8 Great Things to Do in Annapolis Maryland

Fun things to do in Annapolis include visiting the US Naval Academy, sailing on the Chesapeake Bay, seeing USA’s first capital, experiencing the Ego Alley spectacle, and savoring amazing crabs, Irish food and fare, and wonderful ice cream. This Annapolis information is my curated list of fun activities, historic destinations, and tasty dining and drink based on many visits to Maryland’s capital city.

My wife and I were fortunate to be included in the #DCTravelBlogger group hosted by the Annapolis Visitor Bureau. Our 24 hour visit included a stay at the luxurious Hotel Annapolis (formerly Loews Annapolis), which featured this amazing stained glass window in our 5th floor lobby.

picture of stained glass window in Hotel Annapolis by Charles McCool for McCool Travel
places to see in Annapolis: Hotel Annapolis stained glass

Chesapeake Bay Activities

Heck yeah, I can create a separate post of 8 Great Things to Do in Annapolis just on the water. Rent a kayak or SUP. Go fishing or crabbing. Take a boat tour on Harbor Queen. Ride on a classic schooner. Walk the plank and shoot water cannons from a pirate ship. Learn to sail at a sailing school. Ride the water taxi (only $3 across to Eastport, $8 maximum). Sail on a private sailboat (OK, you have to know someone). Swim. Water ski. Windsurf or kite surf. Eat, drink, sun bathe. Hmmm, maybe enough for two 8 great things to do in Annapolis on the water posts.

Sailing on the Chesapeake Bay is a popular Maryland activity
Sailing on the Chesapeake Bay is a popular Maryland activity
sail the Harbor Queen around Chesapeake Bay Maryland
sail the Harbor Queen around Chesapeake Bay Maryland

US Naval Academy

Speaking of water, there is also no denying that Annapolis is a Navy town. While the US Naval Academy is guarded, there are some public entrances and attractions. The easiest and most popular is probably the John Barry gate along Prince George Street near the City Dock area. Commodore Barry was the founder of the US Navy and there is a memorial to him just inside the gate.

US Naval Academy, photo by USNAPrep.com
US Naval Academy, photo by USNAPrep.com

The nearby visitor center has a short film on the history of the US Navy and Naval Academy, poignant displays, and a gift shop. The Admissions Office is on the second deck (upstairs level) if you want to scare—I mean encourage—your children. Worship services and three dining options and are available to visitors. Public tours cost $10.50 per adult.

Ice Cream in Annapolis

The only time I did not see at least several dozen people in line at the Annapolis Ice Cream Company was Sunday morning—before it opened. Walking around, I spotted several other ice cream shops. Did I try any? NO! Obviously I must return to Annapolis.

where to eat in Annapolis: Annapolis Ice Cream Company
where to eat in Annapolis: Annapolis Ice Cream Company
Annapolis Ice Cream Factory line
popular Annapolis Ice Cream Company (with the lurking Maryland State House)
Kilwins Ice Cream Annapolis
Annapolis casual eats: Kilwins Ice Cream

See also 5 Fun Places to Eat in Annapolis Maryland

So Many Irish Pubs

Our #DCTravelBlogger group was treated to lunch at Galway Bay Irish Pub and sampled their Irish egg nog—a great thing to do in Annapolis in winter! Walking around town that afternoon and evening, I said, “there’s another Irish pub” more times than I expected. I did not count but, while researching, found four other Irish pubs (and other non-Irish pubs) and one Irish store. Annapolis also hosts an Irish Festival in July.

Galway Bay Irish Pub, Annapolis MD
Galway Bay Irish Pub, Annapolis
Galway Bay Annapolis egg nog
Annapolis restaurant: Irish egg nog at Galway Bay
Galway Bay Irish egg nog Annapolis
fun place to visit in Annapolis MD is Galway Bay. Try the Irish egg nog – Sláinte

Annapolis History

OK, did you know that Annapolis served as the first Capital of the United States of America? For 9 months at the end of the American Revolution, Congress met at the Maryland State House and Annapolis was the first peacetime capital of the new nation. History oozes from every brick. Visit historic St. Anne’s Church—whose congregation included two Declaration of Independence signers and Francis Scott Key (he wrote the Star Spangled Banner)—the cozy alleys, pre-Revolution taverns, and historic homes.

1747 Pub Annapolis MD
1747 Pub is one of the best places to drink in Annapolis Maryland
Cabbage Alley Annapolis MD
Cabbage Alley in Annapolis
Annapolis MD historic district marker
Annapolis is full of historic district markers
mosaic tile art at St. Anne's Church
look for the vibrant mosaic tile art at St. Anne’s Church

Sailing Hall of Fame

It certainly makes sense that America’s Sailing Capital hosts the National Sailing Hall of Fame. Personally, I like to visit Halls of Fame to be inspired by persons who excel at their passion.

