12 Unforgettable Family Road Trips for This Summer

The classic American road trip is a cherished tradition for families across the nation.

Cruising down scenic highways and stopping to check out whatever catches your attention — whether it's a breathtaking viewpoint, a quirky roadside diner, or a historic landmark — is a fantastic way to discover the U.S. with your loved ones this summer.

It's also an affordable travel option, especially if you use points, rent an RV, or stay at budget-friendly motels or campgrounds along the way. Depending on where you're headed, booking a few hotels ahead might be a good idea, but after that, feel free to be spontaneous. While it might be tough to snag a cheap last-minute hotel in a busy spot like Hilton Head, you’ll likely find plenty of great options in quieter places like Missouri.

Of course, road trips with children come with their own set of challenges, like keeping them entertained and managing potential motion sickness.

Try using a fun, kid-friendly voice on the Waze app for directions to keep everyone laughing. Bring along iPads that attach to the back of the headrests and make a list of classic road trip games like I Spy, 20 Questions, and license plate spotting. Pack your kids’ favorite snacks, plenty of water, and don't forget extra clothing, plastic bags, paper towels, or wipes... just in case anyone feels sick.

It's also a good idea to bring a solid credit card for gas purchases. Check out TPG's guide to the best cards for fuel. You can use the GasBuddy app to find nearby stations offering the best prices.

Now that the practicalities are taken care of, let's dive into 12 iconic summer road trips across the U.S.

Appalachian Highlands to Nashville

Take a scenic route through Appalachia, culminating in a visit to Nashville, with stops in West Virginia and Kentucky. Begin in Charleston, West Virginia, the state capital, where three major highways converge. You can easily fly into West Virginia International Yeager Airport (CRW).

Day One: Arrival in Charleston

Explore West Virginia's stunning Capitol building, which boasts a gold-leaf dome that's 5 feet taller than the U.S. Capitol. Don't miss the West Virginia State Museum, where you can dive into Appalachian history and culture, or the Avampato Discovery Museum, a hands-on science museum for visitors of all ages.

Wander down the charming, tree-lined Capitol Street and grab a bite at one of its many restaurants. For a local favorite, head to Dem 2 Brothers and a Grill for some mouthwatering barbecue.

Charleston offers a variety of major hotel chains for your stay. Use your Marriott Bonvoy points at the Charleston Marriott Town Center (rates start at $124 or 15,500 points per night) or Four Points by Sheraton Charleston (rates start at $114 or 15,500 points per night). Alternatively, redeem Hilton Honors points at Embassy Suites by Hilton Charleston (rates start at $131 or 36,000 points per night).

Day Two: Travel from Lexington to Louisville

From Charleston, take a scenic three-hour drive to Lexington, Kentucky, known as the heart of horse country. Spend time at the renowned Keeneland Racecourse and tour the Kentucky Horse Park. Don't miss the newly revamped Distillery District, where you can enjoy pizza, ice cream, craft beer, live music, and, of course, bourbon.

Next, head to Louisville, just an hour and a half away. Stop for a hearty Southern meal at the Claudia Sanders Dinner House (yes, that Sanders... Claudia was the Colonel's wife).

Louisville is packed with family-friendly activities, such as the Louisville Slugger Museum & Factory, the Kentucky Science Center, and a fun-filled Ohio River cruise aboard the historic Belle of Louisville steamboat.

Stay at the iconic 21c Museum Hotel, which is part of the Accor Live Limitless rewards program (rooms start at $212 per night). This hotel combines contemporary art with comfort, featuring a museum and the celebrated Proof on Main restaurant. For a more classic experience, check out The Seelbach Hilton Louisville, a Beaux-Arts gem dating back to 1869 (rooms start at $133 or 36,000 Hilton Honors points per night). This hotel is known for its elegant, old-world charm, with a stunning lobby adorned with Renaissance-style carvings and a dome made of 800 glass panels.

Day Three: Explore Nashville

Drive south to Nashville, a three-hour journey that leads you to Music City, where you can unwind at Hotel Fraye, part of Hilton's Curio Collection (rooms start at $190 or 57,000 Hilton Honors points per night). If you're looking for a modern stay, check out the new Tempo by Hilton, which opened in February (rooms start at $169 or 50,000 Hilton Honors points per night). Both hotels are located in downtown Nashville, near the famous Ryman Auditorium, Broadway's honky-tonk bars, and great dining options.

While in Nashville, explore its vibrant culture by visiting landmarks like the Country Music Hall of Fame and Museum, Radnor Lake State Park, the Nashville Zoo, and the Grand Ole Opry. Families will love the tech-infused mini-golf experience at Puttshack, and everyone can enjoy the new Nashville Yards development, which will offer a music venue, a cinema, and 350,000 square feet of shopping and dining.

