After living in Maryland for more than a decade, you’d think I’d have explored Annapolis a little more by now. Honestly, I can count on one hand the number of times I’ve spent time wandering around our state’s capital. Somehow, it’s one of those places I’ve always meant to explore more but never quite got around to.

With fall in the air and my 16-year-old daughter starting her very first hospitality job at a Navy football game, I had the perfect excuse to change that. While she spent the day gaining some real-world work experience, I had several hours to myself, and I decided to make a little adventure out of it.

I love having an excuse to get out of the house, discover somewhere new (or somewhere I should know better by now!), browse cute shops, and soak up all the little details that make a place special. And what better time to explore Annapolis than in the fall, when the Great Annapolis Pumpkins, seasonal displays, and cozy small-town charm make everything feel a little more inviting?

So, I set off on a solo day trip with no big agenda — just a little exploring, some shopping, and the freedom to wander wherever the day took me. Sometimes, the best adventures happen when you finally make time for yourself.

About the Great Annapolis Pumpkins

I couldn’t visit Annapolis in the fall without stopping to see the giant pumpkins! I mean, how often do you get to stand next to a pumpkin that weighs half of what a small car does? Every October, these massive pumpkins make their way to Annapolis, with some weighing over 1,000 pounds. I knew they were big, but there’s something about seeing one in person that makes you realize just how enormous they really are. Of course, I had to stop for a few pictures because when you come across pumpkins like these, you can’t just walk by! It was such a fun little fall moment and one of those simple things that made my solo day trip feel special.

You can find the pumpkins at the Visitor’s Center at 26 West Street, Maryland Avenue near 48 Maryland Avenue, Market Space, and MRE Mercantile at 318 6th Street.

Cute Shops and Unexpected Finds in Annapolis

In between my giant pumpkin stops, I explored downtown Annapolis, although the boat show made it a little harder to enjoy the nautical views I love so much about this area. With so much going on, the waterfront wasn’t quite the peaceful backdrop I had in mind, so I decided to switch things up and spend more time wandering through the shops and galleries instead. That turned out to be a lovely way to spend the afternoon! I popped into galleries filled with gorgeous, oversized photographic prints of boats and discovered all sorts of other fun finds along the way.

One thing I really appreciate about Annapolis is how easy it is to explore on your own. You can stroll at your own pace, duck into a shop whenever something catches your eye, and take your time looking around without feeling like you need a set itinerary. There always seems to be something interesting tucked into a window or waiting to be discovered inside a little shop.

If you need a break from walking, there are plenty of nearby restaurants and cozy cafes where you can grab a bite, enjoy a coffee, or simply sit for a while and people-watch. For a solo day trip, Annapolis really does make it easy to fill your day with little discoveries. Sometimes, I think those unplanned stops end up being just as enjoyable as the things you originally came to see.

A Little Solo Time in Annapolis

By the time I wrapped up my day in Annapolis, I was glad I had taken the opportunity to explore on my own. Between the giant pumpkins, browsing the shops and galleries, and simply enjoying a change of scenery, it was a nice reminder that I don’t always need a big plan or someone to join me to have a good day out.

I’ve lived in Maryland for over a decade, and I’m realizing there are still so many places close to home that deserve a little more of my attention. Annapolis is definitely one of them. With its historic streets, charming shops, seasonal attractions, and plenty of places to stop for a bite or a coffee, it’s an easy choice for a solo day trip when you need a little time to yourself.

Sometimes, that’s all a day needs to be: a little wandering, a few unexpected discoveries, and the freedom to do whatever catches your eye. I’m glad I finally made more time for Annapolis, and I have a feeling I’ll be back to explore a little more — hopefully with those beautiful nautical views next time!