Top San Diego Things to Do in May

Enjoy a wine-paired dinner in Estancia’s beautiful outdoor courtyard on May 23.

Star Wars Day celebrations, Mother’s Day brunch, wine pairing dinners, beloved Broadway musicals and more fun things to do are on tap this month. Here are the top 30+ San Diego things to do in May.

Edited by Jordan Fraser.

Mole and Mezcal Dinner
May 2. Puesto welcomes two internationally acclaimed Oaxacan chefs to its La Jolla kitchen to create a traditional Oaxacan meal. For one night only, guests will enjoy a four-course prix-fixe menu, and an optional drink pairing menu. Reservations required. 5 p.m. $30, additional $20 for the drink pairing. 1026 Wall St., La Jolla, 858.454.1260.

Side Barre
May 2. Get pumped up for this fierce, 50-minute, high-energy fitness event held in Side Bar’s recently renovated space to a soundtrack by DJ XP. The total-body workout will target strength, cardio and flexibility for all levels. Afterward, enjoy hosted appetizers, two craft cocktails featuring Suja juice and a swag bag that includes Pure Barre swag and Suja goodies. 5-7 p.m. $40. 536 Market St., downtown. Tickets

Fiesta Old Town Cinco de Mayo
May 3-5. Celebrate Cinco de Mayo in historic Old Town San Diego with four stages for live entertainment, a beer and margarita garden, Lucha Libre matches and the Lowrider Lane car show. Be sure to check out the variety of food and retail vendors, as well as the children’s area at this 36th annual festival. F 4-9 p.m.; Sa 10 a.m.-10 p.m.; Su 10 a.m.-8 p.m. Free. San Diego Avenue between Conde and Twiggs, Old Town, 619.291.4903.

The Boardroom Show Surf Party
May 3. Get an exclusive first look at some of the highlights of this year’s Boardroom Show Surf Expo at this free public event at Del Mar Plaza. Preview the retrospective on Bruce Brown’s life as told by his son in A Life of Endless Summers, The Bruce Brown Project. Plus, a photo slideshow from legendary Surfer magazine photographer Don Balch; a preview of the new surf film Spoons from producers Wyatt Dailey and Justin Misch, a photo slideshow from the archives of Larry “Flame” Moore, music from Tower 7 and beer and taco specials from Pacifica Del Mar. 6:30-9:30 p.m. Free. 1555 Camino Del Mar, Del Mar, 858.847.2284.

Cinco de Mayo in Balboa Park
May 4. Experience a family-friendly fiesta filled with Mexican music and dance performances, colorful horseback riders, strolling mariachis, a fashion show of traditional Mexican dress, hands-on activity booths for kids, arts and crafts vendors, food trucks and more. The day-long celebration culminates with a 5 p.m. concert in Spreckels Organ Pavilion featuring crowd-favorite Jarabe Mexicano. 11 a.m.-6 p.m. Free. Balboa Park, 1549 El Prado, San Diego.

Film & Float: The Empire Strikes Back
May 4. The Force is strong this Star Wars Day with a special poolside screening of The Empire Strikes Back. Bring your own lightsaber or don your best cosplay to storm the Lafayette’s pool deck. Plus, $5 poolside cocktails and bites available from Hope 46. 6-9:30 p.m. Free. Lafayette Hotel, 2223 El Cajon Blvd., North Park.

Rhythm & Brews Music and Craft Beer Festival
May 4. The San Diego Brewers Guild hosts the eighth annual Rhythm & Brews Music and Craft Beer Festival. Listen to live music on two stages from Matt Costa, Low Volts, Francis Blume and more while sampling 100+ brews from over 50 breweries. VIP entrance at noon, event 1-4 p.m. $45 GA, $70 VIP. Historic Vista Village, S. Citrus Ave. and E. Broadway, Vista.