Before heading to Nashville International Airport (BNA), be sure to grab some locally made chocolate treats at the Goo Goo Clusters Shop to sweeten your journey home.

Highlights of Lake Michigan

Take a scenic route along Lake Michigan, starting in Milwaukee, continuing south to Chicago, and then making your way up through Michigan, ending in Traverse City.

Day One: Discover Milwaukee

Arrive at Milwaukee Mitchell International Airport (MKE) and dive into the city's rich cultural scene with a visit to the Lynden Sculpture Garden, the Milwaukee Art Museum, the Milwaukee Public Museum, and the interactive Discovery World Science and Technology Center. Don't miss a frozen custard from Kopp's, and for a unique experience, head to SafeHouse, a spy-themed burger restaurant that kids will absolutely enjoy.

Hyatt enthusiasts can use their points or redeem free night certificates for a stay at the Hyatt Regency Milwaukee (starting at $115 or 6,500 World of Hyatt points per night). Alternatively, Marriott points can be used at the Milwaukee Marriott Downtown (rates starting at $159 or 34,000 Marriott Bonvoy points per night).

Day Two: Chicago Adventure

Drive south for about two hours to reach Chicago, a city brimming with family-friendly activities such as the Shedd Aquarium, the Field Museum of Natural History, Lincoln Park Zoo, and Millennium Park. If you're planning an overnight stay, consider the Pendry Chicago (starting at $242 per night) or the Kimpton Gray Hotel Chicago (starting at $160 or 38,000 IHG One Rewards points per night), both excellent choices for families.

Day Three: Indiana Dunes National Park to Traverse City

From Chicago, take a scenic drive along the lakefront, making a stop at the newly established Indiana Dunes National Park to enjoy some lakeside fun before heading north to the picturesque town of Holland, Michigan. Founded by Dutch settlers, Holland is known for its iconic windmill, annual tulip festival, and Dutch-inspired delicacies, including the famous pastries at deBoer Bakkerij & Dutch Brothers Restaurant.

The stunning lakeshore features Holland State Park, Laketown Beach, Tunnel Park, and a charming red lighthouse.

Traverse City is located 168 miles to the north, and along the way, you can discover a variety of small towns and the scenic Huron-Manistee National Forests.

Once you reach Traverse City, take some well-deserved time to relax on the beach. If you're visiting in late June or early July, don't miss the renowned National Cherry Festival.

For a fun family getaway, consider staying at the Great Wolf Lodge to enjoy its indoor water park, or use IHG One Rewards points to book a stay at Hotel Indigo Traverse City (starting at $144 or 26,000 IHG One Rewards points per night).

Depart from Cherry Capital Airport (TVC).

Big Bend National Park, located in Texas, is a stunning destination.

Stretching for 150 miles along the border between Texas and Mexico, Big Bend National Park offers a breathtaking and adventure-packed road trip.

Day One: From El Paso to Marathon

Fly into El Paso International Airport (ELP), then drive about 300 miles southeast to the remote Big Bend park. Stop for lunch in the artistic town of Marfa at Sentinel or Convenience West for some delicious barbecue. Continue your journey to Marathon, where you can stay at the historic Gage Hotel (rooms start at $229 per night) and dine at the Brick Vault Brewery and Barbecue.

Days Two and Three: Explore Big Bend National Park

Once you're in the 800,000-acre Big Bend National Park, every road you travel offers incredible scenic vistas. The park mainly consists of the Chihuahuan Desert, which stretches alongside the Rio Grande and features the majestic Chisos Mountains. Notable stops include the Ross Maxwell Scenic Drive, the eerie Terlingua Ghost Town, the Santa Elena Nature Trail, zip-lining at Lajitas, and the stunning Boquillas Canyon.

The park is also full of family-friendly hiking routes and boat tours along the Rio Grande for a fun experience for all ages.

For those not into camping, consider staying at the family-owned Big Bend Holiday Hotel, offering charming vintage rooms and beautifully designed casitas (starting at $97 per night). For a more family-friendly experience with amenities like a golf course and swimming pool, stay at Lajitas Golf Resort (starting at $224 per night).

The central coast of California

California's breathtaking coastline offers endless adventure. The central coast, in particular, is perfect for families with plenty of wildlife, history, and spectacular waves. You can fly in and out of Meadows Field Airport in Bakersfield (BFL) or San Luis Obispo County Regional Airport (SLO).

