All Articles An East Coast road trip through hip-hop history

An East Coast road trip through hip-hop history

From Brooklyn to Virginia Beach, this trip pays respect to the genre.

By Iman MilnerJan 17, 2024 9 minutes read
Exterior of the Apollo Theater at sunset

After nearly three decades as an enthusiastic listener of hip-hop’s most prolific voices, it was time to remind myself why I fell in love with the genre. To properly do so, last year my boyfriend and I set off on a 442-mile celebration of the 50th anniversary of one of music’s most celebrated and diverse genres .

Though hip-hop spans communities and continents, deciding where to start this trip down lyrical memory lane was pretty simple. The Northeast is the birthplace of some of the genre's most well-respected artists and noteworthy landmarks. From rap icons whose verses have become synonymous with the music itself to sound architects who have taken hip-hop everywhere from kitchen tables to outer space, few would argue that rap owes endless thanks to the contributions of those who braved cold winters to paint pictures with prose.

We began our journey in its original stomping ground—the Bronx, NY—made our way through New York City’s boroughs, and continued to Philadelphia and Washington, D.C. before ending our hip-hop hooray in Virginia Beach. Ahead, take a look at each of our stops.

DAY ONE: The Bronx and Manhattan

Total mileage: 18.7 miles

Outside Yankee Stadium in the Bronx, New York
Outside Yankee Stadium in the Bronx, New York
Image: Management/Tripadvisor

MORNING: “Once upon a time not long ago…”

Listen to: “Children’s Story” by Slick Rick

Historians have traced hip-hop’s origins to the one-time home of Clive Campbell—who would go on to be known as DJ Cool Herc—and his sister, Cindy, at 1520 Sedgwick Avenue. The apartment building sits in the Morris Heights neighborhood in the Bronx, and a front door emblazoned with the iconic address is accessible from the main street. I recommend snapping a picture at the entrance after grabbing breakfast at Little Italy’s M&G II, where coffee is free every day before 11 a.m. Classic NYC breakfast fare is the perfect fuel for checking out the George Washington Bridge, considered the busiest in the world and name-dropped by rap acts like Redman and Wiki, for major photo ops (about halfway through the walk, just past the first suspension tower, you’ll get the best view) of the city that started it all.

AFTERNOON: “We be the kings of the Boogie Down”

Listen to: “Bronx Tale” by Fat Joe ft. KRS-One

Though many museums include memorable hip-hop collections, the Bronx Museum of the Arts is a great stop for getting a deeper understanding of NYC’s relationship to the genre. It’s also home to tons of photos that capture different eras of hip-hop.

After, take a seven-minute walk up Grand Concourse to Yankee Stadium. Rappers and rap culture alike have made “the Yankee hat more famous than a Yankee can” and a must-have fashion accessory (you can grab one from the pro shop at the stadium or from any of the sidewalk sellers along 161st).

Pro tip: Grand Concourse is also home to the Bronx Walk of Fame where the likes of Kurtis Blow, Kid Capri, and KRS-One are all honored with markers. End the afternoon with a stop at Bronx native Fat Joe’s sneaker store Up NYC to check out the rapper’s Terror Squad Nike Air Force 1 on display and grab some sneaks for yourself.

EVENING: “But ain’t no place like Harlem, man”

Listen to: “Harlem” by Cam’ron

Head into Manhattan for dinner at the famed Harlem hotspot Amy Ruth’s. For more than two decades, this soul-food restaurant has fed locals and tourists alike—just ask rapper Ludacris, whose regular order of four fried chicken wings with added honey is part of the menu. Just know it’s first come, first served and it gets busy on the weekends. Walk to the iconic Apollo Theater, which became a touchstone of Black music and culture following the 1987 premiere of the series Showtime at the Apollo. It’s here where acts like Wu-Tang Clan, The Fugees, and Naughty By Nature pulled major crowds.

If you're truly committed and have energy to spare, zoom down the length of Manhattan and grab a nightcap in the Lower East Side at Las’ Lap. Owned by actor Michael B. Jordan and open late, this spot is a favorite of the who’s who of hip-hop who are known to pop in for the Caribbean-inspired fare (jerk-chicken eggrolls, vegan patties).

Tip: Don’t forget about the tolls that come with traveling between boroughs. If you don't already have an E-ZPass, bring cash. And know that parking can be tough in NYC—find spots and pay close attention to signs. Opt for longer-hour allowances and drop a pin to remember where your car is in case you decide walk around for a while.

Where to stay

Worthy detours along the way

DAY TWO: Brooklyn

Total mileage: 7.7 miles

Ol’ Dirty Bastard mural in Brooklyn, New York
Ol’ Dirty Bastard mural in Brooklyn, New York
Image: Ferga/Tripadvisor

MORNING: “You never thought hip-hop would take it this far”

Listen to: “Juicy” by Notorious B.I.G

After a late night, start the day in the stomping grounds of Christoper “Notorious B.I.G” Wallace at Black-owned Sisters Brooklyn. The savory French toast is a favorite—just the fuel you’ll want for a perfect day spent in the birthplace of some of rap’s legends. Take a 10-minute walk west on Fulton and come face-to-face with the Biggie Mural that hangs above the Lafayette Avenue C train station.

