programs, which are nationally recognized; and high school graduation rates (above 90 percent).

“Many of our graduates have been accepted to elite colleges and universities across the nation,” says Cook. “And our athletic teams continue to excel in the Patroon Conference and advance to state and regional competition.” 

Photo by Ian Poley

Cold Spring

Cold Spring is well-known for its quaintness, but thanks to a community of empowered residents, it has managed to avoid sprawl and has preserved its storybook quality. In 2018, middle school students obtained permission to beautify the train tunnel with a mural and, later in 2019, successfully presented a proposal to the village board for bike racks.

City council members fiercely defend Main Street from chain stores, and they have worked hard over generations to preserve and protect the surrounding natural resources through organizations like the Hudson Highlands Land Trust.

The result is a town where one can stroll through unspoiled neighborhoods of Victorian homes, lay in the grass with an ice cream cone looking across the river to Storm King Mountain, take a kayak ride through the reeds at Constitution Marsh, or scramble up Breakneck Ridge for panoramic views of the Hudson and its Highlands. If you crave the city, the Metro-North can take you there in just over an hour.

The Main Street

Main Street’s natural slope glides pedestrians past little garden cafés (one is even named Garden Café), boutique apothecaries, clothing stores, and pizza and barber shops before landing at the train tracks. Then, if you pass under a the aforementioned tunnel, you’ll find more splendor: a charming little Argentine spot, Rincon Argentino, which has sidewalk tables and a secluded garden; the historic Hudson House River Inn; and the waterfront plaza where kids on scooters circle a little gazebo, all with a magnificent view.

Local resident and author Gretchen Dykstra says, “I don’t think there is anywhere prettier in the Valley.” Dykstra’s favorite spots are Hudson Hil’s, where she meets with a group every morning for breakfast; Split Rock Books, which she says has “become a sort of community center;” and Cathryn’s Tuscan Grill.  

Photo by Hector A. Diaz

The Homes

According to Bill Hussung of Robert A. McCaffery Realty, the median sale price is $540,000. At the time of this interview, there were five homes available, three of which were above $600,000 (one house hitting close to $1.8 million).

“Young couples moving from Brooklyn and Queens are willing to pay the price to live in the village, even if it means a smaller house. They value walkability and amenities more than the house itself,” says Hussung. A home in Philipstown or Nelsonville (still in the school district) can be had for about $400,000-500,000.

The Schools

Every June at graduation, Haldane seniors ring a massive iron bell overlooking the Hudson, signifying their departure from the hillside campus where many have spent their school days since kindergarten. Superintendent Phil Benante tells us that having all grades on one campus “allows high school students to interact with their younger siblings and to maintain relationships with their past-grade-level teachers. It is a very warm environment where meaningful relationships can thrive.”

Students become critical thinkers in their Socratic method circles, innovators in the Discover, Create and Innovate project lab, and involved citizens through their various community-based projects.

Photo by JD Urban Photography


Hudson set the stage for the broader revitalization and gentrification of the Valley’s urban spaces, drawing serious investment, visitors, and new residents from New York City over the last 20 years. Its connections to both New York City and Albany via its Amtrak stop has long made it an arts hub, drawing musicians, painters, gallery owners, and writers.

Not that this is a new phenomenon: Frederic Church’s Olana, both its Ottoman-style home and aesthetically landscaped grounds, are probably the area’s greatest attraction, a piece of high art and world history perched above the city. A number of other parks, nature and wildlife conservation areas, and a boat launch can be found within the Hudson limits, as can a number of big box stores; a brewery; and Basilica Hudson, an arts and events space. The city is also host to Winter Walk, one of the Valley’s oldest and largest holiday festivals, which attracts upwards of 20,000 revelers.

Photo courtesy of Visit Hudson NY

The Main Street

Warren Street — all 1.11 miles of it — has perhaps become the Valley main street, filled with boutiques, antique shops, restaurants, and galleries, many of them housed in historic buildings. The Spotty Dog is the region’s original bookstore-bar, serving up a rotating selection of craft brews in addition to an excellent library of books, as well as art supplies.

Moto Coffee/Machine is a hybrid café/motorcycle shop, competing with a number of excellent coffee shops — including the similarly named Rev Hudson, which has a quiet spot at the top of the street. Hudson Hall at the Historic Hudson Opera hosts concerts, dance events, and education programs, while more off-the-beaten-track places like the Pleshakov Piano Museum serve as testaments to eccentric pursuits. Reliable standbys like Swoon Kitchenbar and Oak Pizzeria Napoletana sit shoulder-to-shoulder with high-class experimental kitchens like Fish & Game.

