When the temperatures cool, the summer crowds disperse, and the trees begin to show their true colors, Annapolis teems with activities and great things to see and do. Whether you love the bustle of the city or prefer the wide-open rural spaces, there’s something here for everyone.
A consensus on the “best” things to do in Annapolis might be impossible, but we’ve put together a list of our favorites to help you enjoy fall in Annapolis:
Why Autumn is the Best Time to Visit Annapolis:
US Powerboat Show, October 3 – 6, 2019: The City Dock is the place to be for all things boating. The Powerboat Show features everything from luxury yachts to high-performance fishing boats, inflatables, marine equipment, and more.
US Sailboat Show, October 10 – 14, 2019: This year, the US Sailboat Show is celebrating its 50th anniversary. As the largest international sailboat show, it is a must-do for sailing enthusiasts. Beyond the boats, enjoy live entertainment, food, shopping, and fun for the whole family.
First Sunday Arts Festival, October 5, 2019, November 3, 2019: Shop and discover the works of local artists and artisans. Located in the first block of West and Calvert Streets, this free event runs from 11 am to 5 pm.
Tour the Historic National Road
As Maryland’s oldest road, the Historic National Road traverses 170 miles, from Baltimore to the Pennsylvania line. The six-hour drive passes by museums, monuments, state parks, and some of the most picturesque scenery you’ll ever experience.
Scenic Railroad Trip for Fall Foliage Viewing
See fall in Annapolis in all its glory with a trip aboard the Western Maryland Scenic Railroad. Leaving from Cumberland, the three-hour train trip takes you through breathtaking views and stops at a few sweet spots along the way.
Spooky walking tours
As the autumn chill settles in, the days grow shorter, and the shadows grow longer. It’s the perfect time for a spooky walk through Annapolis in the fall. Choose from several ghost walks, including a Haunted Pub Crawl and a historic downtown walking tour.
West Annapolis Oktoberfest, September 29, 2019
Celebrate the season at Annapolis Oktoberfest. Enjoy a day of beer, food, and fun for the whole family. This festival on Annapolis Street features more than 130 vendors, a petting zoo, beer trucks, live music, and more.
Maryland Renaissance Festival, Weekends Through October 20
Travel back in time to the year 1532 at the Maryland Renaissance Festival. Whether you go in costume or not, this event offers historic reenactments, jousting, dancing, duels, music, and plenty of food and drink.
When work calls, My Annapolis Office is here to help. What are your favorite fun fall things to do near you or things to do in Annapolis in November? Let us know—reach out today!
