Here are 5 of the top events happening around Hampton Roads in May 2026, based on confirmed event calendars, scale, and local popularity:
🍷 1. Spring Town Point Virginia Wine Festival
📍 Norfolk | May 2–3, 2026
One of the region’s biggest spring festivals. Expect 200+ Virginia wines, live music, food vendors, and waterfront views at Town Point Park. It’s consistently ranked among the top wine festivals in the country.
🎶 2. Beachy Music Weekend
📍 Virginia Beach Oceanfront | May 8–9, 2026
Free outdoor concerts right on the boardwalk featuring beach music bands and tribute acts. A classic kickoff to the summer vibe in Virginia Beach.
🚛 3. Pungo Offroad Monsters on the Beach
📍 Virginia Beach Oceanfront | May 15–17, 2026
Monster trucks on the sand. This is one of the most unique events in the region—high-energy, loud, and very family-friendly.
🎭 4. Tidewater Comicon
📍 Virginia Beach Convention Center | May 16–17, 2026
A major pop culture convention with comics, cosplay, celebrity guests, and gaming. Draws thousands across Hampton Roads every year.
🇺🇸 5. Memorial Day Weekend Salute to Summer
📍 Virginia Beach Oceanfront | May 22–25, 2026
Marks the unofficial start of summer with live music, military tributes, and beach events across the oceanfront.
Bonus (if you want more variety)
Atlantic Coast Kite Festival – colorful, family-friendly (May 2–3)
Bayou Bon Vivant Cajun Music & Food Festival – food + live Cajun music (mid-May)