Places Taylor Swift Fans Should Add to Their Bucket List for a Road Trip

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A road through Hudson Valley

 

Upstate New York



Taylor Swift has mentioned multiple upstate New York locales in her songs, and she filmed “Folklore: The Pond Studio Sessions” at Long Pond Studio near the quaint town of Hudson in Hudson Valley. You won’t be able to visit the studio itself. Still, this picturesque town is filled with fun things to do, like sampling a matcha rose chocolate bar at The Quiet Botanist, visiting the Olana State Historic Site, and shopping at the eclectic boutiques on Warren Street. Hudson Valley is a great New York fall getaway destination if your schedule is flexible. A kaleidoscope of colors greets leaf-peepers, the smell of fresh apples fills the air, and cool, crisp temperatures present the sweater weather you’ve been waiting for — you can finally break out that cardigan!

While you’re there, consider stopping at Samuel’s Sweets Shop, the adorable candy store owned by fellow Swiftie Paul Rudd. It’s in another charming upstate New York town called Rhinebeck, about 25 miles south of Hudson. Play Swift’s “Sweet Nothing” during your drive and prepare yourself for some tough decisions ahead — chocolate, gummies, or popcorn. Drive-in 32 is another recognizable point of interest for fans of the lyric video “This is Me Trying.” Located in Greenville, about 23 miles northwest of Hudson and 30 miles southwest of Albany, its massive screen was featured in the video, making it “the world’s most viewed drive-in screen,” according to the location’s Instagram page. Films are shown here seasonally, beginning in May.

Watch Hill, Westerly, Rhode Island

Rhode Island's Watch Hill Lighthouse

You can’t miss Taylor Swift’s gorgeous, 11,000-square foot Rhode Island mansion — it’s perched by the shore, atop the highest point in Watch Hill. Bought for $17.75 million in 2013 (when Taylor was a mere 23), this Westerly home has been the scene of multiple Independence Day bashes and the star of Swift’s “folklore” hit, “The Last Great American Dynasty.” Known as Holiday House, Taylor brings the history of her home’s former owner, Rebekah (Betty) Harkness, to life in fine, lyrical fashion.



When you’ve finished ogling the fence around Swift’s house (because honestly, that’s the closest you’ll get), head to nearby Watch Hill Beach for a swim before visiting the landmark Watch Hill Lighthouse. Set on a peninsula, this Insta-worthy attraction is accessible year-round from 8 a.m. to sunset. On the other hand, the Watch Hill Lighthouse Museum is open on Tuesday, Wednesday, and Thursday afternoons from July through the week after Labor Day. 

Other fun things to do while in Watch Hill include digging your toes into the soft sand at East Beach, riding one of America’s oldest continuously operating Flying Horse Carousels, and visiting the Napatree Point Conservation Area. When hunger pangs hit, grab a bite at Taylor’s most frequented local restaurant, Olympia Tea Room. She’s been spotted dining at this 100-year-old, family-run establishment with A-list friends like Ed Sheeran, Jack Antonoff, and Hailee Steinfeld.

Long Island, New York

Oheka Castle in Huntington



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Oheka Castle is one of the most stunning places every Swiftie should add to their road trip bucket list. Set on grounds so perfect you won’t find an errant blade of grass, this Elysian retreat is instantly recognizable as part of the remarkable “Blank Space” video set. Oheka Castle stands proudly in Huntington, Long Island, about 37 miles east of Manhattan, making it a perfect place to stop on your way to the Big Apple. Listed on the National Register of Historic Places, this is the second-largest private home in the country and boasts a luxurious hotel, the OHK Bar & Restaurant, and gorgeous gardens. If you’ve got cash to spare, stay the night.

Winfield Hall, also known as the Woolworth Mansion, was used in interior scenes for the same music video. Recently sold for a bargain price of $8.25 million, this Glen Cove estate lies on 16.4 acres just over 16 miles northeast of the castle. It’s privately owned, so catching a glimpse will be tricky. Welwyn Preserve is a short drive away and boasts four wooded nature trails to help stretch your legs. Also nearby is the popular Morgan Memorial Park, where you can enjoy a swim, have a picnic, or sprawl on the beach.

