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Top Things To Do in Virginia Beach in May

things to do in virginia beach may

Last modified: March 21, 2019

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.

13th Annual Virginia Spring Wine Festival

Happening Saturday and Sunday, May 4 - 5, 2019.

First wine festival up is the 13th Annual Virginia Spring Wine Festival. This event will take place the first weekend of May, which will be May 4th and May 5th. 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, though wine sampling does end at 4:00 pm on both days.

Monsters on The Beach

Happening Friday through Sunday, May 17 - 19, 2019.

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 17th through May 19th 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

Happening Saturday, May 11, 2019.

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).

Beach Music Cruise-In

Happening Friday through Sunday, May 10 - 12, 2019.

Check out the hottest of hot rods and most stylish vintage cars around! The Beach Music Cruise-In 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!


Happening Saturday, May 11, 2019.

This family-friendly event invites all truck lovers to gather at Williams Farm Recreation Center: 5252 Learning Circle, Virginia Beach, VA 23462.

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. Low sensory hour from noon - 1:00 pm.

Tidewater Comicon

Happening Saturday and Sunday, May 18 - 19, 2019.

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 will take place the weekend of the 18th and will last all day during both days.

Pungo Strawberry Festival

Happening Saturday and Sunday, May 25 - 26, 2019.

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 25-26th. This year will be the 36th year that the Strawberry Festival will be celebrated! People adore 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

Happening Friday through Sunday, May 24 - 26, 2019.

Towards the end of the 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. 

Patriotic Festival 

Happening Friday through Sunday, May 31 - June 2, 2019. 

The event that concludes the month of May and brings in the month of June is the Patriotic Festival. There's so much fun to have at this annual festival at the oceanfront! Of course there is music, which brings thousands of people to this fun event. There is also a "military zone", mobile tours, and other activities. There will be appearances by the US Marines, Newport Shipbuilders, USO Military Expo, US Air Force Performance Lab, Military Vehicle Display, and much more. 

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.