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 🚢
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 🦀
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 🎮
- Karaoke room
- Video games room
- Original PAC-Man
- Hoop Fever
- 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 ⚓
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 🎻
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 🛶
- Two art galleries featuring local art
- Wedding sites
- Summer camps for all ages
- Six outdoor pavilions
- 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 🎨
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 🧑🌾
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 🍨
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 🎭
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!)