A curated list of notable September events around Annapolis, the Eastern Shore, and nearby areas, featuring community festivals, concerts, sports, theater, fundraisers, family-friendly activities, and more. Event dates may be subject to change.
Maryland Seafood Festival
Celebrate Maryland’s rich maritime heritage at the Maryland Seafood Festival, returning to Sandy Point State Park on Saturday, September 12, from 11 a.m. to 7 p.m. and Sunday, September 13, from 11 a.m. to 6 p.m. This beloved annual tradition features fresh local seafood, live music, artisan vendors, family-friendly activities, contests, and an impressive selection of local beverages. Running alongside the festival, Skipjack Heritage Days invites visitors to experience the Chesapeake Bay’s working waterfront through hands-on exhibits, educational demonstrations, public skipjack sails, and a thrilling skipjack race on Sunday. Whether you’re coming for the crab cakes, waterfront entertainment, or to celebrate the Bay’s enduring traditions, this weekend festival offers something for every member of the family. More info: mdseafoodfestival.com
21st Annual Boatyard Beach Bash
Escape to the islands without leaving Annapolis at the Annapolis Maritime Museum & Park’s 21st Annual Boatyard Beach Bash on Saturday, September 19, from 4 to 10 p.m. This all-inclusive waterfront celebration features performances by world-class musicians and members of Jimmy Buffett’s legendary Coral Reefer Band, including Peter Mayer, Doyle Grisham, Nadirah Shakoor, John Frinzi, Scott Kirby, and more. Guests will enjoy six hours of live music, handcrafted cocktails, gourmet bites, and a laid-back Key West atmosphere, all while supporting the Annapolis Maritime Museum & Park’s educational programs. It’s the ultimate end-of-summer celebration for Parrotheads, music lovers, and anyone looking to enjoy an unforgettable evening on the Chesapeake Bay. More info: amaritime.org
Photo by Megan Evans Photography
Annapolis Run for The Light House - Half | 5k | Walk
Lace up for a meaningful cause at the 17th Annual Annapolis RUN for The Light House on Sunday, September 20, from 8 to 11 a.m. at Quiet Waters Park. Participants can choose from a half marathon, 5K, or walk while enjoying scenic routes through the park and the waterfront community of Hillsmere Shores. Having sold out for the past five years, this popular event brings runners, walkers, and supporters together to raise funds for The Light House, the Annapolis nonprofit dedicated to ending homelessness and poverty in the community. Whether you’re chasing a personal best or simply walking in support of a great cause, every mile helps make a difference. More info: annapolisrunforthelighthouse.org
Photo by Blue Moon Photograhy
EOB’s In Concert at Historic London Town House and Gardens
Enjoy an evening of music, storytelling, and Chesapeake Bay tradition when the Eastport Oyster Boys return to Historic London Town & Gardens on Wednesday, September 9. Beginning at 6 p.m., the beloved Annapolis group will fill the gardens with their signature blend of maritime folk, island rhythms, and good-natured humor, celebrating life along the shores of the Chesapeake. Named the Musical Goodwill Ambassadors of Annapolis and the Maritime Republic of Eastport, the quartet has entertained audiences for more than two decades with an eclectic mix of instruments, lively performances, and tales inspired by the region’s rich maritime heritage. Pack a chair or blanket and enjoy an unforgettable evening of local music in one of Anne Arundel County’s most scenic outdoor venues. More info: oysterboys.com
Navy Football Kicks Off September 5
Experience one of Annapolis’ most cherished traditions as Navy Football returns to Navy-Marine Corps Memorial Stadium on Saturday, September 5, when the Midshipmen kick off the 2026 season against Towson University at 3:30 p.m. Fall Saturdays in Annapolis come alive with pageantry, patriotic pride, and the excitement of college football as fans from across the country gather to cheer on the Midshipmen. Whether you’re a lifelong Navy supporter or experiencing the game-day atmosphere for the first time, the pregame traditions, Brigade of Midshipmen, and electric stadium environment make for an unforgettable start to football season in Maryland’s capital. More info: navysports.com
You’re a Good Man, Charlie Brown
Step into the beloved world of Charlie Brown, Snoopy, Lucy, and the entire Peanuts gang in You’re a Good Man, Charlie Brown, presented by Compass Rose Theater at Annapolis Mall. Running weekends from September 18 through October 4, the award-winning musical features Friday evening performances at 7:30 p.m. and Saturday and Sunday matinees, with additional Saturday evening performances. Filled with heartwarming songs, humor, and timeless life lessons, this family-friendly production celebrates friendship, imagination, and finding joy in everyday moments. Whether you’re introducing a new generation to these iconic characters or reliving childhood memories, this charming musical is sure to delight audiences of all ages. More info: compassrosetheater.org