McCool Travel note: the Sailing Hall of Fame moved to Newport, Rhode Island.

Annapolis MD Winery

Visiting a winery in Annapolis was a pleasant surprise. Our wine flight tasting at Great Frogs was accompanied by local artisanal cheeses, fruit, and marcona almonds. The port wine was my favorite and is sold in cool one quart maple syrup glass containers. I cringed at the $50 bottle price but, you know what, I should have bought one. When I return for my ice cream adventure, I will buy a bottle.

sample great snacks and wines at Great Frogs
sample great snacks and wines at Great Frogs
Great Frogs wine bottles have locally inspired designs
Great Frogs wine bottles have locally inspired designs

People Watching in Ego Alley and Around Town

Ego Alley, a narrow stretch of water off Spa Creek near the Annapolis City Dock, is among the places to see and be seen. In case it is not obvious, boaters and yacht owners show off their craft along ego alley, especially on brilliant weekend days. Pusser’s Caribbean Grille is a remarkable location (along Ego Alley) for a meal, snack, or drink.

Walking around town, mainly along Main Street, on Saturday night and Sunday morning, we saw countless youngsters dressed in their finest white Naval uniforms. Almost all had “Class of 2019” on their name tags, indicating that they are incoming freshmen. Good luck to the new midshipmen! Look for action near the Alex Haley and Kunte Kinte memorial at City Dock. When the crowd is heavy, at least two men are making balloon animals for kiddies of all ages. Buskers (street performers) further congest the already crowded area.

Near Annapolis, you can try our favorite taco tacos. Details at 8 Great Amazing Fish Tacos in US

What are your suggestions for places to visit in Annapolis MD?

8 great things to do in Annapolis, fun activities, historic destinations, and tasty dining and drink in Maryland's capital city.

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40 thoughts on “8 Great Things to Do in Annapolis Maryland”

  1. We love Annapolis when we visited. We did the Harbor Queen tour and enjoyed live music at Galway Bay Pub. Actually there were many places that had live music and the best part was that we could bring the kids along to enjoy the music too.

  2. I still have many states to visit and Maryland is one of them. I had no idea there was so much to do there. I think I would like the sailing museum and I know I’d love the ice cream!

  3. Haha! There’s a Galway Bay in Australia? That’s pretty interesting. Galway’s one of my favorite places in the world. Loved reading about your sailing experience too. Definitely on my to-do list that one!

  4. I’m sure, like many others, I only knew about Annapolis as a Navy town. Loved the idea of the Great Frogs wine and cheese tasting. I agree with you about visiting a Hall of Fame. Wimbledon was so impressive and the Sailing Hall Of Fame would be interesting too.

  5. First I thought by your pictures Annapolis is in Greece. Guess I must work on my geographic skills 😉 #anapolis #greece #maryland

  6. Hmm. Some people seem to think Philadelphia was the first capital of the US. I’m sure there’s all sorts of subtlety and nuances involved in why each city makes this claim. (To perhaps state the obvious, I’m from Philly.) One of my college friends was employed by Maryland’s scenic river program. She got to keep the/an official state canoe in her garage.

  7. You forgot “Arts”! For a smaller city, Annapolis boasts a huge number of performing arts organizations, art galleries, and music venues. My favorite is the Annapolis Summer Garden Theatre, an outdoor community theatre that presents musicals outdoors in the summertime at their historic venue at City Dock. So much fun!

  8. Great timing on your post! We have friends who just moved to Annapolis and we can’t wait to visit them. We’ll definitely share your finds with them and try them out ourselves when we visit.

  9. Well, I’m a little ashamed that I didn’t know that Annapolis was the first US capital m– or maybe I just forgot. I’ve never been to Annapolis and it looks like I’ve been missing out on some great experiences. Would definitely like to try the port. If you’re regretting that you didn’t buy the $50 bottle, it must have been very, very good.

  10. We loved Annapolis- such a historic city. We have the Chesapeake with us every day- we have posters of two of Marion Warren’s famous Chesapeake photos (the Thomas Light, and skipjacks) hanging on our walls, a souvenir from a long ago DelMarVa vacation.

  11. I lived in the D.C. area and then Baltimore for a total of about 15 years and always loved to visit Annapolis. It looks as if it’s added a lot of businesses since then. I got a smile out of the reference to “ego alley” because I’d forgotten about it.

  12. I did not know that Annapolis was the first Capital of the United States of America. But now I do! I’d also love to tour the Naval Academy. Sound like a getaway-worthy city.

  13. I have to admit that I had not heard of Annapolis in Maryland. Like Australia, America is such a large place. I had to google where it was. It does appear that it has a lot going for it, with a water location and rich history

  14. I love the combination of history and new uses. Looks like you had a perfectly delicious day.

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