Spend a day exploring the area’s most picturesque lighthouses and their picturesque surroundings. Begin at Two Lights State Park (free admission), where Maine’s first "twin" lighthouses were erected on the rocky shore in 1928. (The scenery inspired Edward Hopper’s painting Lighthouse at Two Lights.) Trails wind through the 41-acre park, passing abandoned World War II bunkers and picnic tables with Atlantic Ocean views. Head to Fort Williams Park next and climb into the tower of Maine’s oldest lighthouse, Portland Head Light, where a museum ($2 adult admission) stands on what was once a crucial military holding.
Spend an afternoon canoeing and bird-watching at secluded Great Pond. Seaspray Kayaking, based 45 minutes away in West Bath, delivers and picks up canoes ($20 per day, plus $30 for delivery), but call a day in advance to make arrangements. For the quickest access to the trail leading to the pond, park at Fenway Road, off of Fowler Road (see map). Once you’re on the water, watch for common moorhens and least bitterns, two rare marsh species that both reside here.
Take a hike through Robinson Woods, an 82-acre preserve lined with centuries-old trees like eastern hemlocks and red spruces. Grab a self-guided tour map at the information kiosk near the trailhead; it includes ten stations designed to illuminate the lore and biology of native trees. A detailed fourteen-station tree guide is available at the same kiosk or online.
Rent a hybrid or road bike ($25 to $35 per day) from Cycle Mania in Portland and stop by the Cape Elizabeth Land Trust for cycling maps of the area’s many cycling routes. Try the 1.6-mile Spring Point Shoreway Trail, which crosses through a marina and concludes at Willard Beach in South Portland. For a mountain-biking excursion, follow the .8-mile Dyer-Hutchinson Farm Trail, which ambles through forest and connects to the extensive Cape Elizabeth Greenbelt trail system.