Vintage Vacations That Will Give You Intense Nostalgia

From Disneyland to Martha's Vineyard, these are the destinations that inspire wanderlust in generations of travelers.

Travel before the 19th century was limited to the very wealthy. The automobile and its widespread availability after World War II changed that, though, and an era of travel was born.

Cue a generation of family vacations when kids, dogs and luggage were loaded into the family station wagon for a weeklong getaway. Repetitive songs were bellowed over thousand-mile road trips and families came together for new experiences. Air travel and the advent of the Internet means trip-planning that constantly gets simpler. People can go pretty much anywhere at any time and those new experiences—in a seemingly ever-shrinking world—are the name of the travel game.

"Travelers are more savvy and a looking for value added—they want to be sure of having a great experience," said Nancy Gardella, Martha's Vineyard Chamber of Commerce & Tourism director. "Travelers are also more interested in experiences—they want to do [something] special, out of the ordinary things while on vacation. Really, they want to make memories."

These are a few destinations that were immensely popular from the early to mid-1900s. They all offer classic—yet fresh—experiences worthy of being the next visit on any traveler's dream travel list, perfect for making memories.

Martha's Vineyard coast
Martha's Vineyard's ocean-side allure has drawn travelers in for decades. (©Ben Philabaum/Flickr, Creative Commons)

Martha's Vineyard

Martha’s Vineyard was already thriving as a vacation destination in the 1950s, but it was pretty much an under-the-radar destination according to Gardella. Vacationers from the Northeast came to the island—in its secluded location off the Massachusetts coast—to sail and fish. Celebrities like James Cagney and Patricia Neal escaped to the island to relax and it also served as a haven for former President John F. Kennedy and his family.

The making of "Jaws" in 1974—and a few celebrity sightings—brought the island a bit of attention, but for the most part the island remained quiet until the 1990s when President Bill Clinton and his family vacationed there throughout his presidency. The relaxed pace, the deliberately underdeveloped coastline and the miles of hiking and biking trails keep vacationers coming year after year.

“We’re a true island, so the only way to get here is to fly, take a ferry or swim a long way,” said Gardella. “As far as travel trends, I’m delighted to report that the vineyard is truly a three-season destination, so if you’re not tethered to a summer vacation, enjoying the island in the spring and fall is a perfect time to get all the benefits without the crowds.”

Group of adults sitting around an outdoor fire pit on a summer day
As a 1930s movie star you have to be two hours from Hollywood, no further. Where do you go to relax? Palm Springs. (©

Palm Springs

Balmy temperatures and near-daily sunshine earned Palm Springs its travel attraction for generations. The area became a destination in the 1930s as a health resort for Hollywood stars.

"[Studio executives] had a rule that the stars needed to be no more than two hours away in case they needed to be called into the studio," said Mary Jo Ginther, Palm Springs Bureau of Tourism director. "Palm Springs is two hours away." 

Lucille Ball, Dinah Shore, Frank Sinatra and Bob Hope—among other Hollywood elite—built second homes in Palms Springs that are now prime examples of mid-century modern architecture. These abodes have earned Palm Springs its spot on the National Register of Historic Places and a showcase of mid-century modern architecture that draws visitors in from around the country. 

The city is still a playground for Hollywood stars, a place where they can be themselves without worrying about paparazzi. The landscape outside the city offers beautiful hikes and—for shopaholics inside the city limits—there are plenty of unique finds to score. The uptown design district is known to be especially bountiful, not to mention the treasures waiting at the vintage market held the second Sunday of each month.

Route 66
(©Don Harder/Flickr, Creative Commons)

Route 66

Say the word "road trip" and Route 66 is most likely what immediately comes to most Americans' minds with its long stretches of black top and kitschy Americana. From 1926 until it was decertified in 1985, it was a series of highways from Chicago to Santa Monica, California. For many escaping the Dust Bowl in the Midwest, it was the road to hope for a better life in the West. 

The towns along the way welcomed the visitors, offering everything from a tank of gas to a cold drink and a cool dip in a pond. Plenty of landmarks sprang up along the way: the Totem Pole Park, Cadillac Ranch and the Blue Whale to name a few. Many of those same landmarks still welcome motorists taking a trip through America's heartland. While on the road, grab an iconic fried chicken basket, sleep in a wigwam or take in the natural beauty of the Mother Road.

