09/27/2026
HIGHLANDTOWN ALERT!
Found these gems this weekend and had to delve into the history of a restaurant well off enough to gift patrons trinket trays and metal telephone indexes!
(Side note: Jeff was brought home to Foster Avenue as a newborn)
Founded in 1923, Leo F. Winterling and his wife, Mary A. Winterling, opened the establishment initially as the F. & L. Winterling Restaurant (named for their sons).
The restaurant was uniquely built out of two adjoining corner rowhouses in Southeast Baltimore, with a staircase in the dining room leading directly up to the family’s living quarters.
Mary Winterling managed the kitchen and provided the recipes. The restaurant specialized in hearty home-style cooking and was famous for its authentic German dishes—most notably its signature sour beef and potato dumplings—alongside crab cakes and massive homemade pies and desserts.
Heyday and Community Hub: In its mid-century prime, Winterling’s was mentioned in the same breath as legendary Baltimore landmarks like Haussner’s, Marconi’s, and Obrycki’s.
Run later by Leo G. “Skip” Winterling (the founders’ son) and daughter Leah, it became an iconic neighborhood gathering spot. It routinely drew local celebrities, politicians, and sports figures, including legendary sports announcers Chuck Thompson and Charlie Eckman, as well as National Brewing executive Jerry Hoffberger.*
If you’re interested in these bits of Baltimore history, message me and catch them before they migrate to Adamstown. $5 each
*Baltimore Sun reporting