Next, pay a visit to 226 St. James Place—a common stop on walking tours in the area—to lay eyes on the childhood home where Wallace made the memories he’d later turn into some of the most well-known rhymes in all of hip-hop. End the morning with a quick trip to see the Ol’ Dirty Bastard mural made in honor of the founding member of Wu-Tang Clan.

AFTERNOON: “But nobody in rap did it quite like I did it”

Listen to: “Hovi Baby” by Jay-Z

Few rappers have made a bigger impact on hip-hop than Shawn “Jay-Z” Carter and for that reason, no road trip in honor of the genre is complete without a visit to Bed-Stuy, the Brooklyn neighborhood he called home. The famed musician often waxes poetic about his time growing up in the area, leading fans to clamor to be photographed in front of the Marcy Housing Projects sign as proof of having walked the same block as the 23-time Grammy winner. Pro tip: Take a stroll around the building to see signs bearing the rapper’s lyrics.

For a quick lunch, head over to Sweet Chick’s Bedford Avenue location for one of their contemporary takes on the classic chicken and waffles (the Nashville hot and salted caramel will be on your mind for days). This spot is co-owned by rapper Nas, who grew up in Queens. Then, pop over to Adam Yauch Park, the childhood spot of the Beastie Boys’ founding member.

EVENING: “So, when’d you fall in love with hip hop?”

Listen to: “Love Of My Life (An Ode To Hip Hop)” by Erykah Badu ft. Common

From Adam Yauch, take the 10-minute walk to the Brooklyn Heights Promenade—fans of Brown Sugar will recognize this location—for a perfect view of the classic New York skyline. End the night with a short drive to dinner at Junior’s Restaurant in Downtown Brooklyn and order the cheesecake made famous by Bad Boy Records founder Sean “Diddy” Combs during an episode of MTV’s Making The Band. Sampling this NYC original is a must—the receipt hasn't changed since 1950.

Where to stay

Worthy detours along the way

DAY THREE: Philadelphia

Total mileage: 117 miles

Two people sitting outside of Uncle Bobbie’s Coffee and Books in Philadelphia
Shelves of books at Uncle Bobbie’s Coffee and Books
Uncle Bobbie’s Coffee and Books
Image: Courtesy of Uncle Bobbie's Coffee & Books

MORNING: “Expressway, hair back, weaving through the traffic.”

Listen to: “Let Me Blow Ya Mind” by Eve

Hit the road early to beat the morning rush-hour traffic; you’re in for a 2.5-hour drive to Philly, so fire up that classic rap playlist and settle in. Make your first stop at Happy Restaurant in Germantown for a classic counter breakfast (they’re cash only!) of beautifully fluffy eggs and some top-tier pancakes. Then head over to Uncle Bobbie’s Coffee and Books, which is owned by one of hip-hop culture’s most prolific voices, Marc Lamont Hill. Here, you can pick up books from legendary rappers like Philly’s own Black Thought of The Roots.

AFTERNOON: “Back in Philly, we be out in the park.”

Listen to: “Summertime” by DJ Jazzy Jeff & the Fresh Prince

Hop in the car for a quick drive to the Clemente Park and Playground in Fairmont, where Will Smith delivered his iconic “In West Philadelphia, born and raised…” lyrics for The Fresh Prince of Bel-Air. Then take off to the City Center neighborhood to see a mural dedicated to The Roots created by local artists including Tatyana Fazlalizadeh, whose Stop Telling Women To Smile street art set off a cultural reckoning in 2012. The mural holds special significance due to its location near the Philadelphia High School for Creative and Performing Arts (CAPA) where the founding members of The Roots first met.

EVENING: “Representing Philadelphia, you know what I mean?”

Listen to: “You Got Me (Live)” by The Roots ft. Jill Scott

Major mileage awaits so I recommend making it an early night. Opt for reservations at El Vez (not hip-hop-related but far too good to miss) where the tuna-coconut ceviche is delectable. For those taking the trip with friends, the taco tasting platter is perfect for feeding a crowd. End the evening with a quick stop at the nearby Will Smith mural on Gerard Avenue.

Where to stay

Worthy detours along the way

DAY FOUR: Washington, D.C.

Total mileage: 150 miles

Howard University's Founders Library at sunset
Howard University's Founders Library at sunset
Image: Justin D. Knight/Courtesy of Howard University

MORNING: “D.C. Chillin”

Listen to: “Chillin” by Wale ft. Lady Gaga

When it comes to hip-hop, few cities in the Northeast have been able to create a sound as distinctive as that of rappers and producers in Washington, D.C. Home to artists like Wale, Rico Nasty, and Goldlink, and nicknamed “The Chocolate City,” the nation’s capital is a hotbed of musical creativity.

