The Freedom Trail is undoubtedly Boston’s most iconic and popular attraction—a 2.5-mile red-brick path that winds through the city, connecting 16 historically significant sites tied to the American Revolution. Walking the Freedom Trail feels like stepping back in time, and it’s an absolute must-do for anyone visiting Boston, especially for the first time.
We started the trail around 11 a.m., since a lot of the sites like the Old State House and the Old North Church don’t even open until 10. It ended up taking us most of the day—we didn’t make it to the final stop at the Bunker Hill Monument until almost 6 p.m. But we weren’t in a hurry. Since it was our first day in the city, we kept getting sidetracked exploring other places we came across along the way.
Boston is packed with history, and walking the Freedom Trail was such a cool way to experience it. There’s something about seeing these places in person—standing where huge moments in our country’s history actually happened—that makes everything feel more real. It was definitely one of the highlights of our trip.
Tips for Walking the Freedom Trail
Use an audio tour (and here’s a secret free one!)
There are tons of walