Exploring Boston with Kids: Family-Friendly Fun

June 27, 2025June 27, 2025 / Melissa (I Crashed the Web) / Leave a comment

I love Boston! It’s a city full of history, with plenty to do, and easy to get around. Plus, Boston holds a special place in my heart — it’s where B and I met while at Boston College! I love the city, and we recently went back with our kids for the first time. I hadn’t been back since I was pregnant with FW in 2016 and found that the city is still incredibly walkable, packed with history, and surprisingly kid-friendly.

Spending time in Boston looked a little different from it did when I was in my 20s – but there were still so many fun things to do! Whether you’re visiting for the first time or returning with little ones in tow, here are some of our favorite ways to enjoy Boston as a family.

Getting Around

Boston’s public transportation system (the “T”) is easy to navigate and a fun adventure for kids. Ours loved riding the train—and bonus: kids ride free! We just purchased a week-long adult pass and we were good to go for our 7-day stay.

Where to Eat with Kids

The North End (Little Italy)

Whether you’re with kids or not, this charming neighborhood is a must-visit. It’s packed with Italian restaurants, and most are kid-friendly, especially if you dine out for dinner early. A few favorites:

Mike’s Pastry – Iconic cannoli tourist spot. It’s cash only, but worth it! We tried other cannoli places in the North End but this still came out on top.
Pizzeria Regina – Famous Boston pizza with a location in the North End.
Lucia’s – A cozy spot we’ve enjoyed in the past (reservations available).
Nando’s – Great for families! They even made off-menu spaghetti and meatballs for our kids. They also take reservations.

Prudential Center

The food court – Options for even your pickiest eaters.
Legal Sea Foods – I’m not saying this is THE PLACE to go for the best seafood in Boston. Yes, it’s a chain, but it’s a Boston staple with a kids’ menu. They have several spots, but went to the one in the Prudential Center, which is easy to reach by T.

Quincy Market at Faneuil Hall

This is bustling food hall where everyone can find something they love, or at least everyone in our family did. From orange chicken to acai bowls to hot dogs to clam chowder, there really is a great selection here. Warning – if you go on weekends it’s BUSY and hard to find a seat, but weekdays are less packed and more manageable, especially with hangry kids. There are often free samples in the market and street performers outside too!

Ice Cream

We went in the summer, so yes, ice cream deserves a category of its own. Here are a few local spots:

JP Licks – A local ice cream favorite with spots throughout the city.
Gelato in the North End – Always a hit after dinner, if you end up not stopping at Mike’s (or even if you do!).
Jamie’s Ice Cream – Smaller place with outdoor seating in Brookline but right off the T. Their flavors are so good, I love “Dump Him” the most!
White Mountain Creamery – A staple if you’re near BC

Fun Things to Do with Kids

Boston Duck Tour

A land-and-water tour with a pirate guide and lots of quacking. Super touristy, but the kids loved it. Look for early morning discounts or combo tickets with other attractions. We took the 9:30 a.m. tour to snag the early-duck discount. This was one of the highlights of the trip for sure! The kids loved “driving” the boat when it went off the land and into the water.

Boston Public Garden

Ride the swan boats and visit the Make Way for Ducklings statues. A peaceful, picturesque spot for a stroll.

Freedom Trail

Follow the red line through historic sites like Paul Revere’s house. Great for older kids or history buffs. We only did some of this with our kids, since the 3-year-old couldn’t care less – but I’m hopeful my older kids will remember some of what we saw when they learn more about the American Revolution!

Boston Common

America’s oldest public park, and it’s perfect for running around or relaxing.

Newbury Street

Upscale shopping and dining but there are fun kid-friendly stops like a Harry Potter store and Ben & Jerry’s. Beautiful for just walking down on your way to the Boston Public Garden.

Faneuil Hall & Quincy Market

Shops, food, and entertainment all in one place. We got souvenirs, lunch, and walked around a few times. Our kids loved the street performers (and yes, there was some breakdancing involved by my oldest, too!).

