ANNAPOLIS – Festival season is in full swing across Annapolis and Anne Arundel County this September, bringing a vibrant mix of live music, cultural celebrations, heritage events, and family-friendly traditions. Throughout the month, visitors can experience the destination’s unique character and community spirit while enjoying seasonal events and activities across the region.
Visitors Center Happenings in September
Festival season is the perfect time to stop by the Annapolis & Anne Arundel County Visitors Center between events. Open daily from 10 a.m. to 5 p.m., with extended hours until 7 p.m. on Wednesdays during Dining Under the Stars, the center offers local recommendations, featured business activations, and a 24-hour outdoor information kiosk. On September 9, visitors can enjoy a Ballet Theatre of Maryland performance outside the center from 5 to 7 p.m. Throughout September, guests can also contribute to Gallery 57’s America 250: This Is Now interactive community quilt project. Before leaving, take part in the Be Revolutionary: America 250 Exploration Trail, featuring newly added sites through year’s end. Check in at participating locations and stop by the Visitors Center to redeem prizes while exploring Annapolis and Anne Arundel County.
Annapolis Songwriters Festival – Sept. 10-13
The 5th Annual Annapolis Songwriters Festival, presented by Rams Head, BMI, and Visit Annapolis & Anne Arundel County, brings four days of live music, storytelling, and unforgettable performances to venues throughout downtown Annapolis. Inspired by the renowned Key West Songwriters Festival, the event features nationally acclaimed songwriters, chart-topping artists, and more than 50 local musicians performing in intimate venues and free showcases along the city’s walkable “songwriters trail.” Highlights include a headline performance by Young the Giant, along with concerts at Rams Head On Stage, Maryland Hall, Annapolis Summer Garden Theatre, and other iconic Annapolis locations.
Maryland Seafood Festival & Skipjack Heritage Days – Sept. 11-13
Celebrate 60 years of Chesapeake Bay tradition at the Maryland Seafood Festival, at bayside Sandy Point State Park with fresh seafood, live entertainment, chef demonstrations, family-friendly activities, and spectacular Chesapeake Bay views. Marking the festival’s 60th anniversary is a special first-time appearance by “Mama Duck,” a giant 60-foot inflatable duck. Visitors can also enjoy the famous Crab Soup Cook-Off, Oyster & Craft Beer Tent, local artisan vendors, and Chesapeake Bay conservation exhibits. At the same time, Skipjack Heritage Days, celebrates Maryland’s iconic state boat with the largest gathering of historic skipjack vessels, educational displays, hands-on activities, public sails, and traditional skipjack races visible from the festival grounds. Together, these events showcase the rich culture, cuisine, and maritime heritage of the Chesapeake Bay.
Annapolis Baygrass Music Festival – Sept. 19-20
Set up along the sandy shores of the Chesapeake Bay at Sandy Point State Park, the Annapolis Baygrass Music Festival returns for a weekend of bluegrass, Americana, and community celebration. Known for its mission that “Every Jam Heals the Bay,” the festival combines live music, local food and beverages, workshops, family-friendly activities, and Chesapeake Bay conservation efforts. From barefoot dancing on the beach and educational experiences to fresh Maryland seafood and performances on nonstop alternating stages, Baygrass offers a uniquely Annapolis blend of music, culture, and environmental stewardship.
Anne Arundel County Fair – Sept. 16-20
The Anne Arundel County Fair returns to Crownsville September 16-20, 2026, for five days of family-friendly fun, agricultural traditions, and exciting entertainment. Fairgoers can enjoy classic favorites including livestock shows and auctions, 4-H and FFA exhibits, agricultural displays, carnival rides and games, delicious fair food, pony rides, pig races, and the popular Light & Heavyweight Draft Horse Pull. New and returning attractions include the Bullride Mania Rodeo, an interactive kids firefighter show, and a dinosaur show and educational exhibit. Visitors can also enjoy live music and grandstand entertainment, including performances by Anne Arundel County native Luke Borchelt and Oracle the Band. Celebrating the best of Anne Arundel County’s agricultural heritage and community spirit, this beloved annual event remains a highlight of the fall season.
