Madeline Island, Wisconsin
When people imagine an island getaway, they default to images of the azure waters and white sand beaches that constitute the geography of Corona commercials. That makes sense come February, when sun-starvation has taken hold, but many of the best havens to visit in the fall lie far north (or south) of the equator. A prime example: A 14-by-3-mile slice of the north woods floating two miles off Wisconsin's northern tip in mighty Lake Superior. Madeline Island, a former French fur-trading outpost turned vacation destination turned outdoorsman's getaway, offers summer thrills even after the flannel comes out.
To get there, visitors traveling by car take a 25-minute ferry ride from the lakeside town of Bayfield to the docks at La Pointe, the island's commercial hub. There are a few decent accommodations in town, but repeat visitors tend to rent houses or cabins along the more remote shoreline. A kitted-out house with a full kitchen, living room, loft, and a deck for grilling steaks and drinking local beers won't cost much more than a hotel room in Bayfield.
Once settled, weekenders should start exploring. All of the island's restaurants, bars, coffee shops, stores, and outfitters are right in tiny La Pointe, so Main Street is the best place to start. More specifically, the Beach Club's deck, where a relaxed wait staff serves the best Bloody Marys in town, is the ideal place to start. From there, head toward Big Bay State Park, where hiking trails lead up and over giant boulders on their way to abandoned beaches. Dark sand coves give way to craggy cliffs overhanging carved-out sea caves perfect for exploring, and there's a large lagoon where locals rent canoes by the hour to tourists.
After exploring the coast, head to Tom's Burned Down Café in the heart of town. As the name implies, this joint was reduced to ashes decades ago. Instead of sweeping away the twisted car parts, barrels, and debris, someone (presumably Tom) used it to build a makeshift, roof-less, wall-less watering hole complete with fire pits, boat cushion seats, and a small stage for live music. Tom's gets straight-up rowdy in the summertime, but it's still a hopping scene through the fall as islanders chat up the last of the tourists.
Because northern Wisconsin isn't exactly balmy in fall – the mercury is unlikely to climb above 60 degrees, tee times at the excellent Madeline Island Golf Club are easier to book and leaves tend to turn early. The Bayfield Chamber of Commerce predicts that color will peak in mid-October this year, in time for the Madeline Island Fall Fest, which signals the town's unofficial closure for the season and kicks off on the 19th. Travelers don't have to leave, but they might want to: Bars without roofs and wall don't sling beer in the snow.
More information: The closest major city to Bayfield and Madeline Island isn't even in Wisconsin. Fly United or Delta to Duluth, Minnesota, and drive the hour and 40 minutes across the border to the lakeshore.