Photo Credit DANIE Photography
Join Historic Annapolis for the 13th annual Blazers . Bourbon . Cigars on Thursday, September 24, 2026, from 6–9 pm in the picturesque William Paca Garden
Fall is officially here, and there’s plenty happening around Annapolis to celebrate! Spend the week catching live performances, shopping for your next great read, celebrating local art and culture, or getting outside for some fall fun. From the Kunta Kinte Heritage Festival and West Annapolis Oktoberfest to community events, fundraisers, and the final Tunesday of the season, there’s something for everyone. Grab your friends and family and make the most of the first full week of fall!
Imprint 2026 Closing Reception
September 23rd; Maryland Hall for Creative Arts, Annapolis 5:30pm
Celebrate the creativity and craftsmanship behind printmaking at the Imprint 2026 Closing Reception! Take one last look at the exhibition and explore works that showcase the textures, techniques, and possibilities of this dynamic art form. Mingle with fellow art lovers and the creative community while enjoying complimentary refreshments. It’s a relaxed evening to appreciate the incredible work featured throughout the exhibition and send the show off in style.
Program Year Kick Off & Homecoming
September 23rd; Annapolis Maritime Museum & Park, Annapolis 5:30pm
Kick off a new year of leadership and reconnect with familiar faces at Leadership Anne Arundel’s Program Year Kick Off & Homecoming! Meet the new Flagship Class of 2027 while connecting with alumni representing more than 30 years of the program over live music, light appetizers, and drinks. The celebration will also recognize milestone Flagship classes and support local families through a community collection drive benefiting Just One. It’s an evening of connection, celebration, and giving back to the Annapolis community!
Surfrider Annapolis Chapter Social Hour
September 24th; Bread & Butter, Annapolis 6:30pm
Connect with fellow coastal advocates at the Surfrider Annapolis Chapter Social Hour! Learn more about Surfrider’s mission to protect our oceans, waves, and beaches while discovering the programs and volunteer opportunities happening locally. Meet others who care about the health of our waterways and find new ways to get involved in the community. All ages are welcome to stop by, connect, and learn more!
Taste: Celebrate the Chesapeake
September 24th; The Atreeum at Tall Timber, Annapolis
Celebrate the Chesapeake and support the waterways that connect our communities at Taste: Celebrate the Chesapeake! Enjoy an evening of live music, locally inspired food, awards, and conversation alongside fellow conservation supporters. The event brings together people and organizations who share a commitment to protecting the forests, streams, rivers, and resources that make the Chesapeake Bay watershed so special. As the organization’s largest annual fundraiser, every ticket helps support critical conservation work throughout the watershed.
September 24th; William Paca Gardens, Annapolis 6:00pm
Mix, mingle, and raise a glass at Historic Annapolis’ 13th annual Blazers . Bourbon . Cigars! Enjoy tastings of bourbon, whiskey, and other fine spirits alongside premium cigars and bites from some of the area’s top chefs and restaurants. The evening brings together local business leaders, entrepreneurs, professionals, and community members for networking in the beautiful William Paca Garden. Proceeds support Historic Annapolis and its mission to preserve, protect, and connect the city’s history.
You're a Good Man, Charlie Brown
September 25th; Annapolis mall, Annapolis 7:30pm
Spend the weekend with Charlie Brown, Snoopy, Lucy, Linus, and the rest of the Peanuts gang in You’re a Good Man, Charlie Brown! This award-winning musical brings the beloved comic strip to life through baseball games, homework struggles, crushes, catchy songs, and plenty of heartwarming moments celebrating friendship. Catch performances Friday, September 25th at 7:30 p.m.; Saturday, September 26th at 2 and 7:30 p.m.; or Sunday, September 27th at 2 p.m. It’s a nostalgic and fun-filled show for longtime Peanuts fans and a whole new generation to enjoy.
September 25th; Maryland Hall, Annapolis 7:00pm
Meet #1 New York Times bestselling author Jeneva Rose for an evening celebrating her newest release, Sometimes I Scare Myself! Dive into three chilling new horror stories filled with séances gone wrong, sinister houses, mysterious curses, and plenty of unexpected twists. Each ticket includes a pre-signed copy of the new book, a professional photo with Jeneva, special event swag, and general seating. Thriller and horror fans won’t want to miss this chance to celebrate a haunting new release with the author herself!
