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Here’s Why Autumn in Annapolis Might Actually Be Perfect…

There’s nothing quite like autumn in Annapolis—the gorgeous array of golds and reds that decorate the leafy skyline, that cool little snap to the morning air, the rich aromas of pumpkin and spice wafting from shop to shop along the streets of Downtown… It’s a one-of-a-kind experience not to be missed. In fact, one might almost go so far as to say that autumn in Annapolis is perfect.

Here are six events, activities, and things to do this fall in Annapolis.

Attend the Homestead Gardens Annual Fall Festival

autumn in annapolis fun events

It’s the biggest fall festival in the area, and it runs from September 21 through October 27, so you’ve still got a few days to check it out! Located at Homestead Gardens in Davidsonville, the Fall Festival features 15 rides and attractions, live entertainment, plenty of food, carnival games, and more. Definitely a perk of autumn in Annapolis!

Explore Local Work at the First Sunday Arts Festival

browsing local art in annapolis

On the first Sunday of each month, May through November, head to Downtown Annapolis between 11am and 5pm to browse and shop the works of over 130 local artists at First Sunday Arts. There will also be live performances, music, dancing, and more. It’s a great way to get a head start on your holiday shopping!

Take a Guided Walking Tour

taking a historic walking tour

Fall is the perfect time for getting to know the city of Annapolis a little better—the weather is perfect for walking around, the summer crowds are gone, and the fall foliage adds some magnificent color to some of the most popular tour grounds! Tours run through historic downtown, the grounds of the United States Naval Academy, and even the Maryland State House.

Bonus: On November 7 and 8, take a self-guided tour of some of Annapolis’s most beautiful historic homes at Annapolis by Candlelight.

Or Try a Haunted Ghost Story Tour

dogs on a ghost tour

Step your tour up a notch with a haunted or ghost story tour of Annapolis! Take a nighttime stroll through Downtown while learning about the darker parts of the city’s history. Feeling especially bold? Try a Haunted Pub Crawl complete with haunted taverns and restless spirits.

Cheer on the Midshipmen at Navy-Marine Corps Memorial Stadium

navy vs army football game

Catch a home game at Navy-Marine Corps Memorial Stadium to cheer on the home team (or don’t… but prepare to be outnumbered). Games are prefaced with a march-on by a brigade of midshipmen, and rookies perform pushups for every point added to the scoreboard—it’s an experience that’s definitely different from most college football games. Upcoming home games are Saturday the 26th (vs. Tulane) and November 23 (vs. SMU).

Go Leaf Peeping at a Local Park

beautiful fall foliage

Whether you’re looking for a wooded hike or a lovely treed shoreline, the Annapolis area has plenty of places to go exploring and leaf-peeping. Try Sandy Point State Park for some waterside beauty right in Annapolis, or take a short drive to Patapsco Valley State Park for beautiful foliage along the Patapsco River that you can admire right from your car.

Ready to Come Have Some Fun in Annapolis?

Are you looking for Annapolis autumn activities because you’re thinking of buying a home here or relocating to the area? Then it’s time to contact me, Kyle McCarthy. I’d love to help you get to know the area, explore its unique community, and find the perfect place to call home.

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