Orange County, NY, is home to some of the Hudson Valley’s most charming walkable villages. With their turn-of-the-century architecture, preserved main streets, and a blend of residential, retail, and public spaces, these communities capture the perfect balance of small-town character and modern convenience. Whether you’re casually strolling with friends, dining al fresco, enjoying live music in the park, or attending one of the many annual festivals, these villages remind us why Orange County is such a desirable place to live.
Here are three great villages to explore year-round in this coveted corner of NY’s Lower Hudson Valley:
Cornwall & Village of Cornwall-on-Hudson
Set against the backdrop of the Hudson River, the twin communities of Cornwall and Cornwall-on-Hudson offer a walkable blend of history, culture, and natural beauty. Close to Newburgh and New Windsor, this community has roots back to the American Revolution and is both scenic and fun to explore:
To Eat
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Prima Pizza – A local favorite for classic pies and Italian-American comfort food.
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Cornwall Coffee Co. – A cozy spot for your morning brew or an afternoon pick-me-up.
To Do
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Riverlight Park (Cornwall) – A peaceful riverfront space to relax, walk, or picnic.
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Donohue Memorial Park (Cornwall-on-Hudson) – Stunning Hudson River views, especially beautiful at sunset.
Don’t Miss
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Bandstand Concerts – Cornwall-on-Hudson regularly hosts free outdoor concerts at the bandstand, drawing both locals and visitors together for evenings of live music and community spirit.
"Prima, The Friendliest Place in Town", at Prima Pizza. Photo by Jacob Matthews © 2025
Village of Warwick
Known for its historic charm and lively downtown, Warwick is one of the most celebrated walking villages in Orange County. The streets are lined with boutiques, farm-to-table restaurants, and cultural spots that make it a favorite for both residents and visitors. Warwick's agricultural backdrop is on display throughout the village where a vibrant farmers market and and infused country but sophisticated vibe resonate:
To Eat
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Rusty Goat – Creative menu with locally inspired flavors.
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Fetch Bar & Grill – Casual and welcoming, perfect for families and friends.
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Fannie’s American Fare – Homestyle favorites with a modern twist.
To Do
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Veterans Memorial Park – A green space ideal for walking, community gatherings, and seasonal events.
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The Village Green – A hub for concerts, festivals, and public celebrations.
Don’t Miss: Warwick Applefest
Each fall, Warwick comes alive for its famous Applefest, one of the largest and most beloved festivals in the Hudson Valley. Drawing more than 30,000 visitors annually, this celebration showcases the very best of the region:
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Local apples and fall produce
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Artisan vendors and handmade crafts
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Live music and family-friendly fun
If you missed it this year, mark your calendar for next October—you won’t want to miss this annual tradition that celebrates Warwick’s deep agricultural roots and small-town spirit.
"Bellvale Creamery - World Famous Ice-Cream | Bellvale - Warwick, NY" - Photo by Jacob Matthews © 2023
Village of Chester, NY
Just a short drive from Warwick, Chester is another walkable village gem that blends small-town life with a vibrant local scene. Its historic downtown and welcoming main streets make it an easy place to spend an afternoon. What’s more is this quaint village has views over the northern edges of Orange County’s famed “Black Dirt” region and is accessible by the Heritage Trail, Orange County's celebrated rail trail!
To Eat
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Breakfast: Valkyrie Coffee – A local favorite for handcrafted espresso and fresh pastries.
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Lunch: Rustic Wheelhouse – Relaxed dining with hearty, seasonal fare.
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Dinner: Allan’s Falafel – Flavorful Mediterranean dishes and a cozy, laid-back vibe.
To Do
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Community Bandstand – Check the local calendar for concerts and events held in the “Black Dirt” field area—a beautiful open-air venue perfect for summer evenings.
- Ride, jog or walk The Heritage Trail. It runs from Harriman to Middletown and has new extensions that will soon run northeast toward the Washingtonville/Cornwall area.
Don’t Miss
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Grab a cold craft beer at Rushing Duck Brewery, a staple of Chester’s local flavor.
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Take a short walk by the historic Yelverton Inn (please note: it’s privately owned, so admire from the sidewalk). The Inn has a historic marker and has direct links to the American Revolution, and George Washington.
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The recently preserved acreage where Revolutionary War Malitias camped on Main St. Look for the NY State historic blue markers.
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Stop by for a sweet treat after your stroll at American House Ice Cream Shack!
"Valkyrie Coffee Roasters - Chester, NY" Photo by Jacob Matthews © 2024
Living Among These Villages
If you live in Orange County and have never explored these villages on foot or perhaps by bicycle - it’s worth doing. It gives you a sense of place and connection and the local small businesses will thank you for visiting. Walkable villages like Cornwall, Cornwall-on-Hudson, Warwick, and Chester offer more than just day trips—they represent the kind of lifestyle many homebuyers are seeking in the Hudson Valley. From historic homes with character to modern residences near bustling town centers, living in these communities means having dining, shopping, and recreation and American HISTORY right at your doorstep.