Day One: Pismo Beach

Start your journey in Pismo Beach. If you visit between October and February, make sure to see the Monarch Butterfly Grove, where monarchs stop during migration. Then, take a stroll along the Pismo Pier and rent a multi-person surrey to cruise down the boardwalk. Don’t miss dining at Splash Cafe, and treat yourself to the delicious baked goods at Old West Cinnamon Rolls.

For a cozy stay, use your Hilton Honors points at the Hilton Garden Inn San Luis Obispo/Pismo Beach (rooms start at $128 or 34,000 points per night) or opt for the charming and budget-friendly SeaCrest OceanFront Hotel (rooms start at $189 per night).

Day Two: Morro Bay to San Simeon

Continue your adventure on the Pacific Coast Highway, driving just 30 minutes north to Morro Bay. Here, you’ll encounter the iconic Morro Rock, the last of the Seven Sisters — a series of ancient volcanic peaks that stretch from Morro Bay to San Luis Obispo. For a truly magical experience, try to catch it at sunset.

Next, head to Cambria for a dose of rural charm. Spend time with adorable goats, watch cows being milked, and sample fresh cheese at Stepladder Ranch and Creamery. Saddle up for a ride on a majestic Clydesdale horse at Covell Ranch, take in the beauty of Moonstone Beach, and enjoy a delicious meal at Robin's.

Keep heading north to San Simeon, where a visit to the Piedras Blancas Elephant Seal Rookery is a must. Watch the playful seals basking in the sun just off the highway. Then, venture inland to the stunning Hearst Castle, where you can explore 127 acres of lush gardens, grand pools, and winding paths. If you're lucky, you may even spot some zebras on the tram ride to the castle!

For a budget-friendly stay, use 16,000 Choice Privileges points (or $78 per night) at the Quality Inn Near Hearst Castle. For a more upscale experience, try the Cavalier Oceanfront Resort, with rates starting at $169 per night.

Dramatic coastal Maine

The rugged coastline of Maine is lined with dramatic cliffs, crashing waves, and charming lobster shacks, offering a perfect opportunity for a scenic drive along winding roads with breathtaking views of the Atlantic.

Day One: Portland

Begin your journey in Portland, a lively and pedestrian-friendly city known for its vibrant culinary scene. You can fly into Portland International Jetport (PWM) or Boston Logan International Airport (BOS), which is about a two-hour drive south. Manchester-Boston Regional Airport (MHT) in New Hampshire is also a convenient option for Southwest Airlines travelers.

Wander through the charming Old Port district, where you can pick up some fudge for the kids while browsing local pottery and unique jewelry. Don't miss the Children's Museum and Theatre of Maine, and be sure to climb the Portland Observatory for stunning views of the harbor.

Portland is a food lover's paradise with many family-friendly dining options. A few local favorites include Two Fat Cats Bakery, Duckfat, Salvage BBQ, and the newly opened Quanto Basto for delicious Neapolitan pizza.

For a comfortable stay, use your Marriott Bonvoy points at the Residence Inn Portland Downtown/Waterfront (rates from $125 or 41,000 points per night), which features an indoor pool. Alternatively, stay at the stylish and historic Press Hotel (rates from $195 or 52,000 points per night), part of the Autograph Collection.

Day Two: Rockland to Bar Harbor

Travel further north through Freeport and make a stop at the L.L. Bean Outlet before heading to Rockland. Here, you can explore the Farnsworth Art Museum, the Maine Lighthouse Museum, and the Coastal Children's Museum.

Grab a hot dog from Wasses or stop by the Good Tern co-op to pick up picnic supplies, then head to Birch Point State Park for a relaxing day. If you're in town during the summer, don't miss the Maine Lobster Festival in Rockland, typically held from July 31 to August 4.

Drive north from Rockland to Bar Harbor, where you can explore Acadia National Park. Enjoy a variety of outdoor activities including hiking, biking, kayaking, and swimming in Echo Lake. Be sure to stop by the iconic Jordan Pond House for some of the best popovers in Maine. For a seafood treat, visit the new Travelin' Lobster outpost on Main Street.

Book your stay using Hilton Honors points at the Hampton Inn Bar Harbor, open from May to October. With rates starting at $281 or 87,000 points per night, this hotel offers stunning panoramic views of the ocean and mountains, along with two pools to enjoy.

Nature-based fun in Florida

Florida offers much more than just theme parks. For those seeking nature-filled family activities, the state has plenty to offer. This 118-mile route highlights some of the best natural wonders, from Tampa to Fort Myers, alongside some of the Gulf Coast's most stunning sugar-sand beaches. Begin your journey by flying into Tampa International Airport (TPA) and depart from Southwest Florida International Airport (RSW).

