Theme Ride Thursday: 20 Years of Taylor Swift—Ride through the Eras

On October 24, 2006, a 16-year-old singer-songwriter released her self-titled debut album and introduced the world to Taylor Swift. Twenty years later, Taylor Swift has become one of the defining artists of her generation, building a career that has crossed genres, broken records, continually reinvented itself, and created a fandom unlike almost any other in music.

Taylor first made her mark as a country artist, bringing confessional songwriting, catchy country-pop hooks, and stories of teenage life and heartbreak to a massive young audience. Songs like “Our Song,” “Love Story,” and “You Belong With Me” didn’t just find success with country listeners; they crossed over to mainstream audiences and helped introduce a new generation to country music.

She didn’t stay in one lane for long. As her career evolved, so did her sound. Red blurred the lines between country and pop, 1989 marked her full embrace of pop, reputation brought darker electronic influences, and folklore and evermore ventured into indie-folk and alternative sounds. Through every shift, her songwriting has remained at the center of her music. Her ability to move between genres has helped her reach audiences far beyond where her career began.

The accolades tell part of the story. Swift has won 14 Grammy Awards, including a record four wins for Album of the Year, making her the artist with the most Album of the Year wins in Grammy history.

For Swifties, however, following Taylor has never been just about the music.

Part of the fun is looking for the Easter eggs.

From secret messages hidden in the liner notes of her earliest albums to carefully chosen colors, outfits, numbers, lyrics, music videos, and social media posts, Taylor has spent years leaving clues for fans to decode. Being a Swiftie sometimes means being part music fan, part detective. A seemingly insignificant detail can send fans down a rabbit hole, and sometimes the meaning of a clue isn’t revealed until months or even years later.

Twenty years into her career, she’s still doing it. In September 2026, eagle-eyed fans decoded clues that pointed to the word “encore,” and, just days later, Taylor released The Life of a Showgirl: The Encore, expanding her latest album with four new tracks. Even after two decades, Swifties know better than to assume an era is over when they think it is.

That relationship with her fans has become part of the Taylor Swift experience. Every era brings its own sound, aesthetic, stories, symbols, and surprises. Together, those eras have also given indoor cycling instructors an enormous catalog to work with.

So, in celebration of 20 years of Taylor Swift, we’re taking a ride through the eras with one track from each of her 12 studio albums. And if you’re looking for a Swiftie-themed profile, yes, we even have one of those for you! (Scroll down to the bottom to find it.) 

Taylor Swift 

Our Song, Taylor Swift, 3:21, 89 bpm

Start where it all began. “Our Song” captures the country sound and teenage storytelling that introduced Taylor to the world. At 89 bpm, use it as a flat road with intervals at 0:35–1:02 (27s), 1:29–2:55 (26s), and 2:32–3:04 (32s). You can also use it as a warm-up to prepare for the eras ahead.

Fearless 

Love Story (Taylor’s Version), Taylor Swift, 3:55, 120 bpm

One of the tracks that helped take Taylor from rising country star to mainstream phenomenon, “Love Story” gives us a natural climbing rhythm. Ride at 60 rpm with moderate-to-heavy resistance, adding more resistance during the intervals at 1:04–1:20 (16s), 1:56–2:45 (49s), and 3:17–3:50 (33s).

Speak Now

Mine (Taylor’s Version), Taylor Swift, 3:51, 120 bpm

Written entirely by Taylor, like the rest of Speak Now, “Mine” offers another 60 rpm climbing opportunity. This time, make the hill more dynamic. Alternate between seated climbing and standing attacks, adding enough resistance before each transition out of the saddle.

Red

22, Taylor Swift, 3:52, 104 bpm

By Red, Taylor was beginning to move decisively beyond her country roots and toward pop. “22” is playful, instantly recognizable, and perfect for a faster flat road. Ride around 90–100 rpm with moderate resistance, adding leg surges during the intervals at 0:42–1:09 (27s), 1:47–2:41 (54s), and 2:50–3:47 (57s). Return to the beat between efforts.

