Town: Take the exit on AR-64 to venture deep into the Arkansas Wine Trail in Altus, Arkansas. The region reminded immigrants Jacob Post and Johann Wiederkehr so much of their home German and Swiss wine regions that they settled in and began growing grapes in the late 1880s. Both wineries are still there today, along with about a dozen other wineries. A drive through the region is stunning, but a short lunch break or tasting makes this stop truly memorable.

Eat & Drink: Chateau Aux Arc Vineyard and Winery. Just four miles off the road, in the heart of the Arkansas Wine Trail, you’ll find winemaker and Master Sommelier Audrey House’s award-winning vines and wines. The tasting room is open seven days a week, where visitors can sample complex blends, dry reds, and House’s signature Cynthiana wines (which she pioneered to become the state grape of Arkansas).

Do: Sam Walton put Bentonville on the map when he opened Walton’s 5 and 10 in 1951, which would later become the world’s first Walmart. The five and dime store is still there, attached to an authentic soda fountain that serves arguably the best butter pecan ice cream around, but the Walton family in recent years helped to open the architecturally stunning Crystal Bridges Museum of American Art and the family-friendly Amazeum.

Eat & Drink: Join James Beard Award-nominated chef Matt McClure for a culinary experience through farm-fresh regional cuisine with an Indian and Hmong twist (a nod to the families that have settled in Bentonville) inside The Hive at the 21C Museum Hotel. For an ethereal eating experience, book a table at The Preacher’s Son for a gluten-free meal inside a renovated church that includes a speakeasy downstairs for after-dinner tipples.

Stay: The 21C Museum Hotel Bentonville sits just off the main town square of downtown Bentonville and would be on the list of must-see places within the city even if you’re not booking a room within its 104 rooms due to its rotating gallery of art.

Breakfast: The biscuits are huge and the coffee is strong at The Buttered Biscuit, where their strawberry cheesecake pancakes make this restaurant a true indulgence for breakfast.

Town: The boutique shops and antique stores of historic downtown Rogers alone add up to one worth it stop along the way to Eureka Springs, but now the town’s brick-lined streets lead to an award-winning craft brewery and the new headquarters for locally beloved Onyx Coffee Lab.

Eat & Drink: A short drive from downtown Rogers will put you face-to-face with Arkansas’ only working watermill. The War Eagle Mill is a working gristmill (buy organic grain, cereal, and flour on site), and serves one of the best brunches in the state from the restaurant inside (breakfast and lunch also available). Visit the third weekend in October for the mill’s celebrated arts and craft fair.

Nature: War Eagle Cavern is just a two-mile drive off the main road, where you’ll find the only lakeside cavern entrance in the state. Cave tours are available and take you deep within the caverns of this historic spot.

Do: More than 60 natural springs bubble and spring from this quirky Victorian town, where a series of winding staircases guide visitors up and down the steep terrain to boutique shops, family-owned restaurants (chain stores and restaurants are banned in downtown Eureka Springs), and miles of hiking trails. An active artist enclave colors the town with an artsy vibe, but it’s the underground catacombs and sinister story behind the town’s largest hotel that keeps intrigue alive.

Eat & Drink: A bicycle sits on top of the marquee at Sparky’s Roadhouse Café, which is the first sign of this ’50s style diner’s funky decor. Come prepared to sign a waiver if you plan to sample their Stupid Hott Burger with homemade ghost chili salsa, or simply lounge coolly with a cold beer on their open-air patio.

Stay: Known as “The Grand Ol’ Lady of the Ozarks,” the 1886 Crescent Hotel and Spa features 72 guest rooms and 4 luxury lodges on its stunningly landscaped perch overlooking the town of Eureka Springs. The hotel is known as the most haunted hotel in America, where nightly ghost tours uncover the hotel’s haunting past.

Breakfast: The Eureka Springs Coffee House serves freshly-baked cinnamon rolls and muffins alongside a variety of specialty coffee drinks made from Onyx Coffee Lab’s signature roasts.

