Living in Chester, New York

Chester, NY is one of Orange County’s most conveniently located communities. Just off of Route 17, it provides easy access to the New York State Thruway, Routes 84 and 94, and the Bear Mountain Bridge, making it an ideal location for commuters in all directions. Chester is also just a quick drive to the neighboring towns of WarwickLINK TO PAGE, GoshenLINK TO PAGE and Monroe. 

About the Town and its Village and Hamlet

Chester is comprised of the Town of Chester, the Village of Chester and the Hamlet of Sugar Loaf. Each boasts their own conveniences, amenities and vibe – all surrounded by incredible views.

Shopping and Dining

There are several shopping areas within the Town of Chester. Sugar Loaf is a renowned crafts village with quaint shops where artisans sell their wares and tourists come to spend the day strolling the main street, as well as the Sugar Loaf Performing Arts center. The Village of Chester also has a downtown area with its own groups of interesting shops and restaurants. The town itself has plenty of eateries and shopping centers peppered along the main thoroughfare (Brookside Avenue) with anchor chains, grocery stores, pharmacies and more. There are also breweries and a winery where you can relax and unwind.

Recreational Activities

Surrounded by majestic mountains, Chester has several park and recreational facilities, including the Heritage Trail. This 18 mile asphalt and limestone trail, which runs from Middletown to Harriman, is an ideal place for walking, running, biking and rollerblading. It winds through a bird and wildlife sanctuary, historic landmarks, streams, rolling meadows and friendly communities. You can access the trail by the Chester Depot Museum, which has available parking. There are also other popular hiking spots, such as Goosepond Mountain State Park and Birnberg Nature Preserve Trail, which was permanently protected by the Orange County Land Trust. Golf courses, ski trails, and fishing spots are nearby as well.

You can also enjoy other family activities right in the town itself. The Castle Family Fun Center has a game room, go-karts, mini-golf, batting cages and more. There is also a bowling alley and a movie theater.

Schools

The Chester Union Free School District is comprised of Chester Elementary School, Chester Academy Middle School and Chester Academy High School. Many Chester students, however, attend the Warwick Valley School District. It is best to consult with your realtor or the town hall to determine which schools your children would be attending.