As we step into May, Chesapeake offers a variety of events catering to diverse interests. Here are some highlights to mark on your calendar:
Bike Month
Throughout May, celebrate Bike Month by exploring over 12 miles of paved trails in Chesapeake. Enjoy family-friendly biking activities suitable for all ages. It’s a great opportunity to embrace the outdoors and promote a healthy lifestyle. For more details, visit the city’s official events page.
Paddle for the Border
On May 2, 2026, participate in the 21st annual Paddle for the Border event. This 7.5-mile paddle along the Dismal Swamp Canal starts in South Mills, North Carolina, and concludes in Chesapeake, Virginia. It’s a unique way to experience the region’s natural beauty. More information can be found on the city’s special events page.
Chesapeake Jubilee
From May 14 to 17, 2026, the Chesapeake Jubilee returns, offering a wide array of carnival rides, games, and live entertainment. Don’t miss the Annual Shrimp Feast on Thursday and the spectacular fireworks display on Saturday. The event takes place at 900 Greenbrier Parkway. For ticket information and a full schedule, visit the official Chesapeake Jubilee website.
The Gothic Market
On May 30, 2026, from 12:00 PM onwards, the Chesapeake Conference Center hosts The Gothic Market. This event features unique vendors, live music, and themed activities, catering to fans of gothic culture and alternative fashion. It’s an excellent opportunity to explore and support local artisans. More details are available on the event’s page.
These events showcase the vibrant community spirit of Chesapeake. Whether you’re a resident or a visitor, there’s something for everyone to enjoy this May.