The Best 10 Things to Do in Annapolis

Updated July 21, 2020.

Annapolis is the best part of Maryland! It’s an easy day trip from D.C., it’s historic, it’s beautiful, and they have some incredible food! Here’s my quick list of the top things to do in Annapolis. Start planning your trip!

10. Shop and Eat at the PA Dutch Amish Market

Just four miles outside of historic Annapolis is a magical place where calories are plentiful but don’t count, all the food tastes good, and things like “shoo-fly pie” and “whoopee pie” can be bought by the dozen! There is a restaurant, a grab-and-go spot, and multiple shops for everything from cheese to meat to dessert to baking ingredients. And don’t skip the samples!

9. Step into St. Anne’s Church

You can’t miss it, it’s the large, historic church on top of the hill! It was the first church in Annapolis and was founded in 1692, but it’s the third building in this location.

St. Anne’s Historic Episcopal Church

8. Find Some Street Art

Murals have become incredibly popular in recent years, and it’s beautiful! There are some pretty murals around Annapolis, so when you happen upon one, strike a pose!

The Wisteria and Bicycle Mural on East and Fleet Streets!

7. Admire the History

I’m about to shock you… I love history! Is it just me? I don’t think it’s just me. Annapolis is a beautiful 17th century town with pieces from four hundred years of history. George Washington resigned his military commission here in 1783 (unprecedented at the time) at the Maryland State House, four signers of the Declaration of Independence called Annapolis their home, and it was a major shipping town! There is so much history here, you can’t help but see and experience it!

Fall in Historic Annapolis

6. Visit the Hogshead

And speaking of history, it’s pretty rare for a common structure, like a hogshead, to survive since the 18th century! This is a FREE attraction, and it’s kind of fun to see how the “other half” lived and worked hundreds of years ago. It’s certainly different than today! The costumed interpreters inside did a great job of answering questions and making the most of our visit!

The Hogshead

5. Tour the William Paca House

This was an unexpected delight! William Paca was a signer of the Declaration of Independence, and his home is beautifully preserved. It’s one of the best house museums I’ve visited, and I go to a lot of house museums (and I’ve worked in a few, too!). Don’t skip this gem, and make sure you leave time for the gardens out back!

The beautiful gardens out back at the William Paca House Gardens
A perfect spot for photos! That’s my dad sticking out his tongue while I give him a smooch. I can’t take him anywhere. And yet I take him everywhere!

4. Eat Crab Cakes

If you visit Annapolis, but don’t eat a crab cake, did you really go? No! So you’ll need to carve out some time to enjoy a crab cake—or two! You can find them on practically every menu, but the best ones are at the Boathouse and the Iron Rooster!

Crab Cake from The Boathouse, up-close and personal.
Read on: What to Eat in Annapolis

3. Tour the Maryland State House

Little known fact for anyone outside of Maryland who is not a U.S. History teacher: Annapolis is the capitol city of Maryland! The capitol is not Baltimore. As such, the Maryland State House is here, and it’s open for FREE self-guided tours every day of the week! They have some great exhibits, and you can peek into the State House and Senate rooms, too! It’s also the oldest state capitol building in the country!

The Maryland State Capitol
George may be resigning his commission, but I found a typo and Daddy-o seems to be swiping his sword!

2. Eat Breakfast at the Iron Rooster

I normally make a point of eating at a different restaurant every time we eat, get coffee, etc., but I happily went to the Iron Rooster twice! And I will go back again next time I go to Annapolis. They serve breakfast all day, and they have deliciously unique dishes!

Breakfast Ravioli from the Iron Rooster!

1. Tour the Naval Academy

This is one of the best tours I’ve taken in the D.C. area. Our guide was a retired alumnus, and he gave us some great stories about the training, traditions, and legends at the Naval Academy! The best part was seeing their training and sports facility. Or maybe it was seeing the stunning dorm that looks more like a grand train station of yesteryear. Take the tour to see for yourself!

U.S. Naval Academy
Get all the details here! How to Tour the Annapolis Naval Academy

Are you ready to plan a trip to Annapolis? Tell me in the comment section! And while you’re at it, check out my United States Page for more!

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3 responses to “The Best 10 Things to Do in Annapolis”

  1. […] More here: 10 Things to Do in Annapolis […]

  2. This was so cute! Loved the photos. My grandparents just moved to the area so my husband and I came to visit and get their new condo set up. Now that we are all good to go we wanted to explore the area a little. Thanks for the tips!

    1. That is awesome! Annapolis is great, and I hope your grandparents love living there so you can enjoy visiting often!

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