May is when Hampton Roads really comes alive. The weather turns, the waterfront fills up, and suddenly every weekend has three things you want to do. I've lived here for over 20 years and May still surprises me with how much is going on. Whether you're a longtime local or just getting settled in the area, here's a look at what's happening across the region this month.
Festivals & Big Events
• **Spring Town Point Virginia Wine Festival** – May 2–3 | Town Point Park, Downtown Norfolk Waterfront: Kick off the month with a relaxed afternoon along the Norfolk waterfront sampling Virginia wines and enjoying the view. This is one of Norfolk Festevents' signature spring traditions and it draws a great crowd — the setting alone is worth the trip.
• **Atlantic Coast Kite Festival** – May 4–5 | Virginia Beach Oceanfront: A genuinely fun, all-ages event on the Virginia Beach waterfront celebrating the art of kite flying. Between the colorful displays and the ocean breeze, it's a perfect early-May outing for families.
• **Bayou Bon Vivant Cajun Music & Food Festival** – May 15–17 | Town Point Park, Downtown Norfolk Waterfront: Three days of live Cajun and zydeco music, authentic Louisiana food, and good energy along the Norfolk waterfront. This one always brings a festive atmosphere — it's hard not to have a good time.
• **Patriotic Festival 2026 – Country Weekend** – May 22–24 | Norfolk Scope Arena: One of the region's flagship Memorial Day weekend events, this three-day country music festival at Norfolk Scope is a big deal. Multiple acts across all three days with pre-show activities — it draws crowds from all over Hampton Roads and beyond.
• **Jackalope Festival** – May 29–31 | Virginia Beach: A creative, eclectic end-of-May festival featuring arts, crafts, live music, and unique vendors in Virginia Beach. It's the kind of event that feels genuinely community-driven and always has something unexpected to discover.
Live Music & Entertainment
• **Beach Music Weekend** – May 10–11 | 31st Street Park, Virginia Beach Oceanfront: Free live beach music and shag dancing at 31st Street Park, featuring acts like Band of Oz, The Original Rhondels, North Tower, and several others. It celebrates a classic East Coast tradition and it doesn't cost a thing — hard to beat.
• **Country for Kids 2026 Concert featuring Joe Nichols** – May 2026 (date TBD) | Hampton Roads Convention Center: This annual charity concert presented by TowneBank features country artist Joe Nichols and raises money for children's causes. With a silent auction, VIP areas, and a photo booth, it's a great night out for a good cause — check the official Country for Kids website for tickets and full details.
Family, Community & Culture
• **Peninsula Community College Earth Day Event** – May 1 | Peninsula Community College, Newport News (10 a.m.–3 p.m.): A free family event featuring live animal encounters, live music, hands-on environmental activities, food trucks, and local vendors. It's a great way to start the month and get the kids engaged with something meaningful.
• **Hampton Mosaic Festival** – May 2026 (exact date TBD) | Hampton: A free community festival celebrating cultural diversity through music, storytelling, drumming, and dance from Indigenous, Asian, and other global traditions. Hampton does a wonderful job with inclusive community events and this one is a real reflection of that.
• **Hampton Roads Convention Center Community Fair** – May 16 | Hampton Roads Convention Center: A free public fair open to all, connecting community members with local organizations and family-friendly activities. Simple, welcoming, and free — worth a stop if you're in the area.
• **3rd Annual Spring Market on the Farm** – May 16 | Little Acre Farm, Suffolk (9 a.m.–3 p.m.): Now in its third year, this outdoor market at Little Acre Farm features local vendors, food, and farm animals for the whole family. It's the kind of Saturday morning that reminds you why Suffolk is such a special corner of this region.
Outdoor Markets & Weekly Staples
• **Yorktown Market Days – Vintage Market & Car Show** – May 9 | Yorktown Main Street (8 a.m.–12 p.m.): Browse antiques and vintage goods alongside classic cars on display in one of the most scenic historic settings in Hampton Roads. An early Saturday morning well spent.
• **Buckroe Beach Farmers Market** – Every Saturday (excluding May 30) | Buckroe Beach, Hampton (starting 9 a.m.): Fresh produce, baked goods, jarred goods, and crafts from local vendors right by the beach. It's a great weekly ritual and one of my personal favorites — there's just something right about shopping local with a water view.
Honestly, this is one of the things I love most about living and working in Hampton Roads — there is always something going on worth showing up for. It's one of the reasons my clients, once they get settled here, never want to leave.