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Top 8 Festivals and Events in Chesapeake

The Jack Rabbit Team | October 20, 2023 @ 12:00 AM

Chesapeake, Virginia, is a city of about 250,000 residents, and with a quarter of a million people living in the area, there’s always something to do. Today, we want to focus on the city's festivals and events, from its music and arts festivals to its food and heritage celebrations. Let’s explore some of the top events you won't want, whether you live in Chesapeake or you’re a local resident.

  • Chesapeake Jubilee

A beloved annual event held at Chesapeake City Park, the Chesapeake Jubilee takes place in May every year and is a celebration of community, music, and delicious food. You, your family, and your friends can enjoy live music performances by nationally recognized artists, food vendors offering mouthwatering meals and treats, carnival rides, and other fun activities.

  • Chesapeake Bay Wine Festival

Also held in City Park is the Chesapeake Bay Wine Festival, a two-day event featuring a wide selection of wines from local and far-off wineries. Visitors can sample wines and discover new favorites while enjoying live music and food.

  • Chesapeake Spring Arts Festival

Celebrating the local arts scene, the Chesapeake Spring Arts Festival brings together talented artists, crafters, and performers for a weekend of creativity and inspiration. You’ll want to check out the visual art displays, live art demonstrations, interactive workshops, and performances that make this event so special. From the perspective of the participating artists, this festival provides a platform to showcase their work and engage with the community.

  • Chesapeake Restaurant Week

Chesapeake Restaurant Week is a culinary extravaganza that highlights the city's diverse dining scene. It’s a wonderful time to expand your knowledge of what dining experiences Chesapeake has to offer. You’ll likely find a few new places you’ll want to eat at during the rest of the year. Participating restaurants offer special menus and promotions, so locals and visitors get to try new dishes as well as old favorites.

  • Revolutionary Beer Festival

If you're interested in local history and you love beer, then Revolutionary Beer Fest in Chesapeake, VA is a must-attend annual celebration. The event brings together local craft breweries which showcase their finest brews while paying homage to the city's rich Revolutionary War heritage. Visitors will also enjoy live music and the enticing aroma, delicious meals from food vendors, and, of course, locally brewed beer. People of all ages come together here to celebrate and enjoy the vibrant community spirit.

  • Chesapeake Fall Festival

As autumn colors sweep through Chesapeake, the city comes alive with the Chesapeake Fall Festival. This family-friendly event features hayrides, pumpkin patches, live music, corn mazes, arts and crafts vendors, and delicious seasonal treats. It's the perfect opportunity to embrace the fall spirit and create lasting memories with loved ones.

  • Chesapeake Farmers’ Market

Looking for fresh produce, local products, and a welcoming atmosphere? Then visit the Chesapeake Farmers' Market at City Park, where local growers offer seasonal fruits and vegetables, artisanal goods, baked goods, and much more. It's a great place to support local farmers, connect with the community, and enjoy the vibrant market atmosphere.

  • Chesapeake Holiday Craft Show

When winter rolls around, so does the Chesapeake Holiday Craft Show, where artisans and crafters showcase their unique creations. Here, you can purchase handmade gifts, holiday decor, jewelry, clothing, and much more. In Chesapeake, the perfect place to find one-of-a-kind gifts for your loved ones. Visitors also enjoy live entertainment, fare from food vendors, and interactive activities for children. We consider this a must-visit event during the holiday season.

Whether you're a local resident or just visiting Chesapeake, these events will allow you to  immerse yourself in the local culture, connect with the community, and create lasting memories. When planning your trip or looking for local experiences, be sure to check the Events in Chesapeake website for the most up-to-date information on upcoming festivals and events. 

If you live in Chesapeake and need a place to store your surfboards, off-season clothes, or business inventory, then consider us at Jack Rabbit Storage. And, if you have any questions, feel free to email or call us. We’re always happy to help.

The Jack Rabbit Team
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