Two vintage bikes on sand dunes in Cape Cod

The 8 Best Destinations for a Vintage Family Vacation

These vacationlands are making a comeback

We’re dedicating our March features to family travel. Read on for insightful guides to the best road trips for different ages, the best hotels with amenities for children, and the changing face of family trip planning, as well as inspiring stories of traveling with a newborn, family travel post-divorce, the lowdown on family campground culture, and more.

Ah, the good ol’ days of family road trips of yore—towing the Airstream packed with vacation supplies or piling into the family station wagon, perpetually guarding your half of the back seat. Like the faux, wood-paneled family truckster, there are plenty of once-idyllic family vacation destinations that have seen their heyday. But vacationlands coast to coast are experiencing a much-needed renaissance, blending classic American nostalgia with modern demands. This guide includes eight great destinations making a comeback. 

Image of Kaaterskill Falls in the Catskills with text over it

Photo: Carrie Thompson / Getty Images

For over a century, the Catskill Mountains in southeastern New York State have lured city dwellers seeking a summertime respite, birthing a vacation destination rife with family-friendly resorts. By the 1950s, the Catskills were dubbed the "Borscht Belt," as countless Jewish families, predominantly from the Big Apple and its surrounding suburbs, enjoyed summer vacations here. In the late 80s, the blockbuster movie "Dirty Dancing," chronicling the 1963 summertime coming of age of Frances "Baby" Houseman, was set at fictional Catskills resort, Kellerman's Mountain House—and don't forget Steiner's Mountain Resort from "The Marvelous Mrs. Maisel, which was filmed at the real-life Scott's Family Resort. As the decades waned, so did the Catskills' popularity, but there's been a progressive comeback in recent years. Today, families flock here to enjoy the spoils of the great outdoors: hiking, bike riding, whitewater rafting, canoeing, and kayaking. Adventure seekers, however, should head to Hunter Mountain to whiz above the treetops on North America's most extensive zip line canopy course

Image of The docks at Lake Arrowhead Village, surrounded by the forest. With white text over image

Photo: Jo Diongzon / Getty Images

Lake Arrowhead, nestled in the San Bernardino National Forest mountains, was once considered a premier resort town, luring Old Hollywood royalty including Marilyn Monroe, Rock Hudson, and Liberace to enjoy rest and relaxation. Today, the best (and only) way to see the sprawling lakefront homes of the rich and famous is a cruise aboard the Lake Arrowhead Queen, a Mark Twain-esque paddleboat. Landlubbers craving to explore the natural beauty of this mountainous region can embark on a thrilling ATV off-road experience, where breathtaking views stretch from Lake Arrowhead to rugged, snow-dusted mountains as far as the eye can see. Less intense adventure here includes hiking, cycling, fishing, and camping surrounded by tens of thousands of towering trees. SkyPark at Santa’s Village, which opened in 2016, offers year-round mountain biking on 10 miles of groomed trails, zip-lining, rock climbing, archery and ax throwing, and an arena for ice or roller skating (depending on the season). Plus, there are hiking trails through dense forest peppered with tranquil meadows and serene streams and ponds. 

Photo of Beautiful beach grasses waving in the wind and a broken snow fence bathed in late afternoon light with a view of the ocean and birds flying in the sky. White text over the image

Photo: Betty Wiley / Getty Images

Cape Cod has long been the summertime playground for generations of families from Boston and other New England cities—who could forget the images of the Kennedys frolicking on the sprawling compound in Hyannis Port? In the 90s, "Dawson's Creek" fans (and a new generation of fans, thanks to the series being recently released on Netflix) will remember the fictional harbor town of Capeside being the setting for Dawson, Pacey, and Joey's teen love triangle. But today, "going down the Cape" means a wealth of family-friendly experiences no matter what time of year. Dennis Port's Pelham House Resort recently unveiled multimillion-dollar renovations that retain all the charm of a classic Cape Cod family resort with a contemporary coastal vibe. Little ones cool off in the pool while parents sip mudslides on the deck, or the whole gang can soak up the sun at the resort's private beach. After dinner, make s'mores at one of the fire pits on the shores of Nantucket Sound or play a round of mini-golf nearby. Cap the night off with a treat from Sundae School, a classic soda fountain in a retrofitted barn known for its from-scratch ice cream and fresh fruit sundaes. 

