Pilgrim Lake is the largest of Orleans’ freshwater ponds at 43 acres and 34 feet to bottom at its deepest point. Since it is over ten acres, it is a Great Pond owned by the Commonwealth of Massachusetts. Pilgrim has a V-shape (heart shape) with a small island. It is accessible from the end of Herring Brook Way.

There is a town landing including a large swimming beach and restroom facilities, with parking for ~20 cars, at the end of Herring Brook Road. Pilgrim requires a town sticker during the season.

The public beach is used for swimming lessons for all ages during July and August. It has shade trees as well as a full sun beach with picnic tables and restroom facilities. The shallow waters allow easy access for children and elders with mobility issues, with a ramp into the water.