Top 14 Food & Drink Events in Houston This Month: May 2023

Dine on delicious dishes and enjoy our picks for the top food and drink events taking place around Houston in May 2023.

Springtime in Houston is as pleasant as it gets, and this month’s culinary happenings only add to the pleasure.

Kick off May with Cinco de Mayo and Kentucky Derby parties, then continue the fun with a Wine Fest on the Bayou, a Rock and Roll Picnic, Wild Game and BBQ Cook-Off, and more.

Here’s everything you need to eat and drink in Houston this month:

Top 14 Food & Drink Festivals & Events in Houston This Month: May 2023

• Celebrity Chefs Against Cancer at Four Seasons Hotel Houston | Wednesday, May 3 – This fourth annual event features 21 chefs from Houston’s best restaurants, coming together for an unforgettable night of spectacular food, drinks, and impactful fundraising. This year’s chefs include Toro Toro’s Richard Sandoval and Rafael Villalpando, Brennan’s of Houston’s Jose Arevalo, Hugo Ortega of Xochi and more, E.J. Miller of Muse, and Troy Guard of Guard & Grace, among other talents. There will also be an extensive silent auction, and the evening will raise funds to help bring back the joys of childhood to a unique population of children touched by cancer through an urban camp experience. $150 to $2,500. 6:30pm to 9pm.
• Star Wars–Themed Dinner at Max’s Wine Dive on Washington | Thursday, May 4 – Star Wars fanatics can wine and dine at Max’s third annual themed wine dinner, featuring a five-course menu inspired by the iconic films paired with the exclusive labels from the Dive. Costumes are encouraged. Reservations are recommended. $99. 7pm. 
• Cinco de Mayo at Monkey’s Tail | Friday, May 5 – The Mexican American dive bar and cantina is getting the Cinco de Mayo fiesta started early by opening its doors at 11am. In addition to its weekend brunch menu, party goers can expect festive decor including a swag wheel to spin at the door, crawfish and an outdoor burrito and taco stand, specialty drinks, a special $5 holiday menu, and DJ beats and mariachi music throughout the day. 21+ all day. 11am to 2am. 
• Kentucky Derby Party at Permission Whiskey | Saturday, May 6 – Over on White Oak, the bourbon and whiskey bar’s Derby celebration will feature a broadcast of the race, live music and a trumpet player, Derby-themed roses, a festive hat contest and other surprises. Fresh mint julep cocktails will be flowing, and Maker’s Mark will be on site giving away branded swag. General admission tickets can be pre-purchased for $20 at Permission, with limited quantities at the door. Noon to 7pm.
• Kentucky Derby Day Party at Julep | Saturday, May 6 – Houston’s finest Southern cocktail bar is getting down and derby for its annual Kentucky Derby event, inviting guests to break out the derby hats and bowties for a day of mint juleps and fun. Expect house cocktails, Champagne, two main bars, a whiskey bar, tacos from Cochinita & co., a live DJ set, and a live stream of the Kentucky Derby. $20 in advance; $25 at the door. 1pm to 6pm.
• “Derby Down on the Bayou” Wine Fest at Brenner’s on the Bayou | Saturday, May 6 – Wine Fest is back, Derby-style, at Brenner’s on the Bayou, as guests are invited to Derby down, sample the exquisite wine collection from exclusive winemakers, and stroll around the gorgeous scenic grounds. Chef-crafted bites will be served from seven of Houston’s top restaurants including Brenner’s on the Bayou, Grotto Downtown, McCormick & Schmick’s, Cadillac Bar, Willie G’s, Babin’s and a dessert station from chef Eunice Grassa—plus, there will also be a Derby Hat Contest with prizes. $150; $250 for VIP. 2:30pm to 5:30pm.
• I’ll Have What She’s Having Rock & Roll Picnic at Last Concert Café | Sunday, May 7 – Women’s healthcare nonprofit I’ll Have What She’s Having is bringing back its Rock ‘n’ Roll Picnic, featuring an afternoon of music, inspired picnic fare from rockstar chefs and hospitality volunteers, cocktails and art while raising funds for essential healthcare services for our community. This year’s hospitality lineup includes Top Chef’s Dawn Burrell, Houston Dairymaids, Underground Creamery’s Josh De Leon, and many more, with VIP options including a special picnic tiffin by Anita Jaisinghani (Pondicheri), Justin Yu (Theodore Rex) and Ryan Pera (Coltivare). $85 and up; $15 for children. Noon to 4pm.
• Yaga’s Children’s Fund Wild Game & BBQ Cook-Off at Moody Gardens | Friday, May 12 & Saturday, May 13 – The 27th annual Wild Game and BBQ Cook-Off returns to the island; a two-day, family-friendly event to benefit the Yaga’s Children’s Fund and its support of more than 25 Galveston County organizations. The fun kicks off with a VIP Sponsor Party on Friday, followed by a morning 5k fun run and the bbq and wild game cook-off and beer tasting on Saturday. $40 and up. Times vary.
• Texas Crab Festival at Festival Park in Crystal Beach | Friday, May 12 to Sunday, May 14 – Savor crab dishes, live music, and festivities, including carnival rides, art vendors, wiener dog races, and more at the 38th annual festival near Galveston. $20. Times vary.
• Wagyu & Wine Night at R-C Ranch | Wednesday, May 17 – Guests are invited to join R-C Ranch for a tasting event featuring premium wines paired with R-C’s signature Texas Wagyu. $125 and includes a multi-course wagyu dinner with wine pairings. 6pm to 7:30pm.
• 50th Annual Pasadena Strawberry Festival at Pasadena Fairgrounds | Thursday, May 18 to Sunday, May 21 – The annual strawberry fest returns to Pasadena, featuring a weekend of barbecue, carnival rides, a car show, mutton bustin’, a kids zone, and more. Times vary.
• Umami Fest at Railway Heights Market | Friday, May 19 & Saturday, May 20 | No Cover – This umami-packed, Houston Asian-inspired food festival and night market will rock street food and merchandise vendors, artists, night market games and prizes, and entertainment.4pm to 11pm.
• Empty Bowls Houston at Houston Center for Contemporary Craft | Saturday, May 20 – Now in its 17th year and raising $991,293 for the Houston Food Bank, the Empty Bowls event is a unique lunch fundraiser and collaboration between Houston area ceramists, woodturners and artists working in all media and Houston Center for Contemporary Craft. Attendees can enjoy perusing the 1,500+ one-of-a-kind, hand-crafted bowls made and donated by Houston area artists, which are available for a donation to the Houston Food Bank of at least $25 per bowl (100% goes to the food bank). All attendees who purchase bowls can enjoy a simple soup lunch. 10am to 3pm (soup served until it runs out).
• 21st Annual Menu of Menus at Silver Street Studios | Tuesday, May 23 – Sip, sample, and taste your way through more than 40 Houston restaurants at one of Houston’s largest signature culinary extravaganzas. $49 and up. 7pm to 10pm.