Bridgton's winding Main Street (U.S. 302) passes picturesque New England townscapes at every curve. On hot summer days kids dive off the dock at the town beach tucked at the end of Highland Lake, just past storefronts with restaurants, galleries, and shops. Just steps from downtown a covered pedestrian bridge leads to 66-acre Pondicherry Park, a nature preserve with wooded trails and two streams. The town has 10 lakes that are popular for boating and fishing. Come winter, people arrive to ski 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. Come fall, Fryeburg is home to the famed Fryeburg Fair (www.fryeburgfair.com), the region's largest agricultural fair.