This cocktail takes the Daiquiri’s triumvirate of rum, lime and sugar and adds elements from several sours (including the Sophisticate, which was a major influence on this spec) in the Sloppy Joe’s bar manuals from the ‘30s: crème de cacao, vermouth, and egg white. I absolutely love the way this drink turned out, and it’s extra versatile because there are two garnish options: the perennial bitters design or cold weather-friendly dusting of cocoa powder.

The Mary Pickford appears in the Sloppy Joe’s books–a mix of rum, grenadine, pineapple, and maraschino liqueur. I took that inspiration, subbed crème de cacao in for the maraschino, added lime for acid, and a small measure of Cognac for vanilla and dried fruit notes. Pickford was a movie star, director and producer; I named this after her little sister, Charlotte, who was also an actor.

This is a little-known Mojito riff dating from the early 1930s at Sloppy Joe’s. It has everything you’d expect from a Mojito–rum, lime, sugar, mint, and soda–but adds a little bit of “French vermouth,” which I interpret here as blanc (or bianco if it’s an Italian producer). This small change adds a slightly floral note and bolsters the lime’s acidity. I like the channel-knife lime peel garnish here along with a big bouquet of mint, of course.

As you know, my historically-driven palate favors the spirits that were popular in 19th-century juleps, i.e. rye, Cognac, and rum. For my own julep recipe, I wanted to combine these three in equal parts with a favorite amaro (Braulio or dell’erborista are particularly good here, but there are many that would work!). I also decided to make the garnish do a little aromatic work, hence the nutmeg and shaved coffee bean, which hit the nose along with the mint upon first sip. The sherry float also contributes a nice aroma if desired!

This is probably the drink that first comes to mind when you think of juleps (unless your brain is stuck in the 19th century like me)! The bourbon-based julep is the one that has survived into the modern age, thanks in no small part to its connection with the Kentucky Derby. For this recipe, I wanted it to be exceedingly elemental. Since we’ve combined the sugar and mint in our mint syrup already, this julep requires but two ingredients (plus a big bouquet of mint, of course). It is simplicity at its finest!

This recipe, based on one from the 1850s, gives a window into what pre-Civil War juleps looked like after ice had established itself as an essential part of the drink. The mixture of Cognac and rye and the slight presence of Jamaican rum illustrate the julep’s former life as a rum drink and the preference for a brandy base during this period while also foreshadowing the rise of rye juleps that would come after the Civil War (see Dabney Julep from our Pre-Civil War Black Tavern-keepers theme). NB: crushed ice is preferred over pebble here.

What’s a julep before it becomes an iced drink? Why, a Mint Sling, of course! During the eighteenth century the eastern seaboard was awash with minty, rum-based slings that also traveled under the name julep. Because we are used to chilled beverages (especially with juleps on the mind), I decided to give this tavern drink the batch-n-freeze treatment; the result is a very pleasing pour that tastes like an aged rum mojito sans ice and soda.

Sometimes called Black Stripe, this drink is a toddy-like mixture of rum, molasses, and hot or cold water that comes from the same seafaring roots at Calibogus (and, indeed, early versions at sea contained spruce ale). Blackstrap was one of the most popular tavern drinks of the late eighteenth through mid-nineteenth centuries in rural New England. Our version uses nineteenth-century techniques to revive this forgotten Rum Old-Fashioned ancestor.

This drink is another that was emblematic of American culture in the days of the early Republic but has since been forgotten. Popular in winter, as they were traditionally served hot, Apple Toddy recipes, including the one in Jerry Thomas’s 1862 book, typically call for mixing apple brandy with hot water and baked apple, and topped with nutmeg. Our version is a little more complex, with notes of cranberry, vanilla, spices, and ginger.

The Halekulani–a whiskey-based sour with lemon, orange, pineapple, demerara sugar, grenadine, and bitters–has always intrigued me. Another non-rum tropical drink from Hawaiian hotel history, this one originated at the House Without a Key Lounge at Waikiki’s Halekulani Hotel. I decided to turn this into a stirred, spirit-forward drink–the result is a tropical Improved Cocktail with a nod to all of the original elements, plus our banana mix and a touch of absinthe.

I have a deep appreciation for eggnog (and its cousin, Tom & Jerry). Because of my fondness for the holiday classic, I’ve developed several recipe for eggnog over the years, both large-format and single serve. This one combines two of my favorite versions–one with rum, rye, and Cognac and one with sherry and Madeira–and streamlines it into a single-serving variation that has a classic flavor profile with a dried fruit note.

Milk Punch–the kind we now differentiate as “clarified”–goes back to at least the early eighteenth century. It’s made by curdling warm milk in a punch mixture then straining it and, thanks to the magic of science, the milk solids make the mixture clear (hence the term “clarified”). Ours has aged rum, Madeira, lime, green tea, sugar, spices, and, well, milk.

Hot Buttered Rum is a drink that has, blessedly, survived into the twenty-first century thanks in large part to its popularity around the holidays. At its most elemental, it’s just rum, sugar, spices, butter, and hot water. I didn’t want to make this variation too overly complicated, but the walnut liqueur, as well as the pumpkin and miso flavors in the syrup, amp up all the best parts of this simple classic while giving it a bit more dimension.

The Stone Fence is a much-mythologized olde Yankee drink consisting of aged rum and hard cider. Supposedly Ethan Allen and the Green Mountain Boys drank a ton of Stone Fences before storming Ticonderoga. In this simple mix of ingredients, I saw the opportunity to play with a bit of anachronism and apply a nineteenth-century template (the Collins) to this eighteenth-century classic.

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.

The Improved Cocktail was a more complex take on the original formula of spirit, sugar, bitters, and water that first appeared in print in the appendix of Jerry Thomas’s 1876 edition. In 2021, I spent a lot of time with this genre and I produced a template from which I derived recipes for rye, genever, and Spanish brandy iterations. I was pleased to have the opportunity to design one with an aged rum base for this month’s theme.

Smashes were all the rage from the 1830s through the Civil War period. In July 2021, we delved into its history and the (s)mash-up of nineteenth- and twentieth-century styles that produced the modern Smash. This one features my signature presentation and is laced with amaro and fortified wine, just like my on my Derby Smash (bourbon, rabarbaro, blanc vermouth, honey, mint). The “dry orange” bit in the title refers partially to the dry sherry and partially to a soda flavor by Polar, the pride of Worcester, MA.

Tavern culture was deeply tied with ports, in part because some of its most notable drinks were born at sea, but also because so much of taverns’ stock was imported. The combination of rum and brandy was a common one in eighteenth-century punches, and Madeira was a wildly popular imported wine. Our punch is flavored with a plethora of other valuable imports: spices, ginger, lime, and tea.

Bumbo, or “Bombo” is a rum sling sweetened, diluted spirit flavored with spices. Rum was a major force in eighteenth-century life, whether it was imported from the Caribbean (that was the best stuff) or produced locally in New England from molasses, the most famous of which was produced in Medford, Massachusetts. Like the whole toddy-sling family, Bumbo is among the nearest antecedents of the capital-C Cocktail.

The flip began as a sailors’ drink and swiftly infiltrated the taverns of England and “British America.” There, it became a hot drink ー a mixture of ale, spirit, egg, sugar and spices, and sometimes other ingredients. Flips were warmed and frothed by submerging a hot iron poker, called a flip-dog or loggerhead, that had been heated in the tavern hearth. If you’re “at loggerheads” with someone, try offering them a mug of this ー ‘tis hard to stay angry with such a comfort in hand.