Star Wars Cocktails at Prohibition
May 4. Drink the force with Star Wars-themed cocktails created to celebrate the movie franchise during a “May The Fourth Be With You” party. GBOD Hospitality Group beverage director Ryan Andrews has created cocktails inspired by some of Luke Skywalker and Darth Vader’s most famous lines, including “Never Tell Me The Odds” made with a combination of Dobel Diamante GBOD Single Barrel tequila, demerara, Averna and R&D House Bitters and “Let The Wookie Win” made with Havana Club rum, fresh lime, ginger and Fernet. $14. 548 Fifth Ave., Gaslamp Quarter.

Pool House at the Pendry opens to the public on Sundays beginning May 5.

Pool House Sundays
Opens May 5. Head to the Pendry for the most sought after pool party experience in downtown San Diego. Top DJs and live performances will headline during the afternoons while guests enjoy a selection of dining choices, signature cocktails, bottle service options and private cabanas. Su-Th 11 a.m.-7 p.m. 550 J St., downtown, 619.738.7030.

Prohibition Supper Club
May 6. This edition of the monthly Supper Club will highlight DesMaDre artisanal tequilas. Presented as a “reverse pairing” dinner, Prohibition lead bartender Ryan Andrews will craft four unique cocktails using DesMaDre unaged blanco, añejo and reposado tequilas, which will be paired with a four-course meal. 6 p.m. cocktail hour; 7 p.m. dinner. $85. 548 Fifth Ave., Gaslamp Quarter, 619.501.1919.

Gator by the Bay
May 9-12. Come to the largest, most authentic Louisiana-themed music and food festival this side of the bayou. Gator by the Bay features four days of live music with more than 100 musical acts on seven stages; an array of Southern cuisine including 10,000 pounds of fresh crawfish trucked in from Louisiana; dancing and family fun. Th 6-10:30 p.m., F 3:30-10:30 p.m., Sa 10:30 a.m.-8 p.m., Su 10:30 a.m.-7 p.m. $35-$150. Spanish Landing Park, 4300 N. Harbor Drive, San Diego.

Jerry Seinfeld
May 10. As the star, co-creator and namesake of one of America’s most beloved sitcoms, Jerry Seinfeld is famous for his uncanny ability to joke about the like things in life that everyone can relate to. 7 p.m. and 9:30 p.m. $70+. San Diego Civic Theatre, 1100 Third Ave., downtown, 619.570.1100.

Junior League Food and Wine Festival
May 11. Savor sips and bites from San Diego’s top restaurants, breweries, wineries and distilleries at this annual fundraiser by the Junior League of San Diego. Don your Sunday best, bid on silent auction items and listen to live music in the scenic La Jolla Cove. This year, vendors include We Olive, Oceanaire, Pali Wine Co. and Eppig Brewing to name a few. VIP admission 1 p.m., event 2-5 p.m. $85 GA, $110 VIP. Ellen Scripps Browning Park, 1100 Coast Blvd., La Jolla.

Mother’s Day Is Sweet
May 11. Show mom the sweeter side of Oceanside at this unique pop-up with dessert and beverage pairings at sweet stops throughout downtown. Offerings include local dessert tastes from local favorites such as Dani Girl Cake Pops and DoughSide Donuts, plus 1- to 3-ounce sips of local craft beer and wine for the adults and nonalcoholic beverages for all. The event will also include a sidewalk chalk activity for kids. 2-5 p.m. $10-$45. 330 N. Coast Hwy., Oceanside. Tickets

Night Nation Run
May 11. Party hard at this unique 5K run and music festival. Expect lots of music, dancing, party zones, selfie stations, light shows, a lantern land, a bubble world and multiple stages with DJs. Once you cross the finish line, the party continues with the “Epic Main Stage After Party” featuring top headliner DJs, and all the trappings of a traditional music festival. Runners are encouraged to arrive at 6 p.m. for the pre-party, race begins at 7:30 p.m. $29.99-$60. Del Mar Fairgrounds, 2260 Jimmy Durante Blvd., Del Mar.

North Park Festival of Arts
May 11. Enjoy artwork from more than 100 artists including paintings, photography, pottery, handmade jewelry and more. Additional highlights at this diverse annual neighborhood event include a live art block where local street artists will transform everyday items into pieces of art right in front of you; four performance stages with a variety of music; and a craft beer block for guests 21+. 11 a.m.-10 p.m. Free. 30th St. and University Ave., North Park.

