Seven Tips For Walking The Freedom Trail With Kids

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For families visiting Boston, Massachusetts, walking the Freedom Trail with kids is a must! There is so much American history in the city of Boston, and a walk along the Freedom Trail is the perfect way to see all those historical sites.

Why you should consider walking the Freedom Trail with kids

We visited Boston at the end of September, and since we only had a few days to spend, we decided the best way to experience the city was to walk along the Freedom Trail.

My daughter poses along the Freedom Trail (September 2018)

A step back into history

Within the annals of American history, the city of Boston is a prominent presence. The city played a pivotal role in the American Revolution and the birth of the United States.

It was in this city in 1773 that the Sons of Liberty, in a protest against the British imposed taxes on tea, dumped a whole shipment of tea from the East India Company into Boston Harbor.

Boston is also the city where Paul Revere made his famous ride in 1775, alerting Patriot troops of the advancement of the British before the Battle of Lexington and Concord.

As an American, walking along the same streets where these historical events happened, it is truly an incredible experience. I love visiting historical places!

And for kids, it’s a chance to learn about American history in a more interactive way.

An aerial view of Boston (September 2018)

Linking history with the present

The Freedom Trail itself was thought up in 1951 by a Boston journalist, as a way to link up many of Boston’s historical sites. There are 16 historical sites along the Freedom Trail.

You can choose to walk along the Freedom Trail with a guide, complete with 18th century dress, or tackle the trail yourself.

When we were walking the Freedom Trail with kids, we chose to walk without a guide. This allowed us to walk at our own pace, stop at the places we wanted, and skip past the places that weren’t as interesting.

If you’re thinking of walking the Freedom Trail with kids, whether on your own or with a guide, there are a few things to keep in mind to make sure your family has a good time.

It can be a bit challenging for young kids, especially if they’re not used to walking a lot. And there are times when you’re walking along busy Boston streets, so practicing road safety is absolutely prudent.

Tips for walking the Freedom Trail with kids

Those considerations aside, here are my tips for walking the Freedom Trail with kids.

A view of the red brick in Boston while walking the Freedom Trail with kids
The Freedom Trail (September 2018)

Tip #1: Give yourself plenty of time

One of our biggest tips for walking the Freedom Trail with kids is to allow plenty of time to do the whole trail. The Freedom Trail spans 2.5 miles, with about 16 official stops. You want to make sure that you give yourself plenty of time to explore some of those stops.

It took our family about five hours to complete the whole Freedom Trail. We stopped at several points of interests along the way, and also stopped for lunch.

Tip #2: Wear comfortable shoes

Walking the Freedom Trail with kids can be long, and it’s important that you (AND your kids) wear comfortable shoes. The last thing you want are blisters on your little ones’ feet! Look for shoes that provide support, as you’ll most likely log in more than 15,000 steps doing the trail.

The whole trail is paved, so don’t worry about getting your shoes dirty. But do keep in mind that you’ll be walking on some old cobblestone streets, so avoid wearing heels or fancy shoes that may make it difficult to keep your balance. And if you’re pushing a stroller, make sure it can handle those cobblestone streets.

Taking a break on the Freedom Trail (September 2018)

Tip #3: Dress for the weather

Along the same lines as wearing comfortable shoes when you’re walking the Freedom Trail with kids, it’s important to dress appropriately for the weather. You never know what might hit you while you’re out walking!

During our day of walking the Freedom Trail, it turned out to be pretty blustery and cold. Fortunately, we came prepared with jackets. We stayed quite warm, despite the wind.

Tip #4: Bring water

As with any hike that you undertake, it’s important that you stay hydrated while you’re walking the Freedom Trail with kids. The trail can be long, and on hot days, you might actually get dehydrated!

We liked bringing along our GRAYL water filter and purifier bottles because we could refill them wherever we were. You can also just use your own non-disposable water bottle, so as to reduce your environmental footprint.

A child looking at Boston’s Old City Hall while walking the Freedom Trail with kids
Stopping at Boston’s Old City Hall (September 2018)

Tip #5: Brush up on your history

The Freedom Trail takes you to many of America’s historical points of interest in Boston. One thing to do before walking the Freedom Trail with kids is to brush up on your American history.

The Freedom Trail website has brief descriptions of each point of interest along the trail, and its significance in United States history. If you want more in depth information, you can take one of the many Freedom Trail walking tours offered.

Another thing that the kids and I did before walking the trail was to read a book about the American Revolution, to get us in the mood for learning about history.

Tip #6: Check out the points of interests

Walking along the trail is only half the fun of the whole Freedom Trail experience. There are 16 spots along the Freedom Trail, and each one is worth a bit of exploration.

