The top 12 family road trips to enjoy this summer
Embarking on a classic American road trip is a cherished family custom.
Traveling along the country's beautiful highways and stopping to discover sights that pique your interest — such as breathtaking viewpoints, roadside seafood shacks, or historical landmarks — is a fantastic way to explore the United States with your family this summer.
It's also a smart way to save money while adventuring, whether you use rewards points, rent an RV, or find budget-friendly hotels, motels, or camping spots along the route. Depending on how popular your destination is during peak season, it might be wise to reserve your first few hotels in advance. However, leave room for spontaneity; for instance, finding a budget-friendly last-minute hotel in Hilton Head during summer might be challenging, while being flexible in Missouri should be easier.
Naturally, traveling with kids can present some hurdles, such as keeping them entertained and managing potential car sickness.
Consider using one of the entertaining, family-friendly voices in the Waze app for navigation to keep everyone amused. Think about bringing iPads that can be attached to the back of the headrests and prepare a list of car games to enjoy. Timeless classics like I Spy, 20 Questions, and spotting license plates remain as fun as ever. Don’t forget to bring snacks your kids love and plenty of water, along with extra clothes, plastic bags, paper towels, or wipes... just in case someone feels a bit queasy from motion sickness.
It’s also wise to have a reliable credit card for gas refills. Take a look at TPG's guide to the best cards for gas purchases. The GasBuddy app can assist you in finding nearby stations with the lowest prices.
With the logistics sorted, here are 12 timeless summer road trips across the U.S.
From Appalachia to Nashville
A view of the Nashville skyline from the water. TIM SEBRING/EYEEM/GETTY IMAGESDiscover Appalachia, culminating in Nashville, on this journey through West Virginia and Kentucky. Begin your adventure in West Virginia's capital, Charleston, located at the intersection of three major state highways. You can fly into West Virginia International Yeager Airport (CRW).
Day One: Charleston
Check out West Virginia's charming Capitol building, featuring a gold leaf-covered dome that stands 5 feet taller than the dome of the U.S. Capitol; visit the West Virginia State Museum to delve into Appalachian history and culture; and explore the Avampato Discovery Museum, an engaging science museum suitable for all ages.
Take a leisurely walk down tree-lined Capitol Street and pop into one of the many restaurants, or head to the renowned Dem 2 Brothers and a Grill for some delicious barbecue.
Charleston hosts all the major hotel chains. You can use your Marriott Bonvoy points at the Charleston Marriott Town Center (rates starting at $124 or 15,500 points per night) or at Four Points by Sheraton Charleston (rates starting at $114 or 15,500 points per night), or redeem your Hilton Honors points at Embassy Suites by Hilton Charleston (rates starting at $131 or 36,000 points per night).
Day Two: Lexington to Louisville
After leaving Charleston, take a three-hour drive to Lexington, the heart of Kentucky's horse culture. Stop by the renowned Keeneland Racecourse and explore the Kentucky Horse Park, then head to the revitalized Distillery District for pizza, ice cream, craft beer, live music, and bourbon tastings.
Next, embark on a 1.5-hour drive to Louisville, making a pit stop at the Claudia Sanders Dinner House (yes, that Sanders... Claudia was the Colonel's wife) for a traditional Southern family-style meal.
Louisville offers a plethora of family-friendly attractions, such as the Louisville Slugger Museum & Factory and the Kentucky Science Center. Kids will particularly enjoy cruising the Ohio River on the Belle of Louisville, the oldest steamboat in operation.
Consider staying at the original 21c Museum Hotel, part of the Accor Live Limitless rewards program (rooms starting at $212 per night). This hotel features a contemporary art museum and is home to the highly praised Proof on Main restaurant. Alternatively, The Seelbach Hilton Louisville, a Beaux Arts-style hotel dating back to 1869, offers rooms starting at $133 or 36,000 Hilton Honors points per night, complete with classically decorated rooms and stunning public spaces, including an opulent lobby adorned with Renaissance-inspired mahogany and bronze carvings and a vaulted dome made of 800 glass panels.
Day Three: Nashville
Finally, embark on a three-hour drive south to Nashville, the vibrant Music City, where you can stay at Hotel Fraye, part of Hilton's independent Curio Collection (with rates starting at $190 or 57,000 Hilton Honors points per night). Nashville also features a location of Hilton's new Tempo lifestyle brand, which opened in February (starting at $169 or 50,000 Hilton Honors points per night). Both hotels are situated downtown, close to the iconic Ryman Auditorium, numerous restaurants, and the bustling honky-tonk bars of Broadway.
Visitors can experience the city's unique charm by exploring attractions like the Country Music Hall of Fame and Museum, Radnor Lake State Park, Nashville Zoo, and the Grand Ole Opry. Families will love the high-tech minigolf experience at Puttshack. The upcoming Nashville Yards, opening in phases, will feature a music venue, a cinema, and 350,000 square feet of retail and dining options.
