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*Please note – While we make every effort to crosscheck links and event details, we always encourage you to do the same before making final plans. If details are missing or incorrect, please let us know so that we can correct them. Thanks for your help! 

  • Carnival – Annapolis Mall

    Westfield Annapolis Mall 2002 Annapolis Mall Rd, Annapolis, MD, United States

    Come and discover the excitement at the largest carnival in town, happening from June 4 to June 14, 2026 at Annapolis Mall, Annapolis, MD! Brace yourself for heart-racing rides, fun games, tasty food, and lasting memories. Make sure you’re part of the fun—mark your calendars and bring your family for a day full of joy […]

  • Financial Foundations

    Whether you’re 22 and starting out or 50 and planning for retirement, Financial Foundations covers the essential steps to help get your financial priorities in order. Learn the universal process used by CovingtonAlsina, designed to guide you through budgeting, investing, and financial goal-setting, regardless of income or age.

  • What’s Up Media’s Best of Party 2026

    Doordan Institute 2000 Medical Parkway, Annapolis

    What’s Up? Media’s Best Of Party celebrates the best of the area’s restaurants, shops, services, entertainment, and businesses all rolled up into one fantastic fundraising event supporting Charting Careers.

  • Naptown Social Stroll

    Citrus Bros West St

    If you're looking for a fun, low-key way to get outside, meet people, and explore Annapolis, the Naptown Social Strolls are exactly what they sound like — and then some. These community walks bring locals together for a stroll through the streets and neighborhoods of Annapolis, with the focus on connection just as much as […]

  • Carnival – Annapolis Mall

    Westfield Annapolis Mall 2002 Annapolis Mall Rd, Annapolis, MD, United States

    Come and discover the excitement at the largest carnival in town, happening from June 4 to June 14, 2026 at Annapolis Mall, Annapolis, MD! Brace yourself for heart-racing rides, fun games, tasty food, and lasting memories. Make sure you’re part of the fun—mark your calendars and bring your family for a day full of joy […]