U.S. 302 becomes Main Street in picturesque Bridgton, whose 10 lakes are popular for boating and fishing. Steps from the tree-lined downtown with its restaurants, galleries, and shops, a covered pedestrian bridge leads to 66-acre Pondicherry Park, a nature preserve with wooded trails and two streams. On hot summer days, kids dive off the dock at the town's Highland Lake Beach, just north of Main Street at the lake's southern end. Come winter, visitors hit the slopes at Shawnee Peak.
The surrounding countryside is a good choice for leaf peepers and outdoors lovers. A few miles north, Harrison anchors the northern end of Long Lake. In fall, Fryeburg, 15 miles west on the New Hampshire border, is home to the Fryeburg Fair (www.fryeburgfair.com), the region's largest agricultural fair.