Day One: Tampa to Sarasota

Begin your adventure by driving Highway 60 west from Tampa to Clearwater Beach, then head south toward Pass-a-Grille. This 20-mile stretch along the coast features picturesque beaches and waterfront restaurants where you can enjoy fresh grouper straight from the Gulf.

On your return east, follow the signs to Fort De Soto Park. This 1,136-acre park offers beaches, mangroves, bike trails, and historic remnants of a Spanish-American War fort. After exploring, continue south to Sarasota to rest for the night.

For accommodations, use your Marriott Bonvoy points at the Westin Sarasota Downtown (rates start at $195 or 31,000 points per night), or treat yourself to the beachfront Ritz-Carlton, Sarasota (rates start at $538 or 59,500 points per night). The St. Regis Longboat Key Resort will also open soon, so make sure to save your Bonvoy points for this luxurious stay.

Sarasota is home to a wealth of natural wonders. The Ann Goldstein Children's Rainforest Garden at Marie Selby Botanical Gardens, located on Sarasota's bayfront, invites kids to explore a lush rainforest, a fun experience that parents can also enjoy.

Across Sarasota Bay, dive into the world of Gulf of Mexico wildlife at Mote Marine Laboratory & Aquarium. You can also embark on one of Mote's eco-boat tours, led by marine biologists, for a unique exploration of Sarasota Bay.

When it's time to eat, head to O'Leary's Tiki Bar and Grill next to Bayfront Park, which features a playground and walking trails. Alternatively, The Old Salty Dog on Sarasota Bay offers a fun twist, serving kids' meals on frisbees.

Day Two: Sarasota to Fort Myers

On the second day, take Highway 72 inland to Myakka River State Park, where alligators are a common sight basking on the riverbanks. Explore the park's boardwalks and canopy trails, or rent kayaks to glide through the waterways, with options for boat tours too.

Drive south along Highway 41 to reach Fort Myers, where you can meet the gentle manatees at Manatee Park and explore the lush wetlands at Six Mile Cypress Slough Preserve.

Stop by Shrimp Shack for a delicious and quick seafood meal, and for dinner, savor the award-winning pies at Fine Folk Pizza.

Use your Hilton Honors points to stay at the Hilton Garden Inn Fort Myers (rates start at $119 or 33,000 points per night) or opt for Hampton Inn & Suites Fort Myers-Colonial Blvd. (rates start at $115 or 33,000 points per night).

Fun in the Finger Lakes

The Finger Lakes region in western New York is made up of 11 stunning lakes that stretch from Syracuse to Rochester and Elmira-Corning. Though each lake varies in size, they're all surrounded by picturesque towns and vineyards. You can embark on a circular journey by flying in and out of Frederick Douglass Greater Rochester International Airport (ROC), located about an hour and a half from Skaneateles, your starting point.

Day One: Skaneateles

Begin your adventure in the charming town of Skaneateles (pronounced SKINNY-atlas). Start with a stop at Skaneateles Bakery for freshly baked doughnuts and blueberry muffins, then take your treats for a leisurely stroll along the pier by the lake.

Set sail on a boat tour of Skaneateles Lake with Mid-Lakes Navigation — you can even assist the Barbara S. Wiles mail boat in delivering mail to the lakeside cottages.

As the evening sets in, enjoy a film at New York's oldest drive-in theater, Finger Lakes Drive-In, then rest for the night at the cozy The Bond 1835 bed-and-breakfast or Skaneateles Suites. While points hotels are limited in this area, you can use Hilton Honors points for a stay at the Hilton Garden Inn Auburn (rates start at $132 or 38,000 points per night), located north of Owasco Lake, the next lake in line.

Day Two: Seneca Falls to Canandaigua Lake

Take a 22-mile drive west to Seneca Falls to explore the Women's Rights National Historical Park, where the first women's rights convention took place in 1848.

Continue along Route 20 toward Seneca Lake, a prime spot for kitesurfing and windsurfing, or take a relaxing sail with Sail Seneca.

The town of Geneva, located at the top of Seneca Lake, offers delightful dining and shopping experiences, including places like F.L.X. Fry Bird and Kindred Fare. Discover the Seneca Lake Wine Trail with stops at renowned vineyards such as Hermann J. Wiemer Vineyard, Red Tail Ridge Winery, Barnstormer Winery, and Fox Run Vineyards. At the southern end of the lake, you'll find Watkins Glen State Park, famous for its dramatic waterfalls, scenic canyons, and hiking trails.

Drive further west to Canandaigua Lake, where you'll find the stylish Lake House Canandaigua (rates start at $280 per night), part of the Preferred Hotels & Resorts network. This lakeside retreat features a pool and hot tub with stunning views, the Rose Tavern serving farm-to-table cuisine, kayaking, and even a private yacht to explore the lake in luxury.