1989

Style, Taylor Swift, 3:51, 95 bpm

1989 completed Taylor’s transformation into a full-fledged pop star, and “Style” still sounds right at home on a cycling playlist. This song could be used as a warm-up or mid-ride flat. If using it as a working segment, settle into a 95 rpm flat road with moderate resistance. Add small amounts of resistance while maintaining cadence during the intervals at 1:00–1:40 (40s) and 2:22–3:42 (1m 20s), creating strength-focused efforts without changing speed. 

reputation

…Ready for It?, Taylor Swift, 3:28, 80 bpm

The opening track of reputation announced immediately that this was a very different Taylor era. Use the darker, heavier production for a powerful 80 rpm flat road. Start seated with moderate resistance, then progressively add load throughout the track.

Lover

Cruel Summer, Taylor Swift, 2:58, 85 bpm

It took several years for “Cruel Summer” to finally become an official single, but Swifties had already known how good it was. Use it as a warm-up or an energetic flat road at 85 rpm with moderate resistance. Add leg surges during the intervals at 0:29–0:51 (22s), 1:17–1:39 (22s), and 2:05–2:50 (45s), returning to the beat between efforts.

folklore

august, Taylor Swift, 4:21, 90 bpm

The folklore era showed another side of Taylor’s songwriting, arriving with a more intimate indie-folk sound. With its lower energy, “august” works beautifully as a recovery flat road at around 90 rpm. Let riders settle into the music, using the intervals at 0:25–0:48 (23s), 1:09–1:32 (23s), 2:13–3:06 (53s), and 3:27–4:00 (33s) for gentle leg surges while keeping the overall effort controlled.

evermore

willow, Taylor Swift, 3:34, 81 bpm

Continue the moodier storytelling of Taylor’s indie-folk era with “willow.” At 81 rpm, use this as a flat road. Rather than making it a maximal effort, focus on smooth pedal strokes and controlled resistance, letting riders settle into the hypnotic rhythm.

Midnights

Anti-Hero, Taylor Swift, 3:20, 97 bpm

One of Taylor’s most recognizable tracks from Midnights gives us a natural flat-road cadence. With plenty of energy to ride to, “Anti-Hero” works perfectly as a warm-up or a moderate flat, letting the steady beat drive the movement.

The Tortured Poets Department

I Can Do It With a Broken Heart, Taylor Swift, 3:38, 130 bpm

The lyrics tell one story while the bright, energetic production tells another, making this track especially fun in a cycling class. Ride at 65 rpm for a climb. Start with moderate resistance and progressively build the hill, using the increasing energy to take riders toward a strong finish.

The Life of a Showgirl

The Fate of Ophelia, Taylor Swift, 3:46, 124 bpm

Twenty years after her debut, we’ve reached Taylor’s 12th studio album and her latest era. Ride at 62 rpm for a climb, adding resistance during the intervals at 0:47–1:23 (36s), 2:01–2:39 (38s), and 2:58–3:35 (37s), offering riders the option to stand or push harder from the saddle. Return to a moderate climbing resistance between efforts.

Want More Taylor Swift?

Looking for even more ways to bring Taylor Swift into your classes? ICA has featured her music many times over the years. Check out Jennifer Sage’s complete Taylor Swift versus Rock ‘n’ Roll—Fast Flats to Climbs class profile, which pairs Taylor’s fast flats and climbs with classic rock favorites. 

You can also dig into our archives for more individual Taylor tracks and coaching ideas, including “Delicate” in Mainstream Music Monday: Swift Pace, Please! and the more recent “I Knew It, I Knew You” from Toy Story 5.

Are You a Swiftie?

Maybe you’ve been here since the days of cowboy boots, curls, and secret messages hidden in CD booklets. Maybe 1989 made you a fan. Maybe you joined during the folklore era, traded friendship bracelets at the Eras Tour, or found yourself trying to decode an Easter egg you swore you wouldn’t overthink.

However you got here, 20 years of Taylor Swift have given us a remarkable soundtrack, and indoor cycling instructors have plenty of material to keep riding through every era.

And if there’s one thing Swifties have learned over the past two decades, it’s never to assume we’ve reached the end of the story.

After all, there’s always another Easter egg to find.

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