Coney Island, Brooklyn, New York

Friends laughing at Coney Island

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Taylor Swift’s “coney island” takes place in the sometimes seedy, always buzzy New York beach town of the same name. Sung with The National, the lyrics to this track describe the protagonist sitting on a bench amongst “the fast times, the bright lights, the merry-go” as she regrets a doomed relationship. “Fast” is a good word to describe this place. There’s always something happening no matter the season, but summer is the best time to visit for a stereotypical Coney Island experience. Sticky ice cream fingers, sandy swimsuits, and eclectic characters abound on this famed old-school American boardwalk, lined with kitschy shops and greasy restaurants — precisely what you’d want from a seaside locale.

Thrill seekers searching for that “merry-go” Taylor sang about should head to Luna Park, Coney Island’s main attraction. Dubbed one of the best amusement parks in the Northeast, there are rides aplenty to tempt even the most nervous of visitors. If Coney Island feels familiar, that’s because it likely is. This famed Brooklyn beach town has been featured in films and songs for years, and its almost three miles of beach have been considered New York City’s playground for over a century. Tip: The D, F, N, and Q subway trains go straight there, as do numerous buses, which means you won’t have to worry about parking if you’re planning to ditch your car in the city for this portion of your road trip.

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Brooklyn, New York

Woman admiring NYC from Brooklyn

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You’ll need to set aside more than 10 minutes to explore the Brooklyn Taylor Swift alludes to in her lengthy version of “All Too Well.” A song about her short but painful relationship with actor Jake Gyllenhaal, the line “From when your Brooklyn broke my skin and bones” purportedly alludes to the time they spent together in the famous New York City borough. During their months as a couple, Gyllenhaal and Swift explored neighborhoods like Park Slope. 

Still upset about her heartbreak? Shake it off with a visit to Prospect Park. This lush, 585-acre greenspace is Brooklyn’s answer to Central Park. In fact, it was designed by the same architectural genius, Frederick Law Olmsted. A visit to the Prospect Park Zoo will have you forgetting about Swift’s neglected red scarf in no time. Next, go shopping on 5th Avenue (in Park Slope, not NYC) and grab a bite to eat from a local restaurant. 

New York City, New York

A Swiftie on Cornelia Street

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Welcome to New York; it’s been waiting for you! Perhaps the most well-referenced city in Taylor Swift’s lyrics, Manhattan was not only one of the singer’s biggest muses but also one of her homes. The song “Cornelia Street” was named after her former house, 23 Cornelia Street. An unassuming West Village carriage house, this popular spot is frequented by Swifties taking selfies in front of its arched doors. While you won’t be invited in (she no longer lives there, anyway), it’s fun to walk in her footsteps to nearby shops and restaurants in Greenwich Village. Apparently, she frequented Via Carota.

Your next stop should be Electric Lady Studios, where Taylor recorded during late-night sessions. Housing Works Bookstore is another must-visit. It was featured in “All Too Well: The Short Film” and boasts enough books that you’re sure to find at least one to tuck into during your long drive to the next stop on your ultimate Taylor Swift road trip (as long as you’re not driving, that is). Walking the High Line is a fun thing to do on a nice day, plus you’ll be able to sing the line, “I knew you, your heartbeat on the High Line” from the song “Cardigan” as you wind your way through the elevated park. Grab a drink in a “dive bar on the East side” while paying homage to “Delicate.” According to Swifties on Reddit, the bar she references is Lovers of Today. 

Reading, Pennsylvania

The Reading Pagoda in fall

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Taylor Swift grew up on an idyllic Christmas tree farm (yes, the one from the song of the same name) in Reading, Pennsylvania. The location also features in her song “Seven.” Her family later moved to Wyomissing. While you can’t tour her homes, obviously — other families live there — you can roam around her old stomping grounds, enjoying the town’s best attractions and tastiest restaurants.

One place every Swiftie should visit at sunset is the Reading Pagoda. This landmark attraction is beloved for its mountaintop locale (it sits at the summit of Mount Penn) and unique Japanese design. An ideal destination for lovers looking for a romantic spot to unwind, this place offers vistas so beautiful that you’ll hear Swift’s romantic ballad, “You Are In Love,” playing in your head on repeat. Hike through Nolde Forest and get in touch with your natural side at the Hawk Mountain Sanctuary, 29 miles north.