Lake Wallenpaupack, Silver Birches Resort, Hawley, Poconos Region, Pennsylvania, USA with white text over the image

Photo: Jon Lovette / Getty Images

Once synonymous with 7-foot-high, champagne glass-shaped hot tubs, the Poconos rose to fame in the post-World War II era. Resorts with swimming pools reminiscent of wedding bells and heart-shaped (and sometimes vibrating) beds helped earn the region the moniker “the Honeymoon Capital of the World.” With more than 100 ski trails and striking natural beauty, this northeastern nook of Pennsylvania sustained its popularity until the honeymoon was over and its glory days were left behind. However, in recent years, the Poconos have seen a resurgence, with city folk from New York City and Philadelphia making easily manageable drives to its serene waterfalls, whimsical woodlands, and no shortage of antique treasures. Camelback Lodge boats gravity-defying water rides and Flow Rider surfing at its on-site Aquatopia Indoor Waterpark, plus arcades, laser tag, and other smile-inducing experiences. Get to know the region better on a guided family horseback ride, sit back and relax on a train excursion, or plunge 1,600 feet into a mountain to explore a real coal mine dating back to 1855

High Angle View Of Boat Sailing In River in Winter Haven with white text over the image

Photo: Jose Bonilla / EyeEm / Getty Images

Before Walt Disney inextricably linked Central Florida to theme parks, there was Cypress Gardens, located an hour from Orlando on Lake Eloise. In operation from 1936 to 2009, the botanical garden and theme park is considered Florida's first tourist attraction. It featured some 8,000 varieties of flowers from more than 90 countries, as well as the country's first electric boats, which floated through the garden's tropical canals. In 1943, the park launched a water ski show that grew so popular, Winter Haven continues to be known as the "water ski capital of the world." Although the grounds of Cypress Gardens are now home to Florida's newest theme park, LEGOLAND, fret not: The historical gardens were maintained, and in a nod to yesteryear, LEGOLAND hosts daily water ski shows—only with LEGO pirates gliding across the lake. Inspired? The whole family can learn to water ski at nearby Elite Cable Park, where the Get Up Guarantee Package ensures that by the end of the day, you'll be wakeboarding, waterskiing, or kneeboarding with ease. 

Sunrise over boats in the dock in Traverse City with white text over the image

Photo: Alan Tsai / Getty Images

Nestled in the pinky of the Lower Peninsula mitten, Traverse City's first summer vacationers arrived by steamship from Chicago, drawn to the fresh air, beaches, sprawling acres, and soaring pines of "The Third Coast." Those factors—plus Traverse City's unique blend of small Midwestern town charm and micro-metropolitan vibe—still draw people from far and wide. Surrounded by the waters of Lake Michigan, the beach at Clinch Park is conveniently steps from downtown and offers gentle lapping waves, soft sand, and ample space for kids to build sandcastles. The splash pad and picnic pavilion are a family favorite, and the calm water is ideal for stand-up paddleboarding. On the peninsula's western shore, scale the breathtaking mounds of Sleeping Bear Dunes National Lakeshore, some soaring as high as 400 feet. Come July, it's the National Cherry Festival, a week-long celebration of the local cherry harvest dating back to 1925. More than 500,000 visitors flock here annually for the event's concerts, local flavor, and (mostly free) family-friendly happenings. 

Scenic view of lake with trees and mountains in Estes Park. White text over image

Photo: Charles Martinez / EyeEm / Getty Images

Known as the Centennial State's original playground, Estes Park is quintessential Colorado, boasting majestic snow-capped mountains, miles of undisturbed craggy trails, and easy-to-spot wildlife, including elks and bears. Considered the base camp for Rocky Mountain National Park, the Stanley Hotel was considered cutting edge with its electricity, telephones, and every turn-of-the-century amenity when it first opened in 1909. The hotel's grandeur faded by the 70s, but when young author Stephen King stayed the night, he left with inspiration to write "The Shining." Now fully restored, the Stanley Hotel is in partnership with the Kent Mountain Adventure Center, so the whole family can take a guided rock climbing lesson with a pro (the high alpine peaks of the Rocky Mountains are no place to wing it). Other outdoor exploits for families include horseback riding, fly fishing, and whitewater rafting. At Open Air Adventure Park, travelers 5 and up can navigate rope bridges, aerial tightropes, swinging log steps, and moving platforms—at 10 and 21 feet above the ground.

Life guard tower on the Jersey shore

Photo: Gregory Adams / Getty Images

Long before MTV’s reality show bearing its name made this 140-mile coastal stretch synonymous with big hair, perpetual tans, and being overserved, the Jersey Shore has drawn visitors to its dozens of beach towns, windswept beaches, and cool ocean breezes. At the southernmost tip of New Jersey, Cape May has welcomed travelers as early as the 1700s, and Wildwood Crest has been a popular family vacation spot since the 50s. Wildwood is très Insta-worthy, with its family-oriented, two-story motels that are decidedly retro, right down to the faux palm trees and boomerang tables. The StarLux Hotel & Suites has fully embraced its mid-century style and offers complimentary bicycles and beach supplies for guests, an arcade, a 27-hole mini-golf course, and an ice cream parlor. Located within walking distance of the boardwalk, vacation days here get off on the right foot with your morning joe served from an Airstream coffee bar.