The last Pilgrim Progress of this summer will be on Friday August 23rd at 6pm. Come witness this long-running tradition! The Pilgrims' first winter in the New World was brutal - by spring, nearly half of the colonists had succumbed to the elements from lack of proper shelter, or disease. Over one hundred years ago, the Town of Plymouth instituted a recurring event to honor these founders, naming it the Pilgrim Progress Reenactment.