Upcoming Events

Knightongale Farm from above showing the fall colors

Fall is for Festivals

Pumpkin patches, waterfront views, and small-town charm, fall in love with Annapolis & Anne Arundel County this season. Explore can't-miss events and festive happenings all autumn long.

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Blue building with a giant pumpkin in front

Great Annapolis Pumpkins

October 2025. You never know when these 1,000-pound pumpkins will pop up in downtown Annapolis, but they are hard to miss once they do! Sponsored by Visit Annapolis & Anne Arundel County and coordinated through the Downtown Annapolis Partnership, these gigantic gourds make for the perfect fall...

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Adventures For Every Season

 

    crowd of music lovers at Annapolis Songwriters Festival

    Annapolis Songwriters Festival

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

    USNA Football

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

    Annapolis Baygrass Festival

    Three black men singing on a stage at a festival

    Kunta Kinte Heritage Festival

    Blue building with a giant pumpkin in front

    Great Annapolis Pumpkins

    A man holds out a Maryland Blue Crab

    Maryland Seafood Festival

    two men in Medeival garb at a renaissance festival

    Renaissance 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

    People march in the Annapolis Pride Parade holding banneres and signs about LGBTQIA+ rights

    Annapolis Pride Parade & Festival

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

    Military Bowl

    Annapolis Chocolate Binge Festival

    Annapolis Chocolate Binge Festival

    Eastport Yacht Club Parade

    Eastport Yacht Club Lights Parade

    Grand Illumination

    Grand Illumination

    Midnight Madness

    Midnight Madness

    People at a holiday market

    Annapolis Holiday Market

    Lights on the Bay

    Lights on the Bay

    Snowflake Alley

    Snowflake Alley

    Cheesy food from Dry 85

    Annapolis Restaurant Week

    St. Patricks Day Parade

    St. Patrick's Parade and Festival

    Annapolis Film Festival 2025

    Annapolis Film Festival

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

    Annapolis Spring Sailboat Show

    Maryland flag in yellow and red

    Maryland Day

    May Day

    May Day in Annapolis

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

    Commissioning Week

    Worlds Largest Crab Feast

    Annapolis Crab Feast

    Kim Hovell oyster paintings

    Annapolis & Anne Arundel County Arts Month

    Singers performing at Let's Go Music Festival

    Let's Go! Music Festival

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

    Annapolis Pride

    three women wearing sailing gear posing for a celebratory photo on a sailboat for Santa Maria Cup

    Santa Maria Cup

    Explore Our Neighborhoods

    Ariel view of Annapolis City Dock with sunset and clouds

    City Dock

    Main Street, Annapolis

    Main Street

    Eastport

    Eastport

    West Annapolis Petticoat

    West Annapolis

    State Circle/Maryland Avenue

    Maryland Avenue

    A sunset shot of Live! Casino & Hotel

    Arundel Mills

    Things To Do in Annapolis and Anne Arundel County

    People playing craps in a casino

    BWI & Arundel Mills Entertainment District

    Nutcracker - Ballet Theatre of Maryland

    Arts & Entertainment

    Maryland Avenue Shopping

    Shopping

    Guinness - Open Gate Brewery

    Breweries & Pubs

    Arundel Mills - A Shopping Center

    Arundel Mills

    View All Things To Do
    Wilma Lee Halloween Cruise

    Wilma Lee Halloween Cruise

    Candlelight: Halloween Classics

    Candlelight: Halloween Classics

    CP presents Dracula: A Comedy of Terrors

    CP presents Dracula: A Comedy of Terrors

    An aerial view of Annapolis looking from the water to the Maryland State House

    Top 25 Things To Do In Annapolis

    The Maryland State House during the Fall with changing leaves in the foreground

    October Things to Do in Annapolis & Anne Arundel County

    Seafood dip with a cheddar cheese pull of creamy seafood from a black cast iron pan.

    The Top 10 Foods You Must Try in Annapolis, Maryland

    A couple orders wine from the mobile bar at Great Frogs Winery

    Leaf Peeping and Wine Sipping

    Mayo Beach play Area

    7 Off-the-Grid Adventures in Annapolis and Anne Arundel County

    BWI-Airport-2-1

    A Free Ride from BWI Airport to Annapolis

    Read All Blog Posts
    Annapolis and Anne Arundel County Conference & Visitors Bureau Annapolis and Anne Arundel County Conference & Visitors Bureau

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