Town: Ridgedale, Missouri, is home to the Top of the Rock, a scenic overlook at Big Cedar Lodge that offers four levels of viewing balconies to gaze out upon the Ozark Mountains and Table Rock Lake. Spend an hour or two soaking in the views before continuing on toward Branson.

Eat & Drink: The Buffalo Bar at Big Cedar Lodge offers the best views from its outdoor patio, where a menu of classic pub fare and wood-fired pizzas fill the lunch menu.

Detour: The Thorncrown Chapel is in the opposite direction from Branson, but a short detour to see this hidden glass chapel in the woods is worth the trip. The 48-foot chapel is one of three of Arkansas’ glass chapels, all designed by E. Fay Jones. The walk is short from the parking lot at the base of the hill, but the views are spectacular inside and outside of this absolutely inspiring structure.

Do: Branson offers an authentic American small-town charm like few other towns can even imagine. Pies are sweeter in Branson, shopping is friendlier, and the entertainment is as clean as the streets of its historic downtown.

Eat & Drink: Branson Landing is where the nightlife action happens in town, but for an authentic Branson meal, head to the Farmhouse Restaurant to fill up on chicken fried steak, fried okra, and their famous blackberry cobbler.

Stay: The Branson Hotel features nine rooms inside a renovated 1903 historic buildings and is reserved only for adults. For a more family-friendly option, check in to the lakefront condos at Still Waters Resort overlooking Branson’s Table Rock Lake.

Breakfast: Breakfast is served all day at Billy Gail’s Café, where their homemade apple cinnamon rolls weigh a pound and their Billion Dollar Bacon is hearty enough to be an entrée itself.

Town: Thayer, Missouri. This small town is just 10 miles from Grand Gulf State Park, which is more commonly known as the “Little Grand Canyon.” The gulf itself stretches for a mile between canyon walls reaching 130-feet tall, where natural bridges and collapsed caves leave much to be explored.

Eat & Drink: Cross back over the border to Mammoth Springs, Arkansas, to dine al-fresco by the mighty Spring River at Wood’s Riverbend Restaurant. Breakfast is served all day long, but their BBQ ribs will keep you satisfied all the way to St. Louis.

Roadside Attraction/Nature: Elephant Rocks State Park is home to giant red granite boulders that have taken the shape of elephants. Use your imagination to make out the elephant shapes, or simply climb to the top of the 27-foot-tall Dumbo rock for the ultimate bragging rights.

Do: Set along the west bank of the Mississippi River, St. Louis is home to the only National Blues Museum in the country and offers amazing photo ops from either the bottom or top of the city’s famous Gateway Arch. St. Louis is naturally suited for adventures, with its Citygarden, caverns, and nature reserves.

Eat & Drink: It’s the local wild cherry wood used to smoke all the meat at The Shaved Duck that makes all the difference in this award-winning St. Louis BBQ joint. You won’t go wrong with anything from the smoker, but make sure to leave room for their brown butter brussels sprouts and buttermilk cornbread.

Stay: Each of the four rooms within this 19th century home take the name of an iconic location within the city, and add to the charm of the Fleur-de-Lys Mansion, Luxury Inn at the Park. Breakfast is included in the stay, and includes freshly baked breads, locally roasted coffee from Thomas Coffee, and only the freshest local ingredients possible.

Town: Cuba. Cross Cuba off your list…well, at least Cuba, Missouri; this small town is loaded with charisma. Drive along Cuba’s Historic Route-66 for an outdoor art gallery of sorts as you pass by the town’s 12 outdoor murals depicting famous moments in history.

Eat & Drink: Shelly’s Route 66 Café hasn’t changed much since it first opened during this historic route’s heyday. This classic diner serves up hearty breakfasts and daily specials for lunch.

