A Glimpse of Washingtonville
Tucked into the rolling hills of Orange County in the lower Hudson Valley, Washingtonville feels more like a friendly front‑porch community than a stop on a grand travel itinerary.
Yet that’s exactly why it’s such an inviting town to visit. You’re just over an hour from New York City, close to Stewart International Airport, and surrounded by rivers, farms, and mountain views—perfect for a relaxed weekend or quick day‑trip adventure.
While folks searching for homes for sale in Washingtonville often rave about the small‑town vibe, casual visitors discover plenty of top attractions to find, explore, and simply enjoy today.
Explore the Outdoors Around Washingtonville
Mays Field and the Heritage Trail
Locals treat Mays Field like their communal backyard. Y
ou’ll see pick‑up soccer under the lights, parents strolling with coffee, and kids racing to the fenced playground. On the far edge, the paved Heritage Trail slips south toward Chester and north toward Goshen—a beautiful 19‑mile greenway that once carried the Erie Railroad.
Walk, jog, or bike the gentle route for an easy hike past wetlands, wildflowers, and grazing horses before looping back for ice cream in the village.
Brotherhood Winery Grounds
Even before you sample a sip, it’s worth wandering the leafy paths around Brotherhood Winery, America’s oldest continuously operating winery.
Vine rows, stone cellars, and seasonal picnic tables create a storybook backdrop for selfies or a casual sandwich from town. Live‑music lawn parties pop up in summer, and lantern‑lit walks feel downright cinematic in October.
Discover the History and Culture
Brotherhood Winery – America’s Oldest Winery
Founded in 1825 and still turning out crisp Rieslings and bold Baco Noirs, Brotherhood doubles as both tasting room and living museum. Take the cellar tour to see hand‑chiseled tunnels, sip reserve wines, and hear how bootleggers kept the barrels rolling through Prohibition.
The restored chapel hosts small concerts and, rumor has it, the resident ghost of a 19th‑century cooper who never clocked out.
Local Historical Buildings and Churches
Washingtonville’s Main Street still shows off 1800s brick storefronts, clapboard art studios, and white‑steepled churches.
St. Mary’s sports vibrant stained glass, while the First Presbyterian Church (est. 1831) anchors the village green and often hosts seasonal craft fairs.
Wander slowly, because you’ll spot hidden plaques telling tales of blacksmiths, canal diggers, and even an early mission school that once served farmhands’ children.
Eat and Sip Like a Local in Washingtonville, New York
Popular Spots to Eat in Town
Start with hand‑tossed pies at Rustic Wheelhouse in nearby Chester.
For lunch, Fiddlestix Café in Cornwall keeps the brunch crowd happy with thick‑cut French toast and creative salads reviewed here.
Dinner? Washingtonville’s own Copperfield’s gastropub pairs short‑rib poutine with Hudson Valley microbrews, proof that small‑town restaurant culture comes with big‑city flavor.
Where to Grab a Drink or Treat
Need caffeine? Grapevine Café pours maple lattes in a converted railroad station.
Craving dessert? Hop over to Quickway Twin Cone for swirl‑soft serve, a childhood rite for anyone growing up around Washingtonville.
After dark, the taps flow at Long Lot Farm Brewery, whose farm‑to‑glass ales regularly feature live acoustic sets—an easy way to meet local musicians and swap hike stories with fellow travelers.
Seasonal Events and Activities
Fall Festivals and Apple Picking Nearby
When October colors the Maples neon red, Washingtonville turns into postcard country.
Families plan day trips to Apple Ridge Orchards or Lawrence Farms Orchards for apple picking, cider doughnuts, and hayrides with sweeping Hudson Valley views.
In the village, the annual Whoville Celebration dresses downtown in Dickensian costumes and ends with a glittering tree‑lighting event on December streets.
Holiday Lights and Winter Markets
Handmade wreaths, warm cocoa, and Victorian carolers define December weekends.
Pop‑up vendors sell ceramics, honey, and retail crafts under twinkle lights at Veteran’s Square, while horse‑drawn wagons jingling past storefronts offer a unique step back in time.
Neighboring Blooming Grove even runs a friendly house‑decorating contest that lights up snowy lanes each year.
Summer Concerts and Outdoor Fun
July sunsets mean lawn chairs at Vern Allen Park for free Friday concerts. Pack a blanket, grab tacos from a food truck, and let kids chase lightning bugs between songs.
Daytime heat? Cool off while tubing the Moodna Creek or rent a kayak on the Hudson River just nearby in Cornwall Landing.
Day Trips and Nearby Attractions
Got extra gas in the tank? Ten minutes north, Storm King Art Center sprawls over 500 acres of monumental outdoor sculpture, perfect for an artist‑inspired photo safari.
Bargain hunters head to Woodbury Common Premium Outlets for designer deals, while aviation buffs tour historical planes at Stewart Air National Guard Museum.
Hikers chase panoramic trail panoramas on Schunnemunk Mountain, and kids love the drive‑through safari at nearby Animal Adventure Park.
There’s truly plenty of places to turn a single trip into a multi‑stop journey.
Why Washingtonville is Worth the Visit
Big‑city stress evaporates the moment you step onto Main Street’s old brick sidewalk.
There’s plenty to keep you busy, yet you can still slow‑sip a latte, chat with shopkeepers, or simply relax on a bench and watch the world drift by. That blend of history, community spirit, outdoor activity, and a surprisingly top‑rated dining scene makes Washingtonville an essential Hudson Valley destination in 2025.
Whether you’re scouting plenty of places to stay before house‑hunting, or you’re a casual travel user just looking for something fun to do today, this little village delivers a warm welcome and a wide‑open schedule.
FAQ’s About Things to Do in Washingtonville, NY
What’s the best time of year to visit Washingtonville?
Mid‑September through late October offers peak foliage, winery harvest events, and perfect hoodie weather. Summer is lively with concerts; winter brings cozy holiday markets.
Is the Heritage Trail suitable for kids and strollers?
Yes. The surface is mostly paved and flat, making it stroller‑friendly, bike‑friendly, and wheelchair accessible for several miles through the county.
Can I tour Brotherhood Winery without tasting wine?
Absolutely. History buffs often book the cellar tour for its 19th‑century architecture, then browse the gift shop for local jams and artisanal chocolates.
Are there public transportation options to Washingtonville?
Short Line buses run daily from Port Authority in NY, and rideshares from Stewart Airport cost about the same as city taxis. Once in town, everything’s within walking distance.
Where can I find up‑to‑date information on local events?
The Washingtonville Community Events calendar posts festivals, markets, and concerts year‑round, making it a handy one‑stop resource before you plan your calendar Washingtonville Community Eve.
