America's Main Street: 27 ways to get lost on Missouri’s Historic Route 66

By Dawnya Bartsch and Reece Parker

Route 66 has long held a place in America’s collective imagination, pushing much of the country further west in its early years and then epitomizing car culture in the ’50s and ’60s. Coined the Mother Road by John Steinbeck in his 1939 American classic Grapes of Wrath, the famed road was popularized even further by Nate King Cole’s 1946 song “(Get Your Kicks on) Route 66.” The song, which spent eight weeks on the pop charts, led many to refer to the thoroughfare as America’s Main Street. A popular television series called Route 66 ran from 1960 to 1964 and followed three young men driving around America, working odd jobs and helping folks in need.

With all this attention and the car’s growing popularity, filling stations, restaurants, auto camps and souvenir shops began to pop up along the historic route. The road was at its peak popularity post-World War II, when families equipped with jobs, money and a car planned cross-country road trips via Route 66. Eventually, more modern and straight interstates were built, replacing the need for many to travel along the windy roads and through the small towns populating the historic route.

America’s Main Street enters Missouiri right at the Old Chain of Rocks Bridge in St. Louis and winds its way to Springfield before exiting into Kansas. Along the way, there are plenty of sights to see and places to explore. So go get your kicks on Route 66.

Old Chain of Rocks Bridge

245 Miles

Photography by Scott Evers

Once part of the original Route 66, this bridge spans the Mississippi River, connecting Illinois and Missouri, and was originally built for vehicular traffic. The eastern end of the bridge is on Chouteau Island and is part of Madison, Illinois, and the bridge’s western end is on the Missouri shoreline and is part of a park with bike and walking trails between the Gateway Arch and the bridge. It’s known for a 22-degree angle bend that was incorporated into the bridge’s design due to a chain of rocks in the river, hence its name. It’s the start of Route 66 in Missouri. –DB

The Gateway Arch

248 miles

Photography courtesy of Gateway Arch.

As we all know, this landmark needs little introduction. The 630-foot-tall monument, clad in stainless steel, is the world’s tallest arch. It is a National Historic Landmark and was built as a monument to westward expansion. It’s commonly referred to as “The Gateway to the West.” The arch was completed in 1965 and is located at the 1764 site of the founding of St. Louis. It symbolizes a time when the city was the last large metropolitan area for many before they ventured further west and into unsettled land. The arch is right along the old Mother Road and is connected to Old Chain of Rocks Bridge via biking and walking trails. -DB

Route 66 State Park

239 miles

Photography by Adam Knaeabel

Travel through history at Route 66 State Park. Along with camping and boating, the park’s visitor center houses a small museum with an overview of the historic route and displays highlighting various parts of the road and artifacts, such as old neon signs, restaurant menus and brochures. Housed in the former Bridgehead Inn, a 1935 roadhouse that sat on the original Route 66, it can practically be considered a one-stop shop for learning all there is to know about the Mother Road. Along with the visitor center, there are also the usual state park activities in the Meramec River. -DB

Meramec Caverns

242 miles

Meramec Caverns is said to be the “greatest show under the Earth!” The tourist destination has attracted millions of people and was even included on USA Today’s travel bucket list of “60 things to do in America before you die.” This complex cave system, featuring some of the rarest and largest cave structures in the world, runs right under Route 66. The cavern tours are led by trained rangers around a 1.25 mile loop of well-lit halls. However, once the tour is over, there is still so much more to see. Meramec Caverns also has zip lines, campgrounds and a caveman climbing wall—and that’s only the tip of the stalagmite. You will be in awe of Earth’s most scenic underground formations. –RP

Mark Twain National Forest

219 miles

Take some time to unplug and visit the Mark Twain National Forest. Encompassing 1.5 million acres of beautiful wooded land, the Mark Twain National Forest has become a popular destination for all sorts of recreational fun. The forest has over 750 miles of trails for hiking, horseback riding, mountain biking and more. Three hundred and fifty miles of perennial streams flow throughout the grounds, suitable for kayaking, canoeing and floating. Visitors can also see a variety of wildlife including fish, amphibians, reptiles, bald eagles and the occasional black bear. There is no shortage of activities for every member of the family to enjoy. Mark Twain National Forest is a great day-trip destination for a hike, but if you have more time, camp a few nights there and explore all the forest has to offer. Regardless, it is a must-see. –RP

Where to Fuel Up—Sort Of.

