Wine & Food Week is celebrating its twenty-first anniversary this year! Presented by H-E-B, this event comes to town May 28-31 promising an unforgettable experience for gastronomy enthusiasts and wine aficionados alike. Here are 21 Reasons not to miss the 21st Wine & Food Week — And Yes, We're Crushing It!

Girls with wine glasses at Wine & Food Week in The Woodlands, Texas

1. Because 21 Years Deserves a Toast: We’ve been crushing it for over two decades, and this year we’re serving up new tastes and experiences for foodies and wine lovers from novice to expert.

2. The Debut of Crushing It with Cocktails: Wine & Food Week is a fresh, spirited event spotlighting mixology masters and cocktail creativity. Competing for "Best in Glass" and other bartender honors include Danny Velazquez, Beverage Director of The Blind Finch; Carla Espinoza, Partner of I Know The Owner Bar; Afzal Kaba, Beverage Director of Musaafer; Sebastien Escobar, Beverage Director of Monarca Modern Cocina Kitchen; Kiana Carillo from Plume; and more.

3. Sip Over 500 Wines: From bold reds to crisp whites and everything in between, your taste buds are in for a world tour.

4. Celebrity Chefs, IRL: Rub elbows and raise forks with more than 100 culinary icons from across the world, including exotic destinations like Aruba.

5. Chef Showdown—Culinary Combat Live: Watch 40 top chefs go head-to-head for the title of Chef of Chefs and a $5,000 cash prize. Can reigning champ Chef Nancy Manlove hold her title? Who will crush the competition?

Three young people (two men, one woman, all of Asian descent) smile at the camera. The men are dressed in white chef uniforms, and the woman is wearing a white blouse and black slacks. The man on the left is holding a metal pan that reads, "Wine & Food Week | Chef of Chefs, Presented by GOYA | Grand Prize Winner." The man in the middle is holding a glass vase (the trophy) and a solid maroon trophy stand. Behind them is a sheer white curtain and miscellaneous posters for Wine & Food Week.

A young black woman, donning a professional black chef's uniform and white gloves, smiles at the camera as she squeezes an orange paste atop a bite-sized desert.

6. The Grand Tasting Experience: This is the one everyone talks about. You’ll taste why.

7. Crush-Off Grape Stomp: Watch finalists from Can You Crush This Tuesday Trivia try to stomp out the competition at Sips, Suds & Savor to win a weekend staycation at the Bernhardt Winery. Then, dive into the rich story of “vine to glass” with a lively grape stomp demo led by none other than Jerry Bernhardt himself—owner and winemaker extraordinaire.

8. Ladies of the Vine Luncheon: Empowering. Elegant. Effervescent. Join the sisterhood of wine and hear from a power-packed panel including Laura Oskwarek, Winemaker, Silver Oak; Cynthia Lohr, Co-Owner, J. Lohr; Roberta Ceretto, 3rd Generation Family Member, Ceretto Winery; Melissa Phillips Stroud, Vice President, Michael David Wines; Kelly Limbaugh, Vice Chairman - Administration, Winery Relations Committee of the Houston Livestock Show & Rodeo international wine competition.

9. Reserve Tastings: Rare wines. Intimate pours. No velvet rope can hold you back. More than 7,000 bottles of wine will be poured during Wine & Food Week.

10. Food That Stops Time: Crafted by chefs who turn ingredients into unforgettable experiences.

11. Epic Cocktail Moments: Thanks to Crushing It with Cocktails, it’s not just about wine anymore.

12. A Ticket To Aruba Could Be Yours: Aruba is calling. Global wine experiences are all the rage. We’re excited to announce a trip giveaway to Aruba including three nights at the Aruba Marriott Resort & Stellaris Casino with daily breakfasts, plus two tickets to the Wine on Down the Road culinary tour, and a $500 airline voucher for Southwest Airlines. A $3,200 value. Wine & Food Week ticketholders are automatically entered, or you can enter online here.

13. Meet Culinary and Wine Icons Plus Rising Stars: Wine & Food offers a rare opportunity to meet culinary veterans and rising stars alike—all crushing it in the worlds of wine and food. Houston’s first master sommelier Guy Stout is back to unveil his new wine line, Magic Bus, at Sips, Suds & Savor. Chef Lena Le, Chopped Champion Truffle Edition, is one of many fresh faces competing in the Chef of Chefs competition.

Person pouring wine into glass during Wine and Food Week in The Woodlands, Texas

14. Wine Education That Doesn't Feel Like School: Sip, swirl, and soak up knowledge in style.

15. Live Music, DJs, & Vibes: Because good food and drink deserve a great soundtrack, photo ops, and experiences.

16. Winemakers Who Pour with Passion: Chat and chill with the people behind the bottles.

17. Themed Nights That Hit Different Clans: Glam, casual, bold, or bubbly—there's a perfect vibe for every guest.

18. VIP Lounges that Seriously Slay: Elevate your evening with exclusive access and next-level indulgence at the Bayway Cadillac Luxury Lounge.

19. The Woodlands—A Perfect Backdrop: Scenic, upscale, and just far enough to feel like a getaway.

20. You'll Be Part of Something Bigger: Proceeds support local charities and community efforts like New Danville, The Woodlands Arts Council, and Montgomery County Food Bank.

21. FOMO is Real—Don't Miss It: Wine & Food Week only happens once a year!

Six people (three men, two women, all in suits or summer dresses) smile at the camera while holding glasses of white and small plates for tastings. Behind them is a room full of people, also mingling and enjoying Wine & Food Week.

A STELLAR LINE-UP

Event line-up includes Wine Around the World Wednesday; the all-NEW Crushing it With Cocktails, and Sips, Suds & Savor. The week culminates with the grand dame—the elaborate Wine Rendezvous Grand Tasting & Chef Showcase at The Woodlands Waterway Marriott Ballroom, where acclaimed chefs compete for the coveted Chef of Chefs Award and a $5,000 cash prize. Looking for that extra touch of VIP, be sure to get tickets early to the Bayway Cadillac VIP Luxury Lounge with ultra-premium wines but limited space. On June 6, don’t miss the Ladies of the Vine Tasting, Luncheon, & Panel Discussion at The Club at Carlton Woods. Wine & Food Week is truly foodie heaven.