See the 2016 Travel Calendar at a Glance
This picturesque peninsula juts 75 miles into Lake Michigan and is dotted with ice cream stands, mom-and-pop diners, and intimate inns—the natural beauty of the Hamptons with a down-to-earth Midwest vibe. Visitors peak in July (cherry season), and by early October the Wisconsin Scenic Byway is clogged with leaf peepers. But September is the sweet spot: Days hit 70° F, the water is at its warmest, and the crowds are all but gone. Hotel prices are up to 40% or more off their midsummer peak.
|What to do
The shop at Egg Harbor’s Wood Orchard is stocked with cherry-preserved everything: jams, ready-made pie filling, juice, and more. Later in the month, you can pick your own apples at Orchard Country Winery and Market in Fish Creek. Climb nearly 100 steps to the top of the Cana Island Lighthouse, one of 11 in the county, for a bird’s-eye view of Lake Michigan. But the real attraction here is the 300 miles of shoreline and its 53 public swimming beaches, including Whitefish Dunes State Park, with the tallest dunes in the state.
|How to save
Average September hotel rates are around $104 a night, according to travel research site STR, though a waterfront room can run $225. This month, rates at the Landing Resort ($90 a night) and the Newport Resort ($129 a night), both in Egg Harbor, come in 30% to 40% lower than summer stays.
Established in 1906, Wilson’s Ice Cream Parlor in Ephraim offers classic malts, homemade ice cream (served in cones with a jelly bean stashed in the bottom to prevent dripping), and a grand view of the town’s bustling marina ($3.50).
October: Hit the Beaches in Panama City, Fla.