The latest hot spot is The Maker, a restaurant, lounge, café and hotel, bringing even more visitors to town. Despite generally high prices, the art scene remains strong, embodied by its rock, Carrie Haddad, who opened her eponymous gallery — the city’s first — in 1991.

“When I first moved to Hudson,” says Haddad, “most buildings were boarded up, but there still was a lot of activity… I fell in love with the architecture of the city. The older, most beautiful buildings were closer to the river, but the entire mile length of Warren Street was full of treasures. I had found my heaven.”

The Homes

“House prices in Hudson run the gamut from $250,000 to $2 million,” says James Male, principal broker at HOUSE Hudson Valley Realty. “Your average single-family house on the standard lot of 25 feet-wide by 120 feet-deep will start around $400,000, and a fully renovated charmer on a rare larger lot will quickly approach $1 million or more.”

The Schools

“The Hudson City School District is one of the most diverse school systems in the region,” says superintendent Maria Suttmeier, EdD. “It covers urban and rural areas, and there are more than 10 different languages spoken by our students and families. The variety of cultures and backgrounds represented in our schools is impressive for a small city school district and offers unique learning opportunities. Our written curriculum is relevant and rigorous, but the unwritten curriculum of how to accept people from other cultures is a learning opportunity you cannot get elsewhere in the area. We are also proud to have one of the state’s largest solar panel arrays located on the Hudson Junior/Senior High School campus. The 3,800-panel solar field was installed through a grant at no cost to the district and is expected to save up to 60 percent of our energy costs.”

Photo by Stefan Radtke


Quaint” is a word that’s often overused, but it’s completely appropriate to apply it to this hamlet, located within the town of Bedford in Westchester County. With its own Metro-North station, Katonah is only about an hour’s ride from New York City, yet maintains a distinctly countrified feel. For history enthusiasts, there’s the John Jay Homestead, where the first Chief Justice of the Supreme Court lived in the early 1800s.

And music fans will be drawn to the sophisticated offerings at Caramoor Center for Music and the Arts, a dazzling former estate that now hosts performances by world-renowned artists. Families will love the Katonah Museum of Art and nearby Muscoot Farm. Another bonus is that Katonah Memorial Park — with a pool, tennis courts, and ball fields — is walkable from the village hub.

For those planning a picnic, the Town of Bedford’s recreation and parks department offers free use of a “picnic pack” of outdoor-play equipment such as Frisbees, wiffle balls, jump ropes, and bats.

The Main Street

Katonah Avenue is the central street here, an eclectic collection of boutiques, markets, and eateries mostly housed in Victorian-era buildings. The atmosphere is homey, yet upscale — you’ll find independent Weinstein’s Pharmacy instead of a chain drug store, while cozy Sgaglio’s Marketplace provides top-grade meats, homemade stocks, hand-selected fish, and produce.

It even has an old-fashioned hardware store, Kelloggs & Lawrence (operating since 1887), and family-owned Charles Department Store is nearly 100 years old. As far as dining, The Whitlock can’t be beat for providing exceptional fare in a neighborly space. Richard Dwyer, a resident who was also a Katonah police officer for 27 years, says it’s a great sense of community that makes the hamlet so special: “People really care about one another’s situations and are willing to get involved to help.” In addition, he cites Katonah’s unique origins: “It was the first community to be designed by Frederick Olmsted, the broad roads were designed for the sweep of a carriage, and the trees are second-generation growth.”

Photo courtesy of the Town of Bedford Recreation and Parks Department

The Homes

All of the above comes at a price.  “I just met with a client and went from about $600,000 to $999,000, but there are houses on the market that are over a million,” says Rita Carrozza, a licensed real estate salesperson with Houlihan Lawrence. “I just closed on a home that was $400,000, but that was very unusual.”

The Schools

Katonah-Lewisboro School District’s engaged students and dedicated and talented teachers are at the heart of our district’s excellence,” says superintendent Andrew Selesnick. “All teachers are supported by ongoing professional learning as they aspire towards the ideals of our K-L Learning Commitment. The park-like nature of our community affords the district’s five schools spacious, beautiful campuses and an array of nearby museums and environmental opportunities that enrich our curriculum.”

Photo by Ian Poley

New Paltz

New Paltz residents are never more than a glance away from breathtaking views of the Shawangunk Ridge. Its hulking rock face attracts scrappy climbers from all over the country, looking for that full central-nervous-system tingle that comes with a daring climb.

