Lovely brick and clapboard buildings are the highlight of Brunswick's Federal Street Historic District, which includes Federal Street and Park Row and the stately campus of Bowdoin College. From the intersection of Pleasant and Maine streets, in the center of town, you can walk in any direction and discover an impressive array of restaurants, as well as bookstores, gift shops, boutiques, and jewelers.
Below Brunswick are Harpswell Neck and the more than 40 islands that make up the town of Harpswell, known collectively as the Harpswells. Route 123 runs down Harpswell Neck, where small coves shelter lobster boats, and summer cottages are tucked away among birch and spruce trees. On your way down from Cook's Corner to Land's End at the end of Route 24, you cross Sebascodegan Island. Heading east here leads to East Harpswell and Cundy's Harbor. Continuing straight south down Route 24 leads to Orr's Island. Stop at Mackerel Cove to see a real fishing harbor; there are a few parking spaces, where you can stop to picnic and look for beach glass or put in your kayaks. Inhale the salt breeze as you cross the world's only cribstone bridge (designed so that water flows freely through gaps between the granite blocks) on your way to Bailey Island, home to a lobster pound made famous thanks in part to a Visa commercial.