Springfield, Missouri Route 66 Itinerary: How to Spend 1, 2, or 3 Days

Springfield, Missouri, is the Birthplace of Route 66. It’s where, on April 30, 1926, local businessman John T. Woodruff and highway advocate Cyrus Avery sent a telegram that cemented Sixty-Six as the moniker of the new highway that would connect Chicago to Los Angeles.

Springfield celebrates its position in history and road trippers flock to the city to be where it all began. Here you’ll find a mix of classic diners, modern restaurants, neon-lit motels, over-the-top-roadside attractions, interactive murals, fun excursions, informative museums, natural wonders, and whole lot of road. With one foot in the past, one in the present, and an eye on the future, Springfield, Missouri, is a must-stop destination on anyone’s Route 66 road trip.

So where do you start? Whether you plan to spend one, two, three, or more days exploring the city, you can fill your entire itinerary with amazing stops that celebrate the last 100 years of Route 66 and the next. Explore our Springfield, Missouri, Route 66 Itineraries below and start planning your road trip to the Birthplace of Route 66.

Where to Stay in Springfield, Missouri

There is no shortage of options on where to stay in Springfield, Missouri. There are plenty of chain hotels in the area, if that’s your thing. But if you really want to explore Springfield right, book a stay at a classic Route 66 motel or a boutique hotel in a historic space.

Two of the best motels on all of Route 66 are located right in Springfield: Rockwood Motor Court and the Best Western Route 66 Rail Haven Motel.

Rockwood Motor Court is the oldest operating motor court on the Mother Road. Built in 1929, this cozy cluster of Ozark sandstone and red-brick cabins has welcomed travelers for nearly a century. Built in 1938, the Route 66 Rail Haven Motel has long been a favorite stop for travelers rolling through Springfield, Missouri. It features retro decor and you can even book the room that Elvis once slept in (pink Cadillac bed and all).

If you’re planning to spend a lot of time near Park Central Square and want to walk between your hotel and the restaurants and bars in the area, or just want something a little more modern, look towards Hotel Vandivort or Moxy Springfield Downtown.

Housed in a former Masonic Temple with status on the National Register of Historic Places, Hotel Vandivort offers an upscale stay with history. And Moxy Springfield Downtown offers a unique, lively stay close to all the action of downtown Springfield.

Springfield, Missouri Route 66 Itineraries

3-Day Springfield, Missouri Itinerary
Route 66 & Beyond

Springfield 3-Day Itinerary Day 1: Park Central Square

Day one of your three-day Springfield travel itinerary is all about exploring the heart of the city: Park Central Square. This central area is a dining, shopping, and entertainment hub where everything you want to see is just around the corner…and right on Route 66!

Start your morning at breakfast at The European, a sleek, yet cozy, scratch-made kitchen that serves pastries, gourmet desserts, savory and sweet breakfasts, and Lavazza espresso drinks in a historic location. Try the Cacio e Pepe Scramble Bowl or Banana Bread French Toast and pair your meal with their signature Crème Brûlée Breve Latte.

Spend some time wandering the area looking for public art, murals, roadside attractions, and historical markers. Admire the Abou Ben Adhem Shrine Mosque and Calaboose, take pictures with the Greetings From Springfield Mural, and pop into the Route 66 Visitor Center for brochures and advice for your stay. While wandering, keep your eyes peeled for unique artwork that is part of Sculpture Walk Springfield.

To truly appreciate what the Birthplace of Route 66 is all about, take some time to explore Birthplace Plaza, one of Springfield’s newest landmarks in the city that started it all, a permanent civic space honoring Springfield’s role on The Mother Road, commemorated with sculptures, murals, and more. Then, don’t forget to head across the street to take photos with the Birthplace of Route 66 Monument, an interactive Route 66 shield built for souvenir selfies.

Come lunch time pop into Druff’s, a grilled-cheese-focused diner located right in the Woodruff Building where local civic leader John T. Woodruff and Cyrus Avery first proposed for Route 66 to be called Route 66.

After lunch, spend a couple of hours exploring the History Museum on the Square. The local museum takes you through centuries of local history, but for Route 66 travelers, the Birthplace of Route 66 gallery is the main event. With timelines, photos, videos, and recreated neon signs, it shows you how Springfield, Missouri, became the Birthplace of Route 66.