Before departing from Nashville International Airport (BNA), don’t forget to grab some delicious, locally made chocolatey treats at the Goo Goo Clusters Shop.
Lake Michigan highlights
CAVAN IMAGES/GETTY IMAGESFollow the lakeshore on this route that begins in Milwaukee, travels south to Chicago, and then loops back through Michigan, concluding in Traverse City.
Day One: Milwaukee
Arrive at Milwaukee Mitchell International Airport (MKE) and discover the city's Lynden Sculpture Garden, Milwaukee Art Museum, Milwaukee Public Museum, and the interactive Discovery World Science and Technology Center. Don’t miss out on a frozen custard treat at the renowned Kopp's. Kids will definitely enjoy the spy-themed burger restaurant, SafeHouse.
Hyatt enthusiasts can utilize points or their free night certificates for a stay at the Hyatt Regency Milwaukee (with rates starting at $115 or 6,500 World of Hyatt points per night). Alternatively, redeem Marriott points at the Milwaukee Marriott Downtown (starting at $159 or 34,000 Marriott Bonvoy points per night).
Day Two: Chicago
Travel southward for about two hours to reach Chicago, a city brimming with top-notch, family-friendly attractions such as the Shedd Aquarium, the Field Museum of Natural History, Lincoln Park Zoo, and Millennium Park, among others. If you opt to stay overnight, there are plenty of hotel options, with Pendry Chicago (rates starting at $242 per night) and Kimpton Gray Hotel Chicago (starting at $160 or 38,000 IHG One Rewards points per night) being excellent choices for families.
Day Three: Indiana Dunes National Park to Traverse City
From Chicago, take a scenic route along the lakeshore and make a stop at the newly established Indiana Dunes National Park for some lakeside fun before heading to the charming town of Holland, Michigan. This Dutch-founded community on the shores of Lake Macatawa boasts a historic windmill, a tulip festival, and delightful Dutch-inspired cuisine, including classic pastries from deBoer Bakkerij & Dutch Brothers Restaurant.
The picturesque lakeshore features Holland State Park, Laketown Beach, Tunnel Park, and a quaint red lighthouse.
Traverse City lies 168 miles to the north, with many quaint towns and the scenic Huron-Manistee National Forests to discover along the journey.
Upon arriving in Traverse City, you can indulge in some well-deserved beach relaxation. If your visit falls in late June or early July, be sure to experience the annual National Cherry Festival.
For a truly enjoyable family getaway, consider staying at the Great Wolf Lodge to take advantage of its indoor water park, or use your IHG One Rewards points at Hotel Indigo Traverse City (rates start at $144 or 26,000 IHG One Rewards points per night).
Depart from Cherry Capital Airport (TVC) for your flight home.
Big Bend National Park in Texas
Grapevine Hills Trails in Big Bend National Park. NAREN MORUM/500PX/GETTY IMAGESStretching 150 miles along the border of Texas and Mexico, this national park offers a stunning, adventure-packed road trip experience.
Day One: El Paso to Marathon
Arrive at El Paso International Airport (ELP) and embark on a drive of approximately 300 miles southeast to reach the secluded park, making a lunch stop at either the Sentinel or Convenience West for some barbecue in the artistic town of Marfa. Continue on to Marathon, where you can stay at the historic Gage Hotel (rates start at $229 per night) and dine at Brick Vault Brewery and Barbecue.
Days Two and Three: Big Bend National Park
Inside the expansive 800,000-acre park, the breathtaking drive reveals stunning attractions at every corner. Much of the landscape is characterized by the Chihuahuan Desert, which hugs the Rio Grande and features the majestic Chisos mountain range. Key highlights include the scenic Ross Maxwell Drive, the eerie Terlingua Ghost Town, the Santa Elena nature trail, zip lining at Lajitas, and the exploration of Boquillas Canyon.
The park offers numerous kid-friendly hiking trails and boat rides along the Rio Grande, ensuring fun for the whole family.
For those who prefer not to camp, the family-operated Big Bend Holiday Hotel offers vintage accommodations along with charming, well-decorated casitas (rates start at $97 per night). For more family-friendly amenities, such as a golf course and swimming pool, consider staying at the expansive Lajitas Golf Resort (rates begin at $224 per night).
Central California coast
Morro Bay at sunset. MICHAEL XU/EYEEM/GETTY IMAGESCalifornia's stunning coastline offers endless opportunities for adventure. The central region is particularly enjoyable for kids, featuring a wealth of wildlife, historical sites, and, of course, the thrilling sound of crashing waves. You can fly into or out of Meadows Field Airport in Bakersfield (BFL) or San Luis Obispo County Regional Airport (SLO).