During our experience of walking the Freedom Trail with kids, we chose to stop at Faneuil Hall Marketplace. While there, we saw a live demonstration of a printing press, printing a copy of the Declaration of Independence, just like in the 1770’s. What a treat for the kids to be able to see history come alive!

A printing press demonstration at Faneuil Hall (September 2018)

Tip #7: Eat at the eateries along the way

Speaking of Faneuil Hall Marketplace, be sure to give yourself time to check out the eateries along the Freedom Trail. Faneuil Hall, and nearby Quincy Market, has a number of sit down eateries, as well as counter-style places.

By far, our favorite place to eat while walking the Freedom Trail with kids is the Union Oyster House. This restaurant has been in business since 1862, and serves one of our favorite bowls of clam chowder!

An experience to remember

Walking the Freedom Trail with kids is truly an experience to remember. We were so proud of the kids, absorbing the sites as they followed the red line that wound through the old streets of Boston.

I know that we will see many more historical sites during our travels, both in the United States and elsewhere around the world. We are lucky to have this opportunity to experience history!

Do you have experience walking the Freedom Trail with kids? Share it in the comments!

Seven Tips For Walking The Freedom Trail With Kids - The Wandering Daughter

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24 Responses

  1. Good job kiddies! The freedom trail was tiring even for us adults. We really like you tip about eating along the way. Nothing gets me through a long walk like quick doughnut and coffee stop. How Boston is that! I’m surprised no one has made an app for the freedom trail yet…

    Thanks for sharing. Keep travel blogging. Adventure is better shared with friends!

  2. Hello dear Astrid,

    First of all, thanks a lot for this great recommendation about hiking with kids. Even if I don`t plan to walk the freedom trail (I am from Europe) your tipps are really usefull and helpfull ->I do plan a small excursion with my nephew.
    Have a wonderful day

    1. That is so true. Even if they don’t retain all the information and things they saw along the way, they’ll remember that they walked the trail.

  3. I don’t have an experience of walking the Freedom Trail at all (or visiting Boston for that matter), but I would, like you did, take the trail without the guide. It seems more relaxed that way, and I’d surely like to skip dressing up in a 18th century dress! 🙂 I’d like to have a bowl of that clam chowder right now!

  4. I remember walking the freedom trails when we visited Boston and found them such a great way to learn the history of the city whilst also seeing it in person on foot. It looks like such a fun way for kids to learn history too, especially as you can self-guide rather than being constrained on an organised tour.

  5. I’m a huge fan of history and would love to do the Freedom Trail, most likely with a guide, as I always learn so much more. Thanks for all the tips and where to get great clam chowder!

    1. I think there’s a lot you can learn from a guide, especially if you want to do a more deep dive into the Freedom Trail.

  6. “In a protest against the British, they imposed taxes on tea” – as a Brit, this did make me laugh! The freedom trail seems like a very important thing to see and a fascinating discovery of history. I will be sure to walk this on my visit to the States!

    1. I often wondered how the Brits interpreted the American Revolution. I’m sure the history books take a much different stance than what the American history books cover.

  7. Allowing plenty of time to do the 2.5 mile long Freedom Trail is a top tip. I have walked the trail numerous times over the years and can’t tell you how many times I have witnessed kid and parent melt-downs about mile 2 because one parent or another was treating it like a forced march. So many great places to sit and snack or eat along the way that you point out too. Great post!!!

    1. Yup. Fortunately, my husband and I have done the trail before we had kids, so we knew what to expect in terms of how long it would actually take.

  8. We don’t have kids, but as history buffs, it’s good to see that some parents travel with their children and make them explore historical sites! You can certainly be proud that your kids learned so much while walking the Freedom Trail in Boston! 🙂

    1. Since my kids are young, we stuck with easy chapter books and picture books. For example, we read “Revolutionary War On Wednesday” by Mary Pope Osborne. It’s part of the Magic Treehouse series. We also read the book “I Am George Washington” by Brad Meltzer. These books didn’t really take place in Boston, but it did talk about the American revolution. I also read aloud the Declaration of Independence to the kids. I don’t think they understood most of it, but we did talk about what it means for one country to have control of a group of people. Of course, this was also a nuanced subject, because we did discuss that not everyone was given freedom (slaves and Native Americans).

  9. The Freedom Trail has a website  and a Twitter feed. If you follow the full route, plan for 4 hours to allow for walking, reading plaques, spending time inside some of the sights, and taking a serendipitous detour or two. 

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Hi, I'm Astrid

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I'm a travel-loving mom of three from Seattle. Join our adventures as we explore the Pacific Northwest and the world!

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