
Chocolate City hasn’t been majority “chocolate” in over a decade. Yet, despite the unique challenges Black business owners face, there are so many flourishing Black-owned businesses and relics of D.C.’s history that you can completely immerse yourself in the rich past and present of the Black community in D.C.
In honor of Black History Month, we built a full day’s agenda to help you sample some of D.C.’s Black-owned businesses. Mix and match restaurants and activities to keep this going for many more days.
8 a.m.: You have to wake up early if you’re going to squeeze everything in. Grab breakfast at either Butter Me Up (1409 T St. NW) or Roaming Rooster (Multiple locations).
Butter Me Up, owned by founder and CEO André McCain, is an all-day brunch cafe that sources ingredients from other local businesses.
Roaming Rooster, owned by a local Ethiopian family, including brothers Michael and Biniyam Habtemariam, went viral in 2019. Back when local Popeyes were running out of their newly launched chicken sandwiches, a loyal customer suggested people check out Roaming Rooster instead — and the rest is history. They’re now up to more than 10 locations in D.C., Maryland and Virginia.
10 a.m.: After breakfast, get a little physical. You could choose something high energy, like a music-based boxing class at Boombox Boxing Club DC (1221 Van St. SE), or something stimulating but laid back, such as playing indoor simulated golf at CitySwing (901 New York Ave. NW).
Boombox co-owners Reggie Smith and Angela Jennings originally met on Tinder. While there were no romantic sparks, the two finance professionals became fast friends. In 2019, they founded Boombox from their mutual love for boxing, music, and community. Boombox offers group fitness classes and one-on-one personal training.
CitySwing’s founder, Tari Cash, noticed the outsized role of golf in corporate settings, and she set her mind to learning the game to keep up with her male colleagues. The approachable and accessible simulated method enables anyone to learn and practice golf. CitySwing offers private rooms for free-play and one-on-one lessons.

1 p.m.: By now, you’ve certainly worked up an appetite. Venture to Spicy Water African Grill off the U Street Corridor (2019 11th St. NW), MLK Deli in the Congress Heights neighborhood (3113 Martin Luther King Jr Ave. SE), Maker’s Union (664 Maine Ave. SW) at the Wharf, or Negril in Shaw, near Howard University (2301 Georgia Ave. NW).
Spicy Water African Grill features West African-style grilled chicken, shrimp, and beef served with sides such as attiéké, jollof, and fried plantains. MLK Deli serves familiar casual foods like sandwiches, salads, and wings — one go-to is the crab cake sandwich, which come in two sizes. You can of course grab some mambo sauce to go along with anything.
Negril has been a stronghold in the Shaw community for decades. Named after the town on Jamaica’s western coast, the restaurant sells Caribbean dishes and beef patties.
Maker’s Union is a property of Thompson Hospitality, led by CEO Warren Thompson and the largest minority-owned food and facilities management company in the country. While best known for carrying local brews on tap they have a broad array of pub food and other dishes as well.
3 p.m.: The day is hardly over! Spend the rest of the afternoon on a self-guided African American Heritage Tour. There are 15 African American Heritage Trail routes across the city, each with five or more sights essential to understanding D.C.’s role in Black history. To begin, pick a neighborhood from the guide and make your way to the designated starting point. The online guide explains the significance of each stop.
Or if museums are more your speed, you could visit the Smithsonian’s National Museum of African American History and Culture with a free, timed-entry pass. With four massive floors of exhibits that tell the story of the first enslaved people to land in what is now Virginia and expansive exhibits about modern Black culture, there is a lot of information and plenty of reasons to go back.
While on the National Mall, you might join one of the special tours or discussions the National Park Service offers on a variety of Black history-related topics throughout the month. Meet at the bookstore of the Martin Luther King Jr. Memorial on Feb. 29, for example, where a park ranger will lead a discussion on Ella Baker, an activist and organizer who became Dr. King’s executive secretary.

6 p.m.: For the final meal of the day, pop into Cane (403 H St. NE) or its sister restaurant, St. James Modern Caribbean (2017 14th St. NW). Both establishments owned by Jeanine Prime pay homage to her Trinidadian background. Cane features street foods such as jasmine rice bowls paired with oxtail or curried chicken. St. James serves dishes such as beef rib and whole fried snapper.
You could also grab dinner downtown at newcomer Kitchen + Kocktails (1300 I St. NW). The brand, launched and operated by the titular Kevin Kelley, has other locations in Dallas and Chicago. The lively restaurant, bathed in sleek black decor, serves Instagram-worthy dishes like an eight-piece bucket of fried chicken served with a bottle of Moët champagne.
9 p.m.: As this jam-packed, Black culture-focused day comes to an end, you may want to reflect on all you’ve learned and experienced. Or just enjoy the company of your valentine, friends, or loved ones. Head to Hill Prince bar (1337 H St. NE) for a nightcap.
James Beard nominee and Hell’s Kitchen winner Rock Harper — best known for slinging duck-fat-fried chicken sandwiches at Queen Mother’s Kitchen — bought Hill Prince in 2023. The cocktail bar, located in a historic row home along the H Street corridor, boasts a dim, moody atmosphere and is the perfect setting for a chill night.