Although these gas stations don’t actually sell gas anymore, they sure make for a great place to stop. Steeped in nostalgia, these retro petrol stations are windows into the past.

Gary's Gay Parita

About 25 miles west of Springfield stands a replica of a 1930s Sinclair gas station. The site includes original non-working pumps and tons of memorabilia. Although you can’t fill your tank with gas here, you can get a tall glass of lemonade. This is no place for a quick pit stop. It truly feels as if you’re stepping into a bygone era, and there is a lot to explore. Due to its truly classic look, it has rightfully become a popular spot for photo ops.

Spencer Station

Spencer Station, a late-1920s gas station, cafe and barber shop, was a popular stop for travelers on the original Route 66. When the new highway was built, it bypassed the station, leading traffic a different way, and Spencer station eventually closed. Now it’s being meticulously renovated and restored, packed with memorabilia and displays. Although it’s a work in progress, it is open most weekends. Owner Ed Klein, who is restoring much of the property himself, says his policy is to always throw open the doors and talk to anyone who happens by if he’s there.

License Plate Noir

The Route 66 Association of Missouri has gotten the go-ahead from the state to offer a custom license plate for Mother Road history buffs everywhere—well, everyone in Missouri, that is.

More than just a piece of metal, the Missouri Route 66 black plate is a “beacon of the spirit of Route 66 and the spirit it offers to adventurers,” states the association, whose members were the driving force behind getting the new license plate design approved by the state and are using it as a fundraiser for the nonprofit organization. The license plate is available exclusively through the Route 66 Association of Missouri website ( The historic preservation organization was established to preserve, promote and develop the historic route throughout Missouri, and a portion of each license plate sold will head to the organization’s coffers.

The license plate’s design prominently features the number 66 in bold white letters against a black background, with Missouri written across the top and  “Main Street of America” at the bottom. Like all license plates, the black Route 66 plates can be personalized, too.

A Place To Stay

Looking for that true Route 66 experience? Then the Wagon Wheel Motel (901 E. Washington St., Cuba, MO) is the place to be. Built in Cuba, Missouri, in 1938, the Wagon Wheel claims to be the oldest continuously operating motel along the Mother Road, earning it a place on the National Register of Historic Places. When it first opened, it was called the Wagon Wheel Cabins and had nine cottages completely constructed with nearby Ozark sandstone. The iconic and beloved bright neon sign that so many people recognize also harkened its name change, officially becoming a motel.

Highway 66 (now East Washington Street) was Cuba’s main road until Interstate 44 was developed, bypassing the town and the motel. However, current-day Cuba has embraced its Route 66 past, with various themed spots in town that make it a popular spot for roadtrippers. If you plan to stay at the Wagon Wheel, don’t forget to check out the world’s second largest rocking chair at Fanning 66 Outpost; the Weir Station, an old gas station turned restaurant; and the city’s many murals scattered throughout town.

Have a Sip on Route 66

Photography provided

Several Missouri wineries have been established not far from the Mother Road and are worth a little side trip if you’re inclined to do a bit more exploring.

Most have popped up in the St. James area, where soil conditions are more hospitable to growing grapes, including St. James Winery, Meramec Vineyards, Claverach Farm and Eagles’ Landing Wine. A bit further down the road is the Peaceful Bend Winery, which boasts one of the best patio views in the area.

Missouri Wines, an association dedicated to promoting the Missouri wine industry, has created vineyard touring itineraries with Route 66 in mind. 

Jasper County Courthouse

166 miles

Don’t be dissuaded by the name. The Jasper County Courthouse is not just any old courthouse. In fact, if you drive past it, you would probably never guess it was a courthouse. Located in Carthage, this 106-foot-tall building is a sight to see. Inspired by medieval architecture, the castle-like marble building features turrets, towers and arches—all that’s missing is a moat. The building was originally built in 1894 and is on the National Register of Historic Places. The courthouse is rich with historical artifacts that patrons can look at inside, including an original antique elevator. Patrons can also appreciate the old architectural style and view the many memorials across the grounds. –RP

Grand Falls

164 miles

Photography provided

Known as the largest continuously flowing natural waterfall in Missouri, Grand Falls is a must-see for a photo op if you’re traveling on a road trip. The waterfall is located on Shoal Creek, within hiking distance of Wildcat Park. The waterfall flows over a 163-foot-wide ledge of solid chert (a fine-grained sedimentary rock) before flowing peacefully downstream. Get closer to nature and have outdoor fun here. The Grand Falls are technically open year-round, as there are no facilities, but the best time to visit is in the summer, when you can cool off and swim
in the river. –RP

12 places to eat Here’s a list of the top spots to eat when traversing America’s Main Street.

