Classic Antique Car at the fall festival and car show in Chesapeake, VA
Season & Holiday Events

Seasonal and Holiday Events

Whether you’re in town for a holiday or just want to get a feel for the city’s take on the seasons, there are plenty of seasonal and holiday events in Chesapeake to keep you busy year-round.


During summer, Thursdays in Chesapeake are for music lovers. From 5:30 to 8 p.m., head down to the Towne Place at Greenbrier to listen to the free Summer Concert Series. A range of musical acts will perform everything from reggae to rock and roll. Enjoy food and drinks on-site as you dance the night away or sit and groove to your favorite tunes.

Let freedom ring in July by checking out the Celebrate Freedom Concert and Fireworks at Chesapeake City Park. Beginning at 5 p.m., guests can delight in food, fun, and tons of children’s activities. Afterwards, listen to music from the U.S. Fleet Forces Band before settling in on the lawn for an impressive fireworks display.

Another way to celebrate the Fourth of July in Hampton Roads is to head to the Annual South Norfolk Parade & Picnic in the Park. At this free event in Lakeside Park, watch live entertainment, take a paddleboat ride, and chow down on delicious snacks.


For just over a month each fall, Bergey’s Corn Maze opens to give visitors a chance to wind their way through the fields of maize. For $10 a person (children under 4 are free), spend a few hours on the farm enjoying wagon rides, a petting zoo, and tons of terrific photo opportunities. Pumpkins are available to complete your autumn adventure.

Featuring more than 100 vendors, including a Kidz Korner complete with activities for the youngest guests, Chesapeake Jubilee Fall Craft Market is a great place to spend the day doing some holiday shopping, all while supporting local businesses. It all takes place at Chesapeake City Park.

Not done shopping? Spend your weekend at the Holiday Craft Show. Taking place at the Chesapeake Conference Center, you can purchase handmade decorations and one-of-a-kind gifts, from bedazzled hair ties to whittled walking sticks, all from local crafters. Santa will be ready and waiting for toy-requests and photos.


For over three decades, the Chesapeake Christmas Parade has filled the streets with dancers, floats, magic, and tons of holiday cheer. Line up along the route through the heart of Chesapeake to catch a glimpse of elves, reindeer, and Santa himself.

Held annually by the National Audubon Society, Chesapeake’s Christmas Bird Count is the ideal way to see some of the over 200 species of birds flying south for the winter as they migrate across Virginia. Free to participate, this holiday season event is a wonderful way to celebrate nature with family and friends.

A hallmark of winter in Chesapeake is the free Holiday Brass Concert from the Virginia Symphony Orchestra. Catch the holiday spirit with this performance from the brass section of the symphony featuring seasonal classics in styles ranging from traditional to contemporary.


Get out and enjoy springtime in Chesapeake with the Dismal Swamp Stomp. The annual half marathon and 5K is a family-friendly event that takes participants through the scenic greenery of the Great Dismal Swamp

Spring is the time for the Chesapeake Eggstravaganza. This yearly celebration for children under 8 takes place at Chesapeake City Park from 10 a.m. to 1 p.m. Start with pony rides or have your face painted before participating in one of two family egg hunts. Once you’ve gathered your eggs, Peter Cottontail will be there for hugs and photos.

Another sure sign that spring is here is the arrival of the Chesapeake Jubilee. For several days in May, come to Chesapeake City Park for a fair experience featuring tons of rides and games, fireworks, music and entertainment, arts and crafts, a Shrimp Feast, and, of course, plenty of food vendors.

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