Day One: Pismo Beach
Start your journey by heading to Pismo Beach. If your visit falls between October and February, be sure to visit the Monarch Butterfly Grove to witness the migration of monarchs. Next, stroll along the Pismo Pier and rent a surrey for a fun pedal along the boardwalk. Don’t miss dining at Splash Cafe and indulging in the delightful treats at Old West Cinnamon Rolls.
Spend the night using your Hilton Honors points at the Hilton Garden Inn San Luis Obispo/Pismo Beach (rates start at $128 or 34,000 Hilton Honors points per night), or consider the charming and budget-friendly SeaCrest OceanFront Hotel (rates begin at $189 per night).
Day Two: Morro Bay to San Simeon
Next, take the Pacific Coast Highway and drive 30 minutes north to Morro Bay, where you can marvel at the impressive Morro Rock, the final member of the Seven Sisters — a series of ancient volcanoes situated between Morro Bay and San Luis Obispo. Aim to catch a glimpse of it during sunset for a spectacular view.
Afterward, make your way to Cambria for a taste of farm life. Get up close with goats, witness cows being milked, and savor some cheese at Stepladder Ranch and Creamery. Enjoy a ride on a Clydesdale horse at Covell Ranch, wander along the stunning Moonstone Beach, and grab a meal at Robin's.
Continue your journey north to San Simeon, where you can’t miss the barking seals at the Piedras Blancas Elephant Seal Rookery, conveniently located just off the highway. Then, head inland to explore the renowned Hearst Castle, featuring 127 acres of exquisite gardens, pools, and pathways. Keep an eye out for zebras (yes, really!) during your tram ride up to the castle.
For accommodations, you can use 16,000 Choice Privileges points (or $78 per night) to stay at the economical Quality Inn Near Hearst Castle, or opt for a more upscale experience at the Cavalier Oceanfront Resort (rates start at $169 per night).
Dramatic coastal Maine
Portland Head Lighthouse in Maine. NAVINPEEP/GETTY IMAGESMaine's eastern coastline boasts rugged cliffs, crashing waves, and charming lobster shacks, making it the perfect spot for a scenic drive along the winding roads that trace the Atlantic.
Day One: Portland
Kick off your adventure in Portland, a vibrant and walkable city renowned for its fantastic culinary scene. You can fly into either Portland International Jetport (PWM) or Boston Logan International Airport (BOS), which is a two-hour drive to the south. Alternatively, Manchester-Boston Regional Airport (MHT) in New Hampshire is another great option for Southwest Airlines travelers.
Wander through the Old Port district, where you can treat the kids to some fudge while you browse local pottery and jewelry. Don't miss the Children's Museum and Theatre of Maine, and be sure to climb the Portland Observatory for breathtaking views of the harbor.
Portland boasts a vibrant culinary scene with plenty of family-friendly options, such as Two Fat Cats Bakery, Duckfat, Salvage BBQ, and the relatively new Neapolitan pizza place, Quanto Basto.
You can redeem your Marriott Bonvoy points for a stay at the Residence Inn Portland Downtown/Waterfront (starting at $125 or 41,000 points per night), which features an indoor pool. Alternatively, consider the historic and trendy Press Hotel (starting at $195 or 52,000 Marriott Bonvoy points per night), part of the Autograph Collection.
Day Two: Rockland to Bar Harbor
As you head north through Freeport, make sure to stop at the L.L. Bean Outlet before continuing to Rockland. While there, visit the Farnsworth Art Museum, the Maine Lighthouse Museum, and the Coastal Children's Museum.
Grab hot dogs at Wasses or pick up picnic essentials at the local co-op, Good Tern, and enjoy your meal at Birch Point State Park. Don’t forget, Rockland hosts the Maine Lobster Festival every summer from July 31 to August 4.
From Rockland, head north to Bar Harbor and explore the nearby Acadia National Park for a few days filled with hiking, biking, sailing, and kayaking. Don’t miss swimming in Echo Lake and savoring the best popovers in the state at the renowned Jordan Pond House. For your local lobster cravings, check out the new Travelin' Lobster location on Main Street.
Redeem your Hilton Honors points for a stay at the seasonal Hampton Inn Bar Harbor (operating from May to October; rates start at $281 or 87,000 points per night). This hotel offers breathtaking ocean and mountain views along with two pools.
Nature-based fun in Florida
BRIANLASENBY/GETTY IMAGESFlorida offers much more than just theme parks, especially for those seeking family-friendly adventures. If you’re eager to embrace nature, Florida has plenty to offer. This 118-mile journey highlights some of the state's top natural attractions from Tampa to Fort Myers, showcasing some of the finest sugar-sand beaches along the Gulf Coast. To embark on this trip, fly into Tampa International Airport (TPA) and out of Southwest Florida International Airport (RSW).
