Winter Pond, located just north of Winchester Center on either side of Woodside Road, is a charming recreational area. Seasonal activities include bird watching, canoeing and kayaking, sailing, fishing, ice-skating, and unusual opportunities for scenic and wildlife photography. The area is a wonderful natural habitat for wildlife.

Often referred to as Winchester’s hidden treasure, Winter Pond is a classic kettle pond, created in the Ice Age by retreating glaciers. Once much larger, it is about 17 acres in size and is considered a Great Pond of Massachusetts. The Town of Winchester is responsible for its maintenance. Winter Pond is very shallow, approximately 8 feet at its deepest, and has a shoreline of about 1.25 miles, most of which is lined with private residences. Public access to both parts of the pond, Big Winter to the west and Little Winter to the East is on Woodside Road. Wildwood Cemetery borders the easternmost shore of Little Winter.