The Town of Montgomery has three villages within its borders – the villages of Montgomery, Maybrook and Walden. It sits in the northern part of Orange County, bordering the Town of Shawangunk in Ulster County to the north, the Town of Crawford to the West and the towns of Wallkill, Hamptonburgh and New Windsor to the south. Walden is in the north central part of the town, while Montgomery is near the center and Maybrook is in the southeast. A summer colony exists around Lake Osiris in the northern section and large swamps are located in the southern section.
The town has business parks on Bracken, Neelytown and Stone Castle roads. The town is also home to the Orange County Airport, which covers 526 acres at Route 211 and State Route 416. The airport boasts 125,000 takeoffs and landings on its two asphalt runways, annually. Many private jets are stored there as well.
Both the Town and Village of Montgomery are named after Richard Montgomery, a brigadier-general in the Continental Army in the American Revolution. The village’s original name was Ward’s Bridge, named for James Ward, who was one of its first settlers who operated a grist mill. Today, the town’s farmer’s market runs from May through November each year, the Montgomery Village Museum shows off village artifacts of yesteryear, and the Grand Montgomery Chamber Music and Theatre Series offers free concerts at 3 p.m. on Sundays at the Senior Center.