Things to Do in Pittsburgh with Family: Baseball, Anthrocon, and Memories

Looking for things to do in Pittsburgh with family? A Pittsburgh Pirates game, time exploring the city, and an unexpected encounter with Anthrocon gave our family two very different summer experiences—and both became part of the memories our children still connect with Grandma and Grandpa.

This Pittsburgh family travel story is especially helpful for families traveling with grandparents or people with different interests. Baseball fans can head to the game, curious explorers can see what is happening around the city, and everyone can come back together with stories to tell.

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Things to Do in Pittsburgh with Family

Our family discovered two memorable ways to experience Pittsburgh during a summer visit:

1. Go to a Pittsburgh Pirates game and turn an ordinary day at the ballpark into a family tradition shared across generations.
2. Leave room for unexpected Pittsburgh experiences, including the colorful sights and energy surrounding summer events such as Anthrocon.

This is not an exhaustive list of every attraction in Pittsburgh. It is a real family travel story about what happened when two generations, two very different interests, and one summer visit created memories that lasted far longer than the day itself.

That is why this version is useful. You do not have to cram every famous Pittsburgh attraction into one trip. Sometimes the best family itinerary begins with one meaningful activity and enough open space for the city to surprise you.

Why Families Will Love These Pittsburgh Experiences

• Different interests can work together. Not everyone in the family has to spend the day doing the same thing.
• Grandparents become part of the adventure. Familiar activities can become family traditions when one generation shares them with the next.
• The day is easy to personalize. Baseball can be the anchor while other family members explore Pittsburgh in their own way.
• The memories are bigger than the attraction. Our story is not really about a scoreboard or a convention. It is about William and Grandpa.
• Pittsburgh rewards curiosity. Leave a little room in the schedule and you may come home talking about something you never planned to see.

How to Plan a Family Day in Pittsburgh

Start with one anchor activity that matters to your family. For us, that was baseball.

Then build the rest of the day around the people who are actually traveling with you.

1. Choose one must-do Pittsburgh experience.
2. Check current schedules and event dates before leaving home.
3. Let family members split up when their interests are different.
4. Leave unscheduled time for walking, sightseeing, and surprises.
5. Choose a place and time to meet back up.
6. Take the family photo, even when nobody thinks they need another picture.

The goal is not to conquer Pittsburgh before bedtime. The goal is to give everyone something to remember.

Readers Also Plan These Pittsburgh Family Adventures

Baseball is only one piece of our family’s Pittsburgh story. You can also plan a day with our Kennywood Pittsburgh family guide, filled with rides, food, family traditions, and practical tips for visiting with kids.

And because baseball stories tend to run deep in this family, do not miss the story of the day Grandpa Steve shook Joe DiMaggio’s hand. It explains a lot about why sharing baseball with the grandchildren means so much.

Baseball With Grandpa: Our Pittsburgh Summer Tradition

We live in a house that does not eat. drink. breathe. sports.

But baseball?

Baseball is different.

It is not that William is athletic. He is not. It is that baseball is his thing with Grandpa.

Long before William came into this world, Grandpa loved baseball.

Loved it.

A few years after William was born, Grandpa came to visit. I had found cases of old baseball cards—the kind with the gum inside.

They were unopened, which was something I had taken great pride in.

I knew Grandpa would appreciate those cards far more than the cardboard box sitting in my garage, so I gave them to him.

Imagine my shock when I came back into the room and found Grandpa opening the packs like a child at Christmas.

He pointed out, quite reasonably in his mind, that he would never know whether there were any good cards inside if he did not open them.

I suppose that is one way to look at it.

Why Baseball Matters So Much to Grandpa

Grandpa’s baseball story started long before those cards.

One of his most treasured baseball memories came from meeting a legend. At a baseball convention, Grandpa Steve was selected for the chance to have Joe DiMaggio sign a baseball.

When DiMaggio became unsteady as he stood, Grandpa—who was a giant of a man at 6 feet 8 inches—reached out to help him. For one brief moment, the two men clasped hands.

The signed baseball mattered, but the memory mattered more. You can read the full story about Grandpa Steve shaking Joe DiMaggio’s hand.

That is the thing about baseball in this family. The game has a funny way of collecting people, stories, and generations.

Camp Grandma and Grandpa Comes to Pittsburgh

Eventually, we all migrated to the East Coast.

Grandpa and Grandma settled in Pittsburgh. We settled in Virginia.

Every summer, William and MacKenzie go to Camp Grandma and Grandpa. It is a rite of passage in our family and a place where grandparents get to make their own traditions with the grandchildren.

For Grandpa and William, one of those traditions became baseball.

Every year, the two of them go to a Pittsburgh Pirates game.

William absolutely loves this time with Grandpa and wears his Pittsburgh Pirates gear with pride.

Baseball is an activity meant to be shared.

It is hot dogs in the stands.

Wearing team colors.

Cheering loudly.

Watching the scoreboard.

And sometimes having absolutely no idea why a certain call was made but agreeing that the umpire was probably wrong anyway.

These are some of my son’s most treasured memories with his grandpa.

I think the same can be said for Grandpa.

Why a Pittsburgh Baseball Game Became More Than a Game

A family baseball outing works because everyone can enjoy it differently.

One person may care deeply about every pitch. Another may be there for the ballpark food. A child may remember the team colors, the noise, or the giant scoreboard long after forgetting who won.

For William, the most important part was never the final score.

It was that Grandpa was sitting beside him.

Take me out to the ballgame and let the memories begin.

An Unexpected Downtown Pittsburgh Experience: Anthrocon

And sometimes, while you are at the ball game with Gramps, your sister and Grandma find something completely different happening in the city.

