Much of downtown Wiscasset is listed on the National Register of Historic Places, and a ramble among the old captain’s homes and Federal-style mansions is a delightful way to while away an afternoon.
Particularly worth visiting is Castle Tucker (2 Lee St., Wiscasset, 207/882-7169, 11 a.m.–4 p.m. Wed.–Sun. Jun.–mid-Oct., $5), an 1807 captain’s home overlooking the river, with Victorian furnishings and a stunning spiral staircase.
More engaging (and expensive) is the Musical Wonder House (16–18 High St., Wiscasset, 207/882-7163, www.musicalwonderhouse.com , 10 a.m.–5 p.m. Mon–Sat., noon–5 p.m. Sun., tours $10–40), an 1852 mansion filled with antique music boxes and player pianos collected by its eccentric Austrian owner.
Halfway down the Boothbay Peninsula, the Boothbay Railway Village (586 Wiscasset Rd., 207/633-4727, www.railwayvillage.org , 9:30 a.m.–5 p.m. daily, $9 adults, $5 children 3–16, free children under 3) is a required stop for families with children. Trains are, in fact, just the beginning of this 10-acre village that includes a town hall, church, and 26 other structures, as well as dozens of antique cars and firefighting equipment. The namesake railway is a narrow-gauge steam train that takes 20-minute rides around the village.
Down at the end of the point, Boothbay Harbor  is surrounded by four lighthouses that can be viewed by driving around Routes 27 and 96. During summer months, Balmy Day Cruises offers tours of Burnt Island (Pier 8, Boothbay Harbor, 207/633-2284, www.balmydayscruises.com , 7 a.m.–5:10 p.m. daily; 8 p.m. tours available Wed.–Sat. Jul.–Aug.; reduced schedules Mar.–Jun. and Sep.–Nov.; $14 adults, $7 children 3–11, free children under 3), where actors portray the family of an early-20th-century lighthouse keeper, who explains how the beacon actually works.