Day One: Journey from Tampa to Sarasota
Start your trip by taking Highway 60 west from Tampa to Clearwater Beach, then continue south to Pass-a-Grille. This scenic route meanders along a stunning 20-mile stretch of beaches and eateries where you can indulge in freshly caught grouper from the Gulf.
As you make your way back east toward the mainland, look for signs directing you to Fort De Soto Park, which boasts 1,136 acres of beautiful beaches, mangroves, biking trails, and historical remnants from the Spanish-American War. After exploring, drive an hour south to Sarasota for an overnight stay.
Spend your Marriott Bonvoy points at the Westin Sarasota downtown (starting at $195 or 31,000 points per night) or treat yourself to a stay at The Ritz-Carlton, Sarasota (rates from $538 or 59,500 points per night) for beachfront luxury. This year, the new St. Regis Longboat Key Resort will also open, so begin saving your Bonvoy points now.
Sarasota is rich in natural attractions. Kids can explore a rainforest at the Ann Goldstein Children's Rainforest Garden, part of the Marie Selby Botanical Gardens located on Sarasota's bayfront, which parents will also appreciate.
Explore the wonders of the Gulf of Mexico at Mote Marine Laboratory & Aquarium, located across Sarasota Bay, and embark on one of Mote's eco-boat tours led by marine biologists to discover the beauty of Sarasota Bay.
When it's time to eat, visit O'Leary's Tiki Bar and Grill next to Bayfront Park, featuring a playground and walking trails, or head to The Old Salty Dog right on Sarasota Bay, where kids enjoy their meals served on a frisbee.
Day Two: Journey from Sarasota to Fort Myers
On the following day, drive inland along Highway 72 to Myakka River State Park, where alligators bask in the sun along the riverbanks. Stroll along the boardwalks and canopy trails that wind through the wetlands and treetops. You can rent kayaks to paddle through the waterways or join a guided boat tour.
Proceed south on Highway 41 to Fort Myers, where you can observe the gentle giants of the underwater world at Manatee Park and delve into more wetlands at Six Mile Cypress Slough Preserve.
Stop by Shrimp Shack for a quick and delicious seafood lunch, and for dinner, savor the award-winning pizzas at Fine Folk Pizza.
You can redeem your Hilton Honors points at the Hilton Garden Inn Fort Myers (starting rates at $119 or 33,000 points per night) or at Hampton Inn & Suites Fort Myers-Colonial Blvd. (starting rates at $115 or 33,000 points per night).
Adventures in the Finger Lakes
WALTER BIBIKOW/GETTY IMAGESThe Finger Lakes region of Western New York features 11 lakes nestled between Syracuse, Rochester, and Elmira-Corning. While some lakes are larger than others, they are all encircled by delightful towns and wineries. You can take a round trip starting and ending at Frederick Douglass Greater Rochester International Airport (ROC), located about an hour and a half from Skaneateles, your first destination.
Day One: Skaneateles
Begin your adventure in the eastern town of Skaneateles (pronounced SKINNY-atlas) with a visit to Skaneateles Bakery, where you can enjoy their deliciously fresh doughnuts and blueberry muffins. Grab some for a snack as you take a leisurely stroll down the pier and along the lakeshore.
Reserve a boat tour on the lake with Mid-Lakes Navigation — you might even have the chance to assist the Barbara S. Wiles mail boat in delivering mail to lakeside residences.
In the evening, enjoy a film at New York State's oldest drive-in theater, the Finger Lakes Drive-In. Afterwards, unwind at the charming bed-and-breakfast, The Bond 1835, or at Skaneateles Suites. While points hotels are scarce in this area, the Hilton Garden Inn Auburn (starting rates at $132 or 38,000 Hilton Honors points per night) is conveniently located north of Owasco Lake, the next lake over.
Day Two: Seneca Falls to Canandaigua Lake
Travel 22 miles west to Seneca Falls to visit the Women's Rights National Historical Park, the site of the first women's rights convention in 1848.
Continue along Route 20 to Seneca Lake, a fantastic spot for kitesurfing and windsurfing, and consider taking a sailing trip with Sail Seneca.
At the northern end of the lake lies Geneva, featuring delightful restaurants and shops such as F.L.X. Fry Bird and Kindred Fare. Discover the Seneca Lake Wine Trail, making stops at vineyards like Hermann J. Wiemer Vineyard, Red Tail Ridge Winery, Barnstormer Winery, and Fox Run Vineyards. At the southern tip of the lake, you'll find Watkins Glen State Park, renowned for its stunning waterfalls, canyons, and hiking trails.
