Driving the entirety of Route 66 is a formidable achievement, but it’s not like you’d be doing anything new—the legendary king of American road trips covers exceedingly well-covered ground. Shake things up by combining one great American pastime with another: whiskey. There’s never been a better time to take a whiskey road trip; according to the American Craft Spirits Association, there are now approximately 1,600 craft distilleries operating across the country.
Carve your way through the spirit’s source—those famous amber waves of grain—and get a firsthand taste at distilleries conveniently dotting the historic route, all the way from Chicago to Los Angeles. (Over time, most of the famed highway has been replaced by interstates, so you’ll see more signs for I-55 and I-40 than you will for U.S. 66.) And remember, hit the road before you hit the distilleries.
Start your journey just 10 miles north of Chicago in Evanston, Illinois. The one-time seat of the temperance movement is now home to one of the leading craft whiskey distilleries in the United States, FEW Spirits. Tours and tastings are held Wednesday through Sunday, and a range of whiskeys are available, including bourbon, rye, and single malt. FEW’s founder Paul Hletko suggests stocking your motel room at Binny’s in Chicago, one of the country’s leading whiskey retailers, then heading to everyone’s favorite dive bar, Delilah’s, which serves more than 800 whiskeys. Other Chicago distilleries to check out include Quincy Street Distillery and KOVAL.
First stop: St. Louis, MO
Cruise 300 miles down what is now known as I-55 to St. Louis, Missouri. Be sure to take your obligatory photo of the Gateway Arch, then make your way to StilL 630 for a few refreshments. The “630” in the distillery’s name is a nod to the arch’s height, and you’ll notice that you can’t spell “still” (or “distill,” for that matter) without “StL.” The distillery is best-known for its rye whiskey but also produces bourbon, single malt, and a range of flavored whiskeys. Owner David Weglarz leads tours on the weekends; they’re popular, so you should book online in advance to ensure you don’t miss out. If you’re still thirsty after the tour, head to the nearby Square One, a brewery and distillery with a full lineup of pub fare.
Second stop: Springfield, MO
Springfield, Missouri, is only about 200 miles southwest on I-44. Directly in your path, however, just an hour outside of St. Louis, is Bourbon, Missouri. According to the town’s official history, yes, it is named for bourbon whiskey, although there are no distilleries to visit here. But this is a whiskey road trip, so it’s worth stopping to take a photo of the town sign. Another 90 minutes down the road is a second potential detour: the town of Lebanon. It’s home to a Route 66 Museum and one of the bourbon industry’s most prominent cooperages, the Independent Stave Company, which works with big-name brands like Jim Beam and Buffalo Trace. Alas, it doesn’t offer public tours, but perhaps another photo is in order. Finish the drive to Springfield and disembark at Missouri Spirits, producers of bourbon and corn whiskey. Sample its wares in a cocktail—the “Bluebird” is a particularly tasty concoction made with blueberry-infused corn whiskey, fresh lemonade, and a house cherry cordial—served at the full bar and restaurant.
Third stop: Tulsa, OK
Stay on I-44 for an easy three-hour drive, and you’ll arrive in Tulsa, Oklahoma, home to Red Fork Distillery, located directly on the old Route 66. Red Fork produces whiskey and white spirits and became Tulsa’s first distillery since Prohibition when it opened at the end of 2017. Unfortunately, state law blocks distilleries from selling or sampling on-site, although the legislation will be partially loosening by October. To quench your thirst, sample Red Fork and other local whiskeys from the well-appointed list at Valkyrie. There are also plenty of classic Route 66 diversions to check out while you’re in Tulsa, like Totem Pole Park and the Blue Whale.
