Fun Fall Events in Annapolis

Annapolis offers a charming and picturesque setting for visitors and residents to enjoy during the fall season. Here are a few of our favorite events in Annapolis in the fall:  

• Whether you are a boater, angler, or just getting started check out the Annapolis Boat Shows in October.  https://annapolisboatshows.com/
• Check out the the longest international Tug of War over the water on November 5th. The tug teams will line up, some on the Annapolis side and some on the Eastport side. The teams will duke it out by tugging on a giant rope across the “Gulf of Eastport” (aka Spa Creek).  https://www.visitannapolis.org/blog/stories/post/a-brief-history-of-the-tug-of-war/
• Visit the U.S. Naval Academy: Explore the historic campus, attend a football game, or take a guided tour to learn about the academy's rich history. https://www.usna.edu/
• Stroll along the City Dock: Enjoy the scenic waterfront area, watch boats sail by, and grab a meal at one of the many restaurants overlooking the harbor. Market House is our favorite if you are looking for a casual meal. https://annapolismarkethouse.com/  And don't miss the new Goat. https://www.thegoatannapolis.com/
• Take a Boat Tour or Cruise: Enjoy a scenic boat tour of the Chesapeake Bay or take a cruise around the harbor to take in the fall foliage from the water. https://amaritime.org/wilmalee/
• Encourage some friends to join you and sign up for the Chesapeake Bay Bridge Run/Walk. https://www.thebaybridgerun.com/
• Shop at Local Boutiques: Wander through the charming streets of downtown Annapolis and explore the various boutiques, galleries, and specialty shops. https://www.downtownannapolispartnership.org/
• Attend Maryland Ave. & State Circle Fall Festival on October 22.  https://mascma.com/ 
• Hike Bacon Ridge Trails: This beautiful park is an excellent spot for autumn hike. https://www.aacounty.org/locations/bacon-ridge-natural-area
• Friday’s in the fall at Great Frogs WineryJoin us for a tasting, glass, or bottle and relax with local live music on the patio.  No cover fees. Wine friendly snacks available for purchase. Seating on patio is on a first come basis. https://www.greatfrogs.com/events
• Take a Ghost Tour: Learn about Annapolis' haunted history on a guided ghost tour. It's a fun and spooky way to explore the city's darker side. https://toursandcrawls.com/
• Explore Annapolis Maritime Museum: Learn about the maritime heritage of Annapolis through exhibits and educational programs. https://amaritime.org/

Enjoy the season. We love this time of year! 

- Betty and Kate