That’s Entertainment: Dinner for Dozens

Tips for organizing a meaningful, stress-free group gathering

A transformed barn is an ideal venue. Photography by Rob Rich
A transformed barn is an ideal venue. Photography by Rob Rich

What do you do when the guest list grows beyond the confines of your home? The answer is to think outside the box—or, as was the case for this simple but heartfelt dinner for 50, inside the barn. Indeed, sometimes the most unlikely settings can inspire the most delightful gatherings, without breaking the bank. 

While many shudder at the idea of hosting hoards for dinner, there are times when it’s required; think rehearsal dinners or milestone birthdays and anniversaries. But there are also folks blessed with so many friends who all know each other that entertaining everyone in one fell swoop is a total joy. In the iconic film The Wizard of Oz, the Tin Man is told: “A heart is not judged by how much you love, but by how much you are loved by others.” For those who are loved by lots, a big gathering can be a wonderful way to return all that affection.

Takeaway market corn puddings served in the host’s own white ceramic lasagna pans. Photo by Rob Rich
Takeaway market corn puddings served in the host’s own white ceramic lasagna pans.

For this late-summer dinner, the venue was a soaring barn on the grounds of the Southampton History Museum, on the east end of Long Island. Little had to be done in the way of decor beyond going with the flow: rented country-casual blue gingham tablecloths and matching napkins, plus candlelit lanterns brought from home. 

Prosecco pours welcome guests, photo by Rob Rich
Prosecco pours welcome guests

The florals were inexpensive pots of seasonal flowers purchased that morning from a local supermarket. Any big-box building supply store with a garden center would offer the same selection. The key is to think local. If you’re doing this in South Florida, chrysanthemums would look silly, but bougainvillea, hibiscus, or orchids would be lovely, and they can go home with you afterwards. Don’t have access to a barn? Maybe it’s a tiki hut, slat house, or party tent (the most trusted inclement-weather insurance policy).  

The menu for this dinner could not have been easier or better received. It began with pigs in blankets with mustard (a surefire crowd-pleaser), followed by a buffet of crispy fried chicken, St. Louis–style barbecue ribs, hearty corn pudding, and grilled seasonal vegetables. In lieu of a caterer, I ordered takeaway from a market in advance. The chicken and ribs came in foil containers for easy reheating and transferral into my serving pieces. A few days before the dinner, I brought my own white ceramic lasagna pans to the market for the corn puddings. 

Guests enjoyed Prosecco, cocktails, and a buffet of fried chicken, St. Louis–style barbecue ribs, and grilled seasonal vegetables, plus an array of mini desserts presented in lovely étagères. Photo by Rob Rich
Guests enjoyed Prosecco, cocktails, and a buffet of fried chicken, St. Louis–style barbecue ribs, and grilled seasonal vegetables, plus an array of mini desserts presented in lovely étagères.

The desserts came from a much-loved local bakery famous for its lemon squares, raspberry crumble bars, and blondies, all cut into bite-size pieces and served on tiered étagères procured from the same party rental company that provided the tables, chairs, linens, dinnerware, flatware, and glassware. If rentals are budget busters, there are plenty of stylish disposables on the market—chic plastic stemless wine glasses and bamboo plates and flatware are all available online. However, I draw the line at paper dinner napkins. Buy a bunch of inexpensive cloth ones instead. You’ll use them again. 

a buffet of fried chicken, photo by Rob RichPhoto by Rob Rich

The key to pulling this whole shebang off can be summed up in one word: staffing. I was fortunate enough to have been made aware of a crackerjack team of local guys and gals who handled the setup, tended the bar, warmed and plated the food in an adjacent kitchen, circulated throughout the evening pouring wine and clearing glasses and plates, and, best of all, cleaned the whole thing up, returning the venue in better shape than before. If there’s one aspect of entertaining where one should never skimp, it’s staffing. The last thing a host wants is to be left with an unwieldy mess after the last guest has departed, or worse, having to fill in as an extra bartender or busboy. It’s a lot more meaningful to mingle with your guests in a relaxed, gracious manner. 

Since most of us haven’t gathered in groups for what feels like an eternity, now that things are (hopefully) looking up, don’t be shy. Hosting a big shindig doesn’t have to be expensive or backbreaking. Just keep it simple, serve generous amounts of food and drink that you love, have lots of help, and enjoy the experience.

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