Photo Op: Onondaga Cave State Park. The dramatic stalagmites and impressive underground ponds within the Onondaga Caves are just as photogenic as the Vilander Bluff Natural Area that sits above them; although you don’t need to wait for a guide to access the panoramic views of the Meramec River at the top of Vilander Bluff.

Do: Osage Beach is just one of the quaint towns surrounding Lake of the Ozarks, where everything revolves around the water. Speedboats, pontoons, fishing boats, and jet skis can all be rented at an hourly rate, and even the local spas offer floating therapies.

Stay: The Inn at Harbour Ridge is located just outside the city limits of Osage Beach on a lakefront property nearby a community dock and swimming platform. Four guestrooms create a cozy ambiance, while gourmet breakfasts of cheddar omelets or baked cinnamon French toast and peach-smothered sausages fuel guests for a day of adventuring around the lake.

Shop: There are more than 65 stores mapped out along the Osage Beach Outlet Marketplace, where shoppers can score deals on designer handbags or grab a stylish swimsuit for the boat.

Eat & Drink: Set along Historic Route-66 in a ’50s-style diner building, Iggy’s Diner serves breakfast, lunch, and dinner, and hand dips their ice cream for their famous floats, malts, and shakes.

Roadside Attraction: Designed by Precious Moments creator Samual J. Butcher, the Precious Moments Chapel in Carthage, Missouri, is a standalone chapel devoted entirely to the Precious Moments characters the artist created more than 35 years ago. Sistine Chapel-style murals line the inside of the building, while a gift shop sells everything from exclusive figurines to wedding accessories.

Nature: A long viewing platform at the Schermerhorn Park and Cave lets visitors peek inside this half-mile-long cave, where rare species of salamander are protected by the WPA in this unusual habitat. The park is part of the 55 square miles that comprise the Ozarks of Kansas, and this little slice of the state is ripe with caves, sinking streams, and sinkholes.

Do: The historic town of Baxter Springs is just a few miles from the OK-KS-MO Tri-State Marker (stand in three places at one time!), where it sits along Historic Route-66 with preserved gas stations and vintage service buildings. The town’s Native American and Route 66 history are preserved within the Baxter Springs Heritage Center & Museum, where visitors can begin a self-guided drive to 12 different sites along the town’s Civil War trail, including Fort Blair.

Eat & Drink: Rita’s Roost Bistro & Sweet Shop is located nearby the old 1870s Crowell Bank building—legend has it that Jesse James robbed the bank in 1876—where it serves burgers and hot dogs inside its ’50s-themed interior. Finish your float and head next door to the Spinout Arcade for some classic games of pinball, air hockey, and bumper cars.

Stay: The three bedrooms inside the Rose Cottage along Route 66 encompass both floors of this 1899 Victorian home. Spend your morning sipping tea in the dining room while the sound of a vintage record player churning out rhythmic jazz sets the tone for the day as birds bathing just outside the windows in the cottage garden.

Breakfast: Weston’s Route 66 Café offers comfort diner food with friendly service. The coffee is hot, the biscuits are drenched in gravy, and pies are made fresh daily.

Town: The Blue Whale of Catoosa may sound like a mythical creature, but in the town of Catoosa, it’s a local legend. Made from metal and cement, the whale was built in a pond as a surprise anniversary gift in the ’70s but became a secret swimming hole along Route 66. Swimming isn’t allowed any longer, but the spot is a popular picnic area and the whale has its own IG hashtag #bluewhalecatoosa.

Eat & Drink: There are some great diners along this Route 66 town, but if you’re just in it for the whale photo, grab a pineapple whip (or a snow cone topped with Nerds and a Ring Pop) from the Oh Mighty Ices food truck and enjoy your treat around the colorful picnic tables set up for prime whale spotting.

Do: There are more than 130 miles of shoreline surrounding Lake Tenkiller at Tenkiller State Park. Along with watersports and fishing, the clear waters of the lake provide ideal conditions for scuba diving to the lake’s sunken airplane fuselage, school bus, helicopter, and two boats.

