Downtown Annapolis Events: September & October 2023

As we transition from summer to fall, Downtown Annapolis is gearing up for a series of exciting events in September and October 2023. Whether you’re a local resident or a visitor looking to explore the area, The Wright Team of Coldwell Banker Realty has rounded up the events you won’t want to miss.

Mark your calendar for these events and make the most of the Fall season in Downtown Annapolis. Each of these events offers a great opportunity to explore, enjoy, and embrace our vibrant local culture.

Annapolis Songwriter’s Festival (September 14-17):

This is a new event in Annapolis and you will want to check it out.  Modeled after the hugely successful Key West Songwriters Festival, the largest festival of its kind in the world, the Annapolis Songwriters Festival brings our love for music to the bay! With performers like Blondie and LeAnn Rimes, it’s expected to be quite a celebration of musical talent!  Get ready to enjoy diverse genres performing all over Annapolis from City Doc to Maryland Hall and Rams Head.

Haunted History Tour (October weekends):

Join a Haunted History Tour to uncover eerie tales and ghostly legends lingering in Downtown Annapolis. Guided by lantern light, you can explore centuries-old alleys while hearing spine-tingling stories of the city’s past inhabitants. This one is fun for the whole family!

Annapolis Sailboat Show (October 12-16):

Every October, sailing enthusiasts from all over the world converge in Annapolis for the Sailboat Show. This yearly homage to sailing showcases an incredible selection of sailboats. Along the shoreline, rows of show tents are set up, full of cutting-edge nautical gear, accessories, electronics, communication equipment, sails, rigging, educational resources, charter companies, clubs, and more. This is a do-not-miss event for everyone, not just the avid sailor.

Maryland Restaurant Week (September 15 – 24):

Maryland Restaurant Week is an opportunity to indulge in gourmet meals and sample diverse flavors from Annapolis’s finest dining establishments. There are numerous restaurants participating this year, throughout Anne Arundel County.  Be sure to enjoy these 10 delicious days of dining!

Maryland Avenue Fall Festival (October 23):

The Maryland Avenue Fall Festival has become a classic over the years making it one of the events to not miss in Downtown Annapolis during September and October 2023. The festival features live music, family-friendly activities, food, a beer garden, and unique vendors offering antiques, art, fair trade goods, handmade crafts, and sustainable products.

Last but certainly not least, be sure to attend a Navy Football game this season!

That goes without saying in Annapolis. The first game in Annapolis kicks off on September 9th at 3:30 pm against Wagner.

The Wright Team of Coldwell Banker Realty Can Guide You

Whether you are considering home buying or selling now, or in the future The Wright Team of Coldwell Banker Realty is here to help guide you through the entire process. The Wright Team provides residential and commercial real estate services in Annapolis, as well as the surrounding communities in Anne Arundel County. With over 70 years of combined experience in the industry and superior local real estate, the Wright Team specializes in historic homes, new construction projects, marketing homes to sell, and assisting buyers in identifying homes to purchase in the local area. Contact us today!