THE SCENIC ROUTE
5 Fall Foliage Drives
This season's biggest roadside attraction is leaves in brillant shades of crimson and gold. Break for photo ops, refuel on fresh cider and apples, and check in to a cozy inn.
HISTORIC ROUTE 66
Chicago to Los Angeles, 2,448 miles
Immortalized by John Steinbeck in The Grapes of Wrath, this original mega highway has long personified the American dream of escaping hard times and making it big out West. Although you won't find the 84-year-old road on maps anymore (it's been replaced by segments of the Interstate Highway System), you can still follow the classic drive from the small towns of the Midwest and Great Plains through the deserts of the Southwest and on to Los Angeles.
Don't miss: The 400-mile-long Oklahoma portion best embodies the retro spirit most 66 travelers are looking for, with ghost towns like Texola and sightings of Americana such as the 66-foot-tall soda bottle marking Pops restaurant in Arcadia.
Trip tip: Find (and stay on) the historic route with Here It Is! The Route 66 The Map Series ($12), eight foldout maps with full driving directions and recommendations for the most worthwhile stops.
Where to stay: Wicker Park Inn's brick rowhouse has been a fixture of Chicago's leafy Wicker Park neighborhood since the 1890s (1329 N. Wicker Park Ave., Chicago, wickerparkinn.com, from $139). The eight themed guest rooms—from Cape Cod to Provence to Tuscan—are appealingly understated, not kitschy. On the Oklahoma leg of Route 66, the two buildings that compose the present-day Pollard Inn (124 W. Harrison Ave., Guthrie, Okla., pollardinn.biz, from $150) were christened as the Guthrie Savings Bank and the W.N. Wallace Pharmacy in the early 20th century. The bank's original vault stands among multitudes of other historic relics that decorate the halls and guest rooms.
DOOR COUNTY, WISCONSIN
Milwaukee to Peninsula State Park, 170 miles
The upper Midwest does not leap to mind as a hotbed of culinary genius, but you might want to think again. Across western Wisconsin, there's a minor revolution afoot, a movement to bring back the traditional pies, small-batch gins, Cornish pasties, and Danish kringles the area was once known for. On any given Saturday, particularly on the Door Peninsula sandwiched between Green Bay and Lake Michigan, you're almost guaranteed to happen upon roadside fish boils and farm stands loaded with fresh apples, juniper berries, Montmorency cherries, and, of course, artisanal cheeses (it is Wisconsin, after all).
Don't miss: Fruit wines—including raspberry, cherry, and peach—are gaining popularity among oenophiles, and the county's top-rated quaffs are at Door Peninsula Winery (5806 Hwy. 42, dcwine.com). Just north of the town of Sturgeon Bay, the 36-year-old winery recruited California vintner Paul Santoriello, who has made wines for the likes of David Bruce Winery, a pioneer of cutting-edge production techniques.
Trip tip: Indulge in local specialties, like maplewood-smoked whitefish from Charlie's Smokehouse, where the Voight family has been smoking fish since 1932 (12731 Hwy. 42, charliessmokehouse.com, whitefish $5.50 a pound).
Where to stay: The Feathered Star Bed & Breakfast boasts an address in Egg Harbor, one of our newly crowned "Coolest Small Towns in America" (6202 Hwy. 42, Egg Harbor, featheredstar.com, from $120). Named after the historic "feathering" quilting design, the inn has six guest rooms that play into the theme by highlighting unique quilting motifs. At the Lodgings at Pioneer Lane, seven elegant and spacious rooms are each appointed to send guests on a vacation within their vacation: The Sea Chest Room channels Nantucket, the Cabin Room alludes to the Adirondacks, and the Leaf Room is reminiscent of Scandinavia (9998 Pioneer Ln., Ephraim, lodgingsatpioneerlane.com, from $80).