Events to look out for this month around San Diego include Pugchella, Gator by the Bay, North Park Festival of the Arts and Freedom Benefit Concert.
5.1: The Great Love Debate with Brian Howie
One of America’s leading dating enthusiasts hosts an episode of his hit podcast, pitting guys versus gals during a series of interactive improv sketches about love, sex and romantic relationships.
Music Box, downtown, greatlovedebate.com
5.2-6: West Coast Weekender
World-class talent from San Diego’s underground scene performs at this boutique music festival filled with engaging panels, creative workshops and live performances from dusk till dawn.
Viejas Casino & Resort, Alpine, westcoastweekender.net
5.3: Seventh annual Drives for Rides
Do your part to ensure no local children miss a cancer treatment due to lack of transportation by honing your golf game at this tournament supporting the Emilio Nares Foundation.
Maderas Golf Club, Poway, enfhope.org
5.3: Party Like Gatsby
Stand in awe of more than 20 circus, cabaret and vaudeville performers at this immersive, 1920s-themed experience where guests are expected to dress in their finest Gatsby-inspired duds.
Observatory, North Park, partylikegatsby.us
5.3: Secret Society of Adultologists: Garden Party
Discover what makes San Diego’s flora so special by chatting with scientists, artists and gardeners at this adults-only, after-hours garden party peppered with croquet, crafts and creative cocktails.
San Diego Natural History Museum, Balboa Park, sdnhm.org
5.3-5: 36th annual Old Town Cinco de Mayo
The city’s signature Cinco celebration returns with live music, a Lowrider Lane and loads of lucha libre matches, along with food and drink specials at dozens of bars and restaurants.
Throughout Historic Old Town, cincodemayooldtown.com
5.3-5: Beach Soccer Championship
Teams of children, adults and professional athletes put their best feet forward during this beach soccer festival that’s focused on raising funds for local youth programs.
Harbor Beach, Oceanside, beachsoccerusa.org
5.4: 28th annual Pug Party: Pugchella
The pug-centric party is back, sporting a Coachella theme and more than 400 scrunched-face canines competing in costume contests, a cupcake chomp and a wet T-shirt showdown.
Del Mar Fairgrounds, Del Mar, pugsandiego.com
5.4: 10th annual Asian Cultural Festival
Immerse yourself in the diversity of more than a dozen cultures and ethnicities during San Diego’s celebration of Asian Pacific American Heritage, which aims to unify local populations and educate others about the region’s art, history and traditions.
Mira Mesa Senior Center, Mira Mesa, asianculturalfestivalsd.com
5.4: Walk for Animals
Do your part to make San Diego safer for furry companions and wildlife of all types by walking in this event that raises vital funds for the San Diego Humane Society.
Liberty Station, Point Loma, sdhumane.org
5.4: 35th annual Father Joe’s Villages Children’s Charity Gala
Help children experiencing homelessness access the tools they need to build a better future by attending this black-tie event and feasting on an exquisite, three-course dinner paired with signature cocktails and world-renowned wines.
U.S. Grant Hotel, downtown, my.neighbor.org
5.4: Cinco by the Bay
Celebrating Mexico’s rich heritage and culture, this 21+ event includes tastes of the nation’s incredible cuisine alongside sips of agave spirits and set to a soundtrack of traditional tunes.
Embarcadero Marina Park South, Marina District, jamn957.iheart.com
5.4: The Pizza Run 5K
Indulge your obsession with one of Italy’s famous exports at this inaugural 5K fun-run that features pizza tastings from several local restaurants at the finish line festival.
Cathedral Catholic High School, Del Mar Heights, kathyslegacy.org
5.4: San Diego Made Market and Factory Grand Opening
Tour San Diego Made’s spankin’ new facility while browsing wares from more than 80 local makers and getting your fill of food and beer from numerous nearby restaurants.
San Diego Made Factory, Logan Heights, sandiegomade.org
5.4-5: Spring Sprint Triathlon, Duathlon & Aquabike
Now spanning two days, this event, which is suitable for experienced athletes and first-timers alike, ignites San Diego’s triathlon season and marks the first of the city’s annual Triple Crown Series.
