Windham’s activities draw homebuyers and tourists to the Catskills
New Yorkers started vacationing in the mountain town of Windham as early as the 1820s, but the community in the Catskills saw tourism increase to a new level when a ski resort opened in 1960. Many visitors make the two-and-a-half-hour drive from New York City to Windham, where a Main Street of local restaurants and shops is surrounded by slopes, summits and forests that pop with red and orange leaves in the fall. The Windham Mountain Club ski resort is one of the area’s biggest draws, but local recreation extends beyond the slopes to hiking, mountain biking and fishing. While the community sees a slight dip in activity in the spring, its outdoor activities are varied enough to keep homeowners and tourists around for most of the year, says Carol Shaw, owner and broker of Shaw Country Realty and a Windham resident. In fact, she compares Windham to a popular recreation town in the mountains of Colorado. “It’s almost like an eastern Boulder.”
A choice between secluded retreats and houses with resort amenities
Mountainside homes line the roads winding alongside the ski slopes. Condos and townhouses are often part of resort communities with high HOA and condo association fees, but they typically come with amenities such as swimming pools, fitness centers and tennis courts. Single-family chalets tend to be more private. There are more single-family homes to the north; they’re farther from the slopes, but they often have direct views of the mountain. Whether they’re condos, townhouses or single-family properties, homes are commonly designed with features typical of cabins: timbering, stone foundations and A-frame roofs.
Older condos and townhouses have recently sold between $200,000 and $650,000, while newly built townhouses can cost between $1.7 million and $2 million. Single-family properties with less than four bedrooms typically sell between $310,000 and $695,000, while larger homes can fetch between $700,000 and $2.3 million. Some homeowners rent out their properties to vacationers to make extra income, Shaw says. The CAP Index Crime Score is 1 out of 10, lower than the national average of 4.
Skiing and golf at Windham Mountain Club, with more to do in the area
The main draw to the community is Windham Mountain Club’s ski slopes. In 2023, the club created memberships and limited the availability of daily ski passes as the resort rebranded as a semi-private club. With lifetime memberships priced around $200,000, some locals choose to drive from their homes in Windham to surrounding ski resorts, Shaw says. Windham Mountain Club also has an 18-hole golf course that’s open to the public and members, while its horseback riding experience is limited to members and resort guests.
When the snow melts, recreation doesn’t dry up. The mountainous region is known for hiking, and The Windham Path creates a nearly 2-mile trail through meadows and over creeks at the base of a mountain. The gentle terrain makes it a leisurely trek for hikers and cyclists, as well as cross-country skiers. Trout fishers wade into the Batavia Kill, while rowboats and canoes are welcome at North-South Lake, about 15 miles outside of Windham.
Windham-Ashland-Jewett Central School District confined to one campus
Windham-Ashland-Jewett Central School teaches kindergarten through 12th grade, receiving a B grade from Niche. Although the school teaches every grade level, the student population is small enough to keep class sizes compact. At the high school level, more than half of students take college-level courses, whether they’re Advanced Placement classes or dual-enrollment offerings. Dual-enrollment students can earn college credits from institutions such as Columbia-Greene Community College and Syracuse University, potentially graduating from high school with a two-year college degree.
A quaint Main Street among the mountains
The heart of the community was built along Main Street. Mountain peaks poke over the roofs of taverns and shops and rise behind the steeples of Windham-Hensonville United Methodist Church and St. Theresa of the Child Jesus Roman Catholic Church. Tourist dollars support more than a dozen restaurants in the small town. The Chicken Run serves fried chicken and steak and invites country and rock musicians to play multiple nights per week. There’s a small selection of groceries at Main Street Market, a butcher and deli. The closest supermarket is a Hannaford about 15 miles east, or “down the hill,” as Shaw says. “If people are coming up here with a family, we say to stop there first.”
Windham Chamber of Commerce and local venues host events
The Windham Chamber of Commerce puts on community events throughout the year, from free summer concerts at CD Lane Park to the Autumn Affair Fall Fest in October. Farmers, bakers and other vendors sell their goods downtown at the Windham Farmers Market, held Saturday mornings from May to October. Historic homes and barns in the countryside have been converted to event venues, hosting weddings, company retreats and more.
Nearby I-87 leads to New York City, Albany
Windham sits along state Route 23, a highway through the northern section of the Catskills. It’s about 25 miles to Interstate 87, which drivers can take 30 miles north to Albany or 120 miles south to New York City. Planes fly directly to two dozen cities from Albany International Airport. There aren’t any hospitals in the immediate area, so residents must drive 40 miles to Margaretville Hospital for medical care.
![Alex Soderstrom]()
Written By
Alex Soderstrom