If you're looking to earn or redeem Hilton Honors points, consider staying at the Hotel Canandaigua, Tapestry Collection by Hilton (rates start at $124 or 36,000 points per night). This lakeside hotel offers a pool and direct access to the Canandaigua Lady at Steamboat Landing. Don't miss a drive to the southern end of the lake to Naples for a taste of its famous grape pie.

Day Three: Rochester

Wrap up your journey with a visit to Rochester, just 28 miles northwest of Canandaigua. Explore the George Eastman Museum, dedicated to the founder of Kodak, the Strong National Museum of Play, a hands-on museum for toys and games that expanded in 2023, the Susan B. Anthony House, now a museum, and Highland Park, famous for its annual flower festivals.

For a taste of local cuisine, stop by the Rochester City Public Market, a vast farmers market with vendors from all over the region. Be sure to try the city's iconic "garbage plate" at Nick Tahou Hots, the original spot that invented this one-plate meal with potatoes, meat, and various sides.

Use Hyatt points for a stay at the recently renovated Hyatt Regency Rochester (rates start at $105 or 5,000 points per night) or opt for the Courtyard by Marriott Rochester Downtown (rates start at $167 or 16,000 points per night) for a convenient and central location.

The coastline of South Carolina

South Carolina's coastline is home to some of the finest beaches in the South, complemented by incredible food along the way. The adventure begins on Hilton Head Island, where you can fly into either Hilton Head Island Airport (HHH) or Savannah/Hilton Head International Airport (SAV). The journey concludes 220 miles north in Myrtle Beach, where you can catch your return flight from Myrtle Beach International Airport (MYR).

Day One: Hilton Head Island

Start your adventure on Hilton Head Island, soaking up the sun at the popular Coligny Beach Park. For a more peaceful atmosphere, consider heading to Alder Lane or Burkes Beach.

Explore the rich history and culture of South Carolina's Lowcountry and Gullah heritage at the Coastal Discovery Museum. Embrace the region's natural beauty with a visit to the Pinckney Island National Wildlife Refuge and Sea Pines Forest Preserve.

Afterward, savor authentic Gullah dishes at Ruby Lee's or indulge in fresh seafood at Skull Creek Boathouse. For a restful night, stay at a luxurious beachfront resort like Omni Hilton Head Oceanfront Resort (rates from $280 per night), or, if you have Marriott Bonvoy points, consider the Westin Hilton Head Island Resort & Spa (rates from $183 or 40,000 points per night).

Day Two: Charleston

Travel north along Route 17 to the charming city of Charleston. Once there, take a stroll along Museum Mile, where you can visit attractions such as the Charleston Museum, the Children's Museum of the Lowcountry, and some of the city's historical homes and parks. The newly opened International African American Museum, inaugurated in June 2023, stands at a former wharf where enslaved people were once brought ashore.

At the southern tip of the Charleston peninsula, explore The Battery and White Point Gardens, featuring Civil War-era artillery, views of Fort Sumter, and ancient live oak trees. Children will enjoy the South Carolina Aquarium, which includes a delightful touch tank experience.

For more beach fun, head to the 6-mile stretch of Folly Beach and savor a delicious bowl of Frogmore stew at Bowens Island Restaurant, a beloved Lowcountry spot.

Charleston's food scene is nothing short of iconic. Be sure to try Southern specialties and fresh seafood at local gems like Rodney Scott's BBQ, Leon's Oyster Shop, and Bertha's Kitchen. If you're in the mood for something unique, check out the newly opened D.C.-favorite Makan, offering authentic Malaysian dishes focused on local seafood. For breakfast all day, Daps Breakfast & Imbibe serves pancakes, including one made with Fruity Pebbles mixed into the batter.

You'll find plenty of major hotel brands in Charleston, so if you have a preferred loyalty program, book a stay at places like the Charleston Marriott (rates from $152 or 30,000 Marriott Bonvoy points per night) or Hyatt Place Charleston/Historic District (rates from $212 or 15,000 World of Hyatt points per night).

For a more unique experience, Charleston boasts several boutique hotels and historic properties, such as the Palmetto Hotel, The Loutrel, Planters Inn, and The Dewberry. If you're looking for the best of both worlds, consider staying at Mills House Charleston, Curio Collection by Hilton (rates from $283 or 75,000 Hilton Honors points per night).

Day Three: Myrtle Beach

Just before crossing into North Carolina, you'll reach Myrtle Beach, a top destination in South Carolina. While the area boasts some touristy spots like amusement parks, water attractions, chain restaurants, and shopping malls—likely a hit with kids—it also features 60 miles of pristine beach, known as the Grand Strand.

