Top Things To Do in Virginia Beach in May

things to do in virginia beach may

Last modified: March 23, 2018

Looking for things to do in Virginia Beach in May? Here's our list of the top events in our beach city!

Keep reading to see what good times are ahead of us for May 2018 at the beach.

12th Annual Virginia Spring Wine Festival

First wine festival up is the 12th Annual Virginia Spring Wine Festival. This event will take place the first weekend of May, which will be May 5th until May 6th. There will be over 25 local wineries at this wine festival at Town Point Park! Town Point Park is located in Downtown Norfolk, which is only a short drive from Virginia Beach. The short drive here will obviously be so worth it! You can’t beat this wine festival if you love Virginia wines. Wineries from all over the state of Virginia will be in attendance and they are bring their best wines to share. The hours of this event are from 11:00 AM- 6:00 PM on both days.

Monsters on The Beach

If monster trucks are your thing, you won't want to miss this extremely popular Virginia Beach event! Monsters on The Beach is one of the only events in the country that will have you viewing monster trucks in an unlikely arena... the beach. This thrilling Virginia Beach event will take place on May 11th through May 13th on 6th Street at the Boardwalk/Oceanfront. There will be bleachers for the spectators. Monsters on The Beach also gives you the chance to take a ride in a monster truck! Get all the info on this favorite event here.

Neptune's International Spring Wine Fest

The second wine event happening in Virginia beach in May is the  International Spring Wine Fest! Unlike the first wine event of the month, this one will include wines from all over the world. Wines from countries like Chile, Argentina, Italy, New Zealand, and of course France will all be available for sampling and/or purchase! This is an extraordinary day for people who love wine because they can sample so many at one place! The venue of the International Spring Wine Fest is Neptune's Park at the Virginia Beach oceanfront (located at 31st Street). May 12th is the date of this Virginia Beach wine festival!

Beach Music Cruise-In

Check out the hottest of hot rods and most stylish vintage cars around! The Beach Music Cruise-In on Friday, May 18th through Sunday, May 20th will showcase an array of classic automobiles on the Virginia Beach boardwalk. Watch the boardwalk be transformed into a version of Route 66. There will be oldies style music, cars, and entertainment. The car show will be happening all day throughout the weekend. This family-friendly thing to do is free and open to the public. See the list of live performers here!


This family-friendly event invites all truck lovers to gather on Saturday, May 19th at the Princess Anne Recreation Center. You will be able to touch awesome tough trucks like the local fire department's Monster Truck, dump truck, police car, street sweepers, and more! There will be more fun included like a DJ, face painting, and arts and crafts. This is a free event and is open to the public. The Touch-A-Truck event starts at 1:00 pm and ends at 3:00 pm. 

Tidewater Comicon

Cosplay enthusiasts have a blast at the Tidewater Comicon. This favorite thing to do for comic lovers will take place at the Virginia Beach Convention Center. This venue is perfect for the Tidewater Comicon because it is a large ordeal. People dress like their favorite cartoon comic book character. People really take their costume seriously here- and for good reason! There is a costume contest for all who enter. This is a great place to meet others who share the same interests as you. This popular VA Beach event is going to take place May 12-13 all day during both days.

Virginia Beer Festival

Like the first event listed, this Virginia Beer Festival is also going to be held at the Town Point Park in Norfolk, VA. Just a short trip away from the beach (roughly 20 minutes), Town Point Park invites all beer lovers to celebrate good beer on Saturday, May 19th. The Virginia Beer Festival offers beer tastings from local beers, regional beers, and international beers. This is a great place to come if you are looking to sample many beers at once in search of a new favorite! This special beer fest was rated "one of the best beers festivals in the country" by USA Today. Click here to get the times of this famous event.

Pungo Strawberry Festival

Next up is America’s favorite Strawberry Festival! The annual Pungo Strawberry Festival will take place during the last weekend in May, with the dates of May 25-27th. This year will be the 34th year that the Strawberry Festival will be celebrated! People LOVE this event and travel from all over the region to attend. This is one of Virginia’s favorite festivals. There are so many things to buy here, and not just strawberry related! Although, you can buy just about anything strawberry flavored here. Bring the kids for this event for carnival rides and petting zoo areas. There is something for everyone at this famous festival. This festival is free and open to the public.

Salute to Summer

The event that concludes the month of May is the Salute To Summer. Located on the Boardwalk at the Oceanfront, this concert series is dedicated to the men and women who serve our country! This year's Salute to Summer includes live performers that everyone can enjoy. There will be local talents as well as nationally recognized bands. Salute To Summer is a great way to kick off the summer all while celebrating the brave men and women who serve the USA. The dates of this event are May 25-27th. 

There are so many events that you don't want to miss while spending your vacation in VA Beach! Look for more events on the events page on our website. There are new events being added everyday. So make sure to keep coming back!

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Rachel Jones

Rachel Jones is a writer, photographer, and social media expert. She is a graduate of Old Dominion University. She has been working with since 2012.

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