Throughout Mission Bay, springsprinttri.com
5.5: Pendry Pool House Opening
Pendry San Diego opens its Fifth Avenue rooftop oasis by playing host to a series of relaxed daytime and evening events, revolving around an unforgettable bar experience.
Pendry San Diego, Gaslamp Quarter, poolhousesd.com
5.5: 11th annual Miracle Babies Superhero 5K
Don your cape and cowl before heading to this costumed 5K followed by a day full of entertainment, art demonstrations and obstacle courses all benefiting the newborns cared for in local NICUs.
NTC Park at Liberty Station, Point Loma, miraclebabies.org
5.5: Carlsbad Village Faire
The one-day street fair returns to North County with more than 750 unique merchants, an international food center and more than 100,000 visitors from far and wide.
Carlsbad Boulevard at Carlsbad Village Drive, Carlsbad, carlsbad.org
5.5: Vintage Flea Market
More than 100 merchants display their turn-of-the-century to midcentury-modern wares at this free, rain-or-shine event where leashed pups are always welcome.
The Observatory, North Park, sdvintagefleamarket.com
5.5: Third annual Chula Vista Cinco Fest
Get your fill of food, music and interactive experiences at this festival focused on Mexican culture and history, which is expected to attract 15,000 attendees.
H Street at Marina Parkway, Chula Vista, chulavistaca.gov
5.9-12: Gator by the Bay
It’s Mardi Gras all over again at this spirited four-day festival featuring seven stages of zydeco, blues and Cajun music along with free dance lessons and delicious Creole cuisine including 10,000 pounds of live Louisiana crawfish.
Spanish Landing Park, Harbor Island, gatorbythebay.com
5.10-19: Sixth annual San Diego Comedy Festival
Touring headliners and hilarious comedians from around the world showcase their talent and compete for cash during this weeklong laugh-fest.
Comedy Palace, Clairemont Mesa, sandiegocomedyfest.com
5.11: Chicano Federation 50th Anniversary Ball
Bringing together hundreds of business and community leaders, this golden anniversary event pays homage to those who have helped the charitable organization provide comprehensive programs dedicated to affordable housing and quality child development.
U.S. Grant Hotel, downtown, chicanofederation.org
5.11: 23rd annual North Park Festival of the Arts
Join more than 40,000 attendees as North Park’s yearly arts and music festival returns boasting even more mouthwatering cuisine, artistic creations and craft beer than ever before.
University Avenue at 30th Street, North Park, northparkmainstreet.com
5.11: Night Nation Run
Blending a music festival and a fun run, this one-of-a-kind athletic experience includes live DJs, confetti guns, light shows, bubble zones and a surprise headliner at the finish line after party.
Del Mar Fairgrounds, Del Mar, nightnationrun.com
5.11: Cultura Fest SD
Attend an indigenous Aztec blessing ceremony and dance to traditional Cumbia tunes at this Latino festival showcasing Spanish rock bands, authentic arts and a blooming beer garden featuring SoCal cervezas. Grammy and Latin Grammy Award winning singer Lila Downs also performs.
California Center for the Arts, Escondido, artcenter.org
5.12: Mother’s Day Celebration
Treat Mom to a Mother’s Day she won’t soon forget by transporting her to 50 acres of blossoms during the final day of Flower Fields 2019 season.
The Flower Fields, Carlsbad, theflowerfields.com
5.16: 29th annual Bike to Work Day
Grab your helmet, pump up your tires and join the thousands of other San Diegans pedaling to their places of work on this day that encourages locals to consider biking as an affordable and environmentally friendly choice for commuting.
Throughout the County, icommutesd.com
5.17: Interactive Day 2019
Learn to embrace our species’ uncertain future as marketing mavens, inspiring entrepreneurs and brilliant brand managers share their visions of the future.
Hilton Bayfront, downtown, sandiegox.org
5.18: Wine, Women and Shoes
Enjoy an afternoon of fashion, philanthropy and fine wine during this exclusive shopping experience benefiting the nonprofit Voices for Children.
