Happy Labor Day! This holiday is about far more than just taking a day off from school and work — it honors American workers and celebrates the accomplishments of the labor movement throughout the country’s history. Many communities celebrate the occasion with parades, festivals and educational events highlighting local labor efforts.
These Chesapeake-area events are a great way to spend your Labor Day with your family, teaching them about the holiday’s historical significance while still being fun, festive and family-friendly.
Additionally, the Maryland Renaissance Festival and Maryland State Fair are both open on Labor Day, so it’s a great opportunity to visit these popular events if you haven’t had the chance.
As of 2026, Maryland State Fair policy states that all minors under the age of 18 must be accompanied by an adult aged 21 or older. An adult chaperone can accompany up to six minors at a time.
Labor Day Weekend at the Inn at Perry Cabin
Sept. 4-6, 3-6 p.m. Friday, noon-3 p.m. Saturday and Sunday | Saint Michaels
The Inn at Perry Cabin will be celebrating Labor Day all weekend, with live music and special menus available depending on the day.
Free | innatperrycabin.com
Recovery Fest
Sept. 5, 10 a.m.-2 p.m. | Solomons
This free, family-friendly event at the Annmarie Sculpture Garden & Arts Center is all about the recovery resources available to anyone struggling with mental or substance abuse-related disorders, with hands-on learning, a scavenger hunt and plenty of kids’ activities.
Free | annmariegarden.org
Pops in the Park
Sept. 5, 11:30 a.m. | Pasadena
This free America 250-themed concert at Downs Park features classic songs by American composers. Maryland Poet Laureate Lady Brion will also make an appearance and perform original poetry and “Lincoln Portrait” by Aaron Copland.
Free | annapolissymphony.org/events/downspark
Towson Tigers at Navy Midshipmen Football
Sept. 5, 3:30 p.m. | Annapolis
The Towson Tigers football team will face off against the Navy Midshipmen at the Navy Marine Corps Memorial Stadium.
$34.50-$64.50 | navysports.com
67th Annual Deal Island Skipjack Race
Sept. 6-7 | Deal Island
Spend Labor Day Weekend by the waterfront at this skipjack boat festival at Deal Island Harbor, featuring boat races and parades, educational exhibits, a vendor fair and other fun activities.
Free | skipjackheritage.com
Labor Day at Historic Hancock’s Resolution
Sept. 6, 1-4 p.m. | Pasadena
Historic Hancock’s Resolution will be open on Labor Day, offering visitors the opportunity to explore the area’s local wildlife, check out the Quilt Story Trail and take guided tours of the house and gardens.
Free | historichancocksresolution.org
America 250 Labor Day Celebration
Sept. 7, 10 a.m.-6 p.m. | Port Republic
Sept. 7 is the 250th day of the year, and Rolling Acres Farm will celebrate both Labor Day and America 250 on that day. Come down to the farm for the opening weekend of its annual Fall Festival, featuring an America 250-themed corn maze, live music, a petting zoo and other fun attractions.
Free | myrollingacresfarm.com
Grasonville Community Center Annual Labor Day Parade
Sept. 7, noon | Grasonville
Grasonville’s annual Labor Day parade takes place at the Grasonville Community Center, with lineups for parade participants beginning at 9:30 a.m. and the parade itself kicking off at noon.
Free | grasonvillecc.org