Ted Drewes Frozen Custard

6726 Chippewa St., St. Louis

For more than 80 years, the family-owned Ted Drewes Frozen Custard has been serving its popular creamy, cold treats at various spots in the St. Louis area. In 1941, the family decided to open its most popular location on historic Route 66. It’s here that you can get Drewes’ iconic malt known as the concrete, a shake so thick that it is served upside down.

Granny’s Candy Store

1135 Highway W, Sullivan, MO

In need of something sweet? Then Granny’s scratch-made candy is just for you. Located in the Meramec Caverns Visitor Center, not far from Route 66, the shop has display cases brimming with homemade chocolate turtles, roasted nuts and all varieties of fudge, which is sold by weight. The shop is a satellite outlet of Grandma’s Candy Kitchen located in nearby Lake Ozark.

Dowd’s Catfish and BBQ

1760 W. Elm St., Lebanon, MO

Known for its southern fried catfish served with hush puppies, this place is popular with locals and travelers alike. Located right on the old Route 66 and just two blocks of I-44 in Lebanon, it’s often frequented by folks headed to Branson.

Red Onion Cafe

203 E. Fourth St., Joplin, MO

If you’re looking for healthier fare, the Red Onion Cafe, located just a block off Route 66 in a quaint historic brick building in the heart of downtown Joplin, is the place to head. The cafe has a casual, urban feel and an extensive menu, with items such as a mushroom and rosemary garlic keto burger and bacon-wrapped grilled chicken.

Whisler’s Drive-up

300 N. Garrison Ave., Carthage, MO

A true roadside classic, this burger joint has been in business for more than 70 years now, meaning these folks know a thing or two about hamburgers. Locals often grab a bag of burgers to go or sit outside on picnic tables.

Steak ‘n Shake

3755 S Campbell, Springfield, MO

What’s different about this Steak ‘n Shake than the hundreds dotting the Midwest? It has been at this Springfield location on Route 66 since 1962 and is on the National Register of Historic Places. With its large ’60s-era neon sign inviting drivers to come on in, this place definitely feels like it’s from another era.

Yogi’s Pizza

311 W. Jefferson Ave., Conway, MO

It’s a small pizza joint, located in a small town, but it has big pizza taste and an extensive menu. Located just a few blocks off the main route and not as well known as other restaurants along the historic roadway, it’s the perfect place to sate your pizza cravings. If you’re lucky, you’ll be there when the owner is throwing his scratch-made dough in the air, creating the perfect round pizza crusts.

Hopper’s Pub

318 U.S. Route 66 East, Waynesville, MO

The Mother Road runs right through Waynesville, and that’s where you’ll find Hopper’s Pub. This family-friendly restaurant and bar serves much more than your typical bar grub. You’ll find everything from quesadillas and BLTs to a Philly cheesesteak sandwich and buffalo chicken wrap.

A Slice of Pie

634 S. Bishop Ave., Rolla, MO

Sometimes just a slice of pie makes the perfect meal, especially when you’re on a road trip and all rules go out the window. From traditional apple and peach pies to pies with names like Peanut Butter Lust and Baltimore Bomb, the novelty of it all makes it a great stop. This month’s special: Bailey’s Irish Cream Cheesecake.

Missouri Hick Bar-B-Que

913 East Washington Blvd., Cuba, MO

Celebrating 17 years, Missouri Hick is considered one of the best barbecue joints along Route 66. This place serves all the traditional barbecue items, from ribs and smoked chicken to pulled pork and burnt ends. For a real classic dish and one of their specialties, try the pork steak sandwich.

Black Sheep Burgers and Shakes

209 E. Walnut St., Springfield, MO

This trendy spot offers gourmet burgers and—drum roll please—shakes. The burgers are made with Snake River Farms wagyu and angus beef with lots of creative toppings, so if you’re craving more than just a basic cheeseburger, this is the place to go. It’s located in the heart of Springfield’s historic downtown on old Route 66.

The Blue Owl Restaurant and Bakery

6116 Second St., Kimmswick, MO

You must veer off Route 66 just a bit to get to The Blue Owl Bakery and Restaurant in Kimmswick, but setting eyes on one of the bakery’s famous Levee High Apple Pies is worth it. Plus, Kimmswick, an historic town on the banks of the Mississippi River, makes for a great stop even without the pie.