Upcoming Events

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.

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Adventures For Every Season

 

    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

    Participant with hands up in purple jacket is excited to be racing at Bay Bridge Run

    Bay Bridge Run

    Lights on the Bay

    Lights on the Bay

    Snowflake Alley

    Snowflake Alley

    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

    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

    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

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    Watermarks Holiday Candlelight Tour

    Watermarks Holiday Candlelight Tour

    Pride & Prejudice, adapted by Emma Whipday

    Pride & Prejudice, adapted by Emma Whipday

    Holiday Tradition Tours of the William Paca House

    Holiday Tradition Tours of the William Paca House

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

    Top 25 Things To Do In Annapolis

    Ambient lights of red, yellow, orange, green reflecting off of City dock waters

    Things to Do This Holiday Season 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

    The canopy of lights over West Street at night during the Chocolate Binge Festival

    4 Unique Holiday Things To Do in Annapolis

    Naval Chapel Dome - New

    5 Ways to Honor Veterans Day in Annapolis, Maryland

    Annapolis Skyline

    November Things to Do in Annapolis & Anne Arundel County

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

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