Travelers are voting Shawnee Peak and Sugarloaf USA as the best ski resorts in Cumberland County. There are 9 ski resorts near Wakefield a city just 36 km from Cumberland County and 12 ski resorts near Conway which is 38 km distant. The most popular of these are Gunstock Ski Area near Wakefield and Bretton Woods Ski Area in Conway. You can find 14 ski resorts in Maine and 402 ski resorts in the country of United States. Our members favorite in Maine is Saddleback Ski Area and Girdwood is the top pick in United States. Want more? Check out our map of ski resorts in Cumberland County.