For a more peaceful experience, explore the Golden Mile, a no-hotel zone, or head to the sand near 82nd Avenue for the gay-friendly beach. Away from the shore, enjoy the Murrells Inlet Marsh Walk, where you can listen to live music and sip on drinks as you go, or wander the lively Myrtle Beach Boardwalk. Don't forget to try the local barbecue at True BBQ, owned by Joseph and Sheila Evans.

Use your Hilton Honors points to stay at the Hilton Grand Vacations Club Ocean Enclave Myrtle Beach (rates from $161 or 76,000 Hilton Honors points per night), just two blocks from the boardwalk. The all-suite resort features two pools, a kids' activity center, and an oceanfront dining option.

Pacific Northwest parks trip

Oregon boasts some of the most pristine landscapes in the U.S., including the breathtaking Crater Lake National Park. From there, the quaint town of Bend presents a perfect mix of small-town charm set against a striking natural backdrop. For this journey, book a round-trip flight to and from Rogue Valley International-Medford Airport (MFR), located 75 miles from Crater Lake and 172 miles from Bend.

Days One and Two: Crater Lake National Park

Begin your adventure at Oregon's Crater Lake National Park, home to the deepest lake in the U.S. Known for its remarkable purity, the lake is fed by rain and snow that fill the caldera left behind by a volcanic eruption centuries ago. Drive the 33-mile loop road around the crater, pausing to enjoy panoramic views and hike scenic trails. Stay at Farewell Bend Campground or use 30,000 Choice Privileges points for a night at the Sleep Inn & Suites in nearby Chiloquin (or from $150 per night).

Days Three and Four: Bend

On day three, drive 100 miles north to the high desert town of Bend, Oregon. Explore the Bend Ale Trail, which features 30 local breweries. If you're visiting in the fall, check out Smith Rock Ranch for a fun corn maze and pumpkin patches. Wander through the Old Mill District, where you'll find charming shops and restaurants by the Deschutes River, and be sure to visit the High Desert Museum to learn about the region's wildlife, history, and art.

Stay at Hampton Inn & Suites Bend (starting at $124 or 35,000 Hilton Honors points per night) or Residence Inn by Marriott Bend (starting at $140 or 30,000 Marriott Bonvoy points per night).

Next, head to the McKenzie River Valley, home to the picturesque McKenzie River National Recreation Trail. Be sure to visit the stunning Sahalie and Koosah Falls before taking Highway 5 south back to Medford.

A Journey Through Missouri via Route 66

While interstates have largely replaced the classic Route 66, this itinerary will take you on a scenic drive through the historic parts of the highway in Missouri.

Day One: St. Louis

Begin your adventure in St. Louis, known as the Gateway to the West. Upon landing at St. Louis Lambert International Airport (STL), make sure to visit the Gateway Arch National Park, home to the iconic Gateway Arch and the courthouse where Dred Scott, a Black enslaved man, fought for his freedom in the 1840s.

Other must-see spots include the beautiful Missouri Botanical Garden, the Saint Louis Art Museum, and the hands-on City Museum, a quirky attraction made from repurposed industrial materials inside a former shoe factory.

For families with kids, don't miss the Magic House children's museum. For dining, explore the City Foundry Food Hall, Balkan Treat Box, Louie, or the James Beard Award-winning Gioia's Deli. For a taste of classic St. Louis barbecue, head to Pappy's Smokehouse.

Redeem your Hilton Honors points at Embassy Suites by Hilton St. Louis Downtown (from $121 or 40,000 points per night) or World of Hyatt points at the Hyatt Regency St. Louis at the Arch (from $188 or 8,000 points per night), offering stunning views of the Gateway Arch. Marriott Bonvoy points can be used at the Magnolia Hotel St. Louis, a historic hotel in a 1924 building that once hosted Cary Grant (from $135 or 31,000 points per night). New in 2023, the 21c Museum Hotel in the former YMCA building is a stylish option, available with Accor Live Limitless points or starting at $183 per night.

Day Two: St. Louis to Lebanon

Head west on Interstate 44, the modern-day version of the iconic Route 66 in Missouri. Make a stop at Route 66 State Park, and explore quirky roadside attractions such as the Meramec Caverns and the world's second-largest rocking chair.

You'll pass through Cuba, known as the 'Route 66 Mural City', where 14 murals celebrating the town's history are painted on the sides of local buildings along the historic route.