Spinning teacups at Disneyland
The twirling teacups and more iconic attractions still operate at Disneyland, as they have since the park opened in the 1950s. (©Martina Yach/Flickr, Creative Commons)


Walt Disney's vision was a park that parents and children could enjoy together and that park opened in Anaheim, California, during 1955. It featured four different "lands" to explore: Adventureland, Frontierland, Fantasyland and Tomorrowland.

Together, families could ride the Mad Hatter’s teacups, sail on Mark Twain’s riverboat and fly like Peter Pan. The park became so popular that three more areas have since been added: Mickey's Toontown, Critter Country and New Orleans Square. Continued growth saw the addition of Disney California Adventure Park in 2001 on Disneyland’s original parking lot and the park currently offers seven more magical "lands" to play in.

While Disney has added several new parks, a cruise line and more since 1955, the original Disneyland with its iconic Sleeping Beauty Castle and several original 1950s rides—in addition to new, more modern attractions—is still fun for the entire family.

Young girl riding a dolphin at Seaworld San Diego
Ride a dolphin at SeaWorld San Diego. (©Mike Aguilera/SeaWorld San Diego)


SeaWorld theme park in San Diego lets guests interact with nature while giving a lesson on marine life. Originally planned as an underwater restaurant, the park opened in 1964 as three giant aquariums and now features more than 5,700 fish from around the world.

One of the park’s most popular attractions is a water show featuring Shamu, the killer whale. The original Shamu—an orca captured in 1965—died in 1971, but the name has been given to other orcas performing in Shamu shows since then. SeaWorld is phasing out its Shamu shows so the whales currently living at SeaWorld will be the last generation of orca performers.

There are plenty of other reasons to keep SeaWorld on your destination radar. The dolphins and sea lions still perform for audiences. Guests can also play with the friendly dolphins and—for an additional fee—even swim with them. Stroll through the waters of the aqarium to get up close and personal with the sharks—from inside a glass viewing tunnel, of course. For thrill-seekers, hop on a ride like Journey to Atlantis or Shipwreck Rapids.

Lincoln Memorial at night
The national mall in Washington D.C. has attracted travelers for decades. (©Daniel Mennerich/Flickr, Creative Commons)

Washington, D.C.

The story of the United States is told in its captial city through sacred, thought-provoking memorials and monuments. The story is timeless, yet there is always something new to learn. Generations have come to see the classics like the White House, the Washington Monument, Arlington Cemetery, the National Mall and the Vietnam Veterans Memorial.

The history not displayed through granite and stone is told through exhibits in the 17 Smithsonian museums, covering topics ranging from art to national history. Don’t miss classic Smithsonian experiences like seeing the famous Kitty Hawk and Spirit of St. Louis planes at the Air and Space Museum.

After a day of taking in history, watch animals play at the National Zoological Park—home of famous pandas Tian Tian and Mei Xiang. Visit the city in the spring and check out the pretty, pink explosion of cherry blossoms.

Cades Cove in Smoky Mountains National Park
Cades Cove is a beautiful semi-secret tucked into the Great Smoky Mountains National Park. (©turcottes78/Flickr, Creative Commons)

Great Smoky Mountains National Park

The Great Smoky Mountains National Park was established in 1932 and the iconic peaks get their name from a natural fog that hangs low over the range, giving it its signature smoky appearance. The park's popularity in almost every season calls to more than 12 million visitors a year, making it the most visited in the country.

From the park’s creation, vacationers have enjoyed scenic drives and hikes through the park. Haywood County North Carolina early branded itself as "Gateway to the Smokies" and attracted tourists from the start of the park's opening. Mountain towns such as Wayneville, NC and Maggie Valley, NC started getting thousands of tourists a year to stay at quaint mountain cabins and motels.  Artists in Gatlinburg formed a community in 1937 and invited tourists to watch them make their wares. Visitors still shop for handmade items like brooms, quilts, baskets and carved candles. Another hand-made item to sample? Local breweries and wineries have quite the reputation. Get wider views from above the town on the Gatlinburg Sky Lift.

Take a scenic drive about an hour and half southwest of Gatlinburg to tour Cades Cove. An 11-mile loop takes visitors through an 1830s-era Appalachian town with log houses, three churches, a working grist mill and other structures. Bike or hike the loop for the best chance of viewing the area’s wildlife.