36th Annual Kunta Kinte Heritage Festival
September 26th; Navy Marine Corps Memorial Stadium, Annapolis 12:30pm
Celebrate African American history, culture, and community at the 36th Annual Kunta Kinte Heritage Festival! Enjoy a full day of live entertainment across two stages while exploring a marketplace featuring more than 100 vendors. Families can also visit the children’s activity tent and stop by the farmers market, where local farmers will provide free fresh produce. Come together for a vibrant celebration honoring the festival’s theme, “Our Roots. Our Story.”
September 26th; Lawyers Mall Annapolis, Annapolis 12:00pm
Grab your sketchbook and get creative during the Fall 2026 Sketch Crawl! Artists of all experience levels can explore downtown Annapolis on foot, stopping at several nearby spots to sketch or paint the scenes that inspire them. Bring your favorite art supplies and enjoy an afternoon of creativity, fresh air, and local scenery alongside fellow artists. It’s a fun and free way to experience Annapolis from a whole new perspective!
Healthy Forests Workday + NPLD with Arundel Rivers Federation
September 26th; Bacon Ridge Natural Area, Hawkins Rd Entrance, Annapolis 10:00am
Give back to the great outdoors during a special Healthy Forests Workday celebrating National Public Lands Day! Join Scenic Rivers Land Trust and Arundel Rivers Federation to help protect Bacon Ridge Natural Area by removing invasive vines, shrubs, and grasses that threaten native plants. Volunteers will receive guidance on identifying and safely removing invasive species, with mindfulness moments woven throughout the morning to slow down and appreciate the changing forest. Grab your gloves, invite a friend, and spend the morning making a hands-on difference for one of the area’s treasured natural spaces!
Free Community Shredding Event
September 26th; United Bank, Annapolis 8:30am
Clear out the clutter and protect your personal information at this Free Community Shredding Event! Bring outdated bank statements, bills, tax returns, and other sensitive documents to be securely shredded onsite. It’s an easy way to safely dispose of paperwork you no longer need while helping reduce the risk of identity theft. Just remember to bring paper only—no cardboard, metals, or CDs.
Anne Arundel County Literacy Council Annual Book Fair
September 26th; Annapolis Mall, Annapolis 10:00am
Stock up on your next great read at the Anne Arundel County Literacy Council’s Annual Book Fair! Browse thousands of gently used books spanning everything from bestsellers, mysteries, and historical fiction to cookbooks, memoirs, romance, and children’s favorites. Score budget-friendly books, fill a special edition Literacy Council tote, enter gift basket raffles, and enjoy additional activities hosted by Discoveries Library. Best of all, every purchase helps support free adult tutoring programs throughout Anne Arundel County!
September 26th; Ridge Grow, Annapolis 10:00am
Kick off the season with the first Fall Saturday of the year at Ridge Grow! Pick out the perfect pumpkins and spend the day enjoying pumpkin bowling, a corn pit, putt-putt, playground fun, yard games, rotating food trucks, and more seasonal activities. There’s no admission or ticket required, so bring the kids, grab some friends, and settle in for a day of fall fun. Can’t make the first one? Fall Saturdays return every Saturday through the end of October!
Pet Adoption Days in Severna Park
September 26th; Homestead Gardens, Severna Park 10:00am
Meet your new best friend during Pet Adoption Days at Homestead Gardens! Stop by to meet adoptable cats and dogs from Charm Rescue and connect with the people helping these pets find loving forever homes. Whether you’re ready to adopt or simply want to meet some adorable animals, it’s a great opportunity to support local rescue efforts. Guests who complete an adoption application will also receive a special Buy 2, Get 1 Free coupon for Grandma Mae’s canned pet food!
September 27th; West Annapolis – Annapolis St and Giddings Ave, Annapolis 11:00am
Raise a glass and celebrate the season at the West Annapolis Oktoberfest! Enjoy an ice-cold brew from the RAR Brewing and Chessie’s Wharf beer garden while sampling bites from local restaurants and food trucks. Browse a variety of vendors for unique finds and get an early start on your holiday shopping while soaking up the festive atmosphere. With food, drinks, shopping, and fun for all ages, it’s a fall tradition the whole family can enjoy.
September 29th; Back Creek Eastpirt, Annapolis 6:00pm
Close out the season on the water with the final Tunesday by Chronic Sailing! Shawn & Friends will take the floating stage for one last evening of live music surrounded by the beautiful views of Back Creek. Cruise over by boat, kayak, or paddleboard and enjoy the laid-back tunes as the sun sets over the water. It’s your last chance of the season to experience this free, family-friendly Annapolis summer tradition!
