Events

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, DJ 7-27, 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!

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 😎🍺

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 😎🏈

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!

MY PRECIOUSSSSS….. 

Wednesday, November 18th, we’re taking a trip to Middle-Earth for Lord of the Rings Trivia, hosted by Beach Trivia!

Prizes for the winning teams!

FREE TO PLAY!

$9.99 Smashburgers + Fries ALL NIGHT

Family Friendly Fun! 

Assemble the Fellowship and summon your inner Gandalf. 

You shall not pass up this one!

🌊 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!