Satisfy Mom’s sweet tooth in the beautiful setting of San Diego Botanic Garden.

San Diego Botanic Garden’s Chocolate Festival
May 11. Bring Mom for a relaxing day in the garden to sample chocolate from a variety of vendors. Plus, live demonstrations and tips on creating chocolate treats. Participating vendors include Bottega Italiana, Carlsbad Cookie Company, Nibble Chocolate and more. 10 a.m.-4 p.m. Free with paid admission or membership. Tasting and activity tickets sold on site. 230 Quail Gardens Drive, Encinitas, 760.436.3036.

Mother’s Day Champagne Jazz Brunch
May 12. Hornblower’s on-land venue The Abbey offers a rare, refined Uptown option for Mother’s Day. Originally constructed as an Episcopal church, this elegant 1910 landmark is San Diego’s only remaining Classic Revival structure. Treat Mom to bottomless bubbly, an elaborate seasonal buffet, decadent desserts and live jazz entertainment by Republic of Music in this unique setting. 11 a.m.-1 p.m. $55. 2825 Fifth Ave., Bankers Hill, 619.686.8715.

Roald Dahl’s classic book-turned-movie comes to life on stage with songs like “I’ve got a Golden Ticket.”

Charlie and the Chocolate Factory
May 14-19. Based on the beloved story by Roald Dahl, the touring Broadway musical features classic songs from the original film including “Pure Imagination,” “The Candy Man” and “I’ve got a Golden Ticket” alongside toe-tapping new music from the songwriters of Hairspray. See website for show times and ticket prices. Broadway San Diego at San Diego Civic Theatre, 1100 Third Ave., downtown, 619.570.1100.

Art & Empire: The Golden Age of Spain
Opens May 18. Featuring more than 100 outstanding works by leading artists from Spain and its global territories during the pivotal years of around 1600 to 1750, this new exhibit is the first in the United States to expand the notion that the “Golden Age” include the Hispanic world beyond the Iberian Peninsula. See website for hours and ticket prices. San Diego Museum of Art, 1450 El Prado, Balboa Park, San Diego, 619.232.7931.  

Old House Fair
May 18. Discover the charming neighborhood of South Park in a tour of five historic homes at this 21st annual event. Begin at the Rose Wine Bar for a mimosa and a selection of historic home preservation specialists, followed by a bike tour of both historic and modern homes built by notable architects. Or take the trolley through the neighborhood to visit the homes in any order you choose. Each location will feature docent-led education and history. 10 a.m.-4 p.m. $6-$27. The Rose Wine Bar, 2219 30th St., South Park.

Over the Line Tournament and Craft Beer Festival
May 18-19. Kick off summer at the annual Over the Line Tournament with qualifying matches taking place on Saturday and the winning teams returning on Sunday for the final. Competing divisions include Men’s Pro, Men’s Open, Men’s Masters (age 45+) and Women’s Open. Plus, enjoy a craft beer festival that will be held during tournament play featuring local breweries such as Alesmith, Bay City Brewing and Second Chance, along with food trucks to grab a bite to eat. 21+. Sa 7 a.m.-6 p.m. Su 7 a.m.-3 p.m. Team entry $120. Beer Fest GA $35. Mariners Point, Mission Bay Park, 3230 Mariners Way, Mission Bay. Tickets

Celebrate the sixth anniversary of one of San DIego’s prized breweries on May 18.

Saint Archer Brewing Company Anniversary Party
May 18. Celebrate Saint Archer Brewing’s anniversary at this family-friendly event that will feature live music from King Tuff, The Schizophonics and The Anodynes. Also enjoy food trucks, a kid’s area, brewery tours, and a special anniversary beer release of the Hazy Rye with Galaxy Hops IPA which will be exclusively available on draft at the anniversary party. 2-9 p.m. Free. 9550 Distribution Ave., San Diego.

