Fall Fun in Virginia Beach

As the muggy summer heat fades and the coastal air turns crisp, autumn settles into Virginia Beach with a charm that is hard to match. Fall here brings the absolute best of coastal living: uncrowded beaches, comfortable outdoor weather, and a calendar packed with community traditions.

We consider this season the sweet spot for getting out and exploring our city. From oceanfront art shows and wine tastings to farm outings and Oktoberfest celebrations, here is your essential guide to fall fun across Virginia Beach!

Oceanfront Culture & Wine Tasting

The oceanfront completely transforms in autumn, serving as the backdrop for the season's premier outdoor gatherings. First up, the Neptune Festival’s Wine Fest brings regional flavor directly to 31st Street Park. It is an awesome afternoon where you can sample vintages from top Virginia wineries, meet the winemakers, and enjoy live music with unobstructed ocean views. Later in September, make plans to visit for the Neptune Festival Boardwalk Weekend, stretching across more than 30 blocks! The festival features the International Sandsculpting Championship, 200+ artisan booths, live music stages, and the Grand Parade.  

In October, Virginia MOCA’s Boardwalk Art Show returns for its 70th year, lining the oceanfront from 24th to 37th Streets. Browsing original fine art, photography, and hand-crafted sculpture while listening to the surf makes for one of the most refreshing weekend walks of the year.

Seasonal Farm Fun & Family Outings

If your autumn checklist includes pumpkin patches and hayrides, Hunt Club Farm’s Harvest Fair remains the ultimate local destination. Running through early November, this seasonal favorite offers something for every age—from a sprawling pumpkin patch and tree-walk adventures to a hands-on petting farm featuring mini Highland cows. It is a classic tradition for local families looking to spend a crisp afternoon outdoors. For a great community celebration, Virginia Beach Parks & Recreation hosts the Autumn in the Air Festival at Mount Trashmore Park. This family-centered event fills the park with live folk and Americana music, a local craft vendor market, petting zoos, pumpkin bowling, and a stacked lineup of food trucks.

Craft Brews & Culinary Showcases

Fall wouldn't be complete without a proper Oktoberfest, and New Realm Brewing Co. delivers high energy on Craft Lane. Get ready for classic German-style brews, live music, stein-hoisting competitions, family games, and the hugely popular dachshund races.

Food lovers can also look forward to the 2nd Annual Taste of Virginia, a premier culinary showcase bringing together regional chefs, craft beverage producers, and local food artisans to sample farm-to-table dishes and coastal specialties. To top off the season's food lineup, Mount Trashmore Park hosts the Hampton Roads Black Food Festival. This vibrant, family-friendly gathering celebrates Black food culture and entrepreneurship, bringing together dozens of Black-owned food trucks, local restaurants, live DJs, line dancing, and community entertainment