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The road trip, an iconic American family vacation experience, is having a moment. Whether you’re looking to take a trip with your brood in the coming months or planning ahead for when your kids get older, picking an appropriate itinerary for your kids’ age range can mean the difference between a making-memories experience or one you’d all rather forget. Add these road trips to your family’s bucket list at just the right times to maximize the fun for everyone.

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Infants and toddlers

Pacific Coast Highway

This one’s for you, weary parents. This stretch of Highway 1 running up and down the California coastline is an incredibly popular road trip for its breathtaking scenery—just the thing to indulge your tired selves in while your little ones snooze in the back seat. Tackle all, part or—really—as much as you can knowing that this is typically a difficult age for traveling with kids. Buckle in your infant for a midday nap during a drive along the soaring cliffs in Big Sur, or take advantage of the car-accessible beaches and dune areas at Pismo Beach. From late October through February, you can also take your tots to the Eucalyptus-tree filled Pismo Beach Monarch Butterfly Grove, where more than 10,000 of the butterflies migrate each year. Treat your toddler to a visit to the Elephant Seal Rookery at San Piedras Beach in San Simeon, where as many as 17,000 of the adorable, big-nosed creatures head during migration season. If you’re brave enough to give the entire 656-mile north to south trip a try with a toddler, dangle a visit to either Disneyland or Legoland as a reward at the end.

Mount Washington Auto Road  

Little ones get a kick out of the simple pleasures of leaf-peeping, making a fall road trip through New England a perfect choice for this age. Add a little extra fun for the grown-ups by planning a side trip for this scenic drive/thrill ride in New Hampshire. Less than eight miles long, the road climbs 4,600 feet in elevation along narrow mountain roads that you can white-knuckle yourself or hire someone to drive for you. Plan on 30-45 minutes each way. 

Ages 6 to 10

Oregon Coast “The Goonies” Tour

Eighties babies can get nostalgic for the classic 1985 Steven Spielberg film “The Goonies” while taking their own kids on a tour of the lush Oregon Coast. Start in super charming Astoria where you can geek out on pivotal icons from the film including the jailhouse and the so-called Goonies House. The seven-hour coastal route along Highway 101 includes loads of amazing beaches—a favorite from the movie is Cannon Beach, with its legendary 235-foot Haystack Rock that’s home to puffins, starfish and more creatures easily spotted from tide pools. Ecola State Park, also featured prominently in the film, offers amazing views of the rocky coast, and you can even spot whales here in season. Other must-visit spots include Columbia River Gorge, about 30 minutes from Portland, where there are easily accessible hikes to massive waterfalls and the “Fruit Loop,” a 35-mile drive along a stretch loaded with orchards, lavender and berry farms, alpaca ranches and more; and Myrtle Tree Trail, a quarter-mile hike to the world’s largest eucalyptus tree, with branches that span 70 feet across.

Blue Ridge Parkway & Tail of the Dragon

Get your National Parks fix on this roughly 470-mile route connecting Virginia’s Shenandoah National Park to Great Smoky Mountains National Park in Tennessee via North Carolina, along a breathtaking stretch of the Blue Ridge Mountains. It’s a hilly road where the speed limit never goes above 45 mph, and no commercial vehicles (except tour buses) are permitted. Kids in this age group will get a kick out of the National Park Service’s Junior Ranger Program, which requires them to complete a series of activities at each park for patches and certificates, and includes some online features perfect for long stretches in the car. Make pit stops along the way at the Roanoke Pinball Museum, home to 60 playable arcade machines; Sliding Rock Swimming Hole, a 60-foot, smooth rock waterslide near Brevard, NC; and Bristol Caverns, an underground cave in Bristol, Tennessee where you can see massive stalagmites and stalactites. A slight detour to Dollywood, Dolly Parton’s Pigeon Forge theme park, should also garner some cheers from the backseat. 

If you’ve got older kids, tack on a drive along the nearby Tail of the Dragon, an 11-mile long road near Robbinsville, NC on the Tennessee-North Carolina state line, considered a must-do for thrill seekers because of its hair-raising twists and turns. The attraction here is not the scenery, but the road itself.

