Greenville, tucked at the southern end of island-dotted, mostly forest-lined Moosehead Lake—at 75,000 acres, Maine's largest and the largest entirely within New England—is an outdoors lover's paradise. In the mid-1800s, Henry David Thoreau departed from here on two of his three famous trips into Maine's wilderness, led by Penobscot guides Chief Joseph Attean and Joseph Polis. In summer, boating, fishing, kayaking, canoeing, and hiking are popular in Moosehead Lake. Come winter, folks head here for ice fishing, snowmobiling, snowshoeing, and cross-country and downhill skiing—you can enjoy both at Big Squaw Mountain ski area just north of town. Greenville has the best selection of shops, restaurants, and inns in the North Woods region. Restaurants and lodgings are also clustered 20 miles north in Rockwood, where the Moose River flows through the village and—across from Mt. Kineo's majestic cliff face—into the lake. There's also a hip cluster in hiking hub Monson, 14 miles south of Greenville. Maine's 100 Mile Wilderness, home to the most difficult and most northerly stretch of the Appalachian Trial, stretches from here to Mt. Katahdin.


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