For dinner, Civil Kitchen offers the best of both worlds: a modern restaurant on old Route 66 that serves traditional menu with a twist. Try the Banh Mi Tacos with the Seafood Beignets to start. After dinner, see a show at Gillioz Theatre (or at least take a moment to admire the sign all lit up at night) and end the night with a tropical cocktail at The Golden Girl Rum Club (or one of the many other Springfield bars), before heading back to your Route 66 motel for the night.

Springfield 3-Day Itinerary Day 2: Classic Route 66 in Springfield, Missouri

On day two of this 3-day Springfield, Missouri Route 66 itinerary, you’ll be exploring all the best of classic Route 66 in town.

Start your day with a pastry and a Route 66 Kicker to go at Trailer Perk Coffee, a drive through coffee spot on the location of the world’s first drive through, Red’s Giant Hamburg.

As you cruise up and down College Street you’ll find many of the best Route 66 sites in Springfield: the Route 66 Barbershop, the Historic Rock Fountain Tourist Court Motel, the Route 66 Bigfoot Mural, Bud’s Tire & Wheel, the College Street Great Mosaic Wall, the Hubcaps on Route 66 Sculpture, and Birthplace of Route 66 Roadside Park. Have your camera ready and prepare for a lot of pulling over!

Then pull into the Route 66 Car Museum, a privately owned collection of more than 75 classic automobiles, sports cars, and celebrity vehicles spread across 20,000 square feet. Even if you aren’t a “car person” you’ll be impressed with selection and care.

For lunch, head right next door to College Street Café, a 1950s diner serving all the classics you’d expect: meatloaf, country fried steak, chicken tenders, French toast, and a selection of hand-patted burgers with different combinations of toppings. 

After lunch, take a little drive to explore some of the best roadside attractions in Springfield and nearby, like the Giant Fork, the Huge Golf Club at Swing Right Golf, and Gary’s Gay Parita (a recreation of a classic Sinclair service station), and Spencer Station (a renovated 1920s gas station). Consider stops at the 1913 Pythian Castle (you can even book a history tour or ghost tour) or the Air and Military Museum of the Ozarks.

Spend the rest of the afternoon relaxing with a pint in the garden of Mother’s Brewing Company or playing a round of quirky-themed mini-golf at Getaway Golf.

For dinner, try a local delicacy: Springfield-Style Cashew Chicken. Invented in Springfield in 1963, this Chinese-American fusion dish features fried chunks of chicken topped with Chinese oyster sauce, cashews, and chopped green onion. You can try it anywhere on the Cashew Chicken Trail, but you can also try it right on Route 66 itself at New House Chinese Food.

Springfield 3-Day Itinerary Day 3: Beyond Route 66 in Springfield, Missouri

While Springfield is the Birthplace of Route 66, the things to do and see in the area go far beyond the Mother Road. With an extra day in town, you can explore all Springfield has to offer.

Start the morning at Gailey’s Breakfast Cafe. This popular spot serves an eclectic menu in a historic setting (the building was once home to Gailey’s Pharmacy and The Seville Hotel). Try the Breakfast Mac and Cheese, El Jefe skillet (with chorizo, avocado, and queso), or the Freedom Waffle topped with blueberries, strawberries, and whipped cream, made to resemble an American flag.

Spend your morning finding out why Missouri is known as the “Cave State.” Boasting more than 7,000 caves within its borders, you’ll find two to explore right in Springfield. You can’t go wrong with either. The Crystal Cave offers an in-depth look at untouched stalagmites and soda straw stalactites on a walking tour of the depths. And for those who just want to sit back and take it in, Fantastic Caverns is the only tram-led drive-through cave in the U.S.

For lunch, head back to Route 66 for a stop at the Route 66 Steak ‘n Shake. Built in 1962, it is one of the most classic examples of this fast food chain and still features much of its original charm, including an impressive neon sign.

After lunch, there’s more to explore in Springfield, Missouri. Head to one of the most visited tourist attractions in the Bass Pro Shops Outdoor World. More than just a store, this 500,000-square-foot landmark features a plethora of free museums, animal exhibits, and history within its walls. Connected to the store is the Wonders of Wildlife National Museum and Aquarium: a world-class attraction featuring 35,000 live fish, reptiles, mammals, and birds across 1.5 million gallons of water. 

For dinner, head to Black Sheep Burgers & Shakes for a stacked Don’t Go Bacon My Heart burger, shareable Truffle n’ Parmesean Fries, and a boozy (or not so boozy) Elvis milkshake. Drive back to your motel on Route 66, admire its neon sign’s glow one last time, and rest up for your next adventure!

