If you’re looking for fun events in Chesapeake, VA, you won't want to miss the Chesapeake Jubilee, Chesapeake Wine Festival, and Chesapeake Rotary Christmas Parade. There's also the Celebrate Freedom Festival with fireworks and the Symphony Under the Stars featuring the Virginia Symphony Orchestra. Each event offers unique attractions, great food, and a warm community vibe. Stick around to discover more about these exciting gatherings and what they bring to the vibrant Chesapeake scene!
Chesapeake Jubilee
Have you ever experienced the excitement of the Chesapeake Jubilee? Held annually from May 16-18 at Chesapeake City Park, this family-friendly event attracts over 35,000 visitors. Originally celebrated as the city’s 20th birthday in 1983, it’s become a cherished tradition that marks the start of summer. You can enjoy a delicious shrimp feast, thrilling carnival rides, and an exciting BBQ competition. The livestock sale adds a unique touch, and various craft vendors showcase local talent. Don't miss the spectacular fireworks display by Zambelli Fireworks on Saturday, choreographed to music that’ll leave you in awe. This year, part of the event proceeds will go directly to benefit the community and youth development initiatives, as the Jubilee has celebrated the city’s 20th birthday since its inception. Plus, your participation helps support the City of Chesapeake Youth Scholarship Program, making it a worthwhile experience for everyone! Additionally, be sure to check out the Eggspedition event happening the following month, which encourages family participation and outdoor activity.
Chesapeake Wine Festival
After enjoying the lively atmosphere of the Chesapeake Jubilee, you can look forward to another fantastic event in the city—the Chesapeake Virginia Wine Festival. Held annually on the second Saturday in October at Chesapeake City Park, this festival features unlimited tastings from over 20 premier Virginia wineries. Enjoy live music by Lewis McGehee and Friends while browsing the Craft Beer Garden and local vendor offerings. This year, the festival is scheduled for Saturday, October 11, so remember to mark your calendars! Remember, this event is for adults aged 21 and older, so bring your ID. Safety is a priority, with security checks in place and accessible amenities throughout the park. This year's event aims to support local community charities, so grab your tickets early, and join in supporting local charities while savoring great wines! All ticket sales benefit Chesapeake Rotary Club charities, including the main focus on the Chesapeake Regional Healthcare 3D Mammography Van.
Chesapeake Rotary Christmas Parade
The Chesapeake Rotary Christmas Parade is a beloved annual tradition that brings the community together to celebrate the holiday season. Established over 40 years ago, this festive event features floats, musical groups, and vibrant light displays, creating a magical atmosphere. Scheduled for December 6, 2025, the parade kicks off at 6:00 PM, with preparations starting around 5:15 PM. To guarantee safety, roads close at 4:15 PM, and the Chesapeake Police Department enforces regulations to keep sidewalks clear. You’ll find food vendors and restrooms available along the route, enhancing your experience. The parade starts at Mount Pleasant Road and Battlefield Boulevard, so arrive early and enjoy this family-friendly event that embodies community spirit and holiday cheer!
Celebrate Freedom Festival
Following the holiday festivities, Chesapeake residents enthusiastically anticipate the Celebrate Freedom Festival, a vibrant celebration honoring America’s birthday. Set for July 3, 2025, at Chesapeake City Park, this family-friendly event is free for everyone. Paid parking opens at 4:00 PM for just $5 per vehicle, ensuring easy access. From 5:00 PM, enjoy children’s entertainment and delicious food from local trucks. The stage features live music from talented performers like the U.S. Fleet Forces Wind Ensemble. Don’t miss the spectacular fireworks display at 9:30 PM, courtesy of Pyrotecnico. Fireworks display will illuminate the sky following the evening performances. Remember to bring your own chairs or blankets for comfortable seating, and please leave tents and oversized umbrellas at home for everyone's safety. Additionally, attendees can find more information about the event through the city’s website navigation options. Join your community in celebrating together, as this festival continues the tradition of fostering community spirit just like the annual Chesapeake Jubilee does!
Symphony Under the Stars
Embracing the enchanting sounds of summer, Symphony Under the Stars invites you to an unforgettable evening of orchestral music in Chesapeake City Park. Scheduled for June 6, 2025, this annual free concert features the Virginia Symphony Orchestra on the Bagley Stage. Arrive early around 6:30 p.m. to secure convenient parking and enjoy food trucks offering diverse picnic options. Remember to bring your own chairs or blankets, as pop-up tents and oversized umbrellas aren’t allowed. The concert begins at approximately 8:15 p.m., providing a perfect backdrop for a summer night. No tickets are required, ensuring accessibility for everyone. For inquiries, contact Chesapeake Parks, Recreation and Tourism at (757) 382-6411. Enjoy a safe and family-friendly atmosphere as you celebrate music together!
So, whether you're indulging in local wines at the Chesapeake Wine Festival or enjoying the festive lights during the Rotary Christmas Parade, there's always something fun happening in Chesapeake. It’s funny how you can run into friends you haven't seen in ages at these events, right? You never know when a chance encounter will spark a great conversation or lead to a new adventure. Mark your calendar—these annual celebrations are not to be missed!