On the come down, New Paltz provides other ways to balance that invigoration: a pampering at one of the best spas in the country at Mohonk Mountain House, a steaming plate of fresh-rolled pasta at A Tavola Trattoria, a tour of the fine art galleries at SUNY New Paltz’s Samuel Dorsky Museum of Art (including works by Siskind, Tolouse-Lautrec and other world masters), a yoga class at Vitality, or a dance workshop at Unison Arts Center. 

The Main Street

Walking down Main Street, you can tell the people who live among all these amenities full-time by their enlightened glow. The town’s parallel values of creativity and individual voice can also be seen on Main in the anti-war group “Women in Black” who have been protesting in front of the library each week for years, in the most vibrant Pride parade in the Valley, and the New Paltz regatta, where outlandish DIY watercraft thrash down the Wallkill River, which runs past Main, each summer.

Businesses like the New Paltz Hostel and Heady Teddy’s Outfitters imply “college town,” while Main Street Bistro, The Parish (just off Main), and dozens of other restaurants and businesses signal that it is very much a town for adults and families, as well.

John Lefsky, owner of Jack’s Rhythms, a record and book store on Main Street, tells us he came here for college in 1981, from Long Island, and he and many others stayed after graduation because “you can be so close to nature, but also so close to New York City.” 

The Homes

Realtor Dylan Taft of Taft Street Realty tells us, “It is very competitive in New Paltz, and homes don’t last long. Sellers have the upper hand. For family homes expect to pay between $350,000-550,000. Higher-end homes can be priced north of $600,000-700,000, and a handful sell for above a million.

There is a wide range of styles — everything from historic stone 1800s farmhouses all the way up to new energy-efficient construction.

Photo courtesy of New Paltz Central School District

The Schools

“We teach multiple views and value and nurture the diversity of thought in our students,” says recently retired superintendent Maria Rice. “We are one of the few Ulster County schools that offer foreign language beginning in first grade. We have received national ranking for 13 consecutive years by the Washington Post and have been recognized as a Recognition School for high performance and closing the achievement gap by the New York State Education Department.” The district’s middle-level technology program begins in fifth grade, using Project Lead the Way, a program affiliated with the Rochester Institute of Technology, and continues through the high school level. Rice adds: “We have a strong pre-engineering program and college course options for students within our high school, as well as on the campuses of Ulster Community College and SUNY New Paltz.”

Photo by Tim Anderson for Visit Nyack


Once the home of renowned artist Edward Hopper, Nyack is proud of its artistic heritage. Helen Hayes, known as the First Lady of the American Theater, also lived here and founded the Helen Hayes Theatre Company; its offshoot, the Helen Hayes Youth Theatre, was founded in 1998 and is still thriving today. A wide variety of other creative types have also resided here, including actress Rosie O’Donnell and writer Carson McCullers.

The population of Nyack is diverse, as well — nearly one-quarter of residents are black, while nearly 20 percent are Hispanic or Latino. Memorial Park, located close to Nyack’s downtown, is a major recreational and cultural hub, with outdoor concerts and movies, as well as tennis courts, a skateboard park, a butterfly garden, and canoe and kayak launching areas.

For those looking for a more extravagant river adventure, you can take a public sail or private charter with Nyack Boat Charter (they have yachts and tubing, too). Nyack is also known for its many popular restaurants and cafés, boutiques and antique stores, and other arts options such as Elmwood Community Playhouse and Rockland Center for the Arts, in nearby West Nyack. Throughout Nyack, ornate Victorian houses abound, giving the area a charming, stately aura.

The Main Street

A long thoroughfare that slopes to the water, Main Street brims with international flair, thanks to its numerous ethnic restaurants. You’ll find falafel shops, Japanese eateries, French bistros, Thai spots, and more, all within the space of a few blocks. And staples like Hudson House, Communal Kitchen, Boxer Donut, and Pie Lady & Son, attract both tourists and residents.

Small stores rule the roost here, from independent pharmacies and gift shops to Main Street Beat, a boutique offering records, clothing, and books. For nightlife, head to Olive’s or Karma Restaurant, Bar & Lounge.

And for those loving a good street fair, Nyack’s are epic, held from spring through fall, on Main Street, Broadway, and Cedar Street. “Every single time we go into town — or sometimes, just walk out our own front door — we see friends and acquaintances,” says resident Christine Gritmon. “There’s also a feeling of automatic community here. People smile and say hello when passing on the street, even if they haven’t met. I also love how much Nyack loves Nyack. The main internal drama among residents centers around how to ensure Nyack’s continued viability without overdeveloping and losing its community feel.”

