On an unassuming Sunday morning, my friends and I decided to take on a challenge that, until recently, I hadn’t even known existed: the “tip-to-tip” walk of Manhattan. It’s exactly what it sounds like: a journey by foot from the very northern tip of the island to the southernmost point. I learned about the trend through my friends (with some encouragement), and later discovered its pop culture roots in an episode of Broad City, which helped turn this urban pilgrimage into a rite of passage for adventurous New Yorkers.

Don’t get me wrong, I love walking. But 30 kilometers in one day? That sounded excessive, especially for someone like me who avoids running unless absolutely necessary. Still, something about this felt different. Maybe it was the promise of discovery, of tracing the pulse of a city that lives and breathes on its streets. Maybe it was the snacks. Either way, I laced up my sneakers and met my friends at 8 a.m., ready to begin our journey.

There’s no single “right” way to do the tip-to-tip. Some people power through in athletic gear, others turn it into a leisurely, indulgent stroll with coffee breaks, museum visits, and food stops mapped out like sacred rites. We went with the latter. Our strategy: blend culture, carbs, and curiosity. Armed with a Google Map pinned with must-see spots, from TikTok-famous cafes to hidden historical gems, we hit the pavement headed to the Inwood station.

Our Strava route

Here is how our tip-to-tip adventure unfolded

STOP 1: BUUNNI COFFEE

We kicked off with caffeine at Buunni Coffee, a small Ethiopian café known for its ethically sourced beans and vibrant community spirit around 207th street. The beans here are directly imported from Ethiopia, and every cup tastes like it has a story to tell. The space doubles as a platform for cultural events and workshops, grounding it as a true neighborhood anchor. It was the perfect place to start; a quiet hum of music, the smell of freshly ground coffee, and the feeling that the city was just waking up with us.

STOP 2: JAY’S COFFEE

Tucked into a sleepy corner of uptown Manhattan, Jay’s Coffee might not scream “destination,” but trust us, this should be your second spot. Their breakfast burrito is a revelation. Wrapped in a warm tortilla and bursting with flavor, it was hearty enough to power us through the morning leg of the walk. We split one burrito and continued walking.

STOP 3: THE MET CLOISTERS

Next, was the Met Cloisters. Nestled in Fort Tryon Park, the Cloisters Museum is part of The Met but feels like a secret medieval castle hidden in plain sight. Built in the 1930s to resemble a European monastery, it houses art and artifacts from the Romanesque and Gothic periods. We wandered among tapestries, sculptures, and arched stone corridors, and took a quiet break on the terrace overlooking the Hudson River.

The Met Cloisters

STOP 4: CARROT TOP PASTRIES

Fueled by caffeine and eager for a sweet bite, we made our way toward our next stop in Washington Heights. A neighborhood favorite for decades, Carrot Top Pastries is unassuming but legendary. Their carrot cake lives up to the hype: moist, subtly spiced, and not overly sweet. We ordered a slice to share but seriously considered going back for seconds.

STOP 5: LEXINGTON CANDY SHOP

After savoring our carrot cake, we continued downtown, aiming for a nostalgic treat at one of New York’s oldest soda fountains. A bittersweet detour, Lexington Candy Shop was closed when we were heading there. Founded in 1925, it’s one of the last remaining luncheonettes of its kind in New York, with Coca-Cola floats and egg creams served the old-fashioned way. It was a bit of a letdown, but honestly, between the carrot cake and the breakfast burrito earlier, we were already pretty full, maybe skipping another food stop wasn’t the worst thing. Laughing it off, we tightened our laces and headed south, weaving through quieter upper west side streets that felt like their own small-town universe.

STOP 6: MORRIS-JUMEL MANSION

Next, we made our way into a completely different kind of history. Known as Manhattan’s oldest house, the Morris-Jumel Mansion was built in 1765 by British military officer Roger Morris and later became home to the prominent Jumel family in the 19th century. It once hosted figures like George Washington and stands today as a striking example of Federal-style architecture, a rare window into upper Manhattan’s colonial past. On your way there, don’t miss Sylvan Terrace: a cobblestone block lined with restored wooden townhouses that once served as the mansion’s carriage drive. This spot was unique, it felt like stepping back in time.

The Morris-Jumel Mansion & Sylvan Terrace

STOP 7: APOLLO THEATRE

With the morning behind us and music on our minds, we headed toward one of Harlem’s most legendary landmarks. The iconic Apollo Theater needs no introduction, yet it deserves one. A cornerstone of African-American culture, the Apollo has played a vital role in shaping American music and launching the careers of countless Black artists. It rose to prominence during the Harlem Renaissance and has since become a legendary stage. Today, it remains the largest performing arts institution dedicated to Black culture and creativity. One of its most beloved traditions is Amateur Night, held every Wednesday, where emerging talents take the stage to compete for a grand prize of up to $20,000. Standing under its glowing marquee gave us goosebumps—it’s more than a theater; it’s a living archive of Black excellence and cultural history.

Apollo Theatre

STOP 8: LUNCH IN HARLEM

After soaking up the history and energy of the Apollo, our stomachs started rumbling, so we set off in search of some of Harlem’s most famous eats. We had high hopes for lunch at Red Rooster, known for its soulful comfort food and live gospel brunch, and Amy Ruth’s, a staple for fried chicken and waffles. Unfortunately, both were packed. Pro tip: make a reservation if you’re doing this walk on a weekend. We ended up at The Fox, a local spot with decent fare but not quite the culinary climax we’d hoped for.

STOP 9: COLUMBIA UNIVERSITY + CENTRAL PARK

Happily full (or at least satisfied), we wandered north again to explore the intellectual and natural beauty of Manhattan. Strolling through Columbia University’s stately campus offered a moment of quiet grandeur before we dipped into Central Park. By then, the cherry blossoms were in full bloom. The winding paths and fresh air gave our legs a second wind and reminded us why this patch of green in the middle of the chaos is such a treasure.

Central Park

STOP 10: TIMES SQUARE + MARTGARITAVILLE

Yes, it’s chaotic. Yes, it’s touristy. But there’s something electrifying about Times Square, especially after hours of walking. The lights, the noise, the people watching… I love it in an unapologetic way. It captures the surreal energy that only New York can offer. So naturally, I could not miss passing by it. There we stopped by Margaritaville, known for its delicious margaritas, a little sweet, a little kitschy, but a very welcome refresher.

Margarita break at Margaritaville

STOP 11: MAMA’S TOO!

After weaving through the heart of Midtown, we found ourselves craving one last indulgent bite before reaching the finish line. If you’re still standing by this point, reward yourself with a slice from Mama’s Too! in West Village, arguably one of the best pizzerias in the city. The house pizza slice and the Cacio e pepe square are famous, but the Philly cheesesteak sandwich might’ve stolen the show for us.

Mama’s Too! pizza

STOP 12: BATTERY PARK

With full bellies and tired legs, we pushed through the final stretch, winding our way downtown toward the very tip of Manhattan.

Finally, Battery Park. We made it. 30 kilometers, over 50,000 steps, 10 hours of walking, a dozen stops, and more memories than I can count. As we sat there, looking out at the Statue of Liberty, feet aching but spirits soaring, I realized something: you don’t just walk Manhattan, you feel it.

And honestly, I can’t wait to do it all over again.

Anddd we’re done!