Head further west to Canandaigua Lake, where you'll find the elegant Lake House Canandaigua (with rates starting at $280 per night), a member of the Preferred Hotels & Resorts network. This hotel features a lakefront pool and hot tub, the Rose Tavern serving farm-to-table cuisine, kayaks, and a yacht for leisurely explorations of the lake, alongside numerous other luxurious offerings.
If you're interested in earning or redeeming Hilton Honors points, consider the Hotel Canandaigua, Tapestry Collection by Hilton, which offers a lakefront location, a pool, and direct access to the Canandaigua Lady at Steamboat Landing, with rates starting at $124 or 36,000 points per night. Drive to the southern end of the lake in Naples to try its famous grape pie.
Day 3: Exploring Rochester
Wrap up your journey in Rochester, located just 28 miles northwest of Canandaigua. While there, be sure to visit the George Eastman Museum, dedicated to the founder of Kodak; the Strong National Museum of Play, an interactive space for toys and games that expanded significantly in 2023; the Susan B. Anthony House, a historic home-turned-museum of the famed suffragette; and Highland Park, known for its annual flower festivals.
For a taste of local cuisine, head to the Rochester City Public Market, a vast farmers market showcasing regional vendors. Don't miss the city's renowned "garbage plate" at the original Nick Tahou Hots, where you can enjoy a one-plate meal featuring potatoes, meat, and various sides.
Consider using Hyatt points at the newly renovated Hyatt Regency Rochester (rates start at $105 or 5,000 points per night) or stay at the Courtyard by Marriott Rochester Downtown (rates begin at $167 or 16,000 points per night) for a prime location.
The coast of South Carolina
Coligny Beach Park, Hilton Head Island, South Carolina. Photo by MARGARETW/GETTY IMAGESThe South Carolina coastline boasts some of the finest beaches in the South, along with fantastic culinary options. This adventure kicks off in Hilton Head Island, accessible via Hilton Head Island Airport (HHH) or Savannah/Hilton Head International Airport (SAV). Your journey will lead you 220 miles north to Myrtle Beach, so arrange your return flight from Myrtle Beach International Airport (MYR).
Day 1: Hilton Head Island
Begin your day at Hilton Head Island and soak up the sun at the beloved Coligny Beach Park. For a more tranquil atmosphere, consider visiting Alder Lane or Burkes Beach.
Discover the rich Lowcountry and Gullah heritage at the Coastal Discovery Museum, and appreciate the area's stunning landscapes at the Pinckney Island National Wildlife Refuge and Sea Pines Forest Preserve.
Later, indulge in authentic Gullah dishes at Ruby Lee's or savor fresh seafood at Skull Creek Boathouse. Consider staying at a beach resort packed with amenities like the Omni Hilton Head Oceanfront Resort (rates start at $280 per night), or if you have Marriott Bonvoy points, take a look at the Westin Hilton Head Island Resort & Spa (rates start at $183 or 40,000 points per night).
Day 2: Charleston
Travel north along Route 17 to the delightful city of Charleston. While there, you can wander through Museum Mile, a pedestrian-friendly path that features institutions like the Charleston Museum and the Children's Museum of the Lowcountry, alongside historic homes and lush parks. The International African American Museum, which opened in June 2023, is located at a former shipping wharf where enslaved individuals arrived.
The Battery and White Point Gardens, situated at the southern tip of the Charleston peninsula, showcase Civil War artillery, stunning views of Fort Sumter, and beautiful live oak trees. Kids will enjoy the South Carolina Aquarium, which features a fantastic touch tank.
For additional beach time, visit the expansive 6-mile Folly Beach and sample a Lowcountry classic, Frogmore stew, at Bowens Island Restaurant.
Charleston's culinary scene is famous, and you must try the genuine Southern cuisine and fresh seafood. Some top spots include Rodney Scott's BBQ, Leon's Oyster Shop, and Bertha's Kitchen. The popular D.C. restaurant Makan has opened a second location here, offering authentic Malaysian dishes with a focus on local seafood. If your kids are craving pancakes, Daps Breakfast & Imbibe serves breakfast all day, featuring pancakes made with Fruity Pebbles mixed into the batter.
All the major hotel brands are present, allowing you to choose based on your loyalty preferences. You can book a stay at the Charleston Marriott (rates starting at $152 or 30,000 Marriott Bonvoy points per night) or at Hyatt Place Charleston/Historic District (rates from $212 or 15,000 World of Hyatt points per night).
For a unique experience, consider some of Charleston's finest independent boutique and historic hotels, such as the Palmetto Hotel, The Loutrel, Planters Inn, and The Dewberry. For a blend of modern comfort and charm, check out Mills House Charleston, Curio Collection by Hilton (rates starting at $283 or 75,000 Hilton Honors points per night).
