Virginia Beach Halloween Food, Drink, and Parties 2026

Experience the 28th Annual Fall Wine Festival at Virginia Beach Oceanfront. This event offers unlimited wine tastings from over 60 Virginia vineyards, accompanied by live music and delicious food truck fare. New in 2025, zero-proof wine and seltzer options will...

Get ready for a spooktacular two-day Halloween Bar Crawl in Virginia Beach! This event spans October 31st and November 1st, offering a thrilling adventure through the city's nightlife. Attendees receive a custom badge with vouchers for drinks and access to...

Experience the Virginia Aquarium after dark during Sharks After Dark, a special adults-only event for ages 21 and up. Each month features a unique theme, with October's event embracing D&D and Halloween. Enjoy a cocktail while exploring the fascinating marine...

Dare to enter The Shack's Treasure Island Terror, a cursed beachside oasis transformed into a pirate's lair this Halloween. Navigate through eerie sea spirits and swashbuckling revelry. With two nights of music, rum, and legendary costume contests offering $1,000 in...

Gather your team for a thrilling Halloween Puzzle Night at Virginia Beach Winery. Challenge yourselves to complete a spooky puzzle within the fastest time, aiming to beat the record of 54 minutes. Your ticket includes a complimentary glass of wine,...

Uncork a good time at the 15th annual Chesapeake Virginia Wine Festival. Sample unlimited pours from over 20 Virginia wineries and explore international selections. Enjoy live music and chef-driven bites in a festive outdoor setting. This event supports local charities,...

Enter a world where fairytales take a wicked turn at Twisted Fairytales Halloween. This epic event features a massive costume contest with up to $10,000 in cash and prizes, alongside immersive live entertainment including multiple DJs, karaoke, and a silent...

Experience the 37th Annual Town Point Virginia Fall Wine Festival, a premier event along the Downtown Norfolk Waterfront. Over 25 of Virginia's top wineries will be present, offering tastings of more than 200 fine wines. Enjoy live entertainment, browse artisan...

Experience the best of fall at the Portsmouth Fall Wine and Music Festival. This adult-only event features tastings from over 200 fine wines, live music, and a curated selection of vendors. Held at the Atlantic Pavilion Festival Park on the...

Get ready for a spooktacular adult-only Halloween party at the Monster Mash Ball! Don your most creative costume and hit the dance floor to the beats of a live DJ or band. Enjoy themed cocktails, delicious hors d’oeuvres, and a...

Experience the chilling history and spectral residents of Colonial Williamsburg on this adults-only haunted pub crawl. Guides share terrifying tales and local legends as you visit historic bars and eerie locations, enjoying adult beverages along the way. It's a tipsy...