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Events and Things to do in Highland Beach, MD this weekend

Looking for things to do in Highland Beach 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 Highland Beach's most popular events.

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Things to do around Highland Beach

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Frequently asked questions about Highland Beach

What are the best events to attend this weekend in Highland Beach?

The best events to attend this weekend in Highland Beach 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:
  • Halloween Spooktacular!
  • Prosecco & Pastichio Luncheon
  • Homecoming After Dark: The Official Alumni Homecoming Celebration
  • James Ward in Concert

    • Which events are currently trending in Highland Beach?

    Trending weekend events in Highland Beach often reflect seasonal moments, nightlife demand, and popular neighbourhoods, including concerts, parties, and special themed events. The trending searches this month in Highland Beach are:
  • fireworks

    • Which events are coming up in Highland Beach this weekend?

    In addition to what's happening right now, there are many upcoming weekend events in Highland Beach, including live shows, parties, food experiences, and limited-time events. Discover upcoming weekend events you won't want to miss:
  • Amazing Annapolis Scavenger Hunt
  • ⁠Mindful Wellness Walk in Annapolis
  • Men Make Men Sexual Recovery Fall Retreat 2026
  • Haunted Thrift Store Paint Night at Cult Classic Brewing

    • Are there free things to do in Highland Beach this weekend?

    Yes — there are often free things to do in Highland Beach 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 Highland Beach this weekend:
  • Free Events this weekend