crowd of music lovers at Annapolis Songwriters Festival

Annual Events & Festivals in Annapolis & Anne Arundel County

 

What is Annapolis Known For?

We get that question a lot; thankfully, we have curated some of our most popular events and festivals for you to discover here in the heart of Maryland.

Besides our historic charm and travel-friendly airport code, BWI (Baltimore Washington Thurgood Marshall Airport), there is much to see and do in this beautiful seaside town. Annapolis & Anne Arundel County are ideally situated on the Chesapeake Bay, which makes it perfect for concerts, parades, romantic getaways, family trips, and festivals.

Discover the best of the Chesapeake Bay on your next adventure to Annapolis & Anne Arundel County!

    Annapolis Chocolate Binge Festival

    Annapolis Chocolate Binge Festival

    Eastport Yacht Club Parade

    Eastport Yacht Club Lights Parade

    Navy Marine Corps Stadium field on game day at Military Bowl 2019

    Military Bowl

    Video Thumbnail - youtube - Annapolis Restaurant Week 2022

    Annapolis Restaurant Week

    People at a holiday market

    Annapolis Holiday Market

    Snowflake Alley

    Snowflake Alley

    Lights on the Bay

    Lights on the Bay

    Midnight Madness

    Midnight Madness

    Grand Illumination

    Grand Illumination

    St. Patricks Day Parade

    St. Patrick's Parade and Festival

    Annapolis Film Festival 2025

    Annapolis Film Festival

    Maryland flag in yellow and red

    Maryland Day

    Sailboats and catamarans lined up in the water with flags flying up the mast.

    Annapolis Spring Sailboat Show

    May Day

    May Day in Annapolis

    Blue Angel air show flying in 5 opposite directions over U.S. Naval Academy

    Commissioning Week

    A person holds a rainbow flag beneath a rainbow balloon arch.

    Annapolis Pride Parade & Festival

    Let's Go Music Festival Lineup Details

    Let's Go! Music Festival

    Batik workshop at Annapolis Arts Week

    Annapolis Arts Month

    A group of black people in costumes march in the Juneteenth parade in Annapolis, MD.

    Annapolis Juneteenth Parade & Festival

    4th of July Boating Event

    4th of July Weekend

    A group of people wearing crab hats sitting around a table picking crabs

    Annapolis Crab Feast

    Navy Football Stadium, Midshipmen line up on the field before a game

    USNA Football

    two men in Medeival garb at a renaissance festival

    Renaissance Festival

    Three black men singing on a stage at a festival

    Kunta Kinte Heritage Festival

    an aerial view of a harbor and waterfront with a stage lit up at night

    Annapolis Songwriters Festival

    A man holds out a Maryland Blue Crab

    Maryland Seafood Festival

    a bird's eye view of the Annapolis Baygrass Festival at Sandy Point State Park

    Annapolis Baygrass Festival

    Aerial view of Annapolis harbor during sailboat show with loads of boats looking out across the water to the Chesapeake Bay

    United States Boat Shows

    USA BMX

    USA BMX East Coast Nationals

    Runners running across the Chesapeake Bay Bridge

    Bay Bridge Run

    Annapolis City skyline during the holidays

    Winter on The Chesapeake

    Known for its cozy coastal charm, historic streets, and waterfront views, Annapolis is consistently ranked as one of the best holiday destinations in America. Explore our guide to the best holiday events and start planning your winter getaway to Annapolis and Anne Arundel County.

    Plan Your Adventure

    Annapolis and Anne Arundel County Conference & Visitors Bureau Annapolis and Anne Arundel County Conference & Visitors Bureau

    STOP BY OUR
    VISITORS CENTER

    26 WEST STREET
    ANNAPOLIS, MD 21401
    INFO@VISITANNAPOLIS.ORG
    PHONE: 410-280-0445
    FAX: 410-263-9591
    Visit Annapolis icon Visit Annapolis icon

    Annapolis Discovered

    Visit our blog and explore local stories
    Visit Annapolis icon Visit Annapolis icon

    Access Annapolis

    Parking & Getting Around Annapolis

    ©2025 VISIT ANNAPOLIS. ALL RIGHTS RESERVED.