Fall is Here! 

Although the days are shorter, the sunsets are sweeter here in the heart of Maryland. Discover your fall adventure along the shores of the Chesapeake Bay in Annapolis & Anne Arundel County!

View more itineraries on our website!

Things to Do in October

The Great Annapolis Pumpkins, October 3-31

Extend your stay in Annapolis for a weekend of fall festivals and Halloween fun!

You never know when these 1,000-pound pumpkins will pop up in downtown Annapolis, but they are hard to miss once they do! Visit the nearby Maryland Avenue & State Circle Fall Festival on October 23rd, or venture into the county for a hay ride and a pumpkin patch at a local farm. Get lost in the corn maze at the Maryland Corn Maze in Gambrills, or book a haunted ghost tour or pub crawl in the heart of historic Annapolis. For the fearless, stay in a historic inn or bed and breakfast and you may just hear more than your heart go bump in the night!


Book a Hotel + Shuttle Boat Show Package!

Book our exclusive Boat Shows hotel and shuttle package! Stay in the BWI/Arundel Mills entertainment district as you plan your trip to Annapolis for the largest in-water boat show. Located only 20 miles outside of Annapolis...


United States Boat Shows


If you’re tired of haunting your own house this Halloween season, grab your friends and brave the dark streets of Annapolis for a hauntingly good time! Read More...

There are 381 farms and over 28,000 acres of farmland in Anne Arundel County alone and thankfully, many of them open their doors for markets, hayrides, corn mazes, and pumpkin tosses every fall. Read More...

Maryland Renaissance Festival, weekends August 28-October 24 

Hear ye! Hear ye! Leave your modern woes behind and step into 16th-century Revel Grove— the 27-acre village overseen by King Henry VIII. Beginning in August and lasting through the end of October.


Read More

The Bay Bridge Run

Join us in Annapolis on November 11, 2022, for the annual Bay Bridge Run! This epic race takes you across the span of the Chesapeake Bay Bridge for a run that will test your mettle and your fear of heights! Register for this race and book your stay for the perfect fall weekend away!


Learn More

Ready to take in the fall foliage along

the shores of the Chesapeake Bay?


Download your Copy of the 2022 Visitor Guide and start planning

your Fall adventure today!