Naptown Flea
Browse, shop, and celebrate local creativity at Naptown Flea on Sunday, September 13, as Maryland Avenue transforms into a vibrant open-air marketplace from 11 a.m. to 4 p.m. This special collaboration with Lucky Girl Market features more than 60 vendors offering vintage finds, handmade goods, art, and one-of-a-kind treasures, along with food trucks, live music, and tattoo artists. Whether you’re searching for unique pieces or simply soaking up the lively atmosphere, this community market is the perfect way to spend a Sunday supporting local makers and small businesses. More info: instagram.com/naptownflea
Pops in the Park
Celebrate Labor Day weekend with the Annapolis Symphony Orchestra’s annual Pops in the Park, a free outdoor concert series bringing inspiring American music to two Anne Arundel County parks. The festivities begin Saturday, September 5, at 11:30 a.m. at Downs Park in Pasadena before continuing Sunday, September 6, at 5 p.m. at Quiet Waters Park in Annapolis. Inspired by the spirit of America 250, this family-friendly program features works by celebrated American composers, a special performance of Aaron Copland’s Lincoln Portrait narrated by Maryland Poet Laureate Lady Brion, and an opening performance by the Annapolis Symphony Academy Aries Youth Chamber Orchestra. Guests are encouraged to bring lawn chairs, blankets, and a picnic while enjoying food trucks, beautiful park settings, and an unforgettable celebration of music, history, and community. More info: annapolissymphony.org
33rd Annual Bob Ferry Golf Classic
Support the Boys & Girls Club of Annapolis & Anne Arundel County at the 33rd Annual Bob Ferry Golf Classic on Monday, September 14, at The Golf Club at South River in Edgewater. Named in honor of former NBA player and Washington Bullets General Manager Bob Ferry, the tournament celebrates his lasting commitment to mentoring young people and strengthening the local community. Participants will enjoy a day on the course while helping fund programs that empower area youth through education, leadership, and opportunity. Whether you’re registering a foursome or participating as a sponsor, this annual fundraiser is a meaningful way to honor Bob Ferry’s legacy while making a lasting impact. More info: bgcaa.com
Charity Boat Auction
Browse for your next adventure at the Chesapeake Bay Maritime Museum’s annual Charity Boat Auction on Saturday, September 5, from 8 a.m. to 1 p.m. in St. Michaels. A Labor Day weekend tradition for more than 20 years, the event features dozens of donated boats and watercraft available to the highest bidders, with the auction beginning at 11 a.m. Visitors can also explore a flea market-style tag sale filled with used boating gear before or after viewing the vessels. Proceeds from every purchase support the museum’s mission to preserve and share the history, culture, and environment of the Chesapeake Bay. More info: cbmm.org
Photo by Jay Strausser
Annapolis Baygrass Music Festival
Experience two unforgettable days of live music, waterfront views, and Chesapeake Bay culture at the Annapolis Baygrass Music Festival, returning to Sandy Point State Park on Saturday, September 19, and Sunday, September 20, beginning at 10 a.m. each day. This beachside festival brings together nationally acclaimed bluegrass, jamgrass, Americana, and roots artists for performances across two stages while celebrating the beauty and preservation of the Chesapeake Bay. Beyond the music, festivalgoers can enjoy fresh local seafood, craft beverages, yoga classes, family activities, artisan vendors, and educational workshops focused on Bay conservation and mental wellness. With a mission of giving back to both the environment and the community, Baygrass offers a one-of-a-kind festival experience where every jam truly helps save the Bay. More info: baygrassfestival.com
Annapolis Songwriters Festival
Music takes over Maryland’s capital September 10–13 as the Annapolis Songwriters Festival returns for four days of performances throughout downtown Annapolis. Modeled after the renowned Key West Songwriters Festival, the event transforms the city’s intimate theaters, bars, and gathering spots into stages where music lovers can discover the artists, voices, and stories behind the songs. This year’s festival is headlined by Young the Giant, adding another major name to a weekend devoted to live music and the art of songwriting. From intimate performances to bigger shows, the festival offers a unique opportunity to experience Annapolis through music while getting closer to the people who create it. More info: annapolissongwritersfestival.com
Photo courtesy of Annapolis Boat Shows
Annapolis PowerBoat Show
