4872 North Farm Road 125, Springfield, MO 65803

Fantastic Caverns is the only ride-through cave in North America, one of just four in the world. Rather than walking, visitors explore the cave from a propane-powered Jeep pulling a tram, winding past columns formed over thousands of years. The 55-minute tour follows the path of an ancient underground river and stays at a cool, consistent temperature year-round, making it a good option whatever the weather outside.

The cave was discovered in 1862 and has operated as a ride-through attraction since 1962. It sits just north of the city, around a 15-minute drive from downtown Springfield with your Hertz rental, and the shaded picnic areas outside make a good spot to stop before heading back.

200 Central Avenue, White Plains, NY 10606

City Limits Diner has served breakfast, lunch and dinner to Greater Westchester for more than 30 years from its Central Avenue location, and its in-house bakery makes it a useful stop at almost any point in the day. You’ll find all-day breakfasts – customers rave about their burrito – as well as heartier plates for big appetites. Think all-American classics like steak and eggs, or surf and turf. It's the perfect stop-off before setting off towards Tarrytown or further into the Hudson Valley, without having to head back into downtown White Plains first. 

305 East Walnut Street, Springfield, MO 65806

Hotel Vandivort is Springfield’s only AAA Four Diamond hotel, housed in a beautifully restored 1906 Masonic Temple in the heart of downtown Springfield. The building spent decades as office space before a full restoration uncovered its original architectural details, and it’s now listed on the National Register of Historic Places.

The boutique hotel is known for Vantage, its rooftop bar overlooking the Queen City, along with seasonal ingredients  and shareable plates that draw locals as much as guests. It’s around a 15-minute drive from Springfield-Branson National Airport in your Hertz rental, making it a practical, characterful base for exploring the city.

Head south on US-65 and reach the Live Entertainment Capital of the World in under an hour. Branson built its reputation on live music theatres, and Silver Dollar City, the 1880s-themed amusement park built around Marvel Cave, remains the city’s biggest draw. Table Rock Lake offers boating, fishing and swimming just outside town, while Branson Landing’s boardwalk and free fountain show make an easy evening stop. It’s close enough for a day trip but easily worth an overnight stay if you plan to extend your adventure. 

124 miles & 2 hours

Head southwest on I-44 and Highway 71 into Northwest Arkansas, home to Crystal Bridges Museum of American Art. Founded by the Walton family, the museum is free to enter and holds an outstanding collection of American masterpieces, from Norman Rockwell to Andy Warhol, set across a 120-acre campus of spring-fed ponds, sculpture trails and native gardens. Bentonville has also built a reputation as a mountain biking destination, with more than 80 miles of trails around the city. It’s a comfortable half-day drive that rewards a full day once you arrive.

Head north on Highway 13 and I-49 for a longer drive into one of the Midwest’s most underrated cities. Kansas City is known for its barbecue, its fountains, and the Country Club Plaza shopping district modelled on Seville, Spain. The National WWI Museum and Memorial, one of the most comprehensive of its kind anywhere in the world, sits beneath a striking tower in the heart of downtown. It’s a longer drive than the others on this list, but the food, music and culture on offer makes it a worthwhile weekend trip from Springfield.