A Fun Filled Long Weekend in Boston with Kids

Boston is one of the oldest cities in America and has been around since 1630! This East Coast city is full of history and is a treasure trove of adventure, there’s plenty to do with kids here. My family and I (over at www.lifehasitsperks.com) live just outside of Boston and can share with you the perfect long weekend itinerary to do in Boston with kids!

Whether you’re exploring the city’s past, playing outside, or savoring treats, Boston has something for everyone. Here’s how to plan the perfect long weekend, with ideas to plan out your morning, afternoon, and evening fun. And if you wake up one day and it is raining, do not fret, I also have ideas listed for what to do on rainy days too.

Day 1: History Meets Adventure

Morning: Freedom Trail

Start the day with a history lesson disguised as a treasure hunt. The Freedom Trail is a 2.5-mile red-brick path that leads you to 16 historical sites.

My kids love it because they can walk along the trail and stop at places like the Paul Revere House or Boston Commons. My favorite part was walking through the North End and stopping at a local bakery for a fresh cannoli!

If you want to keep it light, just do a portion of it, you don’t have to cover the whole trail!

Afternoon: USS Constitution & Bunker Hill Monument

After a quick bite to eat, take your kids to see the USS Constitution, also known as “Old Ironsides.” This historic ship, located in the Charlestown Navy Yard, is the oldest commissioned warship still afloat. Crazy! Your kids will love exploring the decks and learning about life aboard a ship. From there, it’s a short walk to the Bunker Hill Monument. Climb the 294 steps to the top for stunning views of the city. It’s a fun challenge that even kids can enjoy, and the view is worth it!

Evening: Harborwalk

In the evening, take a stroll along Boston’s Harborwalk. The kids can run around, watch boats, and chase some seagulls. 

End the night with a scoop of ice cream from one of the local shops along the way. If everyone’s still got energy, or your kids are older, hop on a short ferry ride to see the city skyline light up!

Day 2: Hands-On Fun

Morning: Boston Children’s Museum

Kick off the day at the Boston Children’s Museum, one of the oldest and best children’s museums in the country. It’s a three-story playground of hands-on exhibits where kids can climb, explore, and learn. There’s a bubble exhibit that my kids could spend hours in, and the KidPower exhibit is perfect for burning off some energy.

Afternoon: New England Aquarium

In the afternoon, head to the New England Aquarium. There’s a huge central tank filled with all kinds of sea creatures, including Myrtle the Turtle, a crowd favorite. 

Don’t miss the touch tank, where your kids can gently interact with rays and small sharks. Afterward, you can grab lunch at a nearby café on the waterfront.

Evening: Dinner in the North End

Wrap up the day with a family-friendly Italian dinner in Boston’s North End. It will feel as if you hopped on a plane and landed in Italy! Many restaurants are welcoming to kids, and what kid doesn’t love pasta? 

After dinner, treat them to another cannoli from the famous Mike’s Pastry or Modern Pastry. (Honestly, you can’t go wrong with either one!) When in Boston do as the Bostonians do!

Day 3: Parks and Playgrounds

Morning: Arnold Arboretum

If the weather is nice, head over to the Arnold Arboretum in Jamaica Plain. It’s a huge space with walking paths and beautiful trees. It’s great for letting the kids run around, have a little picnic, and maybe learn a bit about nature. You could also rent some bikes for an extra bit of fun.

Afternoon: Boston Tea Party Ships & Museum

After lunch (grab something quick at Faneuil Hall, lots of kid-friendly spots), head over to the Boston Tea Party Ships & Museum. This interactive museum is pure gold for kids. They get to toss “tea” into the harbor, board a ship, and hear exciting stories about the American Revolution.

Evening: Outdoor Movie Night

On summer weekends, Boston often hosts outdoor movie nights in parks like Christopher Columbus Waterfront Park or the Hatch Shell. Bring a blanket, some snacks, and enjoy a movie under the stars. If it’s not movie season, a cozy family movie night at the hotel or home works just as well!

Bonus: Rainy Day Fun

What if it rains? No worries! There are still plenty of indoor options to save the day. Here are some of the best indoor things to do in Boston.

Museum of Science

Boston’s Museum of Science is a hit with kids of all ages. There are interactive exhibits, live animal shows, and even an IMAX theater. Don’t miss the indoor lightning show—it’s one of the coolest things you’ll see. My kids love the “hands-on” science experiments they can try, and there’s always something new to discover.

Sky Zone Trampoline Park

If your kids are bouncing off the walls, take them to a trampoline park! Sky Zone in nearby Everett is an indoor trampoline park where they can jump, flip, and play to their heart’s content. It’s a great way to burn energy, even if the weather’s not cooperating. Another bonus? They’ll likely take a long nap afterward!

Bowling or Arcade Fun

End your rainy day at a family-friendly bowling alley or arcade. There are lots of options, but Kings Dining & Entertainment has bowling, arcade games, and even good food to keep everyone happy. It’s a perfect combo of active and relaxed fun to end the day on a high note.

Pro Tips for Parents

• Get a Go Boston Card: If you plan to visit a few of the bigger attractions (like the Children’s Museum, Aquarium, or Zoo), this card can save you some money. It gives you access to multiple attractions at a discounted rate.
• Use Public Transit: Parking in Boston can be tricky and expensive, so take advantage of the T (Boston’s subway system) when possible. Kids think it’s fun, and it saves you from the parking headache.
• Pack Snacks: Boston is very walkable, but that can mean lots of walking for little legs. I always keep snacks handy for when someone gets “hangry.” Lines for food are always a little too long for them to wait.
• Pick Activities in Small Doses: Some of these places are pretty big, so don’t feel like you need to see everything. It’s okay to pick a few highlights and save the rest for another trip.

Bonus: What If You Have Extra Time?

If you find yourself with a little more time or energy, here are a couple of extra spots to consider:

The Boston Public Library

This might sound boring to kids, but the children’s room at the library is fantastic! They have storytime, crafts, and plenty of cozy reading nooks. Plus, the architecture is stunning, making it a great spot for the whole family.

Harvard Museum of Natural History

Located just across the river in Cambridge, this museum has a jaw-dropping collection of gemstones, fossils, and dinosaurs. My kids love seeing the giant skeletons, and the glass flowers exhibit is a beautiful surprise for the adults.

Fenway Park

If you’re in town during baseball season, catch a Red Sox game at Fenway Park. Even if your kids aren’t huge baseball fans, the energy at Fenway is contagious. Grab some popcorn or a Fenway Frank, and enjoy the experience of one of America’s most iconic ballparks.

Gillette Stadium

For football fans, a visit to Gillette Stadium to see the New England Patriots or New England Revolution (soccer) play is an unforgettable experience. Though it’s a bit outside the city, it’s worth the drive for a lively sporting event your kids will love.

Museum of Fine Arts (MFA)

While an art museum might not seem kid-friendly at first glance, the MFA offers free admission for kids and has fun family programs. There are even scavenger hunts designed to keep kids engaged as they explore the galleries. It’s a great way to introduce them to art in an interactive way.

Conclusion: A Memorable Family Weekend

Boston is the perfect blend of history, education, and fun for families. We really enjoy our trips into the city whenever we get a chance. There is so much to do we didn’t even scratch the surface. 

Whether you’re strolling through a park, exploring a museum, or learning about the city’s past, there’s always something to keep your kids entertained. 

Even if the weather doesn’t play along, Boston’s indoor attractions will save the day. So pack your bags, grab your sneakers, and get ready for a family adventure you’ll never forget!

Read Next:

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26 Best Historic Sites in New England