It is almost time to raise a glass to the end of another incredible summer in Annapolis and Anne Arundel County. Thanks to Labor Day weekend and the lingering warm weather, we are still hanging on to all the outdoor and festival fun before fall officially makes its way into town on September 23. So, break out your boat shoes and flip flops, and enjoy notable events like the Annapolis Songwriters Festival, Kunta Kinte Heritage Festival, Anne Arundel County Fair Week, and Navy Football!  


people in bumper cars at a fair
Anne Arundel County Fair
Image courtesy of Visit Annapolis & Anne Arundel County


Weekend Long Fun 

Weekends in SeptemberMaryland Renaissance Festival (Crownsville) Hear ye! Hear ye! Step into the 16th-century Revel Grove and leave your modern woes behind. RennFest has something for everyone. From turkey legs to toasting with mead to jousting and cheering on your own Kingdom, it is no wonder this immersive experience is one of Maryland's most extravagant and popular events.    

Weekends (and some weekdays) in September – Maryland Corn Maze (Gambrills) It is time to get lost in the great outdoors! Swing by Gambrills to test your luck at the Maryland Corn Maze, indulge in some of fall's finest treats, and take a hayride! Plus, this is your one-stop shop to pick a pumpkin, too!  

September 2 & 3 – Pops in the Park (Pasadena & Annapolis) Join the Annapolis Symphony Orchestra at Downs Park in Pasadena and Quiet Waters Park in Annapolis on Labor Day weekend for two FREE performances! Grab your picnic blanket and listen to renditions of uplifting, danceable pop tunes, patriotic songs, and Broadway music to close out summer!    


Quiet Waters Concert
Summer Concerts at Quiet Waters Park
Image courtesy of Visit Annapolis & Anne Arundel County


September 14 – 17 – Annapolis Songwriters Festival (Annapolis) Get ready for Blondie, LeAnn Rimes, and many other incredible songwriters at one of the premier music festivals on the shores of the Chesapeake Bay in Maryland's Music Capital - Annapolis. Modeled after the hugely successful Key West Songwriters Festival, the Annapolis Songwriters Festival brings the love for live music to the Bay. Like Key West, Annapolis has its own world-renowned watering holes and intimate theater settings, making Maryland's state capital the perfect location for concert enthusiasts to get acquainted with the faces, voices, and stories behind the songs.   

September 23Kunta Kinte Heritage Festival (Annapolis) In September 1987, the Kunta Kinte Celebration was born in Annapolis, Maryland. Now known as the Kunta Kinte Heritage Festival, the festival celebrates the perseverance, education, and cultural heritage of Africans, African Americans, and Caribbean people of African descent. The festival runs all day with live music, vendors of African art, jewelry, handmade goods, dance performances, and activities for children.  

September 30 & October 1 – Annapolis Baygrass Music Festival (Annapolis) Every jam saves the Bay! Sit on the shores of the Chesapeake Bay at Sandy Point State Park and enjoy two days of the best bluegrass music around. Bands playing include Yonder Mountain String Band, Railroad Earth, and artist at large Lindsay Lou. The whole family is welcome at this festival! 


A group of spectators watch a band of musicians on a stage at a festival
Kunta Kinte Heritage Festival
Image courtesy of Christian Smooth for Kunta Kinte Fest.


Signature Events 

Thursdays in September September Sunsets Concert Series (Annapolis) The Annapolis Maritime Museum & Park continues a summertime tradition with its September Sunsets Concert Series! The Tides & Tunes concerts continue with four weeks of great music – from rock to funk to hip-hop – with the incomparable backdrop of the Park Campus. Shows are free; however, donations are gratefully accepted. 

September 8 25th Annual Arts Alive (Annapolis) It is a night to imagine at the 25th Anniversary of Maryland Hall's Arts Alive! Art truly comes alive at this rendezvous where you can mingle with 500 of Annapolis' brightest stars, indulge your senses with the finest food and drink, and dance the night away with various forms of entertainment. Plus, you can win a bucket list trip to a getaway of your choice! 

September 8 & 10 City Dock Concert Series (Downtown Annapolis) The City Dock Concert Series, another Annapolis tradition, wraps up with two more September shows. Join City Dock Tango on September 8 and Severn River Stompers on September 10 at Susan Campbell Park for free family fun. Pack a picnic and enjoy music right on the Chesapeake Bay waterfront.  

September 918th Annual Boatyard Beach Bash (Eastport) Break out your best tropical wear and join members of Jimmy Buffett's Coral Reefer Band at the Annapolis Maritime Museum & Park as you soak in the sounds of Key West. Selling out for the past ten years, this is an Annapolis bash you do not want to miss. General admission tickets include an open bar and a delicious meal.  

