Labor Day Weekend Eventsin Chesapeake 2026

Best Labor Day Parties, Concerts, Festivals & Things To Do in Chesapeake

Chesapeake has no trouble filling three days off, and Labor Day weekend puts plenty of it on the calendar at once. Parades and festivals run through the daytime, parties and concerts take over after dark, and live music shows up in venues across the city. Families can build the afternoon around a food festival or head outdoors and let the kids set the pace. Rather use the long weekend to get away instead? A short getaway is easy from here. See what's on across Chesapeake this Labor Day 2026 and book your tickets before they're gone.