Sports!

Our kids enjoy watching professional sports teams, and Boston has plenty to choose from. Since we went in the summer, we caught a baseball game at Fenway and it was great for the kids to see some ball in America’s oldest ballpark. (See a pattern? Lots of OLD things in Boston!)

Playground & Splash Pad

There are playgrounds throughout the city, but one that we frequented a few times was right outside the Government Center T stop and made for a quick break on our way to and from the T.

Rainy/Hot Day Options

New England Aquarium – A highlight of our trip! Penguins, sea turtles, and touch tanks. Our 3-year-old still talks about touching a sting ray and watching the penguins eat.
Museum of Science – A bit harder to get to, but worth it if you have time.
Boston Public Library – Beautiful and right near the Boston Marathon finish line, which is worth checking out, as well as the memorial.
The Prudential Center – A big, air-conditioned mall with food and shops (mentioned above also).

Bonus: Visit Boston College

If you’re near Chestnut Hill, consider a visit to Boston College! It’s where our story began! Stop by Cleveland Circle for a bite to eat at Pino’s Pizza and let me know if you want other food or coffee recs nearby.

Final Tips

Boston is a city best explored on foot or by T. We’ve driven and parked in our hotel before, but this time we flew into the city and took the T from the airport to our hotel. We also discovered a VERY affordable bus to and from downtown to the airport (Logan Express is FREE to downtown and just $3 to the airport). From Fenway to the North End, everything is accessible and easy to get to! And if you do make it to Mike’s Pastry, grab an extra cannoli for us, it’s now FW’s new favorite dessert!

Here’s some more inspiration from my recent Instagram reel:

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Much Needed Family Time in New York

April 27, 2021April 26, 2021 / Melissa (I Crashed the Web) / 1 Comment

What. A. Wonderful. Weekend.

After a year of pretty much staying put in our house in Cleveland, we FINALLY made it back to New York to see my parents. My brother had flown in from Germany, so we braved the 8+ hour car ride with the two kids to see him and my parents for a quick weekend. We hadn’t been back to New York since December 2019 – it was crazy to think how much has changed since then. Not just with the pandemic, but even with our kids — LM was still nursing, in a crib, in diapers, and not talking; FW could barely remember what my parents’ house looked like, and was hardly independent, etc. Oh yeah, and I was not 6+ months pregnant. It really seems like another lifetime.

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It was a quick trip – way too quick – but so great nonetheless. I got to enjoy home cooked meals and baked goods, quality time with my whole family, and even some runs with my brother. Here’s a little of what the weekend entailed:

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Very Merry Birthday Weekend

January 27, 2020January 26, 2020 / Melissa (I Crashed the Web) / 5 Comments

Happy birthday … to me! My birthday was on Thursday, and I only worked a few hours on Friday, so I had a nice long weekend to celebrate!

In emojis, here’s what the weekend included:🍪🥘🏃‍♀️🍿🦒

So what does that look like in real life? Here’s what that entailed:

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LM Turns One

May 27, 2019May 27, 2019 / Melissa (I Crashed the Web) / Leave a comment

This weekend is brought to you by the letter F. F is for First birthday, Friends, Family and Food — all wonderful things and well, I’m still smiling over what an amazingly wonderful weekend it was.

Friday was LM’s first birthday. That’s right, LM turned one over the weekend and I can’t believe it! While I’m still emotionally recovering, we had a blast celebrating. Friday celebrations started off early – I took the afternoon off and we were able to get the kids early from daycare to spend some time at the playground. Both LM and FW loved the swings.

And then we took LM to get her first ice cream. No photos of her, but FW loved his 🙂

Friday night, B and I actually got in a date night. My parents came into town, so B and I snuck out to grab drinks.

And then we had tickets to see the Indians – they won!

We even made it out for an after dinner drink on East 4th.

Saturday came early (especially after staying out late Friday), but was filled with celebrations — it was LM’s party! She enjoyed her first cake.

