Windham: Trails, Peaks and Winter Sports

Windham offers many different reasons to spend your days outdoors: the marked Escarpment Trail runs through the Windham-Blackhead Range Wilderness, Windham High Peak reaches 3,524 feet, and the Windham Path is a family-friendly loop. There are also winter sports at Windham Mountain Club and a local History Trail. Which side of Windham you focus on may shape your choice of vacation rental or vacation home.

Trails, Peaks and Views

The Escarpment Trail is 23.9 miles long, marked in blue, and runs through the Windham-Blackhead Range Wilderness. Cross-country skiing is permitted in the Wilderness in winter. Windham High Peak can be reached from the Peck Road Parking Area; at 3,524 feet, it offers a clear peak destination for planning an active stay. These options offer different points of focus: a longer marked route, a peak destination, or a seasonal activity in the Wilderness.

The Windham Path offers a different scale: this public, family-friendly loop is 1.5 miles long and lies along Route 23, just outside the village of Windham. It passes through meadows and wooded areas, crosses bridges, and offers views of the Great Northern Catskills. It is also the only public access point to Batavia Kill Stream in Windham. If you’re planning a leisurely bike ride or walk, the path offers a family-friendly option for all ages.

The Windham Multi-Use Path is intended for different seasonal activities: in summer, you can use it for walking and biking, and in winter for cross-country skiing and snowshoeing. Its planned connecting function covers Windham’s, Hensonville’s, and Maplecrest’s residential, business, and activity centers along the Batavia Kill corridor. If you include the Path in your day’s plans, check current trail conditions before setting out.

Local History and More to Explore

The Windham History Trail leads to historic homes and scenic spots. It adds a glimpse of local history to outdoor activities. When planning a trip with several interests, you can weigh whether you want your days to focus more on trails and scenery, local history, or winter sports.

Cycling is also offered in different ways: Windham Outfitters offers custom cycling routes for road biking. If this matters to your plans, check with the provider before your trip for current offerings. When choosing accommodations, it makes sense to decide on your main focus first and then assess the specific location of a vacation rental or vacation home against it, rather than assuming the location will be suitable.

Winter Sports at Windham Mountain Club

Windham Mountain Club’s ski area spans 1,600 vertical feet and covers 285 acres; 97 percent of the terrain is served by state-of-the-art snowmaking. The club offers lift tickets and lessons to the public. Its Ski & Ride School teaches guests of all ages and abilities; individual programs may vary in availability. Adult group lessons for ages 13 and up are for first-time skiers and snowboarders as well as beginners. A lift pass is required and must be purchased at the same time as the lesson. Check current conditions, operations, and lesson details with the provider for your dates.

In the Town of Windham, the club also offers three progressive terrain parks for skiers and snowboarders, from beginners to freestyle experts. Windham Mountain Club’s Snow Tubing Park is located in Windham, about a mile and a half from the Lodge; it operates seasonally and is weather-dependent. These offer additional specific winter activities beyond lessons and ski terrain, and you should check current availability before making plans.

Swimming with Clear Conditions

Nearby, CD Lane Park is in Maplecrest, a hamlet in the Town of Windham. Swimming is allowed only in designated areas when a lifeguard is on duty. Access is seasonal and subject to this condition; check current conditions before visiting. This outing offers a different focus from the trails or winter sports and should be planned around the specific conditions for visiting.

Explore more destinations: Acra, Hensonville, Catskill, Hunter, Prattsville, Palenville, Athens, Cairo.

For the broader travel overview: Greene.