Pickleball and Poolside Cocktails: Host a Courtside Bash (or Group Vacation!) at The Iconic Greenbrier

If you’ve ever dreamed of a place where preppy tennis fantasies, pickleball perfection, and timeless elegance collide—mint juleps in hand, match points on the court, and a heavy pour of Gatsby-level glamour—welcome...

by Cortnie Fausner

TVR Exclusives | Venue Stories

If Wes Anderson directed a tennis club, it would look a lot like this: pastel-preppy charm meets grand Southern hospitality, set against a backdrop of chandelier-lit ballrooms and candy-striped cabanas. But this cinematic stunner isn’t fiction. It’s the real-life masterpiece of the iconic Dorothy Draper, whose signature flair lives on in every manicured garden and every swoon-worthy corner of the estate. Throw in a tennis legacy dating back to the 1800s, and you’ve got the ultimate stage for a country club party, milestone bash, or group getaway that practically begs you to pack your best whites and channel your inner socialite.

Nestled in the rolling Allegheny Mountains of West Virginia, this sprawling estate has been serving legendary leisure since 1778, and let’s just say, it still knows exactly how to throw a proper racquet (pun very much intended).

Classic, Colorful, and Dripping in Southern Charm

The moment you step into Dorothy Draper’s maximalist dream world, you know you’ve entered a place that’s anything but another beige hotel. Here, cheerful florals explode across the walls, bold stripes playfully dance through every corridor, and grand chandeliers cast a glow over chintz-covered everything.

Every corner of The Greenbrier feels like a living 1950s postcard: vintage, playful, and impossibly chic. Whether you’re enjoying one of the resort’s famous mint juleps at the Lobby Bar beneath the original Gone with the Wind chandelier, lounging by the prettiest pool you’ve ever laid eyes on, or playing an afternoon round of croquet in pastels, it all feels like a scene from a Ralph Lauren campaign come to life.

Photos: Molly Carr Photography

Game, Set, Match: Why The Greenbrier is a Preppy Court-Side Dream

For those who love a well-set court as much as a well-set table, The Greenbrier is basically your one-way ticket to preppy paradise complete with impeccable tennis courts, breezy pickleball matches, croquet on the lawn, and poolside spritzes that just taste better in a striped cabana. It’s a destination designed for gatherings, whether you’re planning a wedding, a family reunion, a group getaway, or just a “we deserve this” long weekend with your best friends.

A classic countryside retreat, the resort now boasts eight brand-new indoor pickleball courts, with four additional outdoor courts that debuted in Spring 2025. Tennis enthusiasts will love the five Har-Tru clay outdoor courts, in play for over a century, alongside two indoor courts for year-round rallies.

Group Goals: Step Back in Time (Cocktails Included 🍸)

From tennis courts and croquet lawns to jacket-required dinners at The Main Dining Room and late-night martinis at Draper’s, The Greenbrier is a masterclass in old-school glamour. It feels like stepping straight into a vintage postcard: a 1950s tennis social, bourbon in hand, jazz floating from a grand piano. And those courts? Serena Williams herself has played here.

Group Activity Musts:

Tennis Brunch at The Forum: Pizza, pasta, and endless Aperol spritzes.
Preppy Afternoon Tea: Finger sandwiches, petit fours, and peak genteel vibes.
The Bunker Bar: Yes, there’s an actual Cold War-era bunker under the hotel. And yes, you can tour it.
The Greenbrier Casino: America’s only private casino, with Greenbrier Royale as your velvet-roped escape between plays. Whether you’re riding a winning streak or taking a break from the courts, it’s the place to toast to Lady Luck (or rally for round two).
Café Carleton: Live cabaret, top-shelf sips, and old-school glam every Friday and Saturday night. Named for Greenbrier legend Carleton Varney, it pours fine wines and spirits while the stage lights up from 9 p.m. to midnight.

Perfect for Friend & Family Trips:

Girls’ Getaway? Spa days, cocktails, tennis, and endless cute outfits.
Multi-Generational Family Vacay? Activities for everyone, from kids to grandparents.
Bachelor/Bachelorette Party? It’s basically an elevated adult summer camp—only make it a bygone-era bash. Picture Mrs. Maisel vibes, with cocktails, croquet, and dance floors designed for twirling the night away.

Beyond the Courts: Preppy Pursuits for the Whole Crew

Because let’s be honest. There’s always that one friend who’s here purely for the leisure (respect). The Greenbrier is more than just a tennis haven; it’s a full-blown preppy playground.

Start with croquet and lawn games - pastels highly encouraged, obviously. Tee off at the iconic Old White Course, even if your swing leaves a little to be desired, because the views (and the vibes) are impeccable. Feeling bold? Try your hand at falconry lessons. Because yes, learning to handle a hawk is officially on the vacation agenda.

When it’s time to unwind, book the legendary Greenbrier Sulphur Soak at the spa, a ritual guests have been indulging in since the 1800s. Or go full leisure and order a picnic from one of the resort’s dining outlets. Pack your champagne, claim a spot on the North Lawn, and settle in for an afternoon of Gatsby-worthy lounging, wicker basket and all.

And of course, no tennis weekend is complete without a poolside escape, where cabanas, cocktails, and time-travel feels are the name of the game. At The Greenbrier’s infinity pool, striped umbrellas, sun-warmed loungers, and frozen cocktails steal the show. Pro move: book a private cabana for champagne service, a personal attendant, and a perfectly acceptable excuse to order another round of shrimp cocktail.

From Match Point to Marriage Vows

Picture this: a ballroom wedding beneath sparkling chandeliers and gilded ceilings, or a playful ceremony on the croquet lawn followed by garden party cocktails with Pimm’s Cups and live jazz in the air. Even your welcome party feels like a scene from a vintage daydream. The Greenbrier’s pickleball facility is built with luxe locker rooms, vintage-inspired racquet gear, and a preppy, polo-meets-tennis vibe perfect for playful pre-wedding festivities.

Why it works for weddings:

Stunning outdoor courts framed by classic Southern architecture.
Luxury wedding packages packed with perks.
Iconic decor—from wallpaper to chandeliers—means less fuss, more charm.

For full effect, go all in on Greenbrier glam. Think plaid blazers, crisp whites, gold accents, and just enough Southern belle charm to keep it cheeky. Basically, dress like your grandmother’s debutante photos, but with better cocktails.

Final Verdict: Just Book the Trip Already

If you love linen and the idea of sipping cocktails in tennis whites, The Greenbrier is your kind of place. Pack your best racket, your cutest resort wear, and go live out your White Lotus meets Wimbledon fantasy.

Best Season to Visit: Spring and summer = peak preppy vibes. But fall is stunning, too—imagine golden leaves while playing doubles.