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A Taylor Swift Tour of Cleveland: Local Spots for Every Era

A Swiftie’s Guide to The Land

Image © Gabe Wasylko
Annie Zaleski October 03, 2025

Over the last two decades, Taylor Swift has made her mark on Northeast Ohio, with gigs at small venues (a 2006 appearance at Alliance High School) and large venues alike (a 2018 gig at what’s now Huntington Bank Field). In 2021, she opened the Rock & Roll Hall of Fame induction, performing “Will You Still Love Me Tomorrow” to introduce new inductee Carole King. And now she’s even an honorary Clevelander, given her engagement to a proud Cleveland Heights native, Kansas City Chiefs star Travis Kelce.

Although the Eras Tour sadly didn’t make it to the Land, there are still plenty of ways to celebrate Taylor’s career and catalog in CLE. Upon the release of her 12th album, “The Life of a Showgirl,” enjoy a Swiftie guide to Cleveland, penned by the author of 2024’s New York Times best-seller “Taylor Swift: The Stories Behind the Songs.” (Grab your copy from Mac’s Backs, Amazon, or wherever books are sold.)

Have a drink at Jolene’s Honky Tonk

Album: “Taylor Swift” (2006)

Early on, Taylor was country to her core; in fact, when she was a teenager, she even covered Dolly Parton’s pop breakthrough “Here You Come Again.” What better way to celebrate this era than a visit to the E. 4th Street country hotspot Jolene’s Honky Tonk? In addition to plenty of neon signs and visual references to our lord and savior Dolly, the multi-story bar emphasizes good tunes and places to hang with friends.

Go treasure hunting at Paradise Galleria

Album: “Fearless” (2008)

Paradise Galleria lives up to its name: The 13,000-square-foot space is vintage shopping heaven, whether your style is mid-century modern chic or disco and new wave cool. And if you’re feeling fearless like Taylor, be sure to ride the store’s giant indoor slide down to the basement level, which features even more retro goodies for sale.

Get your goth on at the Dark Wave Dance Cave

Album: “Reputation” (2017)

Taylor’s darkest album, thematically and musically, is 2017’s “Reputation.” (Until the end, which starts to lean back into romance—but that’s another story.) Embrace your not-so-inner moodiness at the periodic Dark Wave Dance Cave events, which offer a curated soundtrack of goth and darkwave tunes.

Soak up art history at the Cleveland Museum of Art

Album: “Red” (2012)

“Red” is Taylor’s most eclectic album—songs touch on rock, pop, folk and country, among other genres—and (of course) one of her most colorful releases. You might consider it the sonic equivalent of the vibrant Cleveland Museum of Art. In fact, the University Circle gem just might be the original Eras Tour; after all, the museum boasts era-spanning exhibitions from the Renaissance, Medieval, Byzantine and Modern eras.

Take in a show at Mahall’s

Album: “Speak Now” (2010)

Taylor is an unabashed fan of the 2000s emo scene—we’re talking Paramore, Dashboard Confessional and The Academy Is…—which is obvious from listening to “Speak Now.” (Those crunchy guitars on “The Story of Us,” anyone?) We think “Speak Now”-era Taylor would love Mahall’s, the vintage bowling alley that offers up vintage shopping and a healthy concert schedule featuring up-and-coming bands.

Have date night at The Judith

Album: “Lover” (2019)

Everything about The Judith screams “perfect date night”: the quaint decor, a well-curated menu nodding to French food, and an atmosphere conducive to deep conversations. It’s a perfect match to “Lover,” which features some of Taylor’s most romantic songs to date.

Learn new wave history at the Rock & Roll Hall of Fame

Album: “1989” (2014)

Taylor was influenced by 1980s icons Peter Gabriel and Annie Lennox when creating the synth-pop smash “1989.” Coincidentally, both artists are (deservedly) in the Rock & Roll Hall of Fame. Dig into Taylor’s other musical inspirations at the Rock Hall, including at an exhibit dedicated to one of new wave’s greatest years, 1984. Bonus: Check out Taylor artifacts throughout the museum, including a dress and throne from the “Look What You Made Me Do” video in the Legends exhibit.

Enjoy our local parks and greenspace

Album: “folklore” (2020)

Although released in July, “folklore” feels like the perfect soundtrack to fall in Ohio: flannel shirts, crunching through leaves, and visiting a pumpkin patch or apple orchard. Cue up the album and take a stroll through some of our local greenspace, whether in the Metroparks, by Lake Erie, or the Cuyahoga Valley National Park.

Grab coffee at Ready Set or Brewella’s

Album: “evermore” (2020)

A companion album of sorts to “folklore,” “evermore” exudes cozy vibes—the ideal atmosphere to grab a drink at one of Cleveland’s many indie coffee shops. If you’re in Lakewood, the adorable Brewella’s offers up a rotating array of seasonal fare (try the pumpkin-kissed Jack-O-Latte) and a curated boutique. Near Gordon Square, meanwhile, the friendly hotspot Ready Set Coffee dishes up delectable breakfast sandwiches and creative coffee drinks.

Album: “Midnights” (2022)

“Midnights’” lyrics were all about the things that keep us up past our bedtimes, both good (romantic ecstasy) and bad (relationship regrets, personal insecurity). Luckily, Cleveland’s late-night scene is far more upbeat. The Tremont stalwart Prosperity Social Club boasts one of the best patios in the city and a menu brimming with hearty comfort food. Over in West Park, the Little Rose Tavern is a welcoming neighborhood bar that books DJs, bands and other events.

Find some literary inspiration at Mac’s Backs Books On Coventry

Album: “The Tortured Poets Department” (2024)

If you’re a fan of tortured poetry, the Coventry anchor Mac’s Backs has you covered—and then some. For more than four decades, the multi-story independent bookstore has been a champion of local authors as well as new releases. Their magazine and used book selections are also tops, meaning you’ll certainly find a piece of writing that piques your interest.

See a show at Playhouse Square

Album: “The Life of a Showgirl” (2025)

“The Life of a Showgirl’s” aesthetic is vintage performance glitz, between Taylor’s Bob Mackie costumes and her visual nods to the theater. The perfect place to celebrate her sophisticated new era? The Land’s own artistic jewel, Playhouse Square. Constructed more than a century ago, the theaters once hosted vaudeville and movies—and now bring in an impressive array of Broadway-caliber musicals and plays. Even the giant outdoor chandelier screams showgirl glam.

 

 

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