For a delicious barbecue fix, swing by Missouri Hick Bar-B-Que. Afterward, continue your drive along part of the original Route 66, passing through the picturesque Mark Twain National Forest and the scenic Devil's Elbow bend on the Big Piney River. The kids will love stopping by the Uranus Fudge Factory for some sweet treats, complete with plenty of playful toilet humor. For an authentic retro experience, book a night at the Munger Moss Motel in Lebanon, which offers Route 66-themed rooms.

Day Three: Springfield

Before leaving Lebanon, make sure to visit the Route 66 Museum located inside the county library. Then, drive about 60 miles southwest to Springfield's Fantastic Caverns, one of Missouri's largest caves. Once in Springfield, enjoy family-friendly activities at the Discovery Center, Wonders of Wildlife, and Dickerson Park Zoo. Grab a burger at Black Sheep, and for a chocolatey treat, stop by Askinosie Chocolate for something sweet.

For a good night's rest, stay at the Best Western Coach House (rates starting at $109 or 20,000 Best Western Rewards points per night) or the Hilton Garden Inn Springfield, MO (rates from $132 or 36,000 Hilton Honors points per night). When you're ready to head home, catch a flight from Springfield-Branson National Airport (SGF).

Badlands and Black Hills of South Dakota

South Dakota’s Badlands and Black Hills are a perfect blend of rich history and stunning natural landscapes, making it a fantastic destination for a family getaway.

Day One: Rapid City to Badlands National Park

Fly into Rapid City Regional Airport (RAP), pick up your rental car, and drive 55 miles east to Wall Drug in Wall, South Dakota. Famous for offering free ice water, 5-cent coffee, and irresistible maple doughnuts, it’s a must-stop. Wall Drug is packed with souvenirs for all ages (so set a budget for the kids), and you’ll find a giant dinosaur and a massive jackalope outside.

From there, head south on Highway 240 to Badlands National Park, where you can explore ancient fossils and encounter wildlife like bighorn sheep, pronghorn antelope, eagles, and buffalo roaming across 244,000 acres of prairie, cliffs, and unique pinnacles. Evenings offer fun programs for kids, including meeting Smokey the Bear, stargazing, and learning about the park's geological wonders.

No need to rough it if you want to stay inside the Badlands. Cedar Pass Lodge offers cozy pinewood cabins with Wi-Fi and porches with deck chairs starting at $220, though you can also camp on-site if that’s more your style. Alternatively, stay at the Best Western Plains Motel in Wall (rates start at $120 or 20,000 Best Western Rewards points per night), just a 10-minute drive from the Pinnacles Entrance.

Day Two: Mount Rushmore to Custer State Park

From here, head west to Mount Rushmore National Memorial in Keystone. This iconic landmark, carved into the peak of Mount Rushmore in South Dakota, took 14 years to complete. It showcases the faces of four U.S. presidents: George Washington, Thomas Jefferson, Abraham Lincoln, and Theodore Roosevelt. Stroll along the Presidential Trail to get up close to the sculpture and spot wildlife such as mountain goats, marmots, and birds.

About 20 miles south, you'll find thousands of buffalo roaming freely at Custer State Park (be cautious as they often wander close to the road). The park is also home to pronghorn antelope, mountain goats, bighorn sheep, deer, elk, wild turkeys, and burros. Explore one of the many hiking trails or enjoy a peaceful boat ride on Sylvan Lake.

Take a break from driving and book an evening Blue Bell Lodge hayride and chuck wagon cookout. This includes a scenic three-hour wildlife tour with cowboy singers and a hearty steak dinner with all the sides. Alternatively, dine at the State Game Lodge Restaurant, located inside the historic Calvin Coolidge 'Summer White House.' Try adventurous game dishes such as rabbit, rattlesnake sausage, elk osso buco, and buffalo short ribs. You can also stay at the State Game Lodge (rates start at $183 per night), which was recently renovated in 2024. Outside the park, Comfort Inn & Suites in Custer (rates start at $127 or 25,000 Choice Privileges points per night) offers a comfortable stay.

Day Three: Crazy Horse Memorial to Rapid City

Take the scenic Needles Highway, surrounded by jagged granite spires, to the Crazy Horse Memorial. This monumental sculpture honors the legendary Native American chief and is still under construction. While there, visit the Indian Museum of North America and the Native American Educational and Cultural Center. Enjoy a delicious lunch at the Laughing Water Restaurant, where you can savor Native American dishes like tatanka stew and fry bread tacos.

Wrap up your adventure in Rapid City. Be sure to visit Tally's Silver Spoon for a delightful breakfast, served until 2 p.m. Indulge in dishes like whole wheat oatmeal waffles or a buffalo hanger steak with eggs. Afterward, take time to explore the expansive Prairie Edge Trading Company & Galleries, home to handcrafted Plains Indian arts, Native American exhibits, and a unique Italian glass bead collection.