Day 3: Myrtle Beach
As you approach the North Carolina border, you'll find yourself in Myrtle Beach, one of South Carolina's most beloved beach destinations. While it features some kitschy attractions like water and amusement parks (which your kids will likely enjoy), along with chain restaurants and shopping centers, it is also home to 60 miles of stunning coastline known as the Grand Strand.
Explore the Golden Mile, which is a hotel-free zone, or head to the beach near 82nd Avenue, known as the gay beach. Beyond the shoreline, take a leisurely walk along the Murrells Inlet Marsh Walk, where you can enjoy live music and refreshing drinks, or meander along the bustling Myrtle Beach Boardwalk. Don't forget to save some appetite for delicious barbecue at True BBQ, run by local favorites Joseph and Sheila Evans.
You can use your Hilton Honors points to book a stay at the all-suite Hilton Grand Vacations Club Ocean Enclave Myrtle Beach (rates starting at $161 or 76,000 Hilton Honors points per night). This property is just two blocks from the boardwalk and features two pools, a kids' activity center, and an oceanfront restaurant.
Pacific Northwest parks adventure
Smith Rock, Terrebonne, Oregon. ESTEBAN MARTINENA GUERRERO/GETTY IMAGESOregon boasts some of the most pristine natural landscapes in the country, including the stunning Crater Lake National Park. From there, the delightful town of Bend offers quaint charm set against a breathtaking natural backdrop. For this journey, book round-trip flights into and out of Rogue Valley International-Medford Airport (MFR), which is located 75 miles from the park and 172 miles from Bend.
Days One and Two: Crater Lake National Park
Begin your adventure at Crater Lake National Park in Oregon, which is renowned for having the deepest lake in the country. Its remarkable clarity comes from rain and snow that fill the ancient caldera formed by a volcanic eruption thousands of years ago. Drive along the park's scenic 33-mile loop road, making stops for breathtaking views and hiking opportunities. Consider camping at Farewell Bend Campground or redeeming 30,000 Choice Privileges points for a stay at the Sleep Inn & Suites in nearby Chiloquin (or book from $150 per night).
Days Three and Four: Bend
On the next day, take a 100-mile drive north to the charming high desert town of Bend, Oregon. Discover the Bend Ale Trail, which boasts 30 breweries. If you’re visiting in the fall, don’t miss Smith Rock Ranch for a fun corn maze and pumpkin patches. Stroll through the Old Mill District's shops and eateries along the Deschutes River and visit the High Desert Museum to learn about the area’s wildlife, history, and art.
Rest at the Hampton Inn & Suites Bend (rates start at $124 or 35,000 Hilton Honors points per night) or the Residence Inn by Marriott Bend (rates start at $140 or 30,000 Marriott Bonvoy points per night).
To wrap up your adventure, make your way to the McKenzie River Valley, featuring the stunning McKenzie River National Recreation Trail. Be sure to enjoy the beautiful Sahalie and Koosah Falls before heading south on Highway 5 back to Medford.
Discover Missouri along the iconic Route 66
Climatron at the Missouri Botanical Garden. KSTEFFENS/GETTY IMAGESAlthough modern interstates have largely taken over this historic route, this itinerary will guide you through scenic portions of the legendary Route 66 in Missouri.
Day One: St. Louis
Begin your journey in St. Louis, known as the Gateway to the West. After landing at St. Louis Lambert International Airport (STL), make sure to visit Gateway Arch National Park, which features the iconic arch and the historic courthouse where Dred Scott, a Black enslaved man, fought for his freedom in the late 1840s.
Don't miss the Missouri Botanical Garden, the Saint Louis Art Museum, and the incredibly interactive City Museum, which is crafted from repurposed industrial materials inside an old shoe factory.
If you're traveling with young children, be sure to add the Magic House children's museum to your itinerary. For dining options, check out the City Foundry Food Hall, Balkan Treat Box, Louie, and the James Beard Award-winning Gioia's Deli. For an authentic St. Louis barbecue experience, visit Pappy's Smokehouse.
Utilize your Hilton Honors points at Embassy Suites by Hilton St. Louis Downtown (starting at $121 or 40,000 points per night) or your World of Hyatt points at the Hyatt Regency St. Louis at the Arch (starting at $188 or 8,000 points per night), which offers stunning views of the famous arch. You can also redeem Marriott Bonvoy points at the Magnolia Hotel St. Louis, a Tribute Portfolio Hotel (from $135 or 31,000 points per night), a historic establishment within a 1924 building that once hosted Cary Grant. In 2023, St. Louis welcomed the 21c Museum Hotel in the former YMCA building, where you can stay using Accor Live Limitless points or from $183 per night.
Day Two: Journey from St. Louis to Lebanon
Head west along Interstate 44, which has taken the place of Route 66 in Missouri. Be sure to make stops at Route 66 State Park and quirky roadside attractions like Meramec Caverns and the world's second-largest rocking chair.