2-Day Springfield, Missouri Itinerary
Classic Route 66 & Local Favorites

Springfield 2-Day Itinerary Day 1: The Heart of Springfield, Missouri

Day one of your two-day Springfield travel itinerary will take you from the center of town to the depth of the Ozarks. Start your morning in Park Central Square, the central area for dining, shopping, and entertainment!

Grab breakfast at The European, a sleek, yet cozy, scratch-made kitchen that serves pastries, gourmet desserts, savory and sweet breakfasts, and Lavazza espresso drinks in a historic location. Try the Sweet Potato Breakfast Bowl or Ricotta Pancakes topped with macerated strawberries and pair your meal with their signature Chocolate Malted Latte.

After breakfast, spend an hour or two exploring the History Museum on the Square. The local museum takes you through centuries of local history, but for Route 66 travelers, the Birthplace of Route 66 gallery is the main event. With a photo display, glowing neon signs, and even an informational video, it shows you how Springfield, Missouri became the Birthplace of Route 66.

After you’ve learned about the Birthplace of Route 66, celebrate it! Head down the block to explore Birthplace Plaza, one of Springfield’s newest landmarks in the city that started it all. It’s a permanent civic space honoring Springfield’s role on The Mother Road, commemorated with sculptures, murals, and more. Then, don’t forget to head across the street to take photos with the Birthplace of Route 66 Monument, an interactive Route 66 shield that makes the perfect backdrop for a souvenir selfie.

When it’s time for lunch, pop into Druff’s, a grilled-cheese-focused diner located right in the Woodruff Building where local civic leader John T. Woodruff and Cyrus Avery first proposed for Route 66 to be called Route 66.

From there, take a little detour to find out for yourself why Missouri is known as the “Cave State.” Boasting more than 7,000 caves within its borders, you’ll find two to explore right in Springfield. You can’t go wrong with either. The Crystal Cave offers an in-depth look at untouched stalagmites and soda straw stalactites on a walking tour of the depths. And for those who just want to sit back and take it in, Fantastic Caverns is the only tram-led drive-through cave in the U.S.

For dinner, head back towards Park Central Square and explore your options. Get the signature chicken and waffles at Civil Kitchen, which offers the best of both worlds as a modern restaurant on old Route 66 that serves a traditional menu with a twist. Or grab a Born in the U.S.A. burger and a Purple Haze Shake at Black Sheep Burgers & Shakes, a rock ‘n’ roll burger joint.

After dinner, see a show at Gillioz Theatre (or at least take a moment to admire the sign all lit up at night) and end the night with a tropical cocktail at The Golden Girl Rum Club (or one of the many other Springfield bars), before heading back to your Route 66 motel for the night.

Springfield 2-Day Itinerary Day 2: The Best of Route 66

Start the second morning of your two-day Springfield, Missouri itinerary at Gailey’s Breakfast Cafe. This popular spot serves an eclectic menu in a historic setting (the building was once home to Gailey’s Pharmacy and The Seville Hotel). Try the Ozark Benedict, Flyin’ Hawaiian Omelet with ham and pineapple, or the Stuffed French Toast with orange marmalade or blackberry jam.

After breakfast, take a cruise up and down College Street to find many of the best Route 66 sites in Springfield: the Bud’s Tire & Wheel, the College Street Great Mosaic Wall, the Hubcaps on Route 66 Sculpture, and Birthplace of Route 66 Roadside Park. Have your camera ready and prepare to pull over a lot!

Next pull into the Route 66 Car Museum, a privately owned collection of more than 75 classic automobiles, sports cars, and celebrity vehicles spread across 20,000 square feet. Even if you aren’t a “car person” you’ll be impressed with selection and care.

For lunch, head right next door to College Street Café, a 1950s diner serving all the classics you’d expect: meatloaf, country fried steak, chicken tenders, French toast, and a selection of hand-patted burgers with different combinations of toppings. 

For an afternoon pick-me-up, grab a Route 66 Kicker to go at Trailer Perk Coffee, a drive through coffee spot on the location of the world’s first drive through, Red’s Giant Hamburg. Then, head a little off Route 66 to one of the most visited tourist attractions in the Bass Pro Shops Outdoor World. More than just a store, this 500,000-square-foot landmark features a plethora of free museums, animal exhibits, and history within its walls. Connected to the store is the Wonders of Wildlife National Museum and Aquarium: a world-class attraction featuring 35,000 live fish, reptiles, mammals, and birds across 1.5 million gallons of water. 

