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10 Tips for Creating the Perfect Tailgate


A tailgater is, first of all, a movable feast. And the more we understand how this movable feast came about and how it has evolved through the years, the better we can go about creating a perfect tailgater. 

The first movable feast was, of course, the picnic. We ate food off a tablecloth or blanket spread out on the grass, but with no table or chairs and at a distance from where we lived. As French impressionists would portray it in their paintings, the best place to have a picnic was a meadow beside a stream. Once the participants finished eating, as they lazed about, they often stripped off their clothes and went swimming—perfect for the era. 

Courtesy of Winterthur

Courtesy of Winterthur

The automobile and spectator sports changed all that. First, the cars—or, more accurately, the station wagons of the 1930s-50s—gave picnics a new perspective. By having a drop-down tailgate, we were presented suddenly with an elevated table upon which to spread our food and drink. As with other forms of human evolution, while picnickers crawled on the ground, tailgating allowed us to stand up, sit up and roam about. 

Afternoon sporting events gave us a reason to tailgate. We showed up early for the game—as did dozens or hundreds of others—to have an early lunch that sometimes became more important than the game itself. Why bother to go inside the stadium when we could eat, drink and talk out here? 

Moreover, sporting tailgaters gave us a way to show off. Within the restrictions of a grassy parking place, when other people walked by, we could show them we were the cleverest, most sophisticated, most upscale, most original tailgaters on the block—break out the champagne, foie gras and fresh-cut roses. 

But even with this sophistication, there had to be a rustic sensibility. We’d all look embarrassed if our tailgater came to resemble our dining room with the walls and ceiling removed. 

Eventually, tailgaters became competitive. “Twenty years ago, I was on the other side as a participant,” says Jill Abbott, who now heads the tailgate competition for the annual Winterthur Point-to-Point races each spring.

For a reggae-themed outing, Abbott painted red peppers on the side of a black Suburban. “We made shot glasses for our drinks out of cucumbers,” she recalls. “At one competition, someone else had a Gen. [George] Patton party and actually brought an army tank.” 

The Winterthur competition has been scaled down somewhat in the years since. Anyone who purchases one of the 500 or so parking spaces is eligible for a “best presentation” award within their 10-by-20-foot space. 

Keeping this in mind, here are some guidelines for having a perfect tailgater—whether it’s in a competition or not and whether it’s for a steeplechase race, a football game or something else: 

A theme helps keep you organized. Without one, you might drag out everything you own that might look sexy or expensive. Having a theme forces you to focus, plus it gives your invited guests something to anticipate. 

Speaking of which, choose your guests carefully. Anyone you feel you have to invite is someone you probably shouldn’t inviteFind another time for paybacks or fulfilling obligations. Assuming you’re going to have a few couples, you should start with a small group that’s comfortable with each other, adding a couple of new people to freshen things up. If you want, you can give guests food or decorating assignments to make them feel more a part of things. 

Carefully plan the logistics. How are you going to get people and things to the venue? How will you stage decorations, plus food and wine service, once you get there? At what point will you declare victory and go home? Make a detailed list. You may want just one official tailgate vehicle—a vintage car is always good, although a military tank might be overdoing things—and have the others park elsewhere. And you should consider buying two spots (a more difficult task if the event is first come, first serve) if you need extra room. 

When it comes to food, mix the edgy with the tried-and-true. Food for most parties is a combination of signature dishes that friends are familiar with, plus a few first-time dishes that keep guests interested. Try to think Italian cuisine and not French. Italians tend to look for daring combinations of a few ingredients—chunks of Parmigiano Reggiano with radishes, for example, or truffles on polenta cakes—as opposed to ornate French-style sauces and many steps of preparation. Talk to your friends in specialty food shops and see what’s new enough that isn’t yet trendy. 

2016 Winterthur Point to Point RacesKeep the words casual elegance in mind. This isn’t a sit-down dinner, so think finger foods, tapas and passed plates. At the same time, choose elegant serving pieces, cutlery and plates. Everything looks good served with modern silver and novelty cloth napkins. Printed menus with details about the gathering are a good idea as a piece of memorabilia for friends. And, as Abbott notes, it’s something that makes your tailgater more memorable to the judges. 

“People shouldn’t think in terms of having an entrée, as such,” says Dan Butler, of the website is BigChefGuy.com, who often prepares catered baskets for tailgaters. “Skewers are always a good way of serving more-substantial food.” 

While Butler says that cooking on a portable grill is doable for pros, some venues don’t permit cooking (check first), “heat neutral” dishes can be elegant without needing anything other than coolers. 

Have finger foods to share with passersby— but not the whole menu. Think of it as trick-or-treat for grownups, something savory or sweet that you can make by the dozens to pass out to friends (or judges) who stop by—a “wow” factor that will make them remember you in one bite. 

Decorate in planes. Don’t have everything at table-top level, and don’t allow things up front to block the view of items in back. And avoid competing colors. Abbott cautions that nothing should be top-heavy and easily tipped over or blown away if the wind comes up. 

Encourage an active—but not boisterous— ambiance. Your group and your space should exude class and a bon-vivant atmosphere. It shouldn’t look like a frat party. Respect adjacent tailgaters and their spaces. Don’t look too comfortable. Tired-looking people reclining everywhere in chairs makes others wonder why any of your guests even bothered to leave home that day. 

Have the weatherman help you plan. How you dress and prepare should match the forecast, whether hot and sunny, windy, chilly, or drizzling. Colorful matching umbrellas can save you from too much sun or rain. If you want to splurge, team jackets with logos can keep everyone warm. 

Plan a takeaway gift that will keep the event in mind. A clever party favor—especially one theme-related—can help everyone recall what fun your perfect tailgater was. It might be a boxed treat, a book or a desk accessory. The true measure of a great tailgater is how you and your guests remember it.