Events

Thursdays every week

Get Twisted, Get Loud — It’s Karaoke Night!

Thursday nights at Calypso are anything but ordinary. Step up, grab the mic, and bring the house down with DJ Julz Gat! From singalongs to showstoppers, the crowd is here for it all.

Pro Tip: nothing pairs better with karaoke than a cold Twisted Tea in hand, grab one for just $4! 

Valentine’s is cute… but Galentine’s is where it’s at. 💕 Join us on Thursday, February 12th from 6p-8p for our first ever Galentine’s Paint & Sip, hosted by local favorite Paint the Town—a girls’ night designed for creativity, cocktails, and connection.

🎨 $45 includes all painting supplies for a 16x20 canvas you’ll take home 🍷 Add our $10 drink package and make it $55 total with two drink tickets included—because painting is better with a sip! Valid for a house beer, house wine or a featured paint night cocktail. Drink tickets expire night of the event, no shots, no doubles. 

✨ Beginner-friendly 💗 Perfect for friend groups 🎉 All the ladies’ night energy

🎟 Tickets available now

 🚨 Ticket cutoff: Tuesday, February 10th

Valentine’s is cute… but Galentine’s is where it’s at. 💕 Join us on Thursday, February 12th from 6p-8p for our first ever Galentine’s Paint & Sip, hosted by local favorite Paint the Town—a girls’ night designed for creativity, cocktails, and connection.

🎨 $45 includes all painting supplies for a 16x20 canvas you’ll take home 🍷 Add our $10 drink package and make it $55 total with two drink tickets included—because painting is better with a sip! Valid for a house beer, house wine or a featured paint night cocktail. Drink tickets expire night of the event, no shots, no doubles. 

✨ Beginner-friendly 💗 Perfect for friend groups 🎉 All the ladies’ night energy

🎟 Tickets available now 🚨 Ticket cutoff: Tuesday, February 10th

Whether you’re single, taken, or ready to mingle, everyone’s invited. Join us Friday, February 13th at 8PM for a Stoplight Party that brings the vibes. Get here & Grab your cup!

Green Cup Means Ready to mingle & Single 

Yellow Cup Means It’s complicated - Ask Me  

Red Cup Means Taken 

Happy Hour specials run until 9PM, then it’s full-on Friday night energy with drinks flowing and the party going strong. No labels, no pressure — just good vibes.

Once again, the Virginia Beach Oceanfront is about to get bold! We’re proud to host Cupid’s Undie Run at Calypso Bar & Grill on

Saturday, February 21st

—and trust us when we say this is one of the most unforgettable events of the year.

From

12PM–4PM

, the party is on. The run kicks off at 2PM, but the vibes start early with drink specials, costumes, music, and hundreds of runners showing up in their undies (or whatever makes them feel unstoppable) for an incredible cause.

Cupid’s Undie Run raises awareness and funds critical research for Neurofibromatosis (NF)

—a group of genetic conditions that cause tumors to grow on nerves throughout the body and can lead to blindness, deafness, chronic pain, learning challenges, cancer, and more. By running loud, proud, and a little exposed, we’re proving that nothing will stop us from pushing toward a cure.

This is a 21+ event, and the whole party lives right here at Calypso.

 Register now, grab your boldest look, and join us for an afternoon that’s equal parts wild, meaningful, and unforgettable.