For dinner, try a local delicacy: Springfield-Style Cashew Chicken. Invented in Springfield in 1963, this Chinese-American fusion dish features fried chunks of chicken topped with Chinese oyster sauce, cashews, and chopped green onion. You can try it anywhere on the Cashew Chicken Trail, but you can also try it right on Route 66 itself at New House Chinese Food.

After dinner, grab a pint in the garden Mother’s Brewing Company before returning to your Route 66 motel. Don’t forget to admire the neon sign one last time before retiring for the night!

As you’re leaving the next day, be sure to look for a few things on the way out, like the World’s Second Largest Fork! If your road trip is taking you west, pull over for Gary’s Gay Parita and Spencer Station. And, if you’re motoring eastward, stop for gas at the Springfield Buc-ee’s.

1-Day Springfield, Missouri Itinerary
The Perfect Route 66 Stop

Springfield 1-Day Itinerary: Route 66 Highlights in Springfield, Missouri

With only one day to explore Springfield, Missouri, there’s a lot to pack in! But this itinerary will have you exploring all the best Route 66 sites in town.

Start your day with breakfast at College Street Café, a 1950s diner serving all the classics. If you get there early enough (between 6:00 am and 8:00am), you can indulge in one of the best deals on the Mother Road: the Early Bird Special. For only $6.99 you can get two eggs your way, a choice of meat, hash browns, and either toast or silver dollar pancakes.

After breakfast, spend a little time cruising up and down College Street to find many of the best Route 66 sites in Springfield: the Bud’s Tire & Wheel, the College Street Great Mosaic Wall, the Hubcaps on Route 66 Sculpture, and Birthplace of Route 66 Roadside Park. Have your camera ready and prepare to stop!

Then make a stop at the Route 66 Car Museum, a privately owned collection of more than 75 classic automobiles, sports cars, and celebrity vehicles spread across 20,000 square feet. Even if you aren’t a “car person” you’ll be impressed with selection and care.

Next, head towards Park Central Square to immerse yourself in the Birthplace of Route 66. For lunch, pop into Druff’s, a grilled-cheese-focused diner located right in the Woodruff Building where local civic leader John T. Woodruff and Cyrus Avery first proposed for Route 66 to be called Route 66.

Take some time to explore Birthplace Plaza, one of Springfield’s newest landmarks in the city that started it all, a permanent civic space honoring Springfield’s role on The Mother Road, commemorated with sculptures, murals, and more. Then, don’t forget to head across the street to take photos with the Birthplace of Route 66 Monument, an interactive Route 66 shield built for souvenir selfies. Then spend and hour or two learning all about the history of Springfield at History Museum on the Square. Their Birthplace of Route 66 gallery displays timelines, photos, videos, and neon signs and shows you how Springfield, Missouri became the Birthplace of Route 66.

For an afternoon pick-me-up, pop into The European for their signature Crème Brûlée Breve Latte or Chocolate Malted Latte and a Ferrero Rocher cake or head to Mother’s Brewing Company to relax with a pint of locally-brewed beer.

For dinner, explore your options. Get the BBQ Pork Belly or Fish Tacos at Civil Kitchen, which offers the best of both worlds as a modern restaurant on old Route 66 that serves a traditional menu with a twist. Or grab a What the Dr. Ordered burger, Sweet Potato Fries, and a Strawberry Fields Forever shake at Black Sheep Burgers & Shakes, a rock ‘n’ roll burger joint.

After dinner, see a show at Gillioz Theatre (or at least take a moment to admire the sign all lit up at night) and end the night with a tropical cocktail at The Golden Girl Rum Club (or one of the many other Springfield bars), before heading back to your Route 66 motel for the night. Don’t forget to admire your hotel’s neon sign one last time before retiring to bed!

As you’re leaving the next day, leave some time in your itinerary to stop for breakfast at Gailey’s Breakfast Cafe or a coffee at Trailer Perk Coffee. And be sure to look for a few things on the way out, like the World’s Second Largest Fork! If your road trip is taking you west, pull over for Gary’s Gay Parita and Spencer Station. And, if you’re motoring eastward, stop for gas at the Springfield Buc-ee’s.