Things to Do in Hampton Roads This Weekend and Beyond

Naval Air Station Oceana, Virginia Beach

Headlined by the U.S. Navy Blue Angels, plus F-22 Raptor and F-35C Lightning II demo teams, with a "Celebrating 250 Years of America" theme. Open to the public; visitors 18 and older must show a physical photo ID to enter the base.

Naval Station Norfolk, Norfolk

Ship tours, static aircraft displays, live entertainment, military demonstrations, a children’s play area, and a chili cook-off on the world’s largest naval station. A great way to get an up-close look at the Navy family in Hampton Roads.

Virginia Beach Oceanfront boardwalk (1st-35th Streets)

The 52nd annual Neptune Festival brings live music, arts and crafters, a kids’ Poseidon’s Playground at 17th Street Park, and the International Sandsculpting Championship (Sept 25-Oct 4) at 24th Street. The biggest weekend of the year at the oceanfront, and it is free to walk the whole thing.

Rudee Loop, Virginia Beach Oceanfront

A free, family-friendly celebration of Filipino and Filipino-American culture with live music, cultural performances, dance, food, and vendors at Rudee Loop.

14th Street Stage, Virginia Beach Oceanfront

A free beachfront concert series on the 14th Street stage. Bring a chair, grab something to eat nearby, and enjoy live local music with the sound of the Atlantic behind the band.

Hunt Club Farm, Virginia Beach

Pumpkin patch, farm tours, pony rides, and carnival rides at a longtime Virginia Beach farm staple. A classic fall outing for the kids (and the kid in you).

Town Point Park, Downtown Norfolk

A Nashville-themed, one-day festival of hot chicken, drinks, and country music on the downtown Norfolk waterfront. A fun, free night out in the heart of the city.

Town Point Park, Downtown Norfolk

Virginia’s biggest Caribbean celebration, with music, food, dance, and culture hosted by the Virginia Caribbean American Cultural Association. The Friday kickoff is ticketed; the Saturday festival runs 12-9pm.

Town Point Park, Downtown Norfolk

A long-running festival built for kids, with interactive activities, entertainment, and hands-on fun along the downtown waterfront. One of the most family-friendly days on the Norfolk calendar.

Town Point Park, Downtown Norfolk

The 38th annual Fall Wine Festival features 25+ Virginia wineries and 200+ wines along the waterfront. An adult-friendly day of local pours, food, and live music.

Chesapeake (city event)

A citywide day celebrating trees with tree-climbing demonstrations, a butterfly exhibit, sawmill demos, and food trucks. Free, outdoors, and good for the whole family.

Portside Park, Portsmouth

A bike ride and walk paired with a music festival along the Portsmouth waterfront. Good tunes, local flavor, and an easy way to spend a September weekend downtown.

Portsmouth City Park

Games, crafts, face painting, bounce houses, hayrides, a petting zoo, a hay maze, food trucks, and live entertainment at Portsmouth City Park. Built for families, and free.

Festival Park, Downtown Portsmouth waterfront

Wine vendors and live entertainment along the downtown Portsmouth waterfront. A relaxed fall afternoon with a harbor view.

Suffolk Executive Airport, 1410 Airport Rd, Suffolk

The Peanut Fest is one of Hampton Roads’ most anticipated fall traditions, with carnival rides, live music, food, and entertainment at the Suffolk Executive Airport. Thursday, Oct 8, is Carload Night. A hometown favorite for nearly half a century.