Do you remember, the 21st night of September? Well, we hope you also remember the other 29 days of September! Let Annapolis and Anne Arundel County heal the sting of the end of vacation season with signature and recurring events that will be fun for the entire family. Whether a weekend getaway is what you are searching for or a local night on the town, Annapolis & Anne Arundel County is the perfect destination for a Fall adventure.


Outdoor seating for wine tasting
Thanksgiving Farms Winery


Fall Adventures


September 17 – November 6 (weekends) - MD Corn Maze (Gambrills) -- People have been getting lost in the 8-acre corn maze for 16 years! Check out the new farm flyer zip line and giant bounce pad in addition to the old favorite pedal tractors, rodeo roping area, giant straw pyramid, tire mountain, and more. They even offer pony rides. Hours: Saturday-Sunday, 10:00 a.m.–7:00 p.m.  


September – November (weekends) - Thanksgiving Farm Winery (Lothian) - Folks near and far have been traveling to this local winery which began growing grapes in 1998. They specialize in Bordeaux red varieties and their historic farm and farmhouse are on the National Register of Historic Places. Stop in for a tasting on Saturdays and Sundays through November from noon until 5:00 p.m. Reservations are strongly encouraged. 


A woman dressed in medieval attire holds flower crowns on her arms
Experience the Maryland Renaissance Festival!


Annual Events & Festivals


September – October – Maryland Renaissance Festival  (Crownsville) - Immerse yourself in one of the most highly anticipated events in Anne Arundel County. With more than 200 professional performers, including knights, kings, queens, and jousters, you will not want to miss this old-world experience full of fun for the whole family. The Renaissance Festival is open for revelers every weekend from September 2nd through October 22nd. Advanced tickets are highly recommended for this popular event. 

September 3 & 10 – Navy Football (Annapolis) – Navy Football kicks off its 2022 season with a home game against the Delaware Blue Hens on Saturday, September 3rd at noon. They will match-up against Memphis on Saturday, September 10 at 3:30 p.m. Go Navy! 

September 14-18 – Anne Arundel County Fair (Crownsville) - Both young and old alike will enjoy daily entertainment, contests, shows, demonstrations, displays, foods and goods offered by a variety of fair vendors at the county’s annual fair. Children 9 and under are free with a paying adult, Age 10 & over, $10.00 each.

September 15-17 Annapolis Songwriters Festival (Downtown Annapolis) - Modeled after the hugely successful Key West Songwriters Festival, the largest festival of its kind in the world, 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 our historic capital on the bay the perfect setting for live music enthusiasts to get acquainted with the faces, voices, and stories behind the songs.


Logo embellishments with text that reads 1st Annual Annapolis Songwriters Festival September 15 thru 17 2022


September 10-30 -- The Radical Voice of Blackness Speaks of Resistance and Joy (Annapolis) – Guest curated by Myrtis Bedolla of Galerie Myrtis, the exhibit features fine art by fifteen Black Maryland-based artists, as well as the Banneker-Douglass Museum’s Fine Art Collection. The Radical Voice of Blackness Speaks of Resistance and Joy examines historic and contemporary themes of Black joy and healing created in opposition to, and in spite of oppression. 

September 24 – Kunta Kinte Heritage Festival (Downtown Annapolis)In September 1987, the Kunta Kinte Celebration was born in Annapolis, Maryland. Now known as the Kunta Kinte Heritage Festival, the event is a celebration of the perseverance, education, and cultural heritage of Africans, African Americans, and Caribbean people of African descent. 

September 24-25 Maryland Seafood Festival (Annapolis) – The festival has been gracing the shores of the Chesapeake Bay since 1966 with delectable crab, oysters, shrimp, mussels, and locally caught fish prepared any way you like it! Come for the food and stay for the views! 


Three black men singing on a stage at a festival
The Kunta Kinte Heritage Festival
Image courtesy of Christian Smooth


Seasonal Signature Events


September 9 Arts Alive Global! Come Sail the World (Annapolis) – "Come Sail the World" at Arts Alive Global! Sponsored by Rams Head Presents, this is Maryland Hall for the Creative Arts’ largest fundraising event of the year. Arts Alive is going worldwide this year. The campus will be transformed into a mini globe offering trips around the world through entertainment, décor, art, food, and cocktails.  

