Sheboygan, WisconsinThe drive: 2.5 hours

Sheboygan has long been known as the home of the bratwurst (and more recently as the go-to spot for Vera Pizza Napoletana–certified wood-fired pizzas at one of my favorite restaurants, Il Ritrovo). But what I love most about this small city halfway between Milwaukee and Green Bay is its lesser-known claim to fame as the Malibu of the Midwest. Thanks to a shoreline that juts into Lake Michigan, exposing it to wind from several directions, Sheboygan is a prime spot to surf when the conditions are just right. 

I’m not brave enough to join in, but it’s fun to have surf culture so close to home. I’ve passed through the area year-round to visit relatives in points north or to pick up kids from summer camp, and have always seen wave riders, no matter the season — in winter, some of them wear two hooded full-body wetsuits to endure water temperatures that can hover in the low 30s. A few years ago, though, I was there during Labor Day Surf Weekend, when surfers from all over descend on Sheboygan. There was a flurry of activity at Eos Surf Shop, a downtown store lined with boards and gear that looks like it belongs in Southern California. But the center of the action was an area called the Elbow at North Beach at Deland Park. I watched as surfers jumped into the lake with their boards from the giant rocks near the shoreline, celebrating the unofficial start of surf season.

I may not see anyone tackle a 30-foot swell when I visit Sheboygan, but the novelty of watching surfers ride waves hundreds of miles from the closest ocean is a quirky-cool phenomenon that never gets old.