B’s mom made the cake and cupcakes – isn’t she amazing?!

LM thought so. She got frosting in her nose 🙂

The weather was PERFECT and FW enjoyed playing with his friends, cousins and of course, me.

After Saturday’s perfect weather, Sunday turned out stormy. We managed to catch a break in the rain and made it to the Zoo with my parents.

LM is still a little too young to enjoy it, but FW had such a blast. His favorite animals are the giraffes and elephants, and he got in some quality time with both.

Monday morning my parents left, and we hit up the local Memorial Day parade. It starts about 2 miles from our house, so B rode with the kids on the bike and I ran over.

Post-parade included some hot dogs at Grandma and Grandpa’s house, followed by a run home.

Aftet naptime, it was time for bbq #2, this time at B’s uncle’s house.

FW had some more fun and food with his cousins and LM did some assisted walking.

And that was the end of our perfect three-day weekend. Cheers to the unofficial start of summer!

Some questions for you:

Did you watch a Memorial Day parade?
Did you get outside this weekend?

Pre-Turkey Weekend

November 18, 2018November 18, 2018 / Melissa (I Crashed the Web) / 12 Comments

It’s THANKSGIVING WEEK! Though I’m not going back home and seeing my family this year (womp womp), I’m still excited for the holiday and spending time with B’s family. FW loves hanging out with his cousins, and well, I love stuffing 🙂

This weekend was another nice weekend at home. I got in a few runs – outside AND inside – and as always, we had some good food. Here are some of the highlights:

A run outside to kick off the weekend. It was cold and wasn’t my fastest run, but it was good to get outside early while everyone was fast asleep.

Friday we celebrated Thanksgiving a little early — at FW’s school! They had a Thanksgiving lunch celebration for the kids and their families.

It was fun to stop by in the middle of the day and grab a quick bite to eat with him.

Friday night we ordered in – Aladdin’s Lebanese food. It’s nice when we can all eat the same thing, but because FW is such a picky eater that rarely happens. He does love their pita quesadillas with fruit, though!

Saturday morning included some dancing.

Followed by cookie baking (with a toddler and baby).

And then naptime.

While LM was napping, I was able to get in a short treadmill run. I did 1.5 miles running, then stopped and got water, walked a bit and did about 1.5 miles more.

After naps, it was time to head outside for a little walk! We all bundled up.

We walked over to my friend Emily’s house to drop off some cookies and FW got to play with her son, Jack. The two of them are about 6 months apart.

That night, B made us some pizza. I LOVE his pizza and this batch was especially good.

Sunday morning we did some more baking. This time, FW and I made lentil, banana and zucchini muffins.

The day also included some indoor playing.

And a short stroller run with the family. FW fell asleep while we were out.

Th rest of the day flew by! It included not only dinner with B’s family, but also a haircut for FW!

At last, he can finally see again!

Questions for you:

Did it start to get cold near you?
How do you feel about running in the rain?
Have you run with a stroller?

I’m linking up with the weekly wraps.

If Life Gives You A Broken Oven … You Go For Some Runs (And A Walk)

November 11, 2018November 11, 2018 / Melissa (I Crashed the Web) / 3 Comments

What a weekend. It was cold (we saw snow flurries on Saturday!) and semi eventful. Why? Well, Saturday our oven broke. In the middle of cooking dinner (baking pizza dough) for B’s family. So that changed up some of our Sunday plans. But I’m getting ahead of myself. Here’s a little look at the past few days:

Thursday morning, I got in a semi-short run (3.11 miles) outdoors. It was chillier than it has been but it wasn’t too cold for me to get outside. B and I both had to be at work early, so I knew I only had 30 minutes or so to get in a workout after feeding LM.

Thursday night, B and I went out on a date night! We saw A Star is Born and then had dinner. Dinner didn’t start until 10 p.m., so needless to say, Friday I was tired! But look at this beer – it came with a toasted marshmallow!

