Like many of the Black culinarians we’re learning about this month, Thomas Downing was not considered a bartender, but a restaurateur who ran an oyster cellar and catering business. But we know he served drinks at his establishment and, as Cobblers were the order of the day, I opted to create one with Madeira and brandy which were en vogue in New York City during Downing’s heyday.

I love the classic idea of having nuts, chocolate, and dried fruit with coffee and port after dinner. For this recipe, I leaned on the idea of Sangarees and Cobblers, layering flavors over a tannic base and drying the whole thing out with a half-ounce of rye. Pebble ice and a very Victorian garnish make this one quite festive indeed.

I love making all manner of Cobblers during the summer when every month brings a new bounty of fresh fruit. But I’ve always wanted to adapt a Cobbler for peak fall and Madeira is the perfect wine for it. I love looking at old pear and apple varietal names and took the name for this drink from a type of pear that’s still grown in western Massachusetts.

I wanted to demonstrate a fancy application for our Club Pimm’s, and I immediately thought of doing a Pimm’s Cup Royale, i.e. topped with Champagne. I also wanted to integrate some of the traditional fruit and mint that are used in Pimm’s Cups and decided a Cobbler format would be the perfect vehicle. Served over crushed or pebble ice, our Pimm’s Royale is, naturally, garnished with abandon.

My devotion to fortified wine and obsession with 19th-century cocktail aesthetics makes the Cobbler one of my favorite genres. This one combines my love of aperitivo and olde American drinks. Classic Torino-style vermouth, Campari, grapefruit, Sfumato, and strawberry made for a great combination, especially ideal for spring.

In this interpretation of a cobbler, smoky Mezcal and piney gin team up with off-dry blanc vermouth, lime, cucumber, and parsley for a verdant spring cocktail.