Immortalized by John Steinbeck’s 1939 book “The Grapes of Wrath”, as well as the 1946 song “(Get Your Kicks On) Route 66”, the highway became one of the most recognized thoroughfares in North America, crisscrossing not just from Chicago to Santa Monica, California, and back again, but also across our hearts (*cue studio audience: “aww!”). And though the highway no longer exists in a technical sense — it was officially removed from the U.S. Highway System in 1985 — stretches of what has become known as “Historic Route 66” in some states are still out there waiting for you.
Read MoreDriver beware, you’re in for a scare… because the folks over at Kayak have put together a truly terrifying cross-country road trip stretching from New England to the West Coast. From haunted inns to creepy cemeteries, and old state hospitals to abandoned amusement parks, the 7,500-mile trip truly checks off every spooky box a Halloween-loving traveler could dream up.
Read MoreWhat’s the first thing you do when planning a road trip? Before picking out stops along the way, before deciding which places you’ll spend the night in, before figuring out how many miles you’ll travel and how many days and nights you’ll be away — before any of that — the very first thing you do is you give your road trip an epic name equivalent to the significance of the marvelous adventure you are about to embark upon.
Read MoreI could not have imagined, even a week ago, that I would be sitting here, in a Starbucks across the street from Chicago Union Station, finishing up the final post of the year as I wait to board a train headed for St. Louis this evening. But that’s how life goes, things can change in an instant.
Read MoreWith the largest road atlas money can buy (thanks, grandma) laid out on the kitchen counter and some fancy new highlighters in hand, I began marking points. I marked places where I knew people, drew lines connecting the dots, checked the mileage with Google Maps to make sure I wasn’t planning ridiculously long drives (I max out at about 14 hours), and started feeling giddy.
Read MoreI took two months to travel to 22 states, putting over 8,500 miles on my car. I went to new places with old friends and old places with new friends. Sometimes I drove 14 hours in a day, others maybe one. I listened to hours of podcasts, audio books, and A LOT of music…
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