The Sneaky Public Drinker's Guide To Impromptu Tailgating

Massachusetts has a lot going for it. First and foremost, it's a really fun word to say. We also have a lot of apples here, plus more peaches than you'd think. And I can't say for certain, but I assume we still have unparalleled access to the Funky Bunch.

But alas, there are also significant downsides to life here in Dunkindise. For instance, Aerosmith sucks (as do the vast majority of state residents who are not in Aerosmith); for all our bluster and self-importance, none of us will ever cast a meaningful vote in a national election; and we don't have high-level football tailgating.

The Patriots play 50 miles outside of Boston in a region that is culturally and geographically more akin to Rhode Island than it is to the rest of Massachusetts. This is reasonable, because Rhode Island's the very feistiest of the New English states and therefore perfectly deserving of football proximity. But most Massholes live closer to the capital, so there's no easy way for us to get drunk in the Gillette Stadium parking lot on a Sunday morning.

College football tailgating seems to be where it's really at, and we're even more screwed on that count. Boston College is private and sectarian, which means most locals have no real connection to the school, and the stadium's rich neighbors have enough juice to keep the party small anyway. UMass, the state's only other Division I school, isn't any good at football or event planning (they play home games a mere 90 miles from campus). It's a shame.

So I blame the shoddy local sports culture for my failure to seize the tailgating opportunity presented a couple Sundays back when I coached my wife and her friend Lauren through a 21.1K in East Boston. The event began and ended at Suffolk Downs, a faded and glorious old horse track with far more parking than would be necessary if Secretariat and Jesus were resurrected for a match race—an ideal venue for a man to hunker down in the far lot and gather his thoughts while tailgating his hangover into submission. (Remember, where I come from we're so tailgate-deprived that "drinking in the parking lot of a sporting venue" counts, no matter how bleak the circumstances.)

But I'd been so focused on perfecting my prerace pep talk ("Left, right, left, right …") that I'd neglected to plan for the lonely and thirsty couple hours I had to fill before my team passed back through the parking lot in need of late-race advice ("Left, right, left, right, 100 yards to the beer tent"). We'd taken the subway, so I had no heavy-machinery restrictions on my drinking, but once the runners were off and I finally realized I'd stumbled upon the perfect tailgating situation, I found myself utterly boozeless four hours before liquor stores opened.

I figured I could ingratiate myself into a coterie of Bad Dads who'd done enough rogue Little League drinking to know how to prepare for this sort of situation, but I couldn't find any. So I did the only decent thing: I got a roast beef sandwich at Target at 8:00 a.m. and reminisced about some of the great sneaky public drinking capers I've pulled in the past, and fantasized about even better days to come.

Although I've never known the pleasures of a real tailgate party, I've had many hundred drinks on the street; I accept that you can't throw a genuine tailgate party without higher order entertainments such as food, sports, and $40 parking, but anyone with a cup, some liquor, and a touch of gumption can enjoy all manner of illicit al fresco cocktails.

Those of you living in civilized zones that trust a body with an open container don't need to resort to subterfuge, but for the rest of us poor suckers, I've compiled a list of makeshift cocktails that sail under the false flag of nonalcoholic drinks.

Note: These recipes work best if you have access to a convenience store-style soda fountain, but they can all be made with a canned or bottled substitute if you're desperate enough to take that decidedly less dignified approach.


The Sidewalk

This broken, beautiful homage to the Sidecar has seen me through many a stroll down Massachusetts Avenue on many a fine fall day, and the construction method serves as a model for all similar drinks. Get yourself two nips of discount brandy—something like E & J or Christian Brothers; no need to break out the Henny for this special occasion—and pour one into the bottom of your ice-filled cup. Then fill near to the brim with the closest thing to lemonade, leaving just enough room for a shot of orange soda and your second dose of brandy. I like to use the medium-size cups for this and all other walktails, but that's a matter of personal taste and thrift. (It's tough to pass up the extra 20 ounces nine more cents gets you, but if you go for the superlarge you might want to add more brandy and walk slower.)

Scum Island

Ice, a nip of light rum, fill with fruit punch, top with a nip of dark rum. If you can't get multiple shades of rum, that means you're probably stuck with all light, which works fine here. And a note for all recipes: If your 7-Eleven guy is the one in the universe who gives a shit what goes on at the Big Gulp station, then you can add all the booze once you get safely back outside. Either way, you're going to want to send your straw on a few laps around the cup to get things properly distributed.

Angry Nerds

Mountain Dew and Jagermeister.

Happy Sammy

Cheap whiskey and ginger ale. This was the favorite drink of my dear and departing street pal, Sammy (though he took his without the cup, ice, and ginger ale).

The Perfumed Pirate

Spiced rum and Vanilla Coke are worthless on their own, but they make a pretty effective team.

Surly Grandpa

Root beer and coffee-flavored brandy. Beware low-watt liquor here. You want some of that old-school shit the snowplow drivers dump in their coffee, such as Allen's (60 proof) or Mr. Boston (70 proof).

The Affordable Care

Dr. McGuillicuddy's and Dr. Pepper.

The Bye Week

Set aside one Sunday afternoon this fall to go apple-picking or park-walking or leaf-looking or some other gentle thing to shake the second-hand concussions out of your NFL-addled brain. But don't go it alone; go it with a cup of your favorite coffee drink deluxed-up with a pumpkin or cinnamon liqueur. Kahlua Pumpkin Spice (or a cheaper knockoff) is right for this sort of endeavor. It's a scant 40 proof, but remember, you're on a cleanse.

Sweet Release

Hemlock and green iced tea.

Pleasant Surprise

Gin and regular iced tea.


None of these drinks employ vodka for the simple reason that you can add vodka to any damn thing and it will be good enough but never great, and we're reaching for the stars here. But yeah, go ahead and use vodka anywhere you see fit. I offer only one bit of pedantry for this style of drinking. If you shoot your liquor and then chase it with your filler, you're doing an entirely different thing. A noble thing, perhaps, depending on your circumstances and objectives, but the shoot-and-chase method isn't having a walktail, it's making a drink in your face.


Will Gordon loves life and tolerates dissent. He lives in Cambridge, Mass., and has visited all of the other New England states, including, come to think of it, Vermont. Find him on Twitter@WillGordonAgain.

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Image by Sam Woolley.