guests looking at merchandise
Around the US,  Boston

The Freedom Trail – North End

To really get a taste of the history of Boston, we started with the Freedom Trail. For me, the trail conjures up visions of the beginning of the United States of America! For my 7 year old grandson, it seemed like a looong walk. So we compromised; we only walked half of the trail at a time, with plenty of stops along the way. Which is the perfect way to do it anyway – if you rush, you can’t spend time getting to know the history of our nation!

When you have finished the North End, you can read my post all about the South End!

Note: I don’t earn commission from any links in this post, but I hope they will be helpful to my readers.

Our first stop was the USS Constitution Museum and Charleston Navy Yard, a National Historical Park. We chose to start our Freedom trail walk there because there is a parking garage nearby. Parking in Boston is not cheap, so plan to shell out $20 to $50 for each full day of parking, or alternately, use public transportation.

The actual ship USS Constitution was in dry dock at the time that we visited, and the ship tours were booked several hours out, so we didn’t choose to go aboard. Make sure to go early in the day to get a tour time if you want to visit!

Tourists with the USS Constitution

The Museum was lots of fun for the kids! There was a model ship exhibit, a walk-thru exhibit that showed life back in the day, and a children’s activity room that we barely had any time for, because we were anxious to get marching on that trail! The Museum could easily take several hours, and if you have a few days, plan to spend some time there.

child with model ship

Part of the fun of the Freedom Trail is following the brick line in the street. Sometimes the line is interrupted, so you have to be on the lookout! The kids had a fun time following the line to see where we were going next!

child on  the Freedom Trail

We were wandering around the North End neighborhoods trying to recover the line when we happened on Regina’s Pizzaria. It was only 3:30 or so, and we debated whether to come back later, but the kids were hungry, so we decided to eat. We ended up waiting in line about 20 minutes, even though the line was short, and when we saw the line later, after our meal, we were glad we had come early! The pizza was delicious, and I especially enjoyed the BBQ chicken pizza. The restaurant was warm and cozy, with the tables placed tightly together, and because of that they don’t allow strollers inside. We thought for a minute that we would have to go somewhere else, but the manager came to our rescue and stored our stroller in a small cubbyhole outside the front entrance!

Patrons at Regina's Pizzeria

“One if by Land, Two if by Sea”

Schoolchildren all over the country have learned this famous couplet regarding the symbol of how the British were marching to Lexington and Concord. On the night of Paul Revere’s ride, two lanterns were hung from the steeple of the Old North Church, as an indication that the British were arriving by sea – across the Charles River.

The Old North Church

We enjoyed visiting the church, sitting in the pews, and perusing the displays that told of Paul Revere and his ride. We got there too late for a guided tour, but we would recommend checking it out!

young boy in pew at Old North Church

Behind the Old North Church sits Captain Jackson’s Historic Chocolate Shop and the printing office of Edes and Gill. We didn’t realize either one of them were there until we followed the Freedom trail behind the Old North Church. Fortunately, they were both open! The printing office had a printing exhibit with an 18th century printing press, where we were treated to a demonstration of the type of printing used to print the Declaration of Independence. *Update – The printing office of Edes and Gill has moved to Faneuil Hall. Don’t miss it!

exhibit of Colonial chocolate

At Captain Jack’s Historic Chocolate Shop, it was fun to hear about the history of one of my favorite treats, and how the early Americans used chocolate. It is very different than our chocolate candy today. We even got to taste a tiny cup of hot chocolate at the end!

Speaking of Paul Revere, you can visit the Paul Revere house further along the Freedom Trail. The house is Boston’s oldest building, having been built in 1680. It’s a quick little self-guided tour with volunteers in each room to tell a little about the home and life in Paul Revere’s time.

Paul Revere's house

Just a block or so away from Paul Revere’s house, and not an official Freedom Trail stop, is Mike’s Pastry. We stopped there for some sweet cannoli and ended up also trying their ice cream, cake, and lobster tails! Everything was so yummy that we make it point to go back whenever we are in Boston.

Man eating a lobster tail pastry

The North Freedom Trail also includes Bunker Hill Monument and Copp’s Hill burying ground, neither of which we had time to visit, since we were only in Boston for half a day. Maybe next time!

For information about the South Freedom Trail read my post here!

Have you visited the north end of the Freedom Trail? What was your favorite place?


  • Vessy Smith

    What a fascinating experience! Thanks for sharing this! I had never heard of The Freedom Trail before, but now I am so interested to check it out. Oh, and that pastry shop looks amazing! 🙂

    • Lori

      Thanks! It is sooo good. Last time we were there we picked up a selection of six items on our way out and ate them at the airport while we waited for our flight. But the freedom trail is well worth a few days by itself!

  • Courtney

    I so enjoy the Freedom Trail. It is a fabulous experience for the children to walk in history, not just read it in books. I will have to check out the pizza place the next time I am in Boston!

  • Lee Anne

    So cool! I was at the USS Constitution but was only able to tour around it quickly because I was working. I would love to take my kids back to see all of this.

  • Leeanne

    We love the Freedom Trail. We’ve done all parts of it at different times and always love it. Next time don’t miss the playground in Christopher Columbus Park or the aquarium. You don’t even have to go in, they have harbor seals in a tank out front.

  • Lisa Manderino

    I love historical travel. I took my two oldest to Boston when they were little but we will have to go back so they can remember it!

  • alison netzer

    Love Boston. You gave me a smile with your visit to Mikes as I used to visit there, but that was at 2am after the bars closed. I went to college in bean town. So fun to give the kids a history tour.

  • Missy

    We have not visited the north end of the Freedom Trail yet. 🙂 This is an adventure that we would enjoy doing. Thanks for the suggestion.

  • kmf

    Great photos! My family and I took the Freedom Trail last May. It was downpouring most of the time, but we still had fun checking out the historical places…especially loved th Paul Revere House.

  • Tara

    Thanks for sharing your version of the Freedom Trail with your kids! My husband and I did this 13 years ago and we’d love to bring our kids next time!

  • Heather

    I love the Freedom Trail. Growing up in Mass, most school aged children take a field trip to Boston and do some part of the Freedom Trail. I love how there are all different types of tours you can take. I would love to do the haunted walking one. BTW, lobster tails are my favorite!