Kunta Kinte Heritage Festival – Sept. 26
Celebrate the rich cultural heritage and enduring legacy of Africans, African Americans, and Caribbean people of African descent at this year’s Kunta Kinte Heritage Festival, which holds special significance as part of the 50th anniversary of Roots. Held annually at the Navy-Marine Corps Memorial Stadium, this volunteer-run festival features live music, dance performances, African art and craft vendors, cultural exhibits, family-friendly activities, and educational programming that honors the perseverance and contributions of the African diaspora. As the culminating event of the Roots50 celebration, this year’s festival carries added significance, bridging past and present through joyful expression and cultural pride. With its vibrant 1970s-inspired aesthetic and community-centered programming, the festival honors this legacy not only through remembrance, but through collective celebration, unity, and a shared commitment to preserving cultural heritage for future generations.
Annapolis & Anne Arundel County Events in September
September 1: TUNESDAY Floating Concert Series with Endless Summer Charters
September 3: Funky Art Club
September 3: Wilma Lee Sunset Cruises
September 3-5: Wilma Lee Heritage Cruises
September 4: Annapolis Sunset Cruise with Live music with Naptown Brass band by Watermark
September 5: Graduate Annapolis x Red Bull Tailgate
September 5: Join Historic Annapolis for- Call the Midwife: Charlotte Small, a Colonial-Era Annapolis Midwife
September 5: What’s the Tea: Tea Culture Around the World at Historic London Town & Gardens
September 5: Pops in the Park – Downs Park
September 5: Release & Restore: An Upper Body Fascial Workshop at Honey’s Harvest Farm
September 5: Scandalous Annapolis by Watermark
September 6: First Sunday Arts Festival on West Street
September 6: First Sunday Farmers Market at Honey’s Harvest Farm
September 6: Foraging Nature Walk at Honey’s Harvest Farm
September 6: Historic Annapolis Dining Etiquette Experience at Federal House Bar & Grille
September 6: Historic Annapolis presents- What’s Brewing: Mrs. Howard’s Coffeehouse
September 6: Pops in the Park – Quiet Waters Park
September 7: Yappy Hour with Capital SUP
September 8: Homeschool: Unravel the Past! at Historic London Town & Gardens
September 8: TUNESDAY Floating Concert with Endless Summer Charters
September 9: Historic Annapolis Presents: Sails, Science, and Stories of Annapolis: Homeschool Program
September 9: River Concert Series: Eastport Oyster Boys at Historic London Town & Gardens
September 10: ArtFarm Annapolis Creative Circle – Monthly Meetup
September 10: Chesapeake Bay Foundation Learning Series: Menhaden Matter
September 10: Wilma Lee Heritage Cruises
September 11: Songwriters on the Severn Cruise with Watermark
Beginning Sept. 11: Colonial Players presents Our Town by Thornton Wilder
September 12: Write by the Bay at Captain Avery Museum
September 12: Historic Annapolis Presents-Chime After Chime: How a Clock Knows the Time
September 12: Join Historic Annapolis in a Revolutionary Walking Tour with Glenn E. Campbell
September 12: MD Connections to the War Between the States- Live Music at Benson-Hammond House
September 12: SUP Yoga with Allie by Capital SUP
September 12: Weird, Wacky, & Unusual History of Annapolis Tour by Watermark
September 13: Bay Bridge Paddle at Sandy Point State Park
September 13: Paint a beautiful tree at Gallery 57 West
September 15: TUNESDAY Floating Concert with Endless Summer Charters
September 17: Colonial Cocktails: Bitters and Booze
September 17: Historic Annapolis Book Club
September 17: Watermen’s Life Morning Tour — Galesville Heritage Society
September 18: Wilma Lee Sunset Cruises
Beginning Sept. 18: You’re a Good Man, Charlie Brown at Compass Rose Theater
September 19: African American Heritage Tour by Watermark
September 19: Hispanic Heritage at Safeway!
