In the winter of 2008 members of the Sterling Ski Club went on a Ski Trip to Europe and while there they met some members of the Winterset Ski Club of Newtown who were skiing at the same resort. By the end of the trip, they had become fast friends and a affiliation between the two clubs was born. Members of either club can take advantage of the other clubs events and trips. Winterset, having no lodge of its own runs a series of day bus trips on weekends to the mountains that are offering CT Ski Council Awareness Days discount tickets as well as overnight trips that Sterling members are entitled to go on. By the same token Winterset Ski Club members may stay at either of Sterling's two Vermont lodges and enjoy all that they have to offer. Below is a list of scheduled trips.