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 might be impossible, but we’ve managed to put together a list of our favorites to help you enjoy the fall in Annapolis:
Fall Festivals in 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 so much 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, but beyond the boats, you can enjoy live entertainment, food and drink, 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, it’s a free event that runs 11 am – 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. From start to finish, the drive will take you six hours. During this time, it will pass by museums, monuments, state parks, and some of the most picturesque country you will ever experience.
Scenic Railroad Trip for fall foliage viewing
See the fall foliage in all its glory with a trip aboard the Western Maryland Scenic Railroad. Leaving from Cumberland, the three-hour train trip takes you through some of the most spectacular scenery while stopping off at a few sweet spots along the way.
Spooky walking tours
As the autumn chill settles in, the days get shorter, and the shadows grow longer. It’s the perfect time for a spooky walk through Annapolis’ ghostly history. There are several ghost walks to choose from, including a Haunted Pub Crawl, and a walk through the historic downtown district.
West Annapolis Oktoberfest, September 29, 2019
Enjoy a day of beer, food, and fun for the whole family. The festival sets up shop on Annapolis Street in West Annapolis and features more than 130 vendors, a petting zoo, beer trucks, music, and more.
Maryland Renaissance Festival, weekends through October 20
Go back in time to the year 1532 and immerse yourself in historic revelry and reenactments of events of that time. Whether you choose to go in costume or not (you can rent period outfits at the Faire), it’s a jolly good time that includes all kinds of entertainment (music, jousting, plays, duels, dancing, and more), food, drink, and shopping galore.
All work and no play? Say it ain’t so! But, when you need to get things done, we’re always here for you at My Annapolis Office. What are your favorite fall things to do in and around our fair city? We’d love to hear about them! Reach out today to connect.