Festivals And Fairs Headline Weekends In September

From jousting to a rodeo, a crab soup cookoff to concerts by the bay, fairs and festivals happening in the greater Annapolis area this month promise fun for all. Merriment abounds every weekend in September, starting with the Maryland Renaissance Festival and culminating with the Kunta Kinte Heritage Festival. Save the date for these family-friendly celebrations around town.

Renaissance Festival

Weekends through October 25

www.rennfest.com

Entering its 50th season, the Maryland Renaissance Festival has returned and runs through the end of October. This year’s “Rennfest” will feature more than 200 professional performers across 10 stages, 140 artisans exhibiting crafts, 42 food and beverage emporiums, five taverns and more. Step back into 1540 and the life of King Henry VIII in the 27-acre Village of Revel Grove and feast on turkey legs; take in armored jousting on horseback; shop wares from sculptors, artists and craftsmen; and enjoy ales and ciders – all right in Crownsville.

Annapolis Songwriters Festival

September 10-13

www.annapolissongwritersfestival.com

The Annapolis Songwriters Festival is headlined by Young The Giant this year and will feature over 100 performing artists, including many local acts. Organized by Rams Head Presents, the festival is modeled after the Key West Songwriters Festival and takes place across the state capital in multiple venues. Music lovers can look forward to becoming acquainted with the faces, voices and stories behind songs.

Maryland Seafood Festival

September 11-13

www.mdseafoodfestival.com

Marking 60 years since its inception, the Maryland Seafood Festival will offer a new experience this year. The festival grounds at Sandy Point State Park will be open on Friday, September 11, and discounts are available for military and first responders in remembrance of the 25th anniversary of 9/11. That evening, live music performances will feature bands representing the four branches of the armed forces. The world’s largest rubber duck will also be on display at this year’s festival, and attendees can look forward to a crab soup cookoff, oyster shucking contest, seafood vendors, artisans, kids’ activities and much more.

Anne Arundel County Fair

September 16-20

www.aacountyfair.org

Five days of fun are in store for county residents at this year’s Anne Arundel County Fair, marking 74 years of the beloved tradition. Fairgoers can meet live animals, explore homegrown and homemade exhibits, observe tractor pulls, compete in pie eating contests, watch pig races, brave rides and more. Opening acts on September 16 will include a rodeo and live performances by local student musicians from Priddy Music Academy, who kick off the event’s concert lineup. Dinosaur and firefighter training shows are new at this year’s volunteer-run county fair.

Annapolis Baygrass Music Festival

September 19-20

www.baygrassfestival.com

Set on the shore of the Chesapeake Bay, the Annapolis Baygrass Music Festival is a two-day showcase of bluegrass, jamgrass, Americana and other music genres performed on two side-by-side alternating stages. This year’s featured artists include Little Feat, Yonder Mountain String Band, Béla Fleck, Sam Bush, Mountain Grass Unit and others. Festivalgoers can also enjoy local food and outdoor activities for all ages at Sandy Point State Park. Baygrass is described as “a vibrant celebration of community, conservation and connection, championing two vital causes — protecting the Chesapeake Bay and promoting mental health awareness.”

Kunta Kinte Heritage Festival

September 26

www.kuntakinte.org

Now in its 36th year, Annapolis’ Kunta Kinte Heritage Festival is a celebration of the perseverance, education and cultural heritage of Africans, African Americans and Caribbean people of African descent. The festival drew over 10,000 people in 2025 and will take place at Navy-Marine Corps Memorial Stadium again this year. Attendees can look forward to live music performances, dancing, food and beverages, arts and craft vendors, children’s activities and more at the volunteer-run festival.