I Love Poke Festival
May 21. Enjoy poke, along with other island-inspired food and desserts, from 30 of San Diego’s top chefs and restaurants while celebrating Hawaiian culture and cuisine. This 10th annual all-ages festival will also feature a food competition, dancing and live music. 6-9 p.m. $75. Bali Hai, 2230 Shelter Island Drive, Shelter Island. Tickets

By The Barrel: Wine
May 23. This month Estancia La Jolla’s four-course dinner series focuses on wine as the featured alcohol pairing. During the dinner, winemakers will guide guests through a selection of award-winning red and white wines from Trinitas Cellars. 21+. 6:30-9:30 p.m. $125 includes valet parking. Estancia La Jolla, 9700 N Torrey Pines Road, La Jolla. Tickets

Executive Chef Jeff Jackson teams up with Liquid Farm founder Jeff Nelson for a dinner and wine pairing.

Signature Wine Dinner 
May 23. Enjoy a mouthwatering multi-course wine-paired dinner overlooking the Torrey Pines Golf Course and Pacific Ocean. The Lodge at Torrey Pines Executive Chef Jeff Jackson will curate a special menu that perfectly complements the flavors in each hand-selected wine by Liquid Farm founder Jeff Nelson, who will also facilitate conversation about the winemaking process and the inspiration behind each wine selected for the evening. 7-9:30 p.m. $185. A.R. Valentien, 11480 N. Torrey Pines Road, La Jolla, 858.777.6635. Tickets

Fiddler on the Roof
Opens May 28. Featuring the Broadway classics “Tradition,” “If I Were a Rich Man,” “Sunrise, Sunset,” “Matchmaker, Matchmaker” and “To Life,” the original production won 10 Tony Awards and became the longest-running Broadway musical of all time. Tony-winning director Bartlett Sher brings a fresh, yet authentic, vision to this musical masterpiece. See website for show times and ticket prices. Broadway San Diego at Civic Theatre, 1100 Third Ave., downtown, 619.570.1100.

Sip the City
May 31. Hosted at the scenic Headquarters at Seaport District, Sip the City features over a dozen of San Diego County’s urban wineries pouring their unique and award-winning wines. Guests will enjoy unlimited wine tastings, light snacks and live music while supporting local winemakers and the flourishing urban wine movement. Participating wineries include BK Cellars, 2 Plank Vineyards, Mission Cellars, Negociant Winery. 5:30 p.m. $29-$59. 789 West Harbor Drive, Seaport Village. Tickets.

Military Appreciation Month Dining Specials
Through May 31. Veterans and active-duty military service members who present a valid military ID will receive a 20 percent discount on all food purchases throughout the month at each of GBOD Hospitality Group’s five restaurant locations: El Chingon, Havana 1920, Monkey King, Mezé Greek Fusion and Dough Nations. See website for location details.

Free Popcorn for Military Appreciation Month
Through May 31. Theatre Box salutes Military Appreciation Month by offering active military personnel and veterans complimentary popcorn throughout the month of May with proof of a valid military ID and the purchase of a movie ticket. Plus, Theatre Box supports members of the military and veterans year-round with 15 percent off food and beverages at Sugar Factory American Brasserie and $10 specially priced movie tickets. 701 Fifth Ave., downtown, 619.814.2225.

Menopause the Musical
Through June 2. Four women meet while shopping for a black lace bra at a lingerie sale at Bloomingdale’s, where this hilarious and heartwarming tale takes place. After noticing similarities, they joke and bond over their woeful hot flashes, mood swings, wrinkles, weight gain and celebrate that menopause is no longer “The Silent Passage.” See website for show times and ticket prices. The Lawrence Welk Resorts Theatre, 8860 Lawrence Welk Drive, Escondido, 760.749.3448.


Photos: Pendry Pool House courtesy The Influence. Chocolate Festival by Lisa Reynolds. Saint Archer Brewing Anniversary Party courtesy Katalyst PR. Signature Wine Dinner courtesy Evans Hotels. By The Barrel: Wine courtesy Estancia La Jolla. Charlie and the Chocolate Factory by Joan Marcus.


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