At Virginia’s iconic steeplechase meets, tailgating isn’t just about parking the car, setting up a few folding chairs and breaking out the cooler to watch the races—it’s a full-blown, competitive race in itself. Tailgate competitions are where racegoers’ creativity, culinary skills and camaraderie shine for both their guests and judges. If you’re aiming to take home the coveted prize for best tailgate this fall, here are some tips to help you stand out from the crowd, create a memorable experience for your guests and most importantly, have fun while doing it.
“For me, it’s a great way to introduce friends to horse sports,” said Aliana Shepard, a teacher from Alexandria, Virginia, whose group of tailgating friends won last year’s competition at the International Gold Cup steeplechase meet at Great Meadow in The Plains. For Shepard, pulling together a prize-winning tailgate is a fun project for friends to share, and she approaches each event with the same enthusiasm and meticulous planning she brings to her classroom.
“There’s a group of us that get together for brunch regularly, and I’d say that’s kind of the core group of my tailgate team,” she explained. “I come up with a list of ideas, and we brainstorm together.”
The group then divides the tasks, with each person contributing according to their strengths—whether that’s crafting decorations, preparing food, or setting up on the day of the event. There’s a way for everyone to contribute, Shepard noted. “Some of the folks I know come on the day of the tailgate—they’re not crafty at all, but they’re tall or they can carry heavy things, so they get that job,” she said.
While Shepard and her team have mastered the art of tailgate organization, judges like Kelly Knight of Rappahannock Cellars in Huntly, Virginia, which sponsors the International Gold Cup meet’s tailgate contest this year, have the final say in what makes a tailgate truly prizeworthy. For Knight, who will be judging her third steeplechase tailgate this year, a great tailgate is as much about the atmosphere as it is about the food and decor.
“The tailgates that we spend the most amount of time at are the ones where all the guests want us to stay, want to talk, want to show us every little detail,” she said. “Tailgating is an experience. It’s not just about the food and drink.”
1. Set Your Scene with a Standout Theme
One of the keys to a winning tailgate, Knight and Shepard agreed, is establishing a cohesive theme that ties everything together. Go for something unique, Shepard advises.
The theme should permeate every aspect of your tailgate, from color scheme to decorations to food and drink. “For our winning tailgate last fall, our theme was Glamour & Magic,” Shepard said. “I like Halloween-y things anyway, so I was able to decorate with sparkly skulls and things off my mantelpiece.”
Knight recalled one tailgate where the guests dressed to suit the theme’s peach color scheme and another where the hostess styled everything around hats.
“She took hats from around the world and from different eras and paired each with a geographically and historically accurate dish,” Knight said. “Every hat was unique. Every dish was unique. She even had custom cocktails that each represented a hat.”
2. Dazzle with Décor
Don’t underestimate the power of a well-decorated tent. You can go ultra; Knight remembered a knockout tailgate hosted by an interior designer who hung a chandelier inside the tent for her party. But Shepard swears by the magic of DIY decor. Once her group decided on the Glamour & Magic them, she said, “I spent a fair amount of time at thrift stores looking for all of the silver platters and silver serving utensils that we used.”
One key, Shepard said, is to add authenticity by bringing in real elements like thrift-store finds or pieces from home. For one herb garden-themed spring tailgate, Shepard’s group labeled their buffet foods using actual garden stakes. “The worst-case scenario for me is if someone were to step in my tent and say, ‘Oh, I saw all of this at the party store,’” she said.
3. Make the Most of Your Menu
Make sure the food is pretty to look at and good to eat, of course, but keep it on theme, too.
“For example, we had a salad, so we cut the mushrooms to look like skulls. That’s a lot easier than it sounds—you just kind of dig out two little eye holes in the mushroom,” Shepard said of her winning Glamour & Magic tailgate, which also featured black squid ink flatbread with a variety of toppings; chocolate skulls with walnut halves for “brains” inside; and apple pie with witchy symbols in the pastry.
Consider dishes that can be prepped ahead of time and don’t require reheating. “We don’t do anything that requires heat or Sterno,” said Shepard—and heating devices or open flames can also violate an event’s tailgating rules, so be sure to check as you plan.
4. Signature Sips
No tailgate is complete without a signature drink (or two). But here’s a twist: offer both alcoholic and non-alcoholic options. “We tend to do one or two of the batch drinks as non-alcoholic and then leave bottles of liquor next to them,” Shepard explained. “Different people will make different combinations, and that becomes kind of a conversation piece, as well.”
For added flair, consider naming your drinks to match your theme, like Shepard’s “Poison Apple” (apple juice and ginger ale with cinnamon sticks and cloves). “If you make a batch drink and give it a fancy name, it presents very nicely,” Shepard said.
Knight noted that a little sparkling wine (she recommends Rappahannock Cellars’ Charmat Blanc de Blanc paired with a charcuterie board) also can add a little celebratory zip to any tailgate.
5. Be Weather-Ready
Steeplechases are often held rain or shine, so be prepared for whatever Mother Nature throws your way. Shepard prioritizes keeping food under a tent, whatever the weather. Bring tablecloths long enough to hide cool, dry storage space under tables. “We might have a big batch of pasta salads sitting in a cooler underneath the table, and then just plate it and serve it during the day,” she said.
6. Bring the Party
Knight’s advice? “Go all out, create an experience, and have fun, because it really is a fun day.”
A light-hearted sense of camaraderie and fun isn’t just good for you; it can make your tailgate a winner. Knight recalled judging one fancy tailgate that won her heart primarily because of its volunteers’ and guests’ enthusiasm.
“I loved that the first person to greet us as we walked in was the bartender, who said, ‘Ladies, can I get you a custom cocktail? Let me show you our signature drink,’” she said. “I mean, every single person in that tent was involved in that tailgate.”
For Shepard and her friends, that fun lasts a couple of months, from initial planning through the day at the races.
“The biggest tip I have is to make it fun,” said Shepard. “For our Glamour & Magic tailgate, we did a bubbling cauldron where we were hot-gluing glass ornaments coming out of a cauldron like bubbles and making little touches like that about a month or two before the actual tailgate. It’s not all a work that week or all on one person, and that's all part of what makes it fun.”
“Tailgating is an experience. It’s not just about the food and drink.”
The first step: Create a unique, cohesive theme.