Empire State Building seen from the Top of the Rock
From the Top of the Rock, New York lays out all its iconic glory. (©Ivan Velazco/Flickr, Creative Commons)

New York City

Few cities have as many famous landmarks as the Big Apple.

Some of those attractions that drew vacationers in the middle of the century still top our list of things to do in New York. The universal symbol of freedom—the Statue of Liberty—has beckoned immigrants and attracted American visitors since 1875. Thousands flock to Times Square every New Year’s Eve for the annual ball drop, but arguably nowhere do lights shine brighter than nearby Broadway. The Empire State Building and the much newer One World Trade Center are two of the tallest buildings in the city, offering spectacular views of the skyline.

You can still take in a Rockettes show at Rockefeller Center, relax in Central Park or take in some of the finest art in the world, just like your grandparents and their counterparts did.

Opulent, mid-century resorts like Kutshers once welcomed families to the Catskills Mountains. (©Forsaken Fotos/Flickr, Creative Commons)

Catskills Mountains

From the 1920s through the 1970s the Catskills Mountains in upstate New York were the premiere vacation spot for Jewish families from New York City, given the moniker of "The Boscht Belt" for the area's popularity. Lavish resort hotels offered all-inclusive luxury vacations—think Kellerman’s resort in "Dirty Dancing," that was actually based on these resorts—and a retreat into fresh air from the big city.

As prejudices lessened and air travel became popular the Catskills fell out of favor as families vacationed elsewhere. Many of the original, iconic resorts fell into disrepair but there are still plenty of family-friendly resorts left in the region for a relaxing getaway.

The unspoiled natural beauty of the mountains offer a serene place to camp or hike, or simply relax. The lakes and streams are prime spots for fly fishing, which got its start in the region. Make sure to leave an afternoon for a leisurely drive past stunning waterfalls and over historic covered bridges dating back to 1800.

Grand Prismatic Spring in Yellowstone National Park
The Grand Prismatic Spring and other natural wonders are only part of the draw to American's oldest national park. (©Clint Losee/Flickr, Creative Commons)

Yellowstone National Park

Yellowstone was the country’s first national park, established in 1872. The completion of the railroad to the park in 1908 doubled the number of visitors and after World War II—when more families owned cars—and visitors poured in to see geysers like reliable Old Faithful, the bears and the gorgeous scenery.

Very little has changed since: The geysers and hot springs still draw vacationers from around the country and visitors can also see steam pools, bubbling mud pots, warm seeps and fumaroles. The 2 million-plus-acre park offers prime camping, hiking, snowmobiling and fishing. For a more refined vacation, spa resorts abound nearby. Resorts like Big Sky Resort in Montana or Jackson Hole Mountain Resort in Wyoming are just a few of the resorts to offer luxury accommodations close to the natural wonder.

Children ride the Maid of the Mist at Niagara Falls
Ride the Maid of the Mist at Niagara Falls. (Courtesy Destination Niagara USA)

Niagara Falls

Niagara Falls has been a popular honeymoon destination since the early 1800s, though it wasn't billed as the "Honeymoon Capital of the World" until the 1900s.

Because of its natural beauty and ease of access, generations of newlyweds celebrated their marriages by the mighty falls. It is still a honeymoon destination, as nearly every hotel offers a honeymoon package and newlyweds can get an official Honeymoon Certificate signed by the mayor. But it's not just for lovers. 

A new trend in the area is more multigenerational visits as baby boomers recall visiting as children and return to share it with their children and grandchildren. It is also very popular with millennials seeking a more active experience. 

"We have several hiking trails along the gorge that range from easy to moderate," said Andrea Czopp, Destination Niagara USA director of communications. "If you can walk, you can hike the trails."

Take the boardwalk to the Hurricane Deck at Cave of the Winds and feel the rush and spray of Bridal Veil Falls. While some experiences remain the same through the generations, some have been upgraded.The Maid of the Mist still rides guests to the base of the falls, but now there are jet boats—one is open and will leave you soaking wet, the other is closed to keep you dry. With 360-degree spins and trips down class-five whitewater rapids, neither are for the faint of heart.

"These things have been here, we're just trying a new way to present them for the modern traveler," said Czopp.