September 13 - 17Anne Arundel County Fair Week (Crownsville) Both young and old will enjoy all that the Anne Arundel County Fair has to offer! From rides, daily entertainment, contests, shows, demonstrations, displays, and food and goods from fair vendors. Take advantage of the last few days of summer in Anne Arundel County with this popular family event! 


Anne Arundel County Fair
Anne Arundel County Fair September 13-17,2023
Image courtesy of Visit Annapolis & Anne Arundel County


Local Festivals & Events 

September 1 & 2Kristen Dickmann Invitational – Navy Women's Volleyball (Annapolis) This four-team invitational will bring volleyball teams from the United States Naval Academy, University of Maryland, Old Dominion University, and Utah Valley University. The free sporting event is perfect for the entire family to experience the Naval Academy, so make sure you get there in time to take a tour of The Yard beforehand! 

September 9 – Navy Football Kickoff (Annapolis) It is a showdown between Navy and Wagner College at Navy-Marine Corps Memorial Stadium. The Midshipmen's 2023 football season kicks off with a 3:30 p.m. game, giving you plenty of time to set up your tailgate and celebrate a new season!    

September 9Living History on Pinkney Street: Meet the Maryland 400 (Annapolis) Visit Pinkney Street and meet the men who would become known as the "Maryland 400" as they prepare to leave Annapolis and talk with their families and see how they prepare supplies for the troops. Learn how the efforts and courage of these men allowed the rest of the Continental Army to escape complete destruction at the first major battle of the Revolutionary War. 


Men in period military costumes walking on a dock past Tall Ships in a harbor
Come see the reenactors of the Maryland 400 on Pinkney Street.
 Image courtesy of Visit Annapolis & Anne Arundel County.


September 10Classic Wooden Boat Regatta (Annapolis) This is one of the best ways to enjoy sailboat races in Annapolis. The Woodwind boats have been invited to participate in the race "Spirit of Tradition Class." Enjoy three laps out on the Severn River with the Woodwind crew while enjoying a boxed lunch, a perfect backdrop for photography, and the thrill of racing on the river! 

September 16African American Heritage Tour (Annapolis) Trace the journey of African Americans and explore their impact nationally and internationally. This 2-hour walking tour, with a period-attired guide, starts at Market House Park across from Annapolis City Dock, where slave ships entered 300 years ago. Plus, learn about famous Marylanders, such as Harriet Tubman and Frederick Douglass, and the Underground Railroad in the Chesapeake Bay region. 

September 22Critter Cruise (Severn River) Get out on the water, enjoy the breeze of the Severn River, and have a fun experience with critters who live in the Chesapeake Bay. Now is your chance to get up close and personal with blue crabs, American eels, oysters, and ospreys and explore the waters around Annapolis. This hands-on, family-friendly learning cruise is perfect for grades 1 –5. 

September 23Bay Bridge Paddle (Sandy Point State Park) Get your paddle on with three tiers of competition out on the Chesapeake Bay. From recreational to elite paddlers, jump on your board and test your skills. Not a paddle boarder? That is perfectly fine! This race allows for other watercraft, including kayaks and surf skis. Register now so you can hit the water in late September!


Schooner Woodwind: Annapolis Sailing Cruises
Classic Wooden Boat Sailing Regatta.
Image courtesy of Visit Annapolis & Anne Arundel County.


September 23Stories & Art in the Galleries: "It's Fall" (Brooklyn Park). Gather at the Chesapeake Arts Center with your little ones and enjoy a reading of "It's Fall." After the story, children will be invited to make their own paper-cut illustrations! This program will coincide with Janelle Washington's "Quiet Terror, Quiet Joy" exhibit. The event is free with advanced registration!  

September 24West Annapolis Oktoberfest (Annapolis) Join in for the kickoff to the Fall Festival season with a day of food, music, some of the area's best vendors, fun for kids, and plenty of German beer! Pack Annapolis Street from 11 a.m. to 4 p.m. and enjoy free parking at this annual festival.  

September 25The Australian Bee Gees Show Stayin' Alive, Mate! Head over to Rams Head on Stage to see The Australian Bee Gees Show! The group has been playing on the world's stage for over ten years, performing for Bee Gees fans, reproducing not just the look but the sound, energy, and magic that the Gibb Brothers have given the world for the past five decades. Tickets are on sale now!  

September 29 Summer Drive-In Movies Under the Stars (Bay Ridge) Who doesn't love an outdoor movie under the stars? Pack up the family with a picnic and chairs and enjoy a free showing of "The Perfect Storm" to kick off the official fall season. This event is free for everyone.  


