Camryn Limousine

Central Virginia & Charlottesville Wine Tours & Limousine Service

Charlottesville Winery Event Calendar

 
Charlottesville is home to some of the most scenic and award-winning wineries in Virginia, and there’s always something happening—from live music and seasonal festivals to private tastings and vineyard dinners. This Charlottesville winery event calendar is updated regularly to help you discover the best wine events happening this week, this month, and throughout the year. Whether you’re planning a weekend getaway, a birthday celebration, or a group wine tour, this guide makes it easy to find events and plan the perfect experience.
 

Group of people enjoying Central Virginia winery event on a Charlottesville wine tour.

Camryn Limousine: Charlottesville’s Top Choice for Custom Wine Tours & Luxury Transportation

 

Upcoming Winery Events in the Charlottesville Area

 

May 2026

 

A rainbow above the Hardware Hills Vineyard and tasting room
Hardware Hills Vineyard

 

June 2026

 

Two glasses of wine featured on the tour, next to a plate of food and a charcuterie board
Pippin Hill Farm

 

July 2026

 

Planning Transportation for Winery Events

Getting to and between wineries in Charlottesville can be tricky—especially if you’re planning to visit multiple locations or attend events with alcohol. Many vineyards are spread out across the countryside, and rideshare availability can be limited late in the evening.

A private car or limo service allows your group to:

-Travel safely between wineries
-Stay on schedule for timed events and reservations
-Enjoy the experience without worrying about parking or driving

If you’re attending multiple events or planning a full-day wine tour, arranging transportation in advance can make a big difference.
 

When to Visit Charlottesville Wineries for Events

Winery events happen year-round, but some seasons are especially popular:

–Spring (April–June): Blooming vineyards and the start of event season
–Summer (July–August): Live music, outdoor tastings, and longer days
–Fall (September–November): Peak foliage and harvest festivals (busiest time)
–Winter (December–March): Smaller, more intimate events and indoor tastings

For the best experience, plan ahead during peak weekends, especially in the fall.
 

FAQs About Charlottesville Winery Events

What are the best wineries in Charlottesville for events?
Some of the most popular include King Family Vineyards, Veritas Vineyard, and Pippin Hill, all of which host regular events throughout the year.

Do I need reservations for winery events?
Many events require tickets or reservations, especially on weekends. It’s best to check ahead and book early.

Are there transportation options for winery tours?
Yes—private transportation services, shuttles, and limo services are popular options for groups visiting multiple wineries.

What should I wear to a winery event?
Most events are casual to semi-casual. Comfortable shoes are recommended, especially for outdoor venues. When in doubt check the winery’s website or call for more information.
 

Plan Your Charlottesville Winery Experience

Whether you’re visiting for a weekend or organizing a special event, Charlottesville’s wineries offer one of the best wine country experiences on the East Coast. Use this calendar to stay updated on upcoming events and start planning your trip.