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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 Highway 20 for the majority of the trip. Plan to dedicate at least two weeks to this adventure to make sure you can enjoy the incredible National Parks, museums, and attractions you ll see along the way, but if you can spare the time, three weeks is ideal. Before you depart, be sure to check everything off this road trip essentials checklist.

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