Exploring the Harpswell Peninsula
There’s no set itinerary for exploring the area. Just drive south from Brunswick on Route 24 or Route 123 until you can’t go any farther, and then backtrack for a bit and strike south again.
Among the “attractions” worth looking for are the wonderful ocean and island views from South Harpswell at the tip of the westernmost peninsula (park and wander around for a bit), and the clever Cribstone Bridge connecting Bailey and Orrs islands. The hump-backed bridge was built in 1928 of granite blocks stacked in such a way that the strong tides could come and go and not drag the bridge out with it. No cement was used in its construction.
A little more than a mile past the bridge, hang a left on Washington Avenue to reach the Giant’s Stairs Trail, a dramatic, half-mile seaside hike with a bunch of great cliffs to clamber around on.

Excursion to Eagle Island
Eagle Island was the summer home of famed Arctic explorer and Portland native Robert E. Peary, who claimed in 1909 to be the first person to reach the North Pole. (We’re still not sure if he did; his accomplishments have been the subject of exhaustive debates among Arctic scholars, some of whom insist he inflated his claims.) Regardless, in 1904 Peary built a simple, shingled home on a remote, 17-acre island at the edge of Casco Bay; in 1912, he added flourishes in the form of two low stone towers. After his death in 1920, his family kept up the home; they later donated it to the state, which has since managed it as a state park, and in 2015, it became a National Historic Landmark. The home is open to the public, maintained much as it was when Peary lived here. Atlantic Seal Cruises (www.atlanticsealcruises.com; [tel] 207/865-6112) leads two 3-hour trips a day from Freeport in the summer, with up to 28 passengers aboard (adults $35, kids 5–12 $25; kids 1–5 $20). Marie L Cruises (www.marielcruises.com; [tel] 207/833-5343) runs out to the island in a cozy former mailboat, with two trips Friday–Sunday in summers from the Dolphin Marina in South Harpswell (adults $30, kids $15). The trip includes a brief coastal tour and 2 hours to wander the island.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.