Spend a night at the historic Hotel Alex Johnson, part of the Hilton Curio Collection. Rates start at $75 or 21,000 Hilton Honors points per night. Enjoy the striking lobby, where Native American-inspired design elements include a chandelier made of spears and an intricately painted ceiling.

Blue Ridge Parkway from Virginia to North Carolina

Stretching over 469 miles, the Blue Ridge Parkway links Shenandoah National Park and Skyline Drive in Virginia to the Great Smoky Mountains National Park in North Carolina, making it one of the most scenic drives in the country. Begin your journey by flying into Charlottesville Albemarle Airport (CHO) or Dulles International Airport (IAD). Your adventure will conclude in Asheville, where you can depart from Asheville Regional Airport (AVL) or the nearby Greenville-Spartanburg International Airport (GSP) in South Carolina, often offering more affordable flight options.

Day One: Journey from Charlottesville to Blowing Rock

Begin your adventure in Charlottesville, Virginia. If your family loves history, take a tour of Thomas Jefferson's Monticello, a UNESCO World Heritage Site and the former president's home. The Virginia Discovery Museum and IX Art Park are also great options for family fun. In downtown Charlottesville, enjoy a leisurely stroll down the pedestrian mall, exploring shops, cafes, and local favorites like Citizen Bar Burger and The Nook. The Dairy Market food hall is another fantastic stop with diverse dining options for all ages.

As you continue along the Parkway, make a stop at Natural Bridge, a stunning limestone arch known as 'Nature's Cathedral.' In Roanoke, stop for lunch at Mama Jean’s BBQ or head to Pop's Ice Cream & Soda Bar, a nostalgic spot with an impressive grilled cheese menu, along with sodas and ice cream. If time permits, consider a visit to the Taubman Museum of Art, where you can marvel at its collection of sparkling Judith Leiber handbags.

Pause for a picture at Mabry Mill, one of the Parkway’s most iconic landmarks. This historic mill, dating back to 1905, is known for selling freshly milled buckwheat flour — the perfect souvenir from your trip.

Cross into North Carolina and arrive in Blowing Rock. Take a stroll down Main Street, where you’ll find quaint gift shops, fudge stores, and antique shops. For dinner, check out Blowing Rock Brewing Company & Inn or Egg Rollin’, where you can enjoy creative takes on egg rolls, sandwiches, and a separate kids’ menu.

Use your IHG One Rewards points to book a stay at the Holiday Inn Express Blowing Rock South (prices start at $112 or 19,000 points per night). Alternatively, enjoy a range of amenities like a spa, kayaks, paddleboats, tennis courts, lawn games, and weekend bonfires at Chetola Resort (starting at $219 per night).

Days Two and Three: Explore Asheville

Start your day with a visit to Tweetsie Railroad, a thrilling train-themed amusement park featuring historic steam trains, Wild West shows, rides, and much more. For those feeling adventurous, hike one of the 11 trails at Grandfather Mountain — and for those not afraid of heights, the Mile High Swinging Bridge offers sweeping views from above.

Next, head to Linville Falls to marvel at the twin waterfalls pouring into Linville Gorge. Continue your journey to Asheville, your final destination. Asheville is a charming mountain town offering attractions like the grand Biltmore Estate, the expansive mansion and grounds of the Vanderbilts; the Asheville Art Museum; the Asheville Pinball Museum; the Western North Carolina Nature Center; and the River Arts District, which is brimming with local artists’ studios. Don't miss the scenic beauty of Pisgah National Forest that surrounds the area.

Asheville also boasts a fantastic food scene, with family-friendly spots like Chai Pani, Neng Jr.'s, Luella's BBQ, White Duck Taco Shop, Baby Bull, Sunny Point Cafe, and Asheville Pizza & Brewing. Be sure to treat yourself with something sweet from Hole Doughnuts, OWL Bakery, and the French Broad Chocolate Factory & Cafe.

Redeem your Marriott Bonvoy points for a stay at the AC Asheville Hotel Downtown, conveniently located with rates starting at $187 or 62,000 points per night. A new Moxy hotel is also opening in August, with nightly rates beginning at $216 (points redemption details are not yet available). Alternatively, you can use Hilton Honors points to book a room at the Foundry Hotel, a former industrial space transformed into a unique hotel within the Curio Collection, with rates from $207 or 60,000 points per night.

The takeaway

Road trips don't have to be about rushing from one stop to the next. The best trips often focus on exploring the beautiful sights and experiences along the way, creating memories that last long after the journey ends.