Annual Events in Chesapeake Virginia include arts festivals, outdoor adventures, food celebrations, concerts, historic commemorations, and holiday traditions. Chesapeake City Park and the Great Bridge area host many of the city’s recurring community gatherings.
The Chesapeake Spring Arts Festival fills Chesapeake City Park with more than 170 artists and crafters. Live music, food, craft beverages, and children’s activities accompany the juried art displays.
Paddle for the Border takes kayakers and canoeists along the historic Dismal Swamp Canal. The 7.5-mile journey finishes in Chesapeake with food, music, and a community celebration.
The Chesapeake Jubilee is a longstanding summer tradition featuring carnival rides, games, food, music, and fireworks. The celebration began in 1983 as part of Chesapeake’s 20th birthday.
KayaXpedition celebrates paddling at Oak Grove Park with kayaks, canoes, music, and food. Visitors can bring their own watercraft or use available equipment during scheduled sessions.
The Chesapeake Farmers’ Market runs seasonally at Chesapeake City Park. Local farmers offer produce, flowers, honey, eggs, meats, preserves, and other locally grown products.
Celebrate Freedom brings patriotic music, children’s activities, food vendors, and fireworks to Chesapeake City Park. The annual celebration traditionally takes place just before Independence Day.
The South Norfolk July 4 Parade and Picnic is an annual patriotic tradition at Lakeside Park. The celebration combines a community parade with outdoor activities and neighborhood festivities.
The Chesapeake Criterium brings fast-paced bicycle racing to the Municipal Center. Additionally, the Teeuwen Memorial Time Trial continues the cycling weekend at Deep Creek Park.
Symphony Under the Stars presents the Virginia Symphony Orchestra at Chesapeake City Park. Families can bring chairs or blankets and enjoy a free evening concert with food trucks nearby.
The Chesapeake Virginia Wine Festival brings Virginia wineries, food, and live entertainment to Chesapeake City Park. Proceeds from the annual Rotary Club event support community charities.
Chesapeake Restaurant Week showcases local restaurants through special fixed-price menus. Participating locations offer breakfast, lunch, or dinner selections during the fall event.
The Chesapeake Jubilee Fall Craft Market brings more than 100 vendors to Chesapeake City Park. Shoppers can browse crafts and gifts while families enjoy food and children’s activities.
The Holiday Craft Show opens Chesapeake’s seasonal shopping calendar at the Chesapeake Conference Center. More than 90 crafters offer handmade gifts, decorations, and specialty items.
Deck the Hall transforms the City Hall grounds into a drive-through holiday light display. On selected evenings, Fa La La Land adds entertainment, food trucks, activities, and visits with Santa.
The Chesapeake Rotary Christmas Parade is a December tradition stretching back more than four decades. Floats, community organizations, performers, and holiday displays travel through the Great Bridge area.
The annual Battle of Great Bridge weekend commemorates the important Revolutionary War victory of 1775. Reenactments, military encampments, artisans, lectures, and children’s activities bring the history to life.
Chesapeake offers recurring events throughout every season. Arts, outdoor recreation, food, history, music, and holiday celebrations provide many ways to experience the city.
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