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Events and Things to do in Annapolis, MD this weekend

Looking for things to do in Annapolis this weekend? Explore our real-time listings for the best concerts, nightlife, and food and drink experiences. From seasonal festivals and comedy shows to free activities, find your next plan with our constantly updated feed of Annapolis's most popular events.

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Things to do around Annapolis

Trends in Annapolis

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Frequently asked questions about Annapolis

What are the best events to attend this weekend in Annapolis?

The best events to attend this weekend in Annapolis include concerts, nightlife experiences, seasonal events, food and drink tastings, and live entertainment happening across the city. According to Eventbrite, some of the best events this weekend include:
  • SIP, PUFF AND BODY PAINT @ Baltimore's BEST Art Gallery!
  • Drag Queen Sip and Paint Baltimore The Drag Queen Paint experience
  • Yoni Yoga Wellness Experience
  • Baltimore |EVERYTHING EYEBROW™ Certification| 8 Methods|School of Glamology

    • Which events are currently trending in Annapolis?

    Trending weekend events in Annapolis often reflect seasonal moments, nightlife demand, and popular neighborhoods, including concerts, parties, and special themed events. The trending searches this month in Annapolis are:
  • mothers day
  • kentucky derby maryland
  • anne arundel county
  • memorial day

    • Which events are coming up in Annapolis this weekend?

    In addition to what's happening right now, there are many upcoming weekend events in Annapolis, including live shows, parties, food experiences, and limited-time events. Discover upcoming weekend events you won't want to miss:
  • Art Unplugged | Open Paint Session
  • Werkin Girls Drag Queen Show Baltimore - An Unforgettable Drag Show
  • Foodies + New Friends: Baltimore Dinner Meetup | 2026
  • Friday Fun and Games: Improv at The Highwire Center!

    • Are there free things to do in Annapolis this weekend?

    Yes — there are often free things to do in Annapolis this weekend, including live music, cultural events, seasonal activities, and community gatherings. Many events on Eventbrite are free or offer free entry options. These are some free events happening in Annapolis this weekend:
  • Free Events this weekend