Eat & Drink: Boats and jet skis can pull right up to the floating deck at Clearwater Café at Pine Cove Marino on Tenkiller Lake, where steaks are cooked to order and onion rings come stacked a foot high.

Stay: RV and tent campgrounds line the park grounds, but it’s the state park’s 38 cabins that offer the best views and plots along the lake. Cabins range from one-bedroom units to three-bedroom units, but all are equipped with heat and air conditioning with linens and bedding for four.

Breakfast: There are few things sweeter than Sweet Nana’s Donuts, other than maybe Nana herself. This mom-and-pop bakery serves full breakfast (bacon, eggs, breakfast burritos, hot coffee, etc.), but the specialty donuts, maple bacon bars, and sausage rolls are among the best sellers.

Town: Fort Smith is the third most populated city in Arkansas, and this quirky town offers everything from an amusement park ride in the middle of its downtown to a museum dedicated entirely to the spot where Elvis Presley got his first buzz cut when joining the Army on March 25, 1958.

Eat & Drink: The cranberry pecan bread at The Bread Box in Fort Smith is legendary around Arkansas. Sandwiches are the specialty at this family-run bakery, like their chicken salad sandwich on cranberry pecan bread or the Amy Joe grown-up grilled cheese with melted cheddar and swiss cheeses on grilled spinach feta bread topped with tomatoes, sliced pickles, and jalapenos.

Do: Located in Central Arkansas’ Ouachita Mountains, Hot Springs is home to some of the most prized thermal waters in the country (143-degrees and packed full of minerals). Run the bases around one of the first MLB Spring Training fields in the country or soak in the gangster history at Bathhouse Row—once a favorite vacation spot for legendary criminals Al Capone, Lucky Luciano, and Bugsy Siegel.

Eat & Drink: The Superior Bathhouse Brewery serves upscale pub food and craft beers brewed from the thermal waters of the National Park inside a renovated bathhouse. Former speakeasy and mobster hangout, the Ohio Club, is still a hot spot for nightlife in Hot Springs.

Stay: The chic Hotel Hale operates inside a renovated bathhouse along Bathhouse Row, where this boutique property features nine modern guestrooms with thermal water bathtubs.

Breakfast: Kollective Coffee and Tea is one of the top third-wave coffee shops in Arkansas, serving organic and local specialties (vegan options available) alongside locally-roasted coffee.

Eat & Drink: Save your appetite on this short stretch to dine in one of Little Rock’s many local restaurants.

Nature: During a fall road trip, stop in at the Roseberry Farms Pumpkin Patch for an authentic Arkansas hay ride and s’mores around the fire.

Do: Little Rock, Arkansas, is a city of tales and trails. The tales begin with the Little Rock Central High School on the U.S. Civil Rights Trail, and the trails begin with the Big Dam Bridge that connects 14 miles of riverside trails throughout the city. The trail connects Little Rock’s bustling River Market district to countless breweries and restaurants and even provides pedestrian/cyclist access to the Clinton Presidential Center.

Eat & Drink: Set inside a repurposed gas station, The Fold: Botanas & Bar is modern Ark-Mex at its finest. The décor is retro-chic and the tacos are served on handmade tortillas and filled with locally sourced ingredients. Order their ground bison burrito and a lemon-rosemary margarita for the full experience.

Stay: The Empress of Little Rock is listed on the National Register of Historic Places for its pure representation of Victorian architecture, where nine rooms and suites create a cozy retreat for guests at this charming bed and breakfast. 

Breakfast: Weekend brunch lines at At the Corner, a Modern Diner extend into the streets of Little Rock’s River Market district, but out in the Argenta Arts District, Saturdays are for all-you-can-eat pancakes over at Mugs Café. During the week this hipster coffee house serves breakfast starting at 7 a.m. and locally roasted coffee all day long.