Photo courtesy of Visit Nyack

The Homes

“You can buy a fixer-upper for around $345,000 to $375,000. That’s going to be a three-bedroom with a bath or a bath and a half — and an actual close, in-town house, walking distance to the village,” says Frank Mancione, an associate broker with Lydecker Real Estate Corporation. “If you go a little farther out, the property will be a bit bigger and go into the mid-$400,000 range. And then after that, you’ve got houses going from $600,000 to a million.”

The Schools

“Nyack offers a wonderfully diverse student enrollment and a very vibrant and active community,” says James J. Montesano, EdD, superintendent of  Nyack Public Schools. “We are a district that believes in 21st century learning. We provide very relevant curriculum offerings — everything from courses like aerospace engineering and biomedical engineering to medical innovations and music composition. We also have a very robust extracurricular program. Our schools are alive after school, too, whether your interests are musical or athletic.”

Photo by Leslie Hill


Somewhere on a New York subway, a commuter is dissociating from the exhaustion of city life; inside her far-away look is rolling farmland, parks with little streams running through them, friendly candy shop clerks and familiar bartenders at sleepy taverns. In Rhinebeck, those people and places all have names.

Residents become regulars at one of the oldest taverns in the country at Beekman Arms (above) get sweets for their grandkids at Samuel’s Sweet Shop, or laze the day away at Thompson-Mazzarella Park. Seasonal activities like Porchfest in the summer and foliage bi-plane rides at the Old Rhinebeck Aerodrome in fall, punctuate the daily offerings. 

The Main Street

Rhinebeck’s main streets — Mill, Montgomery, and Market — have always been shared by weekenders and residents. George Washington and Alexander Hamilton walked the streets and stayed at the inn at Beekman Arms, and celebrities still find its charms the perfect antidote to their busy lives.

The cajoling melodies of street musician “Scott Sax” set a rhythm for pedestrians as they pass between a splendid lunch at The Amsterdam (above, right), to coffee and dessert at Le Petit Bistro, shopping boutique clothing stories, and independent film at Upstate Films just off.

Kristen Wagner of the popular restaurant Terrapin tells us, “It hasn’t changed much since I was a kid. The building Terrapin is in has been here since 1825, and people who come remember going to church here as kids when it was the First Baptist Church of Rhinebeck.”

John Traver, manager and partner of Samuel’s Sweet Shop, says, “It would be unusual to walk down the street without bumping into someone you know.” Traver’s favorite time on Main Street is the ancient Dutch holiday festival Sinterklaas, which was organized by a rich community of creatives and friends who help keep the small town thriving.

Photo by Jennifer May

The Homes

Gail Lee of Berkshire Hathaway says, “The houses in the village were built in the 1800s, with some from the 1950s or ’60s fit in between. Most buyers are families and long-time residents. There has always been a market for second homeowners, but they are not the majority.

Median home price in the village is $529,000 and $364,000 in the surrounding town.” At the time of the interview, prices ranged from $330,000 for a 1,200 sq ft 1960s ranch to $1.125 million for a 4,000 sq ft 1865 five-bedroom Victorian.

The Schools

Superintendent Joe Phelan retired in January after 22 years at Rhinebeck, and is now serving as interim superintendent. He tells us, “Being a small school, kids don’t feel like they are just one in the crowd; they are more likely to reach out to a trusted adult if they are struggling with anxiety or other issues.”

Phelan also describes some unique traditions like the annual 6th grade student circus and Madagascar Day in the middle school, in which kids can meet live lemurs and Madagascar scholars teach them about the culture. Recent programming, like the implementation of Project Lead the Way — a national K-12 model that provides hands-on learning in computer science, engineering, and biomedical science — have kept the small school on competitive ranking lists like those from the Washington Post, U.S. News and World Report and Top Schools in New York State.

Photo by Louise Hutchinson


Tucked within a protective green belt of rolling hills and farmland, Warwick has a calm, close-knit feeling, and is a throwback to unspoiled beauty. Yet this friendly town is anything but sleepy, thanks to a variety of lively stores and eateries in its downtown area, and a plethora of regionally renowned events.

These include the yearly Applefest in October, which ranks as Orange County’s largest festival and includes music and an apple pie-baking contest; and the Hudson Valley Jazz Festival, featuring a lineup of both local and well-known artists. For year-round fun, Warwick’s half-dozen town parks offer a wide variety of activities and amenities, including fishing, cross-country skiing, horseback riding, and golf.

There’s even a town “beach”— a sandy shore on Greenwood Lake, with a lifeguard-supervised swimming area, children’s play area, volleyball court, and a scenic place for a leisurely picnic.

