Events

Turn up your Friday night with DJ Asa at Calypso 🎶🌊

Come early for dinner and drinks, then stick around as DJ Asa takes over and keeps the weekend energy going.

Bring the crew and make a night of it. 😎

Calling all witches, ghouls & lovers of all things spooky 🔮🕸️

Calypso’s Witches Night Out Vendors Market is taking over the beach Saturday, October 24th! 🌙

Shop local vendors, sip on your favorite Calypso cocktails, grab a bite, and spend the evening getting into the Halloween spirit with us. Costumes and your favorite witches are highly encouraged. 🧙‍♀️✨

🛍️ Local Vendors 🍹 Cocktails + Coastal Eats 📅 Saturday, October 24th ⏰ 6:30–9:30 PM

Interested in becoming a vendor? Email calypsovb@mhgva.com for more information.

Stay tuned... more spooky details are brewing. 👀🎃

Turn up your weekend with DJ Ty Street at Calypso 🎧🌴

He will be taking the stage right after our very first Witches Night Out Vendors Market to keep the night going strong. 🌊😎

Every Sunday

🏈 SUNDAY FOOTBALL AT CALYPSO 🌊

Sundays are for FOOTBALL 🏈🍻

Catch all the action at Calypso with the games on our TVs, cold drinks flowing, and plenty of game day bites to go around 🌊

Grab your crew, claim your spot, and spend Football Sunday with the Calypso crew 😎🍗🍺

Every Monday

🏈 MONDAY NIGHT FOOTBALL AT CALYPSO 🌙

Monday nights just got a whole lot better 🏈🍻

Catch Monday Night Football at Calypso with the game on our TVs, cold drinks, and all your Calypso favorites 🌊

Skip the couch, grab your crew, and spend Monday Night Football with us 😎🍺

Join us Wednesday, October 28th at 7PM for FREE to Play Music Bingo!  Prizes are available for winners!  

Beach Trivia will be adding in spooky hits all night long!  

 Grab your crew, and join us while we kick off our spooooky Halloween weekend here at Calypso!  

 Don't forget, we will have $9.99 Smashburgers + Fries available all night too!

Every Thursday

🏈 THURSDAY NIGHT FOOTBALL AT CALYPSO 🍻

Start your weekend a little early with Thursday Night Football 🏈👀

Catch the matchup at Calypso while you grab dinner, sip on something cold, and settle in for a night of football by the oceanfront 🌊🍺

Thursday night plans = handled 😎🏈

 SING IF YOU DARE…  

 Halloween is taking over karaoke!  

 Join Julz Gat Thursday, October 29th at 8PM for a night of spooky vibes, costumes, and karaoke mayhem. 

 Come dressed for the occasion and compete for Best Dressed Singer — winner takes home a gift card!  

 Pick your poison. Pick your costume. Pick your song. The mic is waiting… 

 Psst.. come early and check out our Crabby Thursday specials before taking the stage, crab specials run from 4PM-9PM!

Halloween weekend starts at Calypso 👻🎧

DJ Jerm is back behind the booth to kick off one of the biggest weekends of October. Grab a cocktail, bring your crew, and get ready for a Friday night by the beach.

Consider this your Halloween weekend warm-up. 🌊

 OUR 15TH ANNUAL HALLOWEEN PARTY IS HERE.  

 For 15 years, Halloween has been one of our biggest nights of the year — and on Saturday, October 31st, we’re celebrating the only way we know how: BIG.

Expect spooky cocktails, a live DJ, a packed dance floor, and a night of Halloween madness that keeps going until the very last song.

This is a 21+ event! Costumes are HIGHLY encouraged!

CALYPSO’S OYSTER ROAST IS TURNING 15! 🦪🎉

For 15 years, we’ve been bringing Virginia Beach together at the Oceanfront for a day of oysters, great food, live music, cold drinks, and even better company.

But this tradition has always been about more than the party. Each year, the Oyster Roast supports a charitable cause, giving us the opportunity to give back to the community that has supported Calypso for so many years.

Different causes. Same mission.

BRING OUR COMMUNITY TOGETHER. HAVE A GREAT TIME. GIVE BACK.

And we can’t wait to celebrate 15 years with you! ❤️

Join us on Saturday, November 7th from 12PM-5PM for AYCE Oysters, Pulled Pork BBQ, Southern Fixins', Adult Beverages Provided, Live Music, Fun & More! 

Proceeds from tickets will go directly to the Virginia Beach Jaycees to support their Christmas Shopping Tour Charity, helping create magic for families from our community that are in need this holiday season. 

 🎟️ Tickets Are Now On Sale! 

DD Tickets for guests 21+ are available for $55.  To Purchase a Designated Driver Ticket, CLICK HERE!

🌊 CLOSED FOR A PRIVATE EVENT🌊

Calypso VB will be closed to the public while we celebrate a private event. 

Thank you for understanding, and we look forward to welcoming you all back soon!🥂

🌊 CLOSED FOR A PRIVATE EVENT🌊

Calypso VB will be closed to the public while we celebrate a private event. 

Thank you for understanding, and we look forward to welcoming you all back soon!🥂

For the 5TH YEAR, we’re proud to host Cupid’s Undie Run — a one-of-a-kind run + party raising funds for NF research through the Children’s Tumor Foundation (CTF)! 

 Cupid’s Undie Run brings people together to run, celebrate, and raise money to help advance research, expand knowledge, and improve care for the NF community. 

Thanks to Undie Run heroes, nearly $30 MILLION has been raised since 2010 to help fight NF!  

The party starts at 12PM  

The run kicks off at 2PM  

The party keeps going until 4PM 

 We’re ready to make YEAR FIVE the biggest one yet! Grab your crew, register for the run, and come help us make a difference.   Registration is OPEN NOW! 

Click Here to Register for Cupids Undie Run 2027!