Something like furry gatherings and sightings.

That was how Anthrocon entered our Pittsburgh story.

Anthrocon is an annual summer convention celebrating anthropomorphic characters—human-like animal characters—and the artists, animators, writers, costumers, puppeteers, and fans who enjoy them.

The event is associated with the David L. Lawrence Convention Center in Pittsburgh, and when it comes to town, the experience can spill beyond the convention itself as visitors and families encounter colorful characters around the city.

For Grandma and MacKenzie, it was definitely not the same Pittsburgh experience Grandpa and William were having at the baseball game.

That was exactly what made the day so much fun.

The video captures one of my favorite things about family travel: sometimes the story you tell for years is the one nobody put on the itinerary.

What Is Anthrocon in Pittsburgh?

Anthrocon brings together people who enjoy anthropomorphic animal characters in art, animation, writing, costumes, puppetry, and fandom.

For children who have never heard the word anthropomorphic, the easiest explanation is simple: think of animal characters with human personalities, expressions, clothing, or adventures.

The important thing for families is to check the current event schedule before making plans. Dates, public activities, registration requirements, and event details can change from year to year.

Even when your family is not attending the full convention, a major summer event can change the feel of the city and become part of the travel experience.

Perfect With a Pittsburgh Summer Weekend

A baseball game and an unexpected city event can fill one memorable day, but they also work beautifully as part of a longer Pittsburgh family weekend.

For another family tradition near Pittsburgh, spend a day using our Kennywood Pittsburgh family guide. The park has become another place where our family stories move from one generation to the next.

You can also browse our Pennsylvania travel collection for more places, attractions, and family adventures around the state.

Pittsburgh Family Travel Tips From Our Experience

Let Different Generations Choose Different Activities

A successful family trip does not require everyone to be attached at the hip.

Grandpa and William had baseball.

Grandma and MacKenzie had their own Pittsburgh adventure.

Everyone came back with something to talk about.

Check the Calendar Before You Go

Baseball schedules and major events change, so check current dates before planning your trip.

A busy city event can be the reason you visit—or a surprise you need to plan around.

Leave Room for the Unexpected

Some of the best family travel stories begin with, “We had no idea this was happening.”

Do not schedule every minute so tightly that nobody has time to notice the city around them.

Wear Comfortable Shoes

This may be the least glamorous family travel advice ever written, but tired feet can turn a perfectly nice adventure into a family mutiny.

Take the Picture

The children grow.

The grandparents grow older.

The team changes.

The city changes.

Take the picture anyway.

How to Make a Pittsburgh Trip Meaningful Across Generations

The best multigenerational trips do not have to be elaborate.

Try repeating one tradition every year. Let Grandpa choose the game. Let Grandma choose where to explore. Recreate an old family photo. Tell the children the stories that happened before they were born.

And when a child is old enough to understand why Grandpa cares so much about baseball, tell the story about the giant 6-foot-8 man who once reached out and steadied Joe DiMaggio.

That is how a day trip becomes family history.

Related Pittsburgh and Pennsylvania Travel Posts

Keep planning your Pennsylvania family adventures with these stories and guides:

• Kennywood Pittsburgh Family Guide: Rides, Food, and Tips
• Shaking Joe DiMaggio’s Hand
• More Pennsylvania Travel and Family Adventures

Things to Do in Pittsburgh FAQs

What are some memorable things to do in Pittsburgh with family?

For our family, a Pittsburgh Pirates game and exploring the city during a major summer event created two very different but memorable experiences. Families can also add a day at Kennywood to a longer Pittsburgh-area trip.

Is a Pittsburgh Pirates game a good family activity?

It can be, especially when baseball is connected to a family tradition. Check the current game schedule and ballpark policies before visiting, then leave enough time to enjoy the experience without rushing.

What is Anthrocon in Pittsburgh?

Anthrocon is an annual summer convention celebrating anthropomorphic animal characters and the artists, writers, costumers, animators, puppeteers, and fans who enjoy them.

Where is Anthrocon held in Pittsburgh?

Anthrocon is associated with the David L. Lawrence Convention Center in downtown Pittsburgh. Check current official event information before planning because dates and activities can change.

Can a Pittsburgh family trip work when everyone has different interests?

Yes. Our family split up for different experiences, with Grandpa and William enjoying baseball while Grandma and MacKenzie explored another side of Pittsburgh. Choose a meeting place and let everyone have something they are excited to do.

Is this a complete Pittsburgh itinerary?

No. This is a real family travel story built around two experiences that became meaningful to us. It is meant to help families create a memorable Pittsburgh day without pretending they need to see every attraction in one trip.

When is a good time for a family trip to Pittsburgh?

Summer works especially well for families interested in baseball and seasonal city events. Always check current schedules, event dates, and weather before finalizing your plans.

Final Thoughts on Finding Things to Do in Pittsburgh

When people search for things to do in Pittsburgh, they usually expect a list.

Sometimes a list is useful.

But the places we remember best are often attached to people.

For William, Pittsburgh means wearing Pirates gear and going to baseball games with Grandpa.

For MacKenzie and Grandma, one summer it meant discovering a city filled with walking, talking animal characters they never expected to see.

For me, it means knowing my children were building their own stories with their grandparents.

The ball games will end. The children will grow. Summer will turn into another summer.

But somewhere in our family collection will always be the boy in his Pittsburgh Pirates gear, the grandfather who loved baseball, and the stories they made together.

Next Pennsylvania Adventure to Try

Keep the family memories rolling with more places to explore in our Pennsylvania Travel collection. Start with Pittsburgh, follow the family stories, and leave a little room for the adventure nobody planned.