Pennsylvania-Ohio Amusement Park Tour

A swath of mega-sized amusement parks—plus a few awesome smaller ones—makes a road trip between these states perfect for a family that is crazy for roller coasters. Start at HersheyPark in Hershey, PA, home to the new, 76-foot Candymonium roller coaster that travels at a top speed of 76 mph. Next, head to Cedar Point in Sandusky, Ohio (boasting 18 roller coasters, it’s often considered the coaster capital of the world) by way of two local parks in western Pennsylvania: Lakemont Park in Altoona, where you can ride Leap the Dips, the oldest wooden roller coaster in the world, and Del Grosso’s Amusement Park in Tipton, an theme park especially suitable for younger kids and where the Crazy Mouse Coaster is considered a highlight. End your trip at King’s Island, just outside of Cincinnati. The largest amusement park in the Midwest is home to several coasters, including Diamondback, a 230-foot-high ride with a 215-foot drop at a 74-degree angle. Woah!

Overseas Highway

If your family’s idea of fun veers more toward wild wonders than wild rides, plan a trip along the gorgeous 113-mile road linking 42 islands over 44 bridges through the enchanting Florida Keys. Start just north of the highway at Everglades National Park, a 1.5 million-acre wetland that’s the largest subtropical wilderness area in the United States, and spot manatees, alligators and maybe a Florida panther. Then, stretch out your trip over several days, stopping in Key Largo at John Pennekamp Coral Reef State Park, an underwater park where you can take glass-bottomed boat tours, snorkel and scuba dive to check out 70 nautical miles of underwater beauty; and Marathon to visit The Turtle Hospital, where you might be lucky enough to witness a sea turtle being released back into the wild. End your trip in Key West, the southernmost city in the continental United States, where fam-friendly highlights include the Key West Shipwreck Treasures Museum, where you can see shipwreck artifacts and listen to stories told by actors in period costumes.  


Road to Hana

To do this iconic Maui day trip right you’ll need 10 to 12 hours (or better yet, an overnight stay in Hana so you can really take your time driving there and back), making it most suitable for older kids. The world-renowned, 52-mile Hana Highway connects Kahului with the town of Hana along a twisty road dotted with 59 (mostly one-lane) bridges and often a lot of crowds. But patience is rewarded with an endless array of Mother Nature’s finest offerings, including the black sand beach at Waiʻanapanapa State Park, the Ka’Eleku Caverns (aka the Hana Lava Tube), the stunning, 80-foot Wailua Falls, and Ohe’o Gulch, site of the Seven Sacred Pools—actually dozens of freshwater pools fed by waterfalls. Be sure to stop at at least one of the many roadside stands selling fresh, tropical fruit and banana bread, and download an app or audio guide to customize the trip to your family’s taste. 

Hamilton Highlights

Make an American history-themed road trip a pop-culture one focused on the Broadway smash “Hamilton,” and pat yourself on the back for the parenting win. Start in Yorktown, Virginia with visits to the Yorktown Battlefield, the site of the last major battle of the Revolutionary War, and nearby American Revolution Museum of Yorktown and stop at nearby Colonial Williamsburg, a living history museum where your family can get a sense of what it was like to live in 18th century America. From there, drive to Washington, D.C. to see the Washington Monument, the Thomas Jefferson Memorial  and the National Archives Museum, where you can view the Declaration of Independence, U.S. Constitution and an exhibit called “Behind the Musical: Alexander Hamilton Documents.” 

Next, drive to Philadelphia to visit Independence Hall, where Alexander Hamilton was one of three delegates to the Constitutional Convention, and the U.S. Mint, created at Hamilton’s behest when he served as Treasury Secretary. Then head east, making a pit stop at Hamilton Park in Weehawken, NJ to see the Dueling Grounds where Aaron Burr shot Hamilton. Make your final stop in New York City, stopping at Trinity Church to see the burial sites of Hamilton, his son, Philip, wife Eliza, Angelica Schuyler and Hercules Mulligan. Then it’s the grand finale: tickets to see the musical at Richard Rodgers Theatre in New York City (check the web site to make sure performance have started again; at time of writing, shows were canceled through January 3, 2021). As for getting there, bonus points if you take the A train: Lin-Manual Miranda said he wrote the song “Wait For it” from the show while riding that subway line.

College Tours

Mapping out a college tour road trip is a perfect opportunity to sneak in some quality time with your teen. If your family is just starting the search process, pick a college-dense region like the Boston area to visit a mix of options that are large and small, public and private, and a mix of easy to get into and reach-for-the-stars schools. Once your future co-ed develops a sense of what they like, you can tailor future trips more specifically. Make the most of your visits by researching hotel stays and restaurants that give you a taste of campus culture (The Nittany Lion Inn on the Penn State campus, for example, is a mecca of blue-and-white school spirit), and try to time visits with on-campus sporting events, art shows or other events that interest your teen. 


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