Photo by Robert G. Breese

The Main Street

Amble down Warwick’s Main Street and you’ll discover both cutting-edge stores — such as Kaliada — whose owner, Kaliada Padilla, makes and sells beautiful, unique custom jewelry — and shops imbued with old-time charm. Frazzleberries, a classic gift store, bursts with rustic knick-knacks. Nearby, the Fizzy Lifting Soda Pop Candy Shop purveys bulk candy, novelty items, and, of course, carbonated beverages. Down the street is Fetch Bar & Grill: Sit at the “doghouse” table and a portion of your check will go to the Warwick Valley Humane Society.

Another can’t-miss is Newhard’s, a 35-year-old gift shop/department store. “What makes this town great is that there’s a lot of pride, resourcefulness, and creativity,” says Michael Newhard, the store’s co-owner and mayor of the village. “You have wonderful shop owners and business people, and there’s an old-time vibe — actually, it’s timeless. There’s also a lot of energy here, with people milling about and shopping. There’s lots to do and see.”

The Homes

Homes between $320,000 and $350,000 are a sweet spot for a first-time home-buyer,” says Nancy Sardo, an associate broker with Green Team New York Realty. “They’re on the market and they’re off the market immediately. “If you have a resale in a village neighborhood that’s absolutely beautifully redone, you’re in probably the high three [hundreds].”

The Schools

“We have incredible students and an extremely talented staff,” says superintendent David Leach, of the Warwick Valley Central School District. “That’s coupled with a community that has such rich human capital and expertise that they share with the students. It extends the education beyond the walls of the schools. You have this community that is so supportive and involved in the educational process, whether it’s volunteering time to help in the classrooms or student organizations.”

Photo by JD Urban Photography


The 1969 Woodstock Music and Art Fair did not happen in Woodstock, but the festival gods bestowed a drop from their acid dropper onto its sidewalks, permeating the village with its legacy as the Catskills mountain home of artists and progressives.

Town historian Richard Heppner tells us, “It is great that we are known for music because of the festival, but the art history is even longer and deeper. The Byrdcliffe Art Colony started here in 1902 and The Maverick in 1905. Then Bob Dylan and his crowd came in the ’60s.”

Resident and author Alison Gaylin moved here with her husband more than 20 years ago, “and have found the community to be warm and welcoming from the start. It’s also been a great place to raise our daughter. Though it’s a small town, there are so many activities for artistically inclined kids, whether it’s the Rock Academy or New Genesis Shakespeare, or the many private dance, music and art classes this very creative community offers.” 

Heppner adds traditions such as Santa’s Christmas Eve arrival on Tinker Street — some years by train or climbing down the church steeple — and various community events also make the town special.

The Main Street

There are actually three main streets in Woodstock — Tinker, Mill Hill, and Rock City — that meet in the center of town at the unofficial town hang, Village Green park. The streets are anchored by long-standing institutions like The Golden Notebook (which David Bowie used to frequent) and Joshuas’s Café on Tinker Street, Bread Alone Bakery (pictured at right) and Pegasus Footwear on Mill Hill Road, and the Colony music venue and Family of Woodstock on Mill Hill.

There is a more recent influx of restaurants and cafés that nail the stylized Catskills cabin aesthetic; on the Mill Hill side, Mud Club sits back on a rocky path serving coffee and wood-fired bagels among the exposed beams and rough-hewn textures, and at 1 Tinker, Shindig’s brunch rush huddles onto unfinished wood bench seats for eggs, thick-cut bacon, and buttermilk biscuits. Shindig’s manager and co-owner Allison Garskoff tells us that like-minded people gather at Bread Alone Bakery in the early mornings before work, the “cool bike-riding crowd” hangs out at Overlook Bicycles, run by Billy Denter, and Woodstock Hardware is still drawing homeowners after close to 70 years. 

Photo by Stephanie Fisher-Meyer

The Homes

Ruperto Ifil, of Halter Associates tells us, “For $250,000 you may have to put between 4 and 12 percent investment up front to make it move-in ready. Turnkey ranch-style homes will go for around $350,000, and the price increases to $500,000-600,000 for with arts-and-crafts homes, colonials, and new construction on large plots. A few properties sell for over a million.”

The Schools

Superintendent Victoria McLaren notes that the district is regularly ranked among the top in the area based on state assessments. She attributes that to the hard work of teachers and staff, along with the support of the community.

“We offer a community mentor program for high school students in which the student identifies an area of interest and they are paired with a community member in that field to engage in an exploratory experience. Also, when students want to create a new club to support their interests, such as the Human Rights Club or the Environmental Club, they are encouraged and supported. Our graduating seniors receive an amazing number of scholarships that are funded by our community to help them transition into the next phase of their lives.” 

Read more: These Are the Best Places to Live in the Hudson Valley in 2021

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