Kid Friendly City Guide To Annapolis, MD



Annapolis Family Guide

Today I’m excited to kick off a series kid-friendly city guides from a local’s perspective. I thought it would be fun to start with my home town and since I’m a new mom — I asked my friend Christina of the blog Proper Hunt to chime in on her favorites… she has 4  and 1 year old girls — that’s adorable Cora above! 

Best places for breakfast or brunch with kids? Surprisingly, Pussers, which is right next to the Annapolis Waterfront Hotel, is great to take the kiddos for brunch. We’ve gone several times with friends who also have kids and it’s great because 1) It’s usually not busy — so no waiting which is a huge plus, 2) the view is fantastic, and 3) it’s good food. Another place we like is Iron Rooster. The food is amazing and it’s full of families so you’re not going to stick out like a sore thumb with your kids. The only drawback is that it’s so popular that you’re definitely going to be waiting for a table no matter when you go. — Christina 
We love to bring our niece and nephews to Grumps Cafe — although it’s in a shopping center and not downtown it’s a fun and lively environment for a casual breakfast (the servers wear PJs!). Naval Bagel is also a great casual option for grab & go or eat in. Perfect for a picnic or enjoying downtown on a bench near the water. — Caitlin 
Outdoor dining in Annapolis with kids? Although they are outside of  central Annapolis they are worth the hike — you can’t beat Lures and Old Stein Inn for dining al fresco with kids. Both have extensive menus so you’re bound to find something for everyone in the family, and the outdoor seating is great for kids to have that extra space to move around. — Christina 
Rams Head Tavern has a great patio outside and casual atmosphere. — Caitlin 
Best place for ice cream in Annapolis? Kilwin’s for vanilla ice cream (Cora’s favorite) if we’re downtown or close to it, and Menchies at the Town Center or Sweet Frog’s at the Harbour Center. — Christina 

Our favorite is Annapolis Ice Cream Company — local and freshly made! There’s limited seating so it’s best to plan on eating outside on Main Street. — Caitlin 
Dinner? Squisito off Riva Rd. is an easy go-to for us since it’s close by, but they really have good pastas and pizzas for the price. — Christina 
Boatyard Bar & Grill is a great laid back atmosphere for kids to enjoy and really good food. — Caitlin 

Best place to get crabs with kids in Annapolis? Skip Buddy’s downtown and venture outside of town and try Cantler’s or Mike’s Crab House.  — Caitlin 
Favorite things to do on a rainy day with your kids? Cora is a big fan of going to Barnes & Noble so we’ll do that on rainy days. She’ll look at the books and we’ll get a cookie for her. She’ll even go to the little stage area and give a little performance if she’s in the right mood.  — Christina
There’s also a great bookstore on Maryland Avenue downtown — The Annapolis Bookstore that would make for a nice rainy day activity with older kids. 
Annapolis Culture & History for kids: 
Older children may enjoy visiting the Banneker-Douglas Museum, the state of Maryland’s official museum of African American heritage. 
The William Paca House & Gardens were built in the 1760s and are full of history! If you’re up for walking try one of the Colonial Walking Tours
The Maritime Museum  is a great place for kids to learn about the ecology of the Cheseapeake Bay and Annapolis’ maritime history. 
Best kids shops: For a more European sensibility, Wheat in downtown Annapolis has really sweet clothes for kids. Lil Lamb Boutique off Maryland Avenue is a beautiful shop filled with clothes, books, and gifts for the kids. They also have a back room where they host themed parties for the little ones. I’m hoping that one day we can have a party for Cora there, it’s just so cute! And Franklin’s Toys is a fabulous toy store that has really thoughtful and unique toys, and we always find something there that Cora loves. — Christina 
Any kid-friendly attractions or ideas for people visiting Annapolis with kids? Quiet Waters Park, hands down, is one of the best places to take your kids. You can walk the paths or go to one of the many play grounds that are scattered around the park. One of our favorite things to do there is walk to the South River Overlook to see the boats and to soak in the views of the South River. There’s a really great playground in downtown Annapolis that we’ll go to during the weekends. We’ll spend some time there and then hit up the farmer’s market just across the street and then walk around downtown until it’s nap time. — Christina 
We love to picnic – Jonas Green Park is right on the water with beautiful views you can’t beat. We also like to take out of towners on a boat ride (I’d suggest Watermark Cruises or Schooner Woodwind – be sure to snag tickets ahead of time) or water taxi from the downtown dock — the kids love it! There is also a really fun pirate ship boat for kids! — Caitlin 




Kid Friendly City Guide To Annapolis, MD


  1. McKenzie says:

    Great post thank you!! I have a 6 month old so hes a bit young to do most of these things yet, but we are planning to visit next month and will check out these spots anyway! Do you have any recommendations for trails/parks that are walkable with the stroller?

check it out

Children's books have always had a special place in my heart, and sharing them with my girls is one of my favorite parts of motherhood.  Learn more about my Usborne Books & More business! 

learn more 

Book Club

Keep your kids busy & having fun with a membership to Magic Playbook -- the monthly printable subscription for kids! 

say goodbye to boredom!