North Carolina

Boardwalk in Croatan National Forest

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When asked to write a song for the film “Where the Crawdads Sing,” Taylor Swift — a fan of the book — was happy to oblige and penned a haunting story told from the point of view of the main character Kya, a survivor who lives on a marsh on the outskirts of town. While Swift doesn’t reference a particular place, she does mention North Carolina as a whole: “Carolina stains on the dress she left,” “Carolina creeks running through my veins,” and “Carolina pines” are just a few of the state-centric lyrics she wrote.

We suggest touring cities and parks to get a real taste of life in North Carolina. Unleash your inner child with a visit to Pullen Park, one of the world’s oldest amusement parks in Raleigh, or sing “Getaway Car” in the NASCAR Hall of Fame in Charlotte. The Outer Banks will give you a glimpse into beach life. A visit to Merchants Millpond State Park transports Swifties to a swampland closer to that evoked in Swift’s ethereal song. Then there’s the unmissable Croatan National Forest, a true beauty home to 160,000 acres of pine forest, bogs, swamps, and estuaries. This natural wonderland also boasts a 100-mile Saltwater Adventure Trail, the only one of its kind in the country, that allows visitors to paddle their way through its unique ecosystems.

Nashville, Tennessee

Teen at Swift's Education Center

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It’s almost impossible to avoid Taylor Swift in Nashville — that’s where the singer began her career, after all. From the $4 million Taylor Swift Education Center that she opened in 2013 to the Bluebird Café, where she first performed at 14, plenty of top attractions are devoted to the superstar. Her likeness is even painted on a wall outside Bad Axe Throwing on Fogg Street. The Country Music Hall of Fame boasts multiple Swift displays as well as limited edition concert posters in its Hatch Show Print. This is also where you’ll find the aforementioned Education Center.

Centennial Park is a place every Swiftie should add to their ultimate Taylor Swift road trip bucket list. In addition to being mentioned on “Invisible Strings” (“Green was the color of the grass where I used to read at Centennial Park”), this is where you’ll find a full-size replica of the Parthenon and a newly placed custom bench dedicated by the town to their former resident. Its plaque says, “For Taylor Swift. A bench for you to read on at Centennial Park. Welcome home, Nashville.” Visit in May for an extra Taylor treat. This is the month when Castle Gwynn, the private home featured in Taylor Swift’s “Love Story” music video, is open to the public (on weekends only). A mere 24 miles south of Nashville in Arrington, you can visit this sprawling spot on the way to your next road trip destination.

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Georgia

Moss-draped oak trees, Georgia

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Southern charm oozes from the cities and towns of Georgia, making visitors feel instantly at home — similar to how we feel when listening to Taylor Swift’s lyrics. In the first verse of “Tim McGraw,” she writes, “He said the way my blue eyes shined put those Georgia stars to shame that night.” While not referring to a particular place, we’d suggest visiting a selection of the state’s best cities and countryside to get a real feel for this magical landscape. From Atlanta to Augusta and Tybee Island to the Antebellum Trail, there’s a whole lot to love about Georgia and a heck of a lot to write songs about.

Speaking of songs — friendship and love are recurring themes in Swift’s tracks. That’s why you need to add Savannah to your road trip. One of the friendliest cities in the U.S., you’ll feel as if you’ve instantly connected with locals while visiting this charming city — kind of like the response provoked by “22” or “I’m Only Me When I’m With You.” If that friendship turns into something a little more (à la “It’s Nice to Have a Friend,”) you’ll be in the right place. Savannah’s horse-drawn carriages, moss-draped roads, historic oaks, and Georgian architecture help make this a prime spot for an amorous couples’ vacation. While there, turn up the volume on “Haunted” and visit Laurel Grove Cemetery, which is said to be one of the city’s spookiest locations.

Tupelo, Mississippi

Elvis Presley Birthplace in Tupelo

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If the name Tupelo sounds familiar, it might be because it’s the birthplace of Elvis Presley. Or, more likely, you remember the lyrics, “The stars in your eyes shined brighter in Tupelo,” from “Dorothea.” According to Taylor Swift, the song is about a girl who left her small town for Hollywood, then returns for the holidays and reconnects with an old love. A small city in northeast Mississippi, Tupelo is a great Taylor Swift road trip destination. And it won’t take days to visit the most interesting attractions, which means you can be back on the road to your next stop in mere hours.

