Upper Midwest Travel + Road Trips

Sharing our love of the Midwest

destinations
road trips
Travel maps

FIND YOUR NEXT ADVENTURE IN THE UPPER MIDWEST

Whether you live in or this is your first time traveling in the Upper Midwest, you are in the right place. Stick around and we’ll show you our favorite spots. And give you endless inspiration for your own adventures and road trips. 

Two postcard images of Mel and Craig in front of waterfalls

HI THERE!

We’re Mel and Craig, and we love exploring the Midwest, especially our home state of Wisconsin. We started The Winding Road Tripper to share our favorite Midwest adventures. We aim to spread the word about the amazing things the Midwest offers and help you plan your adventures.

Contact Us

Latest Articles

Image of inside of American Family Field in Milwaukee, WI home of the Milwaukee Brewers

Best Places to Stay in Milwaukee for a Brewers Game in 2024

Image of outside of Milwaukee Public Market with a red sign

14 FREE Things to Do in Milwaukee

Image of inside of 3rd Street Market Hall with people sitting at tables

Unforgettable Experiences for Couples in Milwaukee: A Local’s Guide

Image of red lighthouse in Sturgeon Bay, Wisconsin in Winter. Red Lighthouse is in the distance with a snow covered shoreline in the foreground.

18 Boredom-busting Wisconsin Winter Getaway Ideas

A couple laying on hood of car playing a road trip game

15 Ridiculously Fun Road Trip Games for Two People

Image inside of a brewery tasting room

Best Craft Breweries in Milwaukee: From a Local’s Perspective