Labor Day WeekendEvents in Annapolis 2026

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

Three days off in Annapolis leave room for whatever kind of weekend you're after. Parades and festivals hold the daytime, concerts and parties pick things up after dark, and live music runs through the city all weekend long. With the family along, a food festival or an afternoon outdoors usually settles the question without much debate. Want the long weekend to feel like an actual break? A getaway close by will handle that. See what's on across Annapolis this Labor Day 2026 and book your tickets before they're gone.