A Visitor's Introduction to Windham's Hamlets

A town with two nicknames - "Gem of the Catskills" and "Land in the Sky," as it is perched in the Catskill Mountains - Windham attracts many tourists because of the Windham Mountain ski resort. However, skiing is not the only item on the Windham Things to Do list. While staying at a lovely Windham Bed and Breakfast, visitors can explore Windham's communities and hamlets. Here is BBonline's introductory guide to Windham, Maplecrest and Hensonville, the three hamlets of Windham.


Perhaps named after either the town or county of Windham in eastern Connecticut, as many of the area's early settlers came from that part of the state, the hamlet - more specifically, Main Street's business district - has had various names throughout the years. It was once called "Batavia" after both the Batavia Kill, the stream that courses along the village, and the Batavia Patent, the piece of land on both sides of the stream. Then, it was called Osbornville when, in 1831, Bennet Osborn was named the first postmaster of the post office instituted there. A mere five years later, the name was changed to Windham Centre. In 1873, the word "centre" was dropped and the name was shortened to Windham.

While in the hamlet of Windham, things to do include catching Windham Chamber Music Festival performances at the Windham Civic & Performing Arts Center and driving to Windham Mountain. There you can ski, skate and have winter fun with the whole family.

Windham Chamber Music Festival
740 County Route 32C
Windham, New York 12496
(518) 734-3868

Windham Mountain
33 Clarence D Lane Road
Windham, New York 12496
(518) 734-4300


Named after John Henson, the hamlet's postmaster in 1853, Hensonville is located in the southern part of the town. Prior to that, it was called Bailey’s Four Corners after Ethan S. Bailey, the first postmaster and his house that created 4 corners by standing near the intersection of County Route 65 and State Route 296. Today, it seats the town government.

There is a beautiful Windham Inn located in the hamlet of Hensonville that is worth a visit. While there, you can add several dining options to your Windham things to do list, such as Taste of China, Vesuvio and Kountry Kitchen Ice Cream Parlour & Restaurant.

Taste of China
387 State Route 296
Hensonville, New York 12439    
(518) 734-4800

Vesuvio Restaurant
49 Goshen Road
Hensonville, New York 12439    
(518) 734-3663

Kountry Kitchen Ice Cream Parlour & Restaurant
State Rte. 296 Main St.
Hensonville, New York 12439    
(518) 734-9811


Located 2 miles southeast of Hensonville lies the hamlet of Maplecrest, named after streets lined with maple trees and mountain tops. Before 1921, it was known as Big Hollow, a description the small community nestled in a valley or "hollow" surrounded by the highest peaks in town. Visitors had trekked these mountains because of perceived curative properties high altitude, pure water and clean air were thought to have. It is easy to see how this hamlet earned Windham the nickname "Land in the Sky." The name was changed when using the word "hollow" was thought to dissuade tourists from coming to the place.

While in this hamlet of Windham, things to do are aplenty because Maplecrest is home to C.D. Lane Park. There families can so swimming, canoeing and fishing in C.D. Lane Lake; play sports in the regulation outdoor basketball court, baseball diamond, and soccer field; have picnics and grill barbecues; and take shelter in the pavilion, in case it rains.

C.D. Lane Park
281 County Route 56
Maplecrest, New York 12454
(518) 734-4170