After a nearly three-hour drive (opt for 1-895S for the longest stretch of the trip), grab fuel at Turning Natural’s Capitol Hill location. The menu is full of smoothies and juices that pay homage to rap legends, from "Green Latifah" to "J-Coal." The “Nipsey Blue” smoothie (blue spirulina with pineapple, guava, and more), aptly named in memory of the late rapper Nipsey Hussle, is pleasant and refreshing.

While in the area, set aside an hour to visit the campus of the historically Black college, Howard University, which has been name-dropped by over 30 MCs. The school’s annual homecoming event has also hosted popular acts like Foxy Brown, Cam’Ron, and 2 Chainz.

AFTERNOON: “King of District of Columbia, can’t come here without a permit”

Listen to: “Crew” by Goldlink ft. Brent Faiyaz, Gucci Mane, and Shy Glizzy

In the spirit of the roots of hip-hop, make a stop at Cool Kids Vinyl. Follow the staircase lined with Air Jordans (the most beloved sneaker in hip-hop culture) to this quaint record store, which is decorated with everything from Tupac Shakur bobbleheads to VHS tapes of Belly and Paid in Full. The selection here isn't vast, but true collectors will find rare gems. Then, drive 15 minutes to the National Portrait Gallery, where a larger-than-life painting of rapper LL Cool J by Kehinde Wiley, who also painted former President Barack Obama’s official portrait (also in the museum) features in an ongoing exhibit about 20th-century Americans.

Tip: If you’re visiting D.C. between February and October, check the schedule to see if can catch D.C. United, the professional men's soccer team that's co-owned by the rapper Yo Gotti.

EVENING: “Capital I’m raising like I’m through punctuating”

Listen to: “Beautiful Bliss” by Wale

Make dinner reservations at Bronze, where Afrofuturism—a central theme of hip-hop acts like Common, Outkast, and Erykah Badu—takes the spotlight. Dine on cuisine richly inspired by the African diaspora paired with a rum-heavy cocktail list. On our visit, “The Night has 1K Eyes,” a brown butter–infused bourbon with chai, was the perfect choice to complement the grilled sea bass.

Wrap up the night with drinks at Never Looked Better, where you can order cocktails inspired by your favorite hip-hop songs. Ever stuck in the ‘90s, my choice was a tequila number inspired by Eve’s “Who’s That Girl,” which happened to be playing when we walked in.

Where to stay

Worthy detours along the way

DAY FIVE: Virginia Beach

Total mileage: 249 miles

Mural in the ViBe Creative District, Virginia Beach
Mural in the ViBe Creative District, Virginia Beach
Image: Courtesy of Visit Virginia Beach

MORNING: “When’s the last time you heard it like this?”

Listen to: “When the Last Time” by Clipse

Virginia may not be the first place many people think of when it comes to hip-hop, but some of the genre’s most incredible producers and musical acts hail from the state. Set off bright and early (I-295 avoids tolls) and head south toward Virginia Beach, then grab breakfast at CLTRE. Vegan Joint—it’s one of N.E.R.D. founding members and legendary hip-hop producer Pharrell Williams’ favorite Virginia Beach spots. Go for the black-bean breakfast biscuit or build your own sweet or savory French toast.

Then, head to Virginia Beach Recording Arts to tour the studio where Timbaland made some of the genre’s most innovative and original sounds. Pro tip: e=Email the space beforehand to request a time slot. The super-friendly staff will let you know when all of the spaces are available to visit; you’ll be able to take a look at soundboards, mixing equipment, and recording areas.

AFTERNOON: “And let ‘em explore the words, something like a tourist”

Listen to: “Can I Have It Like That” by Pharrell Williams

Head back to the car for a short drive to the vibrant ViBe Creative District to take in stunning murals honoring hip-hop heroes like Tupac Shakur. Craving some lunch? Head over to Feather ‘N’ Fin Chicken & Seafood to try Virginia native Pusha T’s favorite meal: a boneless breast combo with cheese, hot sauce, honey, and mayo. With lunch behind you, take a ride to the bookstore at Edgar Cayce’s Association for Research & Enlightenment (another Pharrell fave), and then stop by Neptune Park, where you'll see the statue of the Roman god that inspired the name for The Neptunes.

EVENING: “Where you go, remember me, I’m the best thing in history”

Listen to: “All N My Grill” by Missy Elliott

After a long day, unwind with vegan dining at Desmond’s Island Soul Grill. Here, the menu covers traditional Caribbean cuisine with a hip-hop twist. Don’t miss the “Big Poppa,” a portobello mushroom steak with eggs and jelly, named in honor of the Biggie Smalls classic. Another honorable mention is “ATLiens,” named in honor of the rap group Outkast, which features the creamy coconut grits and battered eggplant.

Where to stay

Worthy detours along the way

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