Navy Football Stadium, Midshipmen line up on the field before a game
Navy Football is Back!
Image courtesy of Visit Annapolis & Anne Arundel County.


September 30Navy Football Versus South Florida (Annapolis) The Midshipmen are back in town to take on South Florida in Annapolis! This 3:30 p.m. game leaves you the perfect amount of time to explore downtown Annapolis for lunch before heading over to Navy-Marine Corps Memorial Stadium for kickoff. Go Navy! 

September 30 - Arts in the Park (Brooklyn Park) - The 9th Annual Arts in the Park festival will be bigger and better than ever – with art activities, art and community vendors, food trucks, performances, and more! And it's all free. This event brings 1,000 community residents and visitors together to celebrate, support, and connect through the arts. 

September 1-30Last Days of the Radical Voice of Blackness Speaks of Resistance and Joy (Annapolis) The Radical Voice of Blackness Speaks of Resistance and Joy presents fine art by fifteen Black Maryland-based artists, as well as the Banneker-Douglass Museum's Fine Art Collection, to examine historical and contemporary themes of Black joy and healing created in opposition to and despite oppression. The exhibit will end on September 30, after being open for nearly a year. Make plans to attend the last Artist Talk in the series on September 30 at 11 a.m. This event promises to be a wonderful opportunity to celebrate the culmination of this extraordinary exhibition while connecting with fellow art and history enthusiasts. 

September - Various Dates Check out an Orioles Game (Arundel Mills / BWI Districts) Stay and play in the Arundel Mills/BWI districts and take the MARC train straight to Camden Yards, home of the Baltimore Orioles, who are 1st place in the AL East! The Birds play the Cardinals, Devil Rays, Nationals, and Red Sox this September.


aerial view of Camden Yards
Oriole Park at Camden Yards.
Image courtesy of Visit Annapolis & Anne Arundel County.


Recurring Seasonal Events

Dinner Under the Stars (Downtown Annapolis) On Wednesday and Saturday evenings through September 23, the first block of West Street shuts down to automobile traffic and welcomes visitors to dine, shop al fresco, and even play pickleball under a canopy of white lights reminiscent of the old cities of Europe (weather permitting).   

First Sunday Arts Festival (Downtown Annapolis) Every First Sunday of the month through November, the first blocks of West and Calvert Streets are filled with street vendors, performers, musicians, and more! This festival encourages residents and visitors to shop locally, discover new restaurants, and support the arts (weather permitting).   

Farmers Markets (Countywide) Summertime is the perfect time to set your sights on cleaner eating with a trip to a local Farmers Market. Source organic vegetables and fruit, dairy, meat and poultry, local pies and jams, honey, and more! 


Outdoor dining on West Street in Annapolis, Maryland
Dinner Under the Stars on West Street.
Image courtesy of Visit Annapolis & Anne Arundel County.


Looking Ahead - SAVE THE DATE 

October 5-8 – Annapolis Powerboat Show (Downtown Annapolis) The City Docks of Annapolis will buzz with excitement as boat lovers from around the globe return to celebrate the 50th anniversary of the U.S. Powerboat Show. Spend days exploring powerboats of all varieties and shopping for boat supplies, navigation equipment, and other marine accessories.    

October 12-15 – Annapolis Sailboat Show (Downtown Annapolis) The U.S. Sailboat Show is just three days after the U.S. Powerboat Show—this annual celebration of sailing features floating docks lined with sailboats from manufacturers worldwide. Peruse multihulls, monohulls, cruisers, racers, sailing dinghies, and more. Show tents line the shore, stocked with the latest in nautical gear and accessories, electronics, communication equipment, sails, rigging, education, charter companies, clubs, and more!  

November 12Bay Bridge Run (Chesapeake Bay) The Bay Bridge Run is a 10K race that traverses the eastbound span of the Chesapeake Bay Bridge from Anne Arundel County to Kent Island in Queen Anne's County and finishes with a huge post-race party! Once a year, the bridge shuts down traffic on the eastbound span for a race that tests your mettle and your fear of heights! The views and photo ops abound, and this race is bringing in race enthusiasts from across the country. 

December 9 - Eastport Yacht Club Lights Parade (Eastport) The magical Eastport Yacht Club Lights Parade takes place along the Annapolis Harbor and Spa Creek on the second Saturday in December every year. This annual tradition has been delighting holiday revelers for 40 years! View the parade from the water on your boat, a tour boat, or a charter to experience the holiday spectacle from the water. Or gather with friends and family along the neighborhoods of Eastport and Annapolis, where every street ending at the water offers a perfect view! 

Runners running across the Chesapeake Bay Bridge
The Bay Bridge Run returns on November 12, 2023.
Image courtesy of Bay Bridge Run.