Family Getaway: Kid-Friendly Day Trip to St. Michaels, Maryland


Before becoming a mother, my husband and I loved the freedom we had to jump in the car or on a plane for a last-minute weekend getaway. Post-kids, however, I’ve come to appreciate a simpler form of travel – the day trip. We’re so fortunate DC has lots of great destinations just a few short hours away. One of my favorites is taking a day trip to St. Michaels, Maryland, which clocks in at under two hours from DC.  Here are some of the spots my family and I love visiting when we make a day trip to St. Michaels.

Must-See Stops During Your Day Trip to St. Michaels

There are always great outdoor activities to experience whenever you visit St. Michaels, and lots of great little shops and restaurants to explore. But, here are some of our tried-and-true favorite places my family recommends everyone try at least once when visiting this quaint little town. 

The Inn at Perry Cabin
The Inn at Perry's Cabin - Day Trip to St. Michaels

Almost everyone knows the Inn at Perry Cabin, made infamous as the wedding venue for the movie Wedding Crashers. Whether or not you’re a fan of the movie, it’s absolutely worth a stop whenever you’re in St. Michaels.

We love grabbing a meal at Stars, which has outdoor seating overlooking the water and it’s much more family-friendly than the indoor dining room. Breakfast and lunch are the most budget-friendly meal options, and a kids menu is available at lunchtime for picky eaters. My daughter’s favorites are the gluten-free mac and cheese and the PB&J with natural peanut butter and local jam! 

If you have extra time, consider a sail on one of the Inn’s beautiful sailboats. They offer two-hour excursions at 10:00 AM and 1:00 PM, and another at sunset if you are staying later in the day. You can view the details and pricing information here.

The Chesapeake Bay Maritime Museum

Chesapeake Bay Maritime Museum - Day Trip to St. MichaelsA day trip to St. Michael’s wouldn’t be complete without a trip to The Chesapeake Bay Maritime Museum. It is a must-visit spot when you come to St. Michaels, with exhibits and attractions for all ages. When both my husband and my toddler are entertained, you know it’s good!

Enter through the old drawbridge, and you’ll see a huge array of buildings and ships to explore.

Walk through a real working shipyard, where shipwrights do everything from restoring huge historical vessels (they were working on one from the 1800s last time we visited) to carving out small, traditional wooden canoes. All of the workers are incredibly friendly and knowledgeable, and happy to answer any questions you have about their work.  

Other favorite stops for us include the lighthouse, built in 1879, where you can see what it was like to live as a lighthouse keeper;  and the At Play on the Bay exhibition that traces the Chesapeake’s transformation from working waterway to the getaway it has become today.

At Play on the Bay has interactive exhibits to entertain your littlest kiddos, plus thought-provoking information for adults (and more mature youngsters) to encourage us to think about the effect this transformation has had on both the environment and those still living and working on the Bay.

With a living shoreline to explore and ever-changing special exhibitions, you can easily spend hours here and see something new each time you visit.

Shore Pedal and Paddle

Paddle Boarding - Day Trip to St. MichaelsIf your kids are a little older an adventurous, you’re going to want to get out on the water when visiting St. Michaels! Head over to Shore Pedal and Paddle to rent paddle boards or kayaks.

Head out on your own if you’re feeling adventurous, or organize a tour through the company for a guided adventure.

If you prefer to stay on land, bike rentals are also available.

Ava’s Pizzeria
Ava's Pizzeria - Day Trip to St. Michaels

The first time we visited St. Michaels, we got the same recommendation over and over and over – go to Ava’s Pizzeria! We haven’t been disappointed by a meal here since.

If you’re from Montgomery County, Maryland, you may recognize owner and chef Chris Agharabi from his days at Persimmon in Bethesda. Now, he’s cooking up incredible pizzas (with great wine pairings for the parents) in this lovely little town. It’s definitely worth a visit, whether you’re taking a day trip to St. Michaels or there for a longer stay. 

Few meals are more kid-friendly than pizza, and Ava’s does not disappoint. The boardwalk pizza was designed with kids and mind, plus there are gluten-free options for little ones with sensitive stomachs.

In a hurry? You can call in your order ahead of time or even order to go.

Justine’s Ice Cream Parlor

Justine's Ice Cream - Day Trip to St. MichaelsI don’t know if it’s just me, but a summertime trip to the water always makes me crave something sweet, and Justine’s really hits the spot. Offering special homemade flavors, it’s the perfect treat on a hot and humid summer day on the Bay.

The portions are really large, so you may want to consider sharing or even ordering a kid’s size! Plus, there is not a ton of seating indoors, so we like to grab cones and walk around the town since it’s centrally located on Talbot Street. Or, you can bring your dessert to nearby Hollis Park so your kiddos can play on the swings and slides.

These sweet treats are the perfect way to end a family day trip to St. Michaels, and will leave you dreaming about the next time you can come back to visit!