If you’re new to town, you may not be familiar with these fun family events in the Chesapeake, Maryland and Washington, D.C., area. Here are some can’t-miss events.
Spring: March–May
Annapolis St. Patrick’s Day Parade
Marching bands, bagpipes, floats and associated parties. visitannapolis.org
Annapolis Film Festival
Multi-day event with films, discussions and special events. Various Annapolis locations. annapolisfilmfestival.com
Maryland Day Celebration
Events during a multi-day celebration of the founding of Maryland and a showcase of the area’s history. Southern Anne Arundel County and Annapolis. marylandday.org
Annapolis Spring Sailboat Show
An annual sailboat show that features new and brokerage boats. Meet with boating clubs and charter companies and shop for gear and equipment. Live entertainment, seminars and more. Annapolis City Dock. annapolisboatshows.com
Annapolis Book Festival
Activities, presentations on the craft of writing, book sales and author meetings. The Key School, Annapolis. keyschool.org/community/annapolis-book-festival
St. John’s v. USNA Croquet Match
The “Johnnies” and the “Mids” vie for the annual croquet title while guests enjoy a lawn party. St. John’s College Campus, Annapolis. sjc.edu
May Day in Annapolis
The Garden Club of Old Annapolis Towne invites residents to the Downtown Historic District to put fresh-cut flower baskets outside of their homes and businesses. Downtown Annapolis. visitannapolis.org
Solomons Maritime Festival
Antique boat show, crab picking and oyster shucking, music, demonstrations and more. Calvert Marine Museum, Solomons. calvertmarinemuseum.com
Chestertown Tea Party
Re-enactment of colonial uprising in Chestertown, Maryland. Event includes a colonial parade, street party, raft race, street performances, colonial crafts, food, wine and craft beer tasting. Historic Chestertown. chestertownteaparty.org
Blue Angels Air Show
Blue Angels flight demonstrations over Annapolis as part of USNA Commissioning Week events. Naval Academy and downtown Annapolis. usna.edu
USNA Commissioning Week
Celebrate the graduating class from United States Naval Academy with weeklong events, activities and ceremonies. usna.edu/CommissioningWeek
Annapolis Irish Festival
Irish music, food, activities and more, plus an area for kids. Anne Arundel County Fairgrounds, Crownsville. annapolisirishfestival.com
Oyster Roast and Sock Burning
Sock burning party with live music and oyster roast. Annapolis Maritime Museum. amaritime.org
Summer: June–August
Bowiefest
Local bands, games, rides, arts and crafts fair, food, home expo and more. Allen Point Park, Bowie. cityofbowie.org/783/bowiefest
Eastport A Rockin’
Performances from local bands, vendors, food and a kids’ area. 35+ bands will play live music in a festival made to promote regional music. Back Creek and Second Street, Annapolis. eastportarockin.com
Smithsonian Folklife Festival
A living cultural heritage celebration with music, dance, food and more. The 2025 program will focus on the experience of the next generation. National Mall, D.C. festival. si.edu
July Fourth Celebrations
Fireworks and celebrations in several towns and D.C. Find complete listings at chesapeakefamily.com/july-4
Annapolis Rotary Crab Feast
All-you-can-eat and drink crab feast. Raise money for local nonprofits and enjoy some classic Maryland cuisine. Navy-Marine Corps Memorial Stadium, Annapolis. annapolisrotary.org
Navy Fan Fest
Meet Navy Football players, get autographs and listen to music. Inflatable games and giveaways are available, and the first 250 kids get a free T-shirt. Navy-Marine Corps Memorial Stadium, Annapolis. navysports.com
Maryland State Fair
Classic carnival rides, games, greasy food, exhibits, an animal farm, concerts and more. Maryland State Fairgrounds, Timonium. marylandstatefair.com
Various County Fairs
Entertainment, 4-H and livestock shows, exhibits, games, rides and more. Howard County Fair in August; Anne Arundel County and Calvert County Fairs in September; and others.