Experience the world’s largest in-water powerboat show when the Annapolis Powerboat Show returns to City Dock from Thursday, October 8, through Sunday, October 11, beginning daily at 10 a.m. Stroll the floating docks as Annapolis Harbor transforms into a premier showcase of luxury yachts, fishing boats, cruisers, and the latest in marine technology, accessories, and apparel. Whether you’re a lifelong boater, an avid angler, or simply love being on the water, this internationally renowned event offers the perfect opportunity to explore the boating lifestyle while enjoying the vibrant waterfront atmosphere of downtown Annapolis. More info: annapolisboatshows.com
NextNOW Fest 2026
Experience the intersection of creativity and community at NextNOW Fest, taking place September 9–15 at the University of Maryland in College Park. This free, weeklong arts festival features live music, comedy, visual art, performances, and interactive experiences from innovative artists across the country alongside talented members of the university community. Festival events begin Wednesday, September 9, at 11 a.m., with additional featured performances on Thursday at 1 p.m., Friday at 5 p.m., Saturday at 5 p.m., Monday at 3 p.m., and Tuesday at 5 p.m. Whether you’re a lifelong arts enthusiast or simply looking for an inspiring day out, NextNOW Fest offers something for everyone. More info: theclarice.umd.edu/
Photo by Josh Davidson
Annapolis Sailboat Show
Set sail for one of the world’s premier boating events as the Annapolis Sailboat Show returns to City Dock from Thursday, October 15, through Sunday, October 18, beginning daily at 10 a.m. Explore floating docks filled with sailboats from leading manufacturers around the globe, from sleek racing yachts and cruising vessels to multihulls and sailing dinghies. Along the waterfront, exhibitors showcase the latest in marine technology, sailing gear, charter opportunities, and educational resources, making this internationally acclaimed event a must-visit for seasoned sailors and newcomers alike. More info: annapolisboatshows.com
Art @ the Park
Celebrate creativity in the great outdoors at the 36th annual Art @ the Park, taking place Saturday and Sunday, October 17–18, from 10 a.m. to 4 p.m. at Quiet Waters Park in Annapolis. This beloved fall festival showcases an impressive collection of visual art alongside live music, artist demonstrations, food trucks, and hands-on activities for children, making it a perfect outing for the whole family. Leashed dogs are welcome, and with beautiful park scenery as the backdrop, it’s an ideal weekend to enjoy local art, fresh air, and community. More info: fqwp.org
Frederick’s 25th Annual Oktoberfest
Celebrate German heritage, food, and festive traditions at Frederick’s 25th Annual Oktoberfest on Saturday, October 2 and 3. Attendees will enjoy authentic German cuisine, lively entertainment, and the spirited atmosphere of one of fall’s most beloved celebrations. Bus transportation is available on Saturday for a $10 fee to/from the City of Laurel’s Robert J. DiPiertro Community Center. More info: cityoflaurel.org/parks or frederickoktoberfest.org
Sporting Clay Shoot
Take aim for a great cause at the MTBMA Annual Sporting Clay Shoot on Tuesday, September 15, from 11:30 a.m. to 4 p.m. at The Point at Pintail in Queenstown. This popular event welcomes both seasoned shooters and first-timers for an afternoon of friendly competition, networking, and outdoor recreation, complete with a catered lunch, oyster station, beverages, raffles, and prizes. Proceeds benefit the MTBMA Scholarship Foundation, helping support students pursuing careers in Maryland’s transportation construction industry. Whether you’re competing with colleagues or simply enjoying a day on the course, every shot helps invest in the next generation of industry professionals. More info: mtbma.org
St Lukes Art League Art Show
Discover the work of talented regional artists at the St. Luke’s Art League Labor Day Art Show, held Saturday, September 5, through Monday, September 7, from 11 a.m. to 5 p.m. each day under the tent at St. Luke’s Church in St. Michaels. This beloved outdoor exhibition features more than 300 original paintings created by St. Luke’s Art League members, offering visitors the chance to browse and purchase unique works in a charming Eastern Shore setting. Whether you’re an avid art collector or simply looking for creative inspiration, this annual Labor Day weekend tradition is the perfect opportunity to celebrate local talent. More info: stmichaelsmd.com
The Wailers at Avalon Theater Foundation
Feel the rhythm of reggae history when The Wailers take the stage at the Avalon Theatre in Easton on Thursday, September 24, from 6:30 to 9 p.m. Celebrating the 50th anniversary of the landmark album Rastaman Vibration, the legendary group will perform beloved classics alongside songs from the iconic 1976 release that helped bring reggae to audiences around the world. With a standing-room dance floor in the orchestra section and reserved balcony seating available, this unforgettable evening promises timeless music, positive vibes, and a celebration of Bob Marley & The Wailers’ enduring legacy. More info: avalonfoundation.org
