Things to Do in Chester, NY: Sugar Loaf, Trails and Country Charm

by Ammar Iqbal

By Ammar Iqbal | Real Estate Salesperson, eXp Realty

Chester, NY combines easy highway access with plenty of country charm. It's a convenient place to live, and it has some unique spots that make weekends fun. Here's what locals enjoy in and around Chester.

Explore Sugar Loaf

The hamlet of Sugar Loaf, in the Town of Chester, is known for its arts-and-crafts shops, galleries and small eateries. It's a relaxed place to browse, and the Lycian Centre there hosts performances and shows.

Hike Goosepond Mountain State Park

Goosepond Mountain State Park offers wooded trails and quiet nature right in the Chester area, great for an easy hike or a walk with the dog.

Craft shops in the hamlet of Sugar Loaf, NY

Walk or bike the Heritage Trail

The Orange County Heritage Trail runs through Chester, connecting it to Goshen, Middletown and Monroe. It's a flat, paved path that works for everyone, from runners to families with strollers.

Farm stands and the countryside

The area around Chester has farm stands, open fields and scenic back roads. Warwick's orchards and the black dirt farm region are a short drive away.

Farm fields near Sugar Loaf in Chester, NY

Everyday convenience

Chester has shopping centers, restaurants and services close by, so daily errands are easy. With Route 17 and Route 94 nearby, getting around Orange County is simple too.

Sugar Loaf Mountain above farmland in Chester, NY

Is Chester right for you?

Chester offers a mix of single-family homes, townhouses and condos, which makes it popular with first-time buyers and downsizers. Learn more in my guides on buying a home in Chester, the Village vs. Town of Chester and buying a condo in Chester. You can also visit my Chester, NY real estate page.