September 10 Warriors in the Park (Annapolis) – Join Warrior Music Foundation and MC3 for the 2nd annual Warriors in the Park Concert featuring: Jimmie's Chicken Shack and Pressing Strings. Enjoy live music at StageOne at MC3 as they honor the strong veteran community in Annapolis.  

September 10 Piney Orchard Street Festival (Odenton) – Rain or Shine! Come join the Piney Orchard community in Odenton to celebrate summer. The event includes fun activities for the entire family. Free Admission, a host of vendors, beer and wine, and a band/DJ all day. 

September 10 Boatyard Beach Bash (Eastport) – Featuring Jimmy Buffet's recording and touring band, the Coral Reefers, and other world-class musicians, as well as the emcee and host of Radio Margaritaville, JD Spradlin. General admission includes great music, fantastic food, and signature cocktails on a scenic waterfront campus. Two drink vouchers included! The Boatyard Beach Bash is a fundraising event to support Annapolis Maritime Museum & Park’s environmental education programs.  


DTN - ROS - Ballet Theatre of Maryland
Ballet in the garden at Hammond-Harwood House.
Image courtesy of Ballet Theatre of Maryland.


September 17 Mentalist Brian Curry at Children's Theatre of Annapolis (Annapolis) – CTA is hosting a “For the Love of CTA” fundraising event - the first in more than three years. The event supports CTA’s operating budget, which allows the organization to continue offering high-quality theatrical performances for Central Maryland audiences, as well as performing and technical theatre arts education for area children. 

September 18 Ballet in the Garden (Annapolis) – Ballet Theatre of Maryland dancers will perform in the intimate environment of the historic Hammond-Harwood House Museum garden in the heart of Annapolis.  

September 24 Anne Arundel County African Heritage Festival (Laurel) – The event was created to bring awareness of the African culture, educate individuals on African American heritage, and connect individuals to Anne Arundel County’s many agencies and resources. Attendees can engage with vendors and local businesses while enjoying music, food, and much more.

September 24-25 Wheel of Fortune Live! (Live! Casino in Hanover) – America’s Game® is going on tour! “Wheel of Fortune Live!” will be giving fans a chance to be a part of the excitement when it comes to the Hall at Live! at Live! Casino & Hotel. Join them and take a spin to solve the puzzles in person! Guests can try out for a chance to go ON STAGE and PLAY to WIN BIG at every show.  


Entrance to an entertainment venue at Live! Casino & Hotel
The HALL at Live!
Image courtesy of Live! Casino & Hotel.


September 25 Bay Bridge Paddle (Annapolis) – Water enthusiasts of all ages and abilities are invited to take part in the Bay Bridge Paddle. The event is open to stand-up paddleboards, kayaks, and other paddle craft. Paddling any part of the Chesapeake Bay is a thrilling experience, and launching from Sandy Point State Park is no different. The race brings together all levels of paddlers for a day of camaraderie and fellowship.

September 25 West Annapolis Oktoberfest (West Annapolis) – Join the shops and restaurants of West Annapolis for a fun-filled family celebration featuring food, music, local vendors, and plenty of German beer!

September 27 Tuesday Beer Tasting Sunset Sail (Downtown Annapolis) – Enjoy a Sunset Sail & Beer Tasting on the Chesapeake Bay aboard the 74-foot, classic wooden schooner, Woodwind. Explore new craft brews and learn from a brewery expert who will be on hand to answer your questions.   

September 30 – October 1 Annapolis Symphony Orchestra (Annapolis) -- A rousing season opener celebrates aspects of America. Copland’s El Salón México is a postcard impression of Mexico through its dance hall melodies. Samuel Barber’s Knoxville: Summer of 1915 evokes the tranquil and dreamlike American South. With text taken from the Ellis Island Oral History Project, Peter Boyer’s work tells the stories of seven immigrants from seven different countries who arrived between 1910 and 1940.  