September 19: Poets in the Conversation Room: Robert Pinsky at St. John’s College
September 19: ¡Viva la Música! A Night of Fire & Flair at Maryland Hall
September 19: 21st Annual Boatyard Beach Bash at Annapolis Maritime Museum & Park
September 20: Annual Soup & Chili Cook Off — Galesville Heritage Society
September 20: Anchors + Artisans at Annapolis Town Center
September 20: Naptown Vinyl Record Market at Maryland Hall
September 20: Third Sunday Farmers Market at Honey’s Harvest Farm
September 22: TUNESDAY Floating Concert with Endless Summer Charters
September 26: Anne Arundel County Literacy Council Annual Book Fair at Annapolis Mall
September 26: Fourth Annual Members & Friends Appreciation Day- Live Music at Benson-Hammond House
September 26: Historic Annapolis Presents-Living History on Pinkney Street: Civil War First Maryland Volunteer Infantry Regiment
September 27: Join Historic Annapolis for-La Sylphide Storytime at the William Paca Garden Featuring the Ballet Theatre of Maryland
September 27: West Annapolis Oktoberfest
Select days in September: Chesapeake Bay Bridge Cruise by Watermark
Select days in September: Scenic Severn River Cruise by Watermark
Select days in September: Thomas Point Lighthouse Cruise by Watermark
Mondays: Monday History Sunset Sails by Schooner Woodwind
Mondays: Coffee, Crafts, & Cruisers
Wednesdays: Dinner Under the Stars
Wednesdays: Carload Crazies Skate
Wednesdays-Sundays: Resin Art Workshops by The Resin Room
Thursdays: September Sunsets Music Series at Annapolis Maritime Museum Park
Thursdays-Mondays: Best of Annapolis Tour: Colonial Annapolis State House & U.S. Naval Academy
Thursdays-Mondays: Colonial Annapolis & Maryland State House
Fridays: Sunset Cruise by Endless Summer Charters
Fridays: Friday Night Slice
Fridays: Spirits & Spirits by Watermark
Fridays: Social Bridge at Captain Avery Museum
Fridays: Friday Night Sunset Music Cruise by Watermark
Saturdays: Chesapeake Bay Experience by Endless Summer Charters
Saturdays: Annapolis Sunset Cruise by Watermark
Saturdays: Kid’s Activity Lab at Captain Avery Museum
Saturdays: Open Hours at Captain Avery Museum
Saturdays: Historic Ghost Tour by Watermark
Sundays: Anne Arundel County Farmers Market
Daily: Annapolis Harbor & USNA Cruise by Watermark
Daily: America’s 250 Harbor Cruise by Darling Charters
Daily: Annapolis Darling Sunset Cruise by Darling Charters
Daily: Chesapeake Sunrise Photographic Experience by Darling Charters
Daily: Private Daytime Charter by Chesapeake Classic Yacht Charters
Daily: Private Sunset Charters by Chesapeake Classic Yacht Charters
Daily: Team Building at Monster Mini Golf Crofton
Daily: Annapolis Scavenger Hunt: Red Bricks & Blue Views
Daily: Puzzling Adventures Scavenger Hunt
Daily: AudaTours Naval Academy Audio Tour: Legends & Landmarks of Anne Arundel Unveiled
About Visit Annapolis & Anne Arundel County
Visit Annapolis & Anne Arundel County (VAAAC) is a nonprofit, partnership-focused destination marketing and management organization dedicated to fostering a welcoming destination and promoting tourism for visitors, partners, and the community. The tourism and hospitality industry in Annapolis and Anne Arundel County significantly impacts Maryland’s economy. In 2024, visitor spending injected $4.3 billion into the state economy, attracting more than 7.2 million visitors, and sustaining more than 27,000 jobs (both directly and indirectly), according to the 2024 Economic Impact of Tourism in Maryland Report. That daily impact — an average of $11.9 million in visitor spending — strengthens small businesses, supports the hospitality workforce, and enhances quality of life for residents across the region. For more information, please visit www.VAAAC.org.
