Fall Events Coming to Annapolis, Maryland

Blazers, Bourbon, Cigars

• When: Thursday, September 27, 2018 6pm- 9pm
  
  
• Where: William Paca House and Garden, 186 Prince George Street
  
  
• Tell me more: Coming up soon! This event is the 5th annual premier gentlemen’s only evening. Join other 21 and older men for a night of bourbon, scotch, rum tastings, cigars, and an assortment of outstanding food from some of the area’s finest chefs. This is a great opportunity to try out some of the local vendors of Annapolis.

Boat Shows

• When: Annapolis Powerboat Show Oct. 4-8
  
  
• United States Sailboat Show October 11-14
  
  
• Where: City Dock, Annapolis, MD
  
  
• Tell me more: October is a unique month for boaters in Annapolis because both the powerboat and sailboat show take place, creating an exciting time for residents and visitors of the capital city! Boats are situated in the water along the dock for viewing, with around 100 sailboats to choose from and every style of motor and ocean-going yacht you can name. Powerboats come in my sizes, ranging from 8′ to 90′ in diameter. In addition, pop up shops have an assortments of gifts to purchase from navigational equipment to clothing, gear and other boating additions.

Maritime Republic Tug of War

• When: November 3, 2018
  
  
• Where: Maritime Republic of Eastport
  
  
• Tell me more: Known as the Slaughter Against the Water, this Annapolis event based on the rivalry between The City of Annapolis and Eastport, is not one to miss this autumn! The 19th year battle of two sides of Annapolis will take place on November 3rd, then shortly after, everyone will enjoy food, beverages, music and dancing. It’s a fun way to celebrate a little bit of history, remembering how Eastport announced a symbolic war of independence after the Eastport bridge was temporarily shut down in the year 1997.

Other Fall Annapolis Events:

• First Sunday of each month May – November
• Maryland Renaissance Festival – August 25 – October 21
• Historic Hauntings Ghost Tour – October 13th
• Homestead Gardens Fall Festival – September 22 – October 28
• Oyster Festival – October 21
• Annual Annapolis by Candlelight – November 2 – 3