Surfing on Lake Michigan is a year-round obsession. For some, anyway. "The only thing that stops us up here is ice," says Ryan Gerard, owner of Third Coast Surf Shop in New Buffalo, a one-stoplight town about 90 minutes from Chicago. The key to November surf, the best of the year, is wind. "November’s more likely than any other month to bring the weather systems we need to create waves," says Gerard. When the elements cooperate, grab a 6.5-mm wetsuit, 7-mm gloves and boots, and make for the lee of a pier or jetty to surf the swell that wraps around the obstruction. New Buffalo’s South Jetty is Gerard’s favorite local break. Between sets, settle in at the Harbor Grand Hotel (doubles from $149; harborgrand.com) and try the tacos at Rios for lunch and pasta at Brewster’s Italian Café for dinner.
The 473-foot Texas Clipper once ferried troops to Iwo Jima and shuttled the wounded home. In the 1950s, she pleasure-cruised the Mediterranean. But for the past year the Clipper has rested 17 nautical miles off South Padre Island in 67 feet of water. According to Tim O’Leary of American Diving, she’s "the biggest fish-attracting device in Texas." AD offers a new all-day, three-dive trip—two to the ship, one to an oil rig—called Tons of Steel ($200; divesouthpadre.com). Divers on the reefed Clipper spot red snapper, turtles, and sharks, but the ship is so large "you can dive a hundred times and still not see everything," O’Leary says. For a friendly beachfront vibe, crash at the Wanna Wanna Inn (doubles from $70; wannawanna.com).
Choose your weapon: mountain bike, kayak, or hiking boots. Cane Creek State Park, in the Mississippi Delta south of Pine Bluff, is a multisport playground. By mountain bike, ride the rolling 15.5-mile Cane Creek Lake Trail through a maze of small creeks and deep draws, crossing three suspension bridges en route. Hike that same trail and return to Cane Creek State Park campground, near the park entrance, to settle in for the night. On day two, you can slalom the lake’s lily pads and bald cypresses in a kayak while watching ospreys, woodpeckers, herons, kingfishers, and wintering bald eagles (camping, $17; kayaks, $15; arkansasstateparks.com/canecreek).
Kentucky, with its sandstone arches and Native American echoes, could be called the Utah of the East. There are over 150 delicate spans within a ten-mile radius of Natural Bridge State Park, and even more rock shelters—cavelike indentations that once housed local tribes. Sand Gap Trail (7.5 miles) is the park’s best hike, starting out in a valley full of eastern hemlock and winding through mixed woods before reaching the bridge. "The terrain is extremely rugged," says naturalist Brian Gasdorf. "Even our ‘easy’ trails are rough." Hemlock Lodge has doubles starting at $85 (parks.ky.gov/findparks/resortparks/nb).