It’s no secret that the Elvis Presley Birthplace is one of the main attractions in Tupelo. The town’s link to “the King” is a huge tourist draw. The estate includes a museum devoted to Elvis’ personal history, career, and childhood home. When you’ve had enough hip wiggling for one afternoon, plug the Natchez Trace Parkway into your GPS. This journey would be perfectly accompanied by a Taylor Swift soundtrack filled with songs of travel and adventure. Cue up “Out of the Woods,” Begin Again,” “Wildest Dreams,” and “The Lucky One” to start. Then, get ready to be awed by the most scenic roads as you wind your way through the majestic landscapes of Tennessee, Alabama, and Mississippi.

Las Vegas, Nevada

Women driving in Las Vegas

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Close your eyes and picture Las Vegas. We bet you’re envisioning bursting fountains, bright lights, and eclectic performers. This desert wonderland is a city of juxtapositions, secrets, seduction, and a whole lot of fun. It’s also referred to in the chorus of Taylor Swift’s massive hit, “Karma”: “Flexing like a Vegas acrobat, Me and karma vibe like that.” Sin City is filled with fun places for Swifties to visit, and they don’t all involve gambling, drinking to excess, or getting hitched at a drive-thru chapel.

Just because Taylor isn’t performing during your visit doesn’t mean you must forgo music. Plenty of amazing performers are ready to wow you with their talents in this epic weekend getaway destination. Book a show while you’re in town. Whether you visit the avant-garde Sphere or catch a superstar singing at the Colosseum at Caesars Palace (“Hello from the other side,” Adele), you’ll love being immersed in sound.

Not Swiftie enough for you? Ditch your heels and head to Exotics Racing, where you can feel the power behind the wheel of a Ferrari, Lamborghini, or McLaren. Tay Tay would definitely approve of that experience. On “Red,” she sings, “Loving him is like driving a new Maserati down a dead-end street.” And don’t forget “Getaway Car.” Depending on how much fun you have, you might need one of those!

Los Angeles, California

Taylor Swift at The Grove

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There’s no denying Taylor Swift’s strong bond with Los Angeles. She highlights the City of Angels on “Invisible String,” Sunset Boulevard and Vine Street are both mentioned in “Gorgeous,” and of course, there’s her “Delicate” music video that features the plush Millennium Biltmore Los Angeles hotel and Golden Gopher bar. Since Taylor croons “Whiskey on ice, Sunset and Vine,” you should probably visit Sunset & Vinyl, a funky ’70s lounge hidden inside 800 Degrees Hollywood. While in town, don’t miss the Los Angeles area’s must-see attractions like the Hollywood Walk of Fame, Hollywood Sign, Universal Studios, and Disneyland. Also, catch a flick at AMC The Grove 14. Taylor attended the premiere of her “The Eras Tour” concert movie here with Beyoncé.

And don’t miss out on a drive along the PCH (Pacific Coast Highway)! This stunning route offers spectacular views that can soothe your soul — rugged bluffs, the iconic Bixby Bridge, and sparkling ocean waves. Make Malibu a day trip destination from Los Angeles. About 36 miles southwest of downtown, you’ll likely recognize Point Dume State Beach from the “22” music video. Pack a swimsuit and towel so you can take a well-earned dip in the ocean. FYI, Swifties recommend listening to these ideal songs on a long, scenic drive: “The Best Day,” “Betty,” “Cowboy Like Me,” “Dorothea,” and “Ivy.”

Dave Pennells

By Dave Pennells

Dave Pennells, MS, has contributed his expertise as a career consultant and training specialist across various fields for over 15 years. At City University of Seattle, he offers personal career counseling and conducts workshops focused on practical job search techniques, resume creation, and interview skills. With a Master of Science in Counseling, Pennells specializes in career consulting, conducting career assessments, guiding career transitions, and providing outplacement services. Her professional experience spans multiple sectors, including banking, retail, airlines, non-profit organizations, and the aerospace industry. Additionally, since 2001, he has been actively involved with the Career Development Association of Australia.