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Every editorial product is independently selected, though we may be compensated or receive an affiliate commission if you buy something through our links. Get your kicks on America's original road trip—this 2,448-mile journey from Chicago to Santa Monica is a trip down memory lane of our nation's history. Emma Kumer/rd.com The Mother Road. America’s Highway. The Main Street of America. The Will Rogers Highway. Route 66 goes by many names, but no matter how travelers refer to it, there’s one constant everyone can agree on: “Historic Route 66 is the quintessential American experience,â€...

Your Guide to an Oregon Trail Road Trip Tamara Gane Oregon Trail route The Oregon Trail Road Trip starts in Cannon Beach on the rugged coast of Oregon and takes you through Idaho, Wyoming, Nebraska, Iowa, Illinois, Indiana, Ohio, Pennsylvania, and New York before finally ending in the seaside community of Provincetown, Massachusetts. Along the way, you'll see mountains, wildlife, raging waterfalls, stunning hiking trails, prehistoric fossils, historic sites, and eat some of the best food you've had in your life. The journey is almost 3,300 miles, plus side trips, following Hig...

Your Guide to a Great Northern Road Trip Tamara Gane Suggest time: 2-3 weeks The Great Northern Road Trip is an adventure you'll never forget. You'll start in the state of Washington and follow U.S. Highway 2 for the majority of the journey until you end in Maine. Along the way, you'll spend time in beautiful cities, pass over mountains, lakes, valleys, badlands, natural marvels, historical sites, and even cross the border into Canada. Before you get started, here's everything you need to plan a road trip, including budgeting, planning your route, choosing the right car, utili...

Every editorial product is independently selected, though we may be compensated or receive an affiliate commission if you buy something through our links. Allard1/Getty Images Explore dazzling cities, charming small towns, National Parks, historic sites, and some of the best views in the country on this epic cross-country road trip. Route Distance: about 3,600 miles Suggest time: 2-3 weeks The Great Northern Road Trip is an adventure you’ll never forget. You’ll start in the state of Washington and follow U.S. Highway 2 for the majority of the journey until you end in Maine. Along the way,...

Your Guide to the San Juan Skyway Road Trip Reader's Digest Editors There’s gold in these hills The locals call their homeland "Colorful Colorado," and a drive around the San Juan Skyway loop proves the aptness of the nickname. As you climb from dusty lowlands to snowy peaks, you'll see nearly every shade possible in nature's kaleidoscopic palette, from creamy sands and rusty bluffs to multi-hued alpine meadows. Winding through a section of the Rocky Mountains from New Mexico into the southwest corner of Colorado, the San Juan mountains were the site of Colorado’s gold and...