Annapolis Symphony Orchestra
The Annapolis Symphony Orchestra



Recurring Events


Live Music at Pirate’s Cove! (Galesville) – Enjoy live music dockside by the West River in scenic Galesville at Pirates Cove on Friday and Saturday evenings and Sunday afternoons.  Sing along with local singers/songwriters and all-around entertainers performing covers of rock and folk favorites. Enjoy nightly food and drink specials.  

Annapolis Sunset Cruise with Live Music (Downtown Annapolis) – Watch the sunset and the lights of Annapolis Harbor during a 90-minute Annapolis Sunset Cruise. Enjoy live music from your favorite local Maryland musicians as you relax with a cool drink. Beverages and snacks are available for purchase from the fully stocked bar. 

A Day on the Bay to St. Michaels (Downtown Annapolis) – Cruise across the Chesapeake Bay to St. Michaels on the Eastern Shore. The quaint historic village of St. Michaels offers fresh seafood, boutique shopping, and historic sites within walking distance during your approximately three hours of leisure time ashore. Admission to the Chesapeake Bay Maritime Museum is included. 

Food Trucks (Greater Annapolis and Severna Park) – Discover new cuisine on Friday nights with a visit to as many as ten food trucks at the site of the Anne Arundel County Farmers’ Market at the corner of Harry Truman Parkway and Riva Road in Annapolis. On Tuesday evenings, head to the grounds of the Earleigh Heights Volunteer Fire Company in Severna Park to enjoy cuisine from 24 food trucks in rotation.  


A yellow and white doughnut Food Truck
Blondie's Doughnuts
Image courtesy of Christian Smooth


Annapolis Tours & Crawls Ghost Tour (Downtown Annapolis) – Take a leisurely ghost walk through the historic downtown district on a spine-tingling journey into Annapolis’ dark and troubled history, while meeting some of our more spirited residents and visiting their most horrific haunted sites! Inquire about their Haunted Pub Crawls for a delightful evening of spirits and spirits! 

Summer Concerts at Quiet Waters Park (Greater Annapolis) – The Annapolis Symphony Orchestra will perform the final Friends of Quiet Waters Park outdoor concert of the season on September 4 from 5:30 p.m. until 7:00 p.m.   

Sunset Paddle at Capital SUP - Quiet Waters Park (Greater Annapolis) – Paddle as the sun goes down and fills the sky with color! Group sunset paddles will close out the day in serenity, with SUPs, kayaks, and canoes available. The guides also will take paddlers into Loden Pond, which is normally off-limits for regular rentals! 

Thomas Point Shoal Lighthouse Tours (Annapolis) – Tours depart the Annapolis Maritime Museum at 9:00 a.m. and noon on a first-come basis. After a 30-minute boat ride, you will get to experience the National Historic Landmark that is still used for navigational purposes.  


Thomas Point Lighthouse - Thomas Point Lighthouse
Thomas Point Lighthouse
Image courtesy of Bob Peterson.


SoFo Summer DriveIn Movies (Annapolis) – Enjoy free monthly outdoor movies on the last Friday of the month at Bay Ridge Shopping Center along the South Forest Drive Corridor. Movies start at dusk after 90-minutes of live music.  Food and drinks are available for purchase from Grumps Café. 

Wildberry Field Market (Crownsville) – Join Wildberry Farms for their weekly Saturday Field Markets featuring more than 30 vendors and food trucks, Wildberry Farms' limited seasonal produce, farm-fresh eggs, and flowers. The weekly rain date is Sunday from 9:00 a.m. until 1:00 p.m.  

Dinner Under the Stars (Downtown Annapolis) – On Wednesday evenings and select Saturdays through September 24, the first block of West Street in the heart of downtown Annapolis closes to automobile traffic and welcomes visitors to dine and shop al fresco under a canopy of white lights reminiscent of European open-air cafes. Treat yourself to an evening with family and friends enjoying live music and art demonstrations against the backdrop of Historic Annapolis.   

ArchiTrex (Downtown Annapolis) – Join Annapolis Tours® by Watermark® for their award-winning ArchiTrex tour developed in partnership with Historic Annapolis. Learn about the city’s most notable and celebrated examples of 17th and 18th-century architecture. Hear stories that go beyond the structures to include insights into the lives of Annapolis' builders and dwellers spanning more than 300 years.  

