Sess’ restaurant, which was located at 1639 Division Street in Old West Baltimore, was arguably the top Black restaurant of the Jim Crow era. This image was from an ad in the AFRO (circa 1945). According to historian Philip Merrill, “They kept an ad in the Afro and the commercial image of their restaurant was captured by black photographer, E Victor Wright Studio of Old West Baltimore.” (Courtesy Nanny Jack & Company)

By Sean Yoes
AFRO Senior Reporter

Black Baltimore has experienced a particularly virulent version of segregation that continues to resonate and in some ways, devastate to this day.

When Baltimore Mayor Barry Mahool instituted the city’s housing segregation ordinances on May 15, 1911, “…for preserving peace, preventing conflict and ill feeling between the White and Colored races in Baltimore City, and promoting the general welfare of the city by providing, so far as practicable, for the use of separate blocks by White and Colored people for residences, churches and schools.”

It was the first segregation ordinance in the nation and with it came the obvious indignities of second class citizenship and systemic White supremacy that are the hallmarks of Jim Crow. Yet, in hindsight so many now see racial segregation as the “gift and the curse” for Black America of the 20th century becaused it compelled our communities  to build and strengthen our own businesses and institutions. And the Black community of Old West Baltimore was one of the most thriving in the United States during the Jim Crow era.

In many ways the heart of Old West Baltimore was that community’s glittering, world-renowned gem of culture and entertainment Pennsylvania Avenue. For many, the way to the heart is through the stomach, and Pennsylvania Avenue, and many of the adjacent streets nearby were home to some of the best Black restaurants in the DMV region.

For most, the top Black restaurant in Baltimore during the time of Jim Crow was Sess’, located at 1639 Division Street, between Druid Hill and Pennsylvania avenues. Its close proximity to the Avenue’s world-renowned entertainment “chitlin circuit” made it a natural go to for some of the most dynamic artists of the era, including Baltimore’s Billie Holiday, Dinah Washington, Redd Foxx, Billy Eckstine, Sarah Vaughan, Pearl Bailey and a phalanx of other Black entertainment icons.

According to Philip Merrill, the owner of Nanny Jack & Co., who is one of the foremost historians on Old Black Baltimore, the restaurant was owned by William Sessoms and his family, who opened it in the early 1940’s.

“The restaurant was a major hotspot for entertainers from the Royal Theater, Negro politicians could be seen dining, as well as students and staff from Carver, Dunbar and Douglass high schools, just to name a few,” Merrill said in his blog, “Old West Baltimore.” “The Sessoms family also lived in Old West Baltimore at 1919 Division Street, within walking distance of their business.”

Perhaps the most enduring Black restaurant from the time of legally enforced segregation was Sampson’s, which was located at 944 W. Fayette Street. It was opened in the 1950’s by J.A. Duke Martin, the owner and operator, and lasted more than five decades when it closed in 2006. The building was ultimately demolished in 2007, allegedly to make way for the University of Maryland Biopark expansion.

But, in its heyday, Sampson’s served up scrumptious, authentic soul food like, smothered pork chops, chitterlings (chitlins’), collard greens, hog maws and other down home classics. The restaurant was also famous for having a bakery and customers could watch the eatery’s bread and rolls being made.

In her book, African-American Entertainment in Baltimore, Rosa Pryor-Trusty, who for decades wrote the “Rambling Rose” arts and culture column for the AFRO, shouts out several Avenue nightclubs. Two of those clubs/restaurants stood out particularly for their delicious food.

The Alhambra, located at 1520 Pennsylvania Ave. and Vilma’s Restaurant and Tavern, located at 2242 Pennsylvania Ave., both were known for serving up fantastic seafood. And specifically, both the Alhambra and Vilma’s were famous for their outstanding crab cakes. 

Many remember two soul food independent chain restaurants in Baltimore: the Soul Shack and Leon’s Pig Pen.

There were two Soul Shack restaurants that featured classic soul food fare like fried chicken, collard greens, cornbread and potato salad. One was located at 228 N. Monroe Street and the other was inside the legendary Lexington Market. Both were operated by Kenneth Bryant and Glendora Cox.

Leon’s Pig Pen at its pinnacle of popularity had six locations (two of the most popular were on Greenmount Ave. on the eastside and Liberty Heights Ave. on the westside) around the city in the 1970’s. Not surprisingly the main attraction at Leon’s Pig Pen, owned by Leon Speight was barbeque pork and beef ribs, which were known to be some of the best on the East Coast. And the Pig Pen was popular with Baltimore residents from the loftiest corridors of power to the projects.

Perhaps the last soul food survivor connected to the golden era of Black owned restaurants in Baltimore is the iconic Five Mile House.

“The Five” as it is known to its legions of devotees over the decades is a nightclub/restaurant located (and still operating) at 5302 Reisterstown Road in Northwest Baltimore.

Westley B. Johnson, who was one of Baltimore’s most prominent and enigmatic Black businessmen opened the Five Mile House in 1973, and ran it until his retirement in 1999. Countless power lunches, business deals, dubious agreements and clandestine rendezvous took place at the Five over the decades. The menu was pretty simple (fried chicken, fish, shrimp, collard greens, etc.), but under Johnson’s ownership the food was always delicious.  The galaxy of Black politicians, lawyers, judges and businessmen who frequented the Five Mile House always paid homage to Johnson, who was a former Baltimore police officer.

“Westley taught us how to do business,” said Dan Henson, one of those legendary political figures who was the commissioner of Baltimore’s Department of Housing and Community Development under Mayor Kurt Schmoke. “He never talked much, we learned by example. Every night he made his customers feel like guests in his home. He tracked every penny the tavern took in and every business expense he paid.”

The history of the Five Mile House is the stuff of legend, arguably the last gem of Old Black Baltimore’s glorious legacy of restaurants and nightclubs.


Sean Yoes

AFRO Baltimore Editor