Artscape
Three-day free outdoor arts festival featuring visual and performing arts, fashion, hands-on projects, children’s entertainers and more. Baltimore. artscape.org
Fall: September–November
Maryland Renaissance Festival
Return to the Middle Ages in an English village with shows, games, attractions and more. Crownsville. rennfest.com
Army’s Annual Army Ten-Mile Race
Participants include military, civilians, wheelchair athletes and wounded warrior athletes. ATM’s mission is to support Army outreach, build morale and promote physical fitness. Pentagon, Washington, D.C. armytenmiler.com
USNA Homecoming Weekend
Homecoming/Alumni Weekend: Join alumni and current cadets at your home away from home for a weekend of memories old and new, plus cheer on Navy football! U.S. Naval Academy. usna.edu
Maryland Seafood Festival
Seafood, demonstrations, competitions, music, a crab soup cookoff, crab derby and more. Sandy Point State Park, Annapolis. mdseafoodfestival.com
Kunta Kinte Heritage Festival
Celebration honors and recognizes African culture, people and the diaspora including Kunta Kinte, a slave brought to Annapolis. City Dock, Annapolis. kuntakinte.org
Patuxent River Appreciation Day
Boat building, canoe rides and harbor cruises, demonstrations, wine tasting, music and more. Calvert Marine Museum, Solomons. calvertmarinemuseum.com
Sultana Downrigging Festival
Ships, schooners and wooden boats join the schooner Sultana in Chestertown for dock tours, public sails, performances, dock dog competition and other activities. Chestertown. sultanaeducation.org
American Indian Festival
Music, dancing, storytelling, demonstrations and more showcasing Native American Culture, especially the Eastern Woodland. Patuxent River Park, Upper Marlboro. pgparks.com
Maritime Republic of Eastport’s Tug of War
A former feud over colonial lordship is now fought out over a fun tug of war across Spa Creek pits in Annapolis and Eastport with team competitions. Eastport and Annapolis City Dock. themre.org
USNA Halloween/All Saints’ Day Concert
The USNA annual Halloween Concert is a spectacular event of music, light, drama and dance. One of the most popular events on the Yard! usna.edu/Music/signature/halloween.php
Grand Illuminations and Tree Lightings
Lightings of town and attraction Christmas trees in November. Visit chesapeakefamily.com/holiday-lights
Winter: December–February
New Year’s Eve Celebrations
Towns and attractions ring in the new year with special celebrations, often
with early celebrations for families. Find listings at chesapeakefamily.com/new-years
Army-Navy Game
A Rivalry for the Ages. For more than a century, they’ve been at it. The Black Knights against the Midshipmen. Army vs. Navy—the greatest rivalry in sports. armynavygame.com
Midnight Madness
Stores stay open late for holiday shopping, entertainment, snacks and drinks on select Thursdays. Downtown Annapolis, downtownannapolispartnership.org/midnight-madness, and in Historic Ellicott City, visitoldellicottcity.com
USNA Presents “Handel’s Messiah”
Continuing a long-standing tradition, the USNA Glee Club combines with the Annapolis Symphony Orchestra and world-class soloists to present selections from Handel’s beloved “Messiah” on Saturday evening and Sunday afternoon in the beginning of December. usna.edu/Music/signature/messiah.php
Gingerbread House Show and Contest
Enter and/or vote for your favorite gingerbread houses. Darnall’s Chance House Museum, Upper Marlboro. history.pgparks.com
B&O’s Magical Holiday Express
Trains of all sizes, holiday festivities in the roundhouse and children’s activities. B&O Railroad Museum, Baltimore. borail.org
Holiday Light Displays and Shows
Several drive-through or walk-through holiday light displays celebrate the season. For complete listings and information, visit chesapeakefamily.com/holiday-lights
National Menorah Lighting
Music, latkes and donuts, games and a lighting of the menorah. White House Ellipse, D.C. nationalmenorah.org
Military Bowl & Parade
Parade features the Budweiser Clydesdales. Football game between ACC and AAC teams. Downtown Annapolis and Navy-Marine Corps Memorial Stadium, Annapolis. militarybowl.org
Polar Bear Plunge
Plunge into the Chesapeake Bay, and enjoy a festival afterward. Raises money for Special Olympics Maryland. Sandy Point State Park, Annapolis. plungemd.com
Chesapeake Family Life KIDS FEST
Feb. 24. Camps, STEAM Activities, summer programs, hands-on fun and giveaways. Pip Moyer Recreation Center, Annapolis. chesapeakefamily.com/kidsfest
