Bar Harbor: 270 miles NE of Boston; 160 miles NE of Portland
Mount Desert Island is home to spectacular Acadia National Park, and for many visitors, the two places are one and the same. Yet the park's holdings are only part of the appeal of this popular island, which is connected to the mainland by a short causeway. Besides the parklands, there are scenic harbor-side villages and remote backcountry roads aplenty, lovely B&Bs and fine restaurants, oversize 19th-century summer "cottages," and the historic tourist town of Bar Harbor.
Mount Desert Island is split in two by an inlet. Most of the park's land is on the eastern side of the island, though there are some vast holdings in the west, too. The eastern side is much more heavily developed. Bar Harbor is the island's center of commerce and entertainment, a once-charming resort now in danger of being swallowed up by T-shirt and trinket shops. The western side has a quieter, more settled air and teems with more wildlife than tourists; here, the villages are mostly filled with fisherman and second-homers rather than actual commerce.
The island isn't huge -- it's only about 15 miles from the causeway to the southernmost tip at Bass Harbor Head -- yet you can do an awful lot of adventuring in such a compact space, and see many different kinds of towns and landscapes. The best plan is to take it slowly, exploring if possible by foot, bicycle, canoe, and/or kayak, giving yourself a week to do it. You'll be glad you did.
See It, Say It: What's for Mount Des-sert? -- There is some debate about how to correctly pronounce the island to which I'm referring in this section. The name is of French origin; technically, it should be "Mount days-airt," but nobody says it that way anymore. Some locals say "Mount des-sert," like what you have after dinner, which is pretty close to the French way of saying things. (Notice the accent on the last syllable.) However, plenty of tourists, transplants, and locals also say dez-ert (like the Sahara), and that's not wrong . . . after all, that's how it's spelled. Pretty confounding.