As you drive, you'll pass through Cuba, known as Route 66 Mural City, where 14 vibrant murals illustrating the town's history adorn the buildings along the route.
If you're in the mood for barbecue, make a stop at Missouri Hick Bar-B-Que. Once you're back on the highway, experience a segment of the original Route 66 as it winds through the scenic Mark Twain National Forest and the Devil's Elbow curve along the Big Piney River. Treat the kids to some fudge at the Uranus Fudge Factory (filled with toilet humor that they'll definitely enjoy). For a truly nostalgic stay, book a Route 66-themed room at the classic Munger Moss Motel in Lebanon.
Day Three: Springfield
Before departing from Lebanon, be sure to visit the Route 66 Museum located inside the county library. The following day, drive about 60 miles southwest to explore Fantastic Caverns, one of Missouri's largest caves, situated just outside Springfield. Once in Springfield, both kids and adults can enjoy the Discovery Center, Wonders of Wildlife, and the Dickerson Park Zoo. Don't forget to grab burgers at Black Sheep, and for dessert, swing by Askinosie Chocolate for a sweet treat.
Stay at the Best Western Coach House, where rates begin at $109 or 20,000 Best Western Rewards points per night, or opt for the Hilton Garden Inn Springfield, MO, with rates starting at $132 or 36,000 Hilton Honors points per night. You can book your flight home from Springfield-Branson National Airport (SGF).
Badlands and Black Hills of South Dakota
The early morning light illuminating the Badlands. GETTY IMAGESThis area of South Dakota is rich in history and natural wonders, making it a fantastic destination for family vacations.
Day One: Journey from Rapid City to Badlands National Park
Arrive at Rapid City Regional Airport (RAP), then pick up your rental car and head 55 miles east to Wall Drug in Wall, South Dakota. Known for its complimentary ice water, 5-cent coffee, and mouthwatering maple doughnuts, it also offers a plethora of souvenirs (so set a budget for the kids), an animated dinosaur, and a giant jackalope in the back.
Continue south on Highway 240 to Badlands National Park, where you and your children can discover ancient fossils and observe wildlife such as bighorn sheep, pronghorn antelope, eagles, and buffalo across its 244,000 acres of stunning prairie, sharp cliffs, and unique pinnacles. In the evening, there are activities for kids to meet Smokey the Bear, gaze at the stars, and learn about the park's geological history.
You don't have to sacrifice comfort to spend the night in the Badlands. Cedar Pass Lodge offers cozy pinewood cabins starting at $220, complete with Wi-Fi and porches with deck chairs. For those who prefer camping, there are also campgrounds available. Alternatively, you can stay at the Best Western Plains Motel in Wall, just a 10-minute drive north of the Pinnacles Entrance, with rates starting at $120 or 20,000 Best Western Rewards points per night.
Day Two: Journey from Mount Rushmore to Custer State Park
Next, head west to Mount Rushmore National Memorial in Keystone. This iconic monument, carved into the peak of Mount Rushmore, took 14 years to complete and showcases the faces of four 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 like mountain goats, marmots, and various birds.
About 20 miles to the south, witness thousands of buffalo roaming freely in Custer State Park (be cautious, as they often wander onto the roads), along with pronghorn antelope, mountain goats, bighorn sheep, deer, elk, wild turkeys, and burros. You can also explore various hiking trails or enjoy a serene boat ride on Sylvan Lake.
Take a break from driving and book an evening hayride and chuck wagon cookout at Blue Bell Lodge, which features a scenic three-hour wildlife tour accompanied by singing cowboys, followed by a steak dinner complete with all the trimmings. Alternatively, dine at the State Game Lodge Restaurant, located within Calvin Coolidge's "Summer White House." Their unique menu includes game dishes like rabbit and rattlesnake sausage, elk osso bucco, and buffalo short ribs. You can also stay overnight at the State Game Lodge (rates start at $183 per night), where the rooms were recently renovated in 2024. Outside the park, Comfort Inn & Suites in Custer offers rates starting at $127 or 25,000 Choice Privileges points per night.
Day Three: Journey from Crazy Horse Memorial to Rapid City
The Needles Highway, framed by towering needlelike granite spires, will take you to the Crazy Horse Memorial, where you can admire the remarkable ongoing sculpture dedicated to the legendary Native American chief. While there, be sure to visit the Indian Museum of North America and the Native American Educational and Cultural Center. Enjoy lunch at the on-site Laughing Water Restaurant, which serves Native American dishes such as tatanka stew and fry bread tacos.