Del Mar Plaza, Del Mar, speakupnow.org
5.18: Armed Forces Appreciation Day
Express your admiration for Camp Pendleton’s active-duty personnel and their families during this daylong celebration chock full of music, food and military displays.
Pier View Way at Coast Highway, downtown Oceanside, oceansidechamber.com
5.18: Chula Vista Community Fun Run
Runners, walkers and parents with strollers are invited to weave through 5 kilometers of various sporting venues at Chula Vista’s premier training facility.
Elite Athlete Training Center, Chula Vista, chulavistaca.gov
5.18-19: 40th annual Fiesta Del Sol
This free, two-day music festival showcases an eclectic selection of live performances along with various vendors, oodles of art exhibits and gourmet food trucks galore.
Fletcher Cove, Solana Beach, fiestadelsol.net
5.19: Grand Avenue Festival
Browse through handcrafted wares from hundreds of merchants, treat your taste buds to bites of international cuisine and swing your hips to loads of live music at Escondido’s famed festival.
Grand Avenue, downtown Escondido, escondidochamber.org
5.19: 33rd annual Bay Bridge Run/Walk
Show your support for San Diego’s Navy personnel during this 4-mile, one-of-a-kind run-walk across the iconic Coronado Bay Bridge toward the Island’s Tidelands Park.
Tidelands Park, Coronado, navybaybridgerun.com
5.24: 15th annual Freedom Benefit Concert
Rock out aboard the USS Midway during this annual fundraiser featuring a live performance by the rock band Daughtry.
USS Midway, Embarcadero, midway.org
5.25: San Diego Black and White Boat Party
Dress to the nines in a binary combination of white and black — or risk standing out like a sore thumb — while aboard this Latin Boat cruise.
Hornblower Yacht, Little Italy, saboronthebay.com
5.25: 11th annual Santee Street Fair & sixth annual Craft Beer Festival
Join more than 30,000 attendees at one of East County’s annual event featuring local breweries, 300 food vendors and oodles of live entertainment.
Town Center Parkway & Riverview Parkway, Santee, santeestreetfair.com
5.25: Sing Dance Crawl
Round up your most patriotic pals for this high-energy Americana-themed party taking place at three downtown venues and bringing locals together for a good time and a great cause.
Various venues around downtown San Diego, singdancecrawl.com
5.25, 26: Dip Day Club Opening Weekend
Sycuan gets in on the pool party action with the Memorial Day Weekend launch of Dip Day Club, a monthly, adults-only party at the casino’s Retreat Pool & Cabanas. Sunday’s headliner? DJ Snoopadelic, a.k.a., Snoop Dogg.
Retreat Pool & Cabanas at Sycuan Casino Resort, El Cajon, retreatpoolsd.com
5.30-31: Concentration 2019
Cannabis extractors and analytical scientists problem-solve, collaborate and advance solutions for conquering core challenges during this breakthrough event assembling the industry’s brightest minds for two days of exclusive content, keynote seminars and interactive exhibits.
Pala Resort & Casino, concentration2019.com
5.30-6.2: 2019 Celebrity Championship
Rub elbows with more than 50 high-profile celebs, and forge new friendships with the rich and famous during this four-day golf extravaganza paired with nightly parties and free events throughout the week.
Singing Hills Golf Resort, Sycuan Resort & Casino, celebritychampionship.com
5.31-7.4: San Diego County Fair — Ozsome!
Following a theme inspired by The Wonderful Wizard of Oz, the county’s signature summer event returns to Del Mar with an impressive lineup of concerts, comedians and deep-fried cuisine.
Del Mar Fairgrounds, Del Mar, sdfair.com
SPORTS HOME GAMES
Padres Home Games
5.3-5 vs Los Angeles Dodgers
5.6-8 vs New York Mets
5.16-19 vs Pittsburgh Pirates
5.20-22 vs Arizona Diamondback
5.31-6.2 vs Florida Marlins