As the capital of Maryland with close proximity to Baltimore and Washington DC, Annapolis is a bustling city that’s wonderful to live in and visit. Nestled on the Chesapeake Bay, this historic city has charming architecture but still has modern features.

Whether you’re planning your first visit to Annapolis or you’ve lived in the area your entire life, there’s no shortage of exciting places to explore. Our Annapolis-based team put together this list of 10 fun things to do in Annapolis!

1) Take a Cruise on the Chesapeake Bay 🚢

We’d be remiss not to mention spending time out on the water of the beautiful Chesapeake Bay. Whether you go by yourself, with a friend or loved one, or with a large group, these boat rides aren’t to be missed.

The two companies we recommended checking out are Watermark and Schooner Woodwind. Watermark provides more classic yacht cruises, while Schooner Woodwind offers unique sailboat cruises.

Head out at golden hour to catch the beautiful sunset!

2) Enjoy Fresh Crab at Cantler’s Riverside Inn 🦀

We won’t lie— the seafood scene in Maryland is unmatched, and there are dozens and dozens of incredible restaurants to visit. Today, we’re featuring Cantler’s Riverside Inn, which is a fantastic, old-school Maryland crab house.

Crab is the main focus of this delicious restaurant, but there are still yummy menu options for “land lovers.” You can’t miss this Annapolis staple, especially if you’re visiting from out of town. If you want to eat hardshell crab legs but have never done it before, they even offer crab opening tutorials!

3) Play Old School Video Games at Game On 🎮

Do you like arcades and bars? Then you don’t want to sleep on the Annapolis arcade bar Game On. Indoors, they have a wide range of games and features, including:

  • Karaoke room
  • Video games room
  • Pinball
  • Skeeball
  • Original PAC-Man
  • Hoop Fever
  • Tetris
  • Super Mario Brothers
  • NFL Blitz 4-player
  • And much, much more!

Outdoors, they have giant Jenga, foosball, ringtoss, and cornhole. Game On has daily drink specials (like $1 mimosas on Sundays!) and a Tuesday Skeeball League that you can join. Fun times are guaranteed!

4) Tour the US Naval Academy ⚓

On just about every “What to Do in Annapolis” list, the US Naval Academy makes an appearance. But since this activity is so unique to Annapolis, we also had to include it. Whether you’re a long-time resident or a tourist, you should prioritize touring the Naval Academy.

As Annapolis is considered the “Sailing Capital of the World,” it makes sense why the Naval Academy is based here. You’ll love seeing the historical highlights and learning about the midshipmen experience. Unless you want to visit as a potential student, you should book a 90-minute walking tour that’s open to the public. Find tickets here!

5) Check Out the Annapolis Symphony Orchestra 🎻

For something you don’t do every day, pay a visit to the Annapolis Symphony Orchestra. With a wide range of musical events, from solo pianists to full orchestra presentations, there’s no shortage of concerts for classical music lovers.

And if you have a child who’s a budding musician, they can participate in private lessons from orchestra-leading musicians through the Annapolis Symphony Academy. Pretty cool, huh?

6) Go Kayaking at Quiet Waters Park 🛶

Boasting an impressive 340 acres of stunning park land, Quiet Waters Park is one of the most visited parks in Anne Arundel County. There are many wonderful features at this park, including:

  • Two art galleries featuring local art
  • Wedding sites
  • Summer camps for all ages
  • Six outdoor pavilions
  • Playground
  • Dog park & dog beach
  • Concert stage
  • Ice skating rink
  • Paved trails
  • Quiet Waters Cafe

And, of course, boat rentals! You can rent canoes and kayaks to take out on Harness Creek and South River. This is one of our favorite ways to spend a summer afternoon. Just keep in mind there’s a $6 entry fee to the park!

7) Try to Find as Many Murals as You Can 🎨

Thanks to the Art in Public Places Commission, Annapolis is covered in impressive outdoor murals. You don’t need to pay an entry fee to view this art behind closed doors. Instead, it’s free and accessible for anyone to view.

Make a scavenger hunt game out of this activity, and try to spot as many murals as you can around town. View a list of just some of the most recent public murals here.

8) Visit the Pennsylvania Dutch Farmer’s Market 🧑‍🌾

It’s no secret that the Amish community is known for its amazing baked goods, produce, and furniture crafting. Hailing straight from Lancaster, Pennsylvania, the Pennsylvania Dutch Farmer’s Market is held right here in the Annapolis Harbour Center.

Known locally as “The Amish Market,” this large farmer’s market features fresh produce, homemade snacks, chemical-free meats, and handmade furniture! All of the Amish merchants are from Lancaster, PA, but we’re lucky enough to host them every Thursday, Friday, and Saturday.

9) Treat Your Sweet Tooth at Annapolis Ice Cream Company 🍨

There’s never a wrong time for ice cream. And since Annapolis Ice Cream Company has been voted “Best Ice Cream” in Annapolis for 18 years in a row, we feel pretty confident in saying you need to check this place out.

Their homemade ice cream is made on-site daily— the only ice cream store in Annapolis to do so! With more than 40 creative, rotating flavors, you’re sure to satisfy your sweet tooth here.

10) See a Show by The Colonial Players 🎭

The Colonial Players were founded in 1949 by local residents who wanted to bring high-quality live theatre to what was then a very small town. Now, more than 70 years later, this historic gem still puts on live plays that charm locals and visitors alike.

Try something different and support the amazing local talent in Annapolis!

Support Local in Annapolis

We hope you feel inspired by this list of fun things to do in Annapolis. It’s very rewarding to support local businesses like the ones on this list, and we hope you’ll support local in the other facets of your life, too. If you ever need roofing or home improvement support in Annapolis, you can rely on the dedicated team at Vanguard General Contracting.

Reach out for a free project estimate! (We may need to get ice cream together once your project is complete!)