Events

Swap the couch for a lawn blanket and meet us under the open autumn sky at Chesapeake City Park! This year, we’re celebrating our 15th anniversary and going all out. From noon until sunset on one unforgettable Saturday, we’ll be pouring bold reds, crisp whites, blush rosés, and global stand-outs. Trade cramped tasting rooms for open-air elegance, where sommelier-level pours are served in real glassware. Two live bands will roll out feel-good sets from the main stage, keeping the groove alive from first pour to last call. The afternoon is fueled by chef-driven bites, artisan desserts, and Insta-ready food trucks, all leading up to golden-hour clinks that wrap up just as the sun dips. Plus, don’t forget to stop by our tent to register to win various prizes, including tickets to Busch Gardens and Haunted Hunt Club Farm!

Your ticket unlocks unlimited sips from over 20 of Virginia’s top wineries. But the adventure doesn’t stop there—passport-hop through our new International Wine Village for pours from every continent. If wine isn’t your speed, don’t worry; we’ll also have a craft beer garden on site. Theme outfits always rule the park, so feel free to dress it up and get festive, but “come-as-you-are” is always welcome. Mark your calendar for a celebration of wine, food, and music that you won’t want to miss!

Ready to join the celebration? Click here for more information.

Celebrate the best of Portsmouth at the first-ever High Street Fest! Join us on October 18 from 12 pm to 5 pm at High & Court Streets for a day of high-energy fun. This is your chance to get out and enjoy a great day with friends, family, and neighbors!

You won’t want to miss the live music stages and an all-day market with over 60 vendors. You can shop from local artisans and grab a bite to eat from the best local eateries. There’s fun for everyone, so come on down! We’ll see you there!

Click here to learn more.

Are you ready for a Ghouling Good Time?!

Get ready for Ghent’s largest Halloween street party and costume contest… Masquerade in Ghent!

Pre-Judging for Costume Contest: 6:00pm
Parade: 6:30pm

After the parade, get ready for a monster mash with live music. Plus, there will be activities for kids, refreshments and adult beverages.

Masquerade in Ghent is free and open to the public. Ample parking can be found along the streets and parking lots. Don’t miss the frightfully, fun-tastic time at this year’s Masquerade in Ghent!

Masquerade in Ghent is proudly presented by the Ghent Business Association.