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Things To Do

Things to do in May

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

The Great Love Debate with Brian Howie
The Great Love Debate with Brian Howie

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

West Coast Weekender
West Coast Weekender

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

Drives for Rides
Drives for Rides

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

Party Like Gatsby
Party Like Gatsby

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

Secret Society of Adultologists: Garden Party
Secret Society of Adultologists: Garden Party

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

Old Town Cinco de Mayo
Old Town Cinco de Mayo

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

Beach Soccer Championship
Beach Soccer Championship

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

Walk for Animals
Walk for Animals

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

Father Joe’s Villages Children’s Charity Gala
Father Joe’s Villages Children’s Charity Gala

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

Cinco by the Bay
Cinco by the Bay

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

San Diego Made Market and Factory Grand Opening
San Diego Made Market and Factory Grand Opening

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

Spring Sprint Triathlon, Duathlon & Aquabike
Spring Sprint Triathlon, Duathlon & Aquabike

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

Pendry Pool House Opening
Pendry Pool House Opening

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

11th annual Miracle Babies Superhero 5K
11th annual Miracle Babies Superhero 5K

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

Carlsbad Village Faire
Carlsbad Village Faire

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

Gator by the Bay
Gator by the Bay

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

San Diego Comedy Festival
San Diego Comedy Festival

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

North Park Festival of the Arts
North Park Festival of the Arts

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

Night Nation Run
Night Nation Run

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

Cultura Fest SD
Cultura Fest SD

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

Bike to Work Day
Bike to Work Day

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

Wine, Women and Shoes
Wine, Women and Shoes

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

Armed Forces Appreciation Day
Armed Forces Appreciation Day

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

Fiesta Del Sol
Fiesta Del Sol

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

Grand Avenue Festival
Grand Avenue Festival

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

Bay Bridge Run/Walk
Bay Bridge Run/Walk

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

Freedom Benefit Concert
Freedom Benefit Concert

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

San Diego Black and White Boat Party
San Diego Black and White Boat Party

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

Santee Street Fair and Craft Beer Festival
Santee Street Fair and Craft Beer Festival

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

Sing Dance Crawl
Sing Dance Crawl

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

Concentration 2019
Concentration 2019

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

2019 Celebrity Championship
2019 Celebrity Championship

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

San Diego County Fair
San Diego County Fair

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

San Diego Padres
San Diego Padres