Friday night was not as I intended. We ended up having to take LM into the dr because of a bad cough that was giving her a hard time breathing. She’s okay, but it’s so hard seeing babies sick – she hasn’t been herself and clearly is hurting 😦

Saturday was when the said oven incident occurred. BC was playing Clemson, so B invited his brother (who went to BC also) and the rest of his siblings and a few friends over to watch the game. We had planned on cooking pizza for everyone when the oven door just fell off. And when B tried to put it back together, we discovered that pieces had disintegrated!

We decided to order in instead, and still got to watch the game. FW hung out with his cousins and stayed up until half time.

The game didn’t quite end as I would’ve liked but it is always fun hosting people in our house. Our apartment was always too small to have to many people over.

Sunday, after the oven incident and some other things that were happening, I just had to get in a run. I knew it would make me feel at least a littke better. So while B and FW were at Home Depot, LM went down for a nap and I got in few easy treadmill miles.

Then, when FW was napping later I couldn’t help myself and got in a few more miles. I mean, look at the weather – it was so nice out! And running really does keep me sane.

We also were able to get on a little walk. It was chilly, but felt good to get out as a family. And it meant we had a relatively active weekend!

After that, it was time for dinner with B’s family. We celebrated B’s dad’s birthday and FW got to hang out with his cousins again.

3 runs, 1 walk and a broken oven … that about sums up the past few days!

Questions for you:

Has a major appliance you use broken down? What did you do?
What temps make you decide to run inside?
Have you seen A Star Is Born? What did you think?

I’m linking up with the weekly wraps.

My Kind of Weekend

October 7, 2018 / Melissa (I Crashed the Web) / Leave a comment

It was a GREAT weekend in CLE. It was warm (in the 70s and 80s!!) for October, my parents were in town, I got in some good quality time with the kids AND we were able to celebrate LM’s baptism.

It was great to celebrate with my mom – three generations in one photo 🙂

After the baptism, we had everyone over our house for chili, cornbread, chips, veggies …

And look at this cake! B’s mom made a GREAT cassata cake.

We all enjoyed the food.

Sunday, B had tickets to the Brown’s game (and they WON!), so FW and LM and my parents and I went to the Zoo!

FW’s favorites are the elephants and the giraffes.

I LOVE having my family in town, and FW really enjoyed spending time with his Nonna and Grandpa. And LM is so much bigger than the last time they were in town, so it was fun to have them interact with her.

What a wonderful weekend – family, good food and good weather. I couldn’t ask for much more ❤

Another Wintry Weekend In the CLE

February 11, 2018February 11, 2018 / Melissa (I Crashed the Web) / 8 Comments

Is anyone else sick of this winter? It has been cold and icy and snowy here for weeks and I’m so ready for warm weather and sunshine and a clear sidewalk to walk and run on!

Okay – enough complaining I suppose. Because despite the weather, it was still a good weekend spent with B and FW. I was sick most of the weekend, so it was pretty laid back and low key.

We of course had to start the weekend by celebrating National Pizza Day with my favorite pizza- Marottas!

Saturday, B made FW and I some pancakes to kick off breakfast. Fun fact- I never used to like pancakes or sweet stuff for breakfast- I was much more of a savory breakfast food lover – until pregnancy.

We spent some time later that afternoon at the West Side Market; we used to shop there all the time when we lived downtown, but now we only make it there maybe once every other month or so.

And of course we had to visit Rising Star for some coffee and chocolate milk (tea for me from Cleveland Tea Revival).

After the Market it was time to hit up the Great Big Home and Garden Show! I had won tickets in an online giveaway from Cleveland Magazine and it was a great way for us to get in some running around time and get Francis moving even with the cold weather.

Saturday night, B made us dinner – spaghetti, meatballs and homemade sauce.

Sunday morning we decided it was warm enough and finally not snowing/icing/raining/sleeting/etc. to go for a walk, so we walked to brunch!