Conclude your trip in Rapid City. Don't miss breakfast at Tally's Silver Spoon, which serves breakfast until 2 p.m. and offers dishes like whole wheat oatmeal waffles and buffalo hanger steak with eggs. Make sure to leave time to explore the vast Prairie Edge Trading Company & Galleries, which showcases handmade Plains Indian arts and crafts, Native American galleries, and a library of Italian glass beads.
Stay overnight at the historic Hotel Alex Johnson, part of the Hilton Curio Collection (with rates starting at $75 or 21,000 Hilton Honors points per night). Take in the stunning lobby, which showcases Native American-inspired features, including a chandelier crafted from spears and a beautifully painted ceiling.
Blue Ridge Parkway stretching from Virginia to North Carolina
The Blue Ridge Parkway's Linn Cove Viaduct gracefully hugs the cliffs of Grandfather Mountain. PETER UNGER/GETTY IMAGESThe 469-mile Blue Ridge Parkway, linking Shenandoah National Park and Skyline Drive in Virginia to Great Smoky Mountains National Park in North Carolina, is renowned as one of the most picturesque drives in the United States. To start your journey, fly into Charlottesville Albemarle Airport (CHO) or the larger Dulles International Airport (IAD). Your adventure will conclude in Asheville, allowing you to depart from Asheville Regional Airport (AVL) or the nearby Greenville-Spartanburg International Airport (GSP) in South Carolina, which often offers more affordable flight options.
Day One: From Charlottesville to Blowing Rock
Begin your adventure in Charlottesville, Virginia. If your family has a passion for presidential history, don't miss a tour of Thomas Jefferson's Monticello, the former president's residence and a UNESCO World Heritage Site. The Virginia Discovery Museum and IX Art Park also offer engaging experiences for the entire family. In the downtown area, take a leisurely stroll along the pedestrian mall to explore shops, cafes, and restaurants such as Citizen Bar Burger and The Nook. Another family-friendly spot is the Dairy Market food hall, featuring a variety of options all in one location.
Continue your journey along the parkway to Natural Bridge, a towering limestone arch known as "Nature's Cathedral." In Roanoke, stop for lunch at Mama Jeans BBQ or the nostalgic Pop's Ice Cream & Soda Bar, which boasts an extensive grilled cheese menu alongside sodas and ice cream. If time permits, check out the Taubman Museum of Art, where you can admire a collection of dazzling Judith Leiber handbags.
Take a moment to snap a photo at the scenic Mabry Mill, one of the most iconic landmarks along the parkway. Established in 1905, this quaint millhouse offers freshly milled buckwheat flour — a perfect souvenir to bring home.
As you cross into North Carolina, your next stop will be Blowing Rock. Stretch your legs on Main Street, where you'll discover gift and souvenir shops, fudge stores, and antique boutiques. For dinner, consider dining at Blowing Rock Brewing Company & Inn or Egg Rollin', which offers creative takes on the egg roll, in addition to sandwiches and a dedicated kids' menu.
Redeem your IHG One Rewards points for a night at Holiday Inn Express Blowing Rock South (rates starting at $112 or 19,000 points per night). Alternatively, enjoy a stay at Chetola Resort, where you can take advantage of amenities such as a spa, kayaks, paddleboats, tennis courts, lawn games, and weekend bonfires (rates starting at $219 per night).
Days Two and Three: Explore Asheville
On the following morning, head to the Tweetsie Railroad, an amusement park themed around trains that features historic steam locomotives, Wild West shows, and various rides. If your children are adventurous, consider hiking one of the 11 trails at Grandfather Mountain — for those who aren't afraid of heights, the Mile High Swinging Bridge offers stunning panoramic views.
Next, make your way to Linville Falls to witness the stunning twin waterfalls cascading into Linville Gorge. After that, continue your drive to Asheville, your ultimate destination. Asheville is a delightful mountain town boasting attractions like the 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 filled with artists' studios, alongside the beautiful Pisgah National Forest.
Asheville is also known for its vibrant food scene, with popular kid-friendly options including Chai Pani, Neng Jr.'s, Luella's BBQ, White Duck Taco Shop, Baby Bull, Sunny Point Cafe, and Asheville Pizza & Brewing. Don’t forget to indulge in treats from Hole Doughnuts, OWL Bakery, and French Broad Chocolate Factory & Cafe.
Consider using your Marriott Bonvoy points at the conveniently located AC Asheville Hotel Downtown (rates start at $187 or 62,000 points per night). In August, a new Moxy hotel will open in the city, with rates starting at $216 per night (point values are not available yet). You can also redeem Hilton Honors points at the Foundry Hotel, a transformed industrial building that is now part of the Curio Collection (rates start at $207 or 60,000 points per night).
In summary
Road trips don't have to consist of speeding through miles just to cover the most distance. Some of the most memorable journeys embrace a different approach, emphasizing the incredible sights and experiences encountered along the way.
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