Catch an early flight in to make the most of your first day in St. Louis, Missouri, starting at the city’s most recognizable landmark, Gateway Arch National Park. Buy tickets and timing online in advance to ride the tram to the top of the 192-meter monument for sweeping views over the Mississippi River and the Old Courthouse below. There are no tickets required for sightseeing and the museum at the base of the arch. Nearby, you can hop on a paddlewheel boat for a tour of the Mighty Mississippi. From there, head to the Anheuser-Busch St. Louis Brewery, where free tours cover more than a century of brewing history and include a stop at the on-site Clydesdale stables and a tasting room pour at the end. Spend the afternoon exploring downtown; top attractions include the quirky and interactive City Museum and the compelling National Blues Museum.

On your second day in St. Louis, branch out to dive into the city’s Route 66 history, starting with a stroll across the Old Chain of Rocks Bridge. In its heyday, the bridge carried Route 66 travelers from Illinois into Missouri across the Mississippi River. Cruise another stretch of historic Route 66 in the Maplewood neighborhood. Pop in and out of locally owned shops selling artisan food, books and crafts, and check out friendly cafes and breweries. You’ll also find plaques that recognize Maplewood businesses that served travelers on the Mother Road. In the evening, set aside some time for dinner, drinks and entertainment in the Delmar Loop neighborhood. Check the schedule for the Duck Room at Blueberry Hill for live music in a venue Chuck Berry played regularly. Keep an eye out for stars on the St. Louis Walk of Fame as you mosey down the boulevard. The next morning, you’ll set off toward the Ozark Mountains, where mysterious caves and lake country await.

Trade the St. Louis skyline for limestone bluffs and open water as you enter the lush rolling hills of the Ozark Mountains. At Lake of the Ozarks State Park, Missouri’s largest state park, hike along a shoreline trail or rent a boat to explore the lake’s famously winding 1,850 kilometers of shoreline. Just south, Ha Ha Tonka State Park holds the ruins of an early 20th-century stone castle, built by a Kansas City businessman and gutted by fire in 1942. Wander the surrounding walking trails and observation deck perched above the spring-fed lake. Nearby, check out another of Missouri’s famed underground attractions in the limestone reaches of Bridal Cave. Before settling in for the night at a lakeside lodge or cabin, grab a laid-back dinner and score some souvenirs at Bagnell Dam Strip or in Osage Beach.

Settle into Tulsa with an evening among its Route 66 icons. Buck Atom’s Cosmic Curios greets visitors with towering space-themed statues out front and a shop full of retro souvenirs inside, while the nearby Route 66 Historical Village tells the city’s transportation story through restored rail cars and roadside memorabilia. Grab dinner at the Mother Road Market food hall, then close out the night with live music at Cain’s Ballroom, the historic dance hall that has hosted acts from Hank Williams to Jack White since 1924. The next morning, snap a photo with the 22-meter Golden Driller statue before heading to Cyrus Avery Centennial Plaza, where bronze sculptures honor Avery at the intersection where his vision for the highway first took shape. The Bob Dylan Center houses one of the world’s largest collections of the singer-songwriter’s personal archives, a fitting stop in a city that has become a hub for American music. Break for lunch at French Hen, then spend the afternoon at The Outsiders House Museum, the restored filming location from S.E. Hinton’s novel and its 1983 film adaptation. Cap the day with dinner at Bull in the Alley before the final leg to Oklahoma City.

After an overnight rest, close out the trip in Oklahoma City with a morning of ranching history and an afternoon of downtown energy. Start at Historic Stockyards City, a neighborhood that encompasses the region’s modern West energy. Its centerpiece is Oklahoma National Stockyards, one of the world’s largest cattle markets where you can watch live cattle auctions every Monday and Tuesday. Nearby, find your own piece of the West, including cowboy hats, boots and other cowboy-inspired trinkets at local shops. The district’s dining options include Cattlemen’s Steakhouse, the city’s oldest restaurant, and McClintock Saloon & Chop House, home to a 15-meter oak bar. Next, carve out some time for the National Cowboy & Western Heritage Museum, which traces the art and culture of the American West across galleries of paintings, sculpture and rodeo memorabilia. Spend the afternoon browsing the independent shops and colorful murals of the Uptown 23rd District. For the evening, head downtown for a stroll along the Bricktown Canal, where a water taxi links restaurants, bars and entertainment venues in a converted warehouse district. If this is the end of your journey, catch a flight home from Will Rogers International Airport or continue your Route 66 road trip into Texas and New Mexico.