FW got tired of walking, so B carried him. He then fell asleep in the carrier

We split some eggs and a lemon crepe. FW was suspicious of the crepe until I told him it was like a cookie 🙂

Sunday afternoon after our walk was pretty lazy. I got in some rest, some baking and some peanut butter making.

I realize I can’t remember the last time I bought any nut butter at the store! I got my Vitamix about a year ago and it has been the only way we’ve been doing peanut or almond butter. I LOVE having it and need to use it more!

Sunday night included dinner with B’s family and that was about it. We watched the Olympics with them for a little bit – it was the first time I’ve watched any of the events! I need to start getting into them.

Some questions for you:

Are you watching the Olympics?
What type of nut butter(s) do you like?

I’m linking up with the weekly wraps!

Some NEWS (Here We Go Again!)

January 31, 2018January 31, 2018 / Melissa (I Crashed the Web) / 6 Comments

For those of you that don’t know, B, FW and I have some EXCITING news to share.

We are well onto our way in expecting Baby #2!

It’s pretty evident that I’ve been hiding a baby, as you can sorta see in the above photo.

Can’t really see it? Okay, how about now? (Took the sweater off)

Yup! There it is – baby #2 has been hiding. So here are some of the updates for you:

Baby #2 is due at the end of May.
Once again, B and I are not finding out if it’s going to be a boy or a girl.
I’m feeling overall okay. I felt much more nauseous at the beginning of the pregnancy, and now I’m feeling much more tired. I’m still waiting for the second trimester high to kick in … but, I’m thinking that life with a toddler may be preventing that from happening! #sotiredallthetime
I’m still running! It is MUCH harder for me this time around, and I’m much slower than I was last pregnancy, but I’m happy to be still running (or walk/running) these days, even if it has been a lot of treadmill runs.

We have so much to do before baby #2 arrives at the house! We have to move FW into a toddler bed (and get him one of those …), we have plans to move him into a different room (the baby will get his room, as it has a built-in diaper changing table that B made), and a few other things. Oh, and somewhat finish our third floor and convert it into a guest room …
I had no idea the we’d need so much stuff for baby #2 – we were super minimalistic with FW because we were in a tiny apartment, but now that we have a house there are some basic things we’ll need that are still big ticket items – like a comfy chair for the new baby’s room for late night nursing! (In the apartment, I just used our current living room chair)
We probably have a boy’s name picked out, but still no girl’s name. It was the opposite with FW – we had a girl’s name (which B now no longer likes) but no boy’s name.

So there you go – the news is out! What questions do you have for us? Any tips for being pregnant AND having a toddler? Or surviving life with two kids?

I’ll leave you with this- a photo from when FW was just a newborn. Wow- time flies and I can’t believe we will have another one here in must be few months!

Weekends with a 13-month-old Baby

July 23, 2017July 23, 2017 / Melissa (I Crashed the Web) / 4 Comments

FW is officially 13 months. No longer an infant, he’s even older than a year right now. He’s almost a toddler! How did that happen?! Anyway, before I get too mushy, here’s a little about our weekend. For having nothing planned, the weekend ended up being pretty busy and flew by. We did some housework, went for a long walk (since I’m still not running), and had some good food.

Saturday I babysat FW while Brian did some housework. So naturally we started the day off with some banana pancakes.

It rained most of the morning, so we were stuck reading and playing inside. But as soon as it cleared up, we went for a walk.

While FW took his afternoon nap, I did some meal prep – cauliflower tots were a success (If only FW liked them …).

The afternoon also called for a bath. I think FW rocks a mohawk pretty well 🙂

B finally got home and brought us pizza. Mama Santa’s was delicious as always.

We ended the night catching up on Game of Thrones. I can’t believe we’re finally up-to-date on all the seasons!

Sunday, the weather was gorgeous, so we spent some time outside. FW loved splashing around the fountains and splash pad!

We ended up taking a pretty long walk that afternoon. My piriformis has been bothering me, so I haven’t been running at all – but we did get in a long walk! Unfortunately, my piriformis started bothering me toward the end. But it was a pretty day!