Fourth stop: Oklahoma City, OK
Oklahoma City is only another 100 miles due west on I-44, and this stretch of Route 66 is dotted with kitschy stops such as the wacky Pops 66 Soda, purveyors of a staggering 700 soft drinks, the Seaba Station Motorcycle Museum, and the Milk Bottle Grocery building, named for the huge metallic milk bottle that has adorned its roof for the past 80 years. Just outside of OKC, in Moore, you’ll find Scissortail Distillery, which is run by a team of combat veterans and produces Leadslingers Bourbon and Fighting Spirit Rye. In Guthrie, about half an hour north of OKC, Prairie Wolf Spirits offers gin, vodka, and coffee liqueur in addition to M Whiskey, its blend of bourbon and rye. It also has an exciting sorghum rum release on the way, with sorghum sourced from the Seminole Nation. As in Tulsa, distilleries here are hamstrung by Oklahoma state laws, so head to OKC’s Stag Lounge, a cigar lounge and cocktail bar, to taste some of its 350 whiskeys, or Power House, for a cocktail and a bite.
Fifth stop: Amarillo, TX
Back on the road, 250 westward miles on I-40 lands you in Amarillo, Texas. It’s an ideal stopping point, but there are no distilleries here, so give your liver some rest and dive deep into Americana. Amarillo is home to the Route 66 Sixth Street Historic District, which is lined with a dozen notable buildings and historic sites to see as well as plenty of shops and restaurants. There may be no distillery here, but this doesn’t have to be a completely dry stop: Don’t miss the aptly named Whiskey River.
Sixth stop: Albuquerque, NM
Keep heading west on I-40 for another 300 miles and you’ll find yourself in Albuquerque, New Mexico. Get a true taste of the Southwest with the New Mexico Blue Corn Whiskey at Left Turn Distilling. Named for the Bugs Bunny “shoulda taken a left turn at Albuquerque” gag, Left Turn offers tours Tuesday through Saturday. At Broken Trail Spirits you can get hands-on in the production of your own micro-batch of whiskey; the team will mature the resulting five-liter barrel in their warehouse for you until its ready to drink. (It’s the perfect excuse to plan a second visit down the road to pick up your barrel.) Then head to The Hangar, a beer and liquor shop inside the Historic El Rey Theater building. Behind the shop’s faux freezer-room door, a fingerprint scanner unlocks access to the hidden basement whiskey bar dubbed Braise. The members-only club does take reservations from nonmembers for a few hours in the early evening on weeknights; be sure to snag a spot ahead of time.
Second-to-last stop: Flagstaff, AZ
You’ve been close friends with I-40 for days already, so why say good-bye now? Stick with your pal for another 325 miles west until you reach Flagstaff, Arizona. About 30 minutes outside of town, you’ll find Grand Canyon Brewery, which just added a distillery component to its successful brewpub. The young distillery currently offers white spirits and an unaged corn whiskey, but bourbon and single malt whiskey are on the way. Consider stopping for a few drams at the Uptown Pubhouse, which has several hundred whiskeys on offer, or try the Annex Cocktail Lounge, which incorporates its quality whiskey selection into can’t-miss craft cocktails. Don’t forget to take a selfie with the 20-foot tall lumberjack now residing outside the Skydome at Northern Arizona University; the Route 66 icon initially stood at the Paul Bunyan Cafe.
Last but certainly not least is the longest stretch of your journey. A final 450-mile push takes you from I-40 to I-15 and finally puts you on I-10, heading straight into the City of Angels. After that kind of drive, you’ll need a drink, so plan ahead and secure a reservation at Mulholland Distilling’s new Mulholland Room in the Arts District. The space is open for private events and small group meet-and-greets and hangouts. Maybe you’ll get to meet actor and co-owner Walton Goggins, who is known for unforgettable roles on shows including Justified and The Shield. After resting up for the night, you may want to hit the beach and enjoy the L.A. sunshine before heading to Greenbar Distillery to enjoy a tour, a tasting, and a hands-on cocktail class offered on Fridays and Saturdays. Because sometimes the best way to ensure you get the cocktail you need after a 2,000-mile road trip is to make it yourself.