City Dock Concert Series (Downtown Annapolis) – Through September 9, Sunday nights are rocking with free entertainment at Susan Campbell Park at Annapolis City Dock from 6:00 p.m. until dusk.  


First Sunday Arts Festival by Bob Peterson
First Sunday Arts Festival


First Sunday Arts Festival (Downtown Annapolis) –The first Sunday of each month from May through November, the first blocks of West and Calvert Streets are filled with street vendors, performers, musicians, and more. In a festive celebration of the arts, thousands of visitors enjoy an afternoon of al fresco dining, live entertainment, and an opportunity to explore the works of more than 100 artisans and craft vendors 

First Sunday Market at Honey's Harvest Farm (Lothian) – On the first Sunday of each month from 11:00 a.m. until 3:00 p.m., Honey’s Harvest features more than 20 local farmers, artisans, brewers, bakers, distillers and their amazing local and organically and/or non-GMO cultivated products, including pastured proteins, local mushrooms, live plants, elderberry syrup, local honey, the harvests of local watermen, homemade baked goods, jams and jellies, vegetables, herbal teas, jewelry, goat’s milk soap, beer, artisan woodcrafts, upcycled’ lamps, and so much more! 

Anne Arundel County Farmers' Market (Annapolis) – Help the Anne Arundel County Farmers’ Market celebrate its 40th year! In honor of the occasion, they’ve expanded their events calendar to include a host of family-friendly celebrations to compliment the ever-changing seasonal variety of farm favorites available. Take advantage of this opportunity to purchase some of the best local products Annapolis and Anne Arundel County have to offer. 

Sunday Fun Day Sails (Downtown Annapolis) – Celebrate Sunday Fun Day with bubbly, mimosas, bloody marys, local craft beers, and wines  while sailing the Chesapeake Bay aboard the 74-foot Schooner Woodwind and Woodwind II.


Schooner Woodwind: Annapolis Sailing Cruises

The Schooner Woodwinds under sail on the Chesapeake Bay.


Monday History Sunset Sails (Downtown Annapolis) – Annapolis Sailing Cruises features a history-slanted sunset sail on Monday nights May through September. Experience the historic Annapolis skyline that has welcomed ships for centuries as you sail past the United States Naval Academy and into the Chesapeake Bay. Come listen to the stories that make up the fabric of history in this terrific bayside town. 

Farm to Table Series with Graze Gourmet (Crownsville) – Enjoy a farm-fresh meal as you’ve never experienced it before out on the farm. Each meal will be crafted by Chef Adrienne Shoots of Graze Gourmet with ingredients sourced completely from Wildberry Farm and served in the grove in the shade of towering trees. 

African American Heritage Tour (Downtown Annapolis) – Trace the journey of African Americans and explore their impact nationally and internationally. Offered in partnership with the Kunta Kinte-Alex Haley Foundation and named a “Heritage Award Winner” by Chesapeake Crossroads, the two-hour walking tour starts at Market House Park across from Annapolis City Dock, where slave ships arrived 300 years ago. Your period-attired guide will highlight the importance of the Underground Railroad in the Chesapeake Bay region.  


Quiet Waters Concert
There's always live music in Annapolis & Anne Arundel County.


Cars and Coffee (Annapolis) – Calling all classic car enthusiasts. Browse an amazing display of different makes, models, and years of vehicles in the west lot of Annapolis Town Center every Sunday.  

Fundraising BEER GARDENS (Gambrills) – Enjoy delicious food, refreshing drinks, lawn games, live music, and more at a fundraiser for the Johns Hopkins House.  

Arundel Preserve Concert Series (Hanover) – The Hotel at Arundel Preserve is presenting complimentary entertainment on select evenings, wrapping up with a concert by Firekite on September 22. Musicians offer a variety of classic sounds perfect for a casual family outing or outdoor happy hour. To add to the festivities, food, and dessert trucks as well as an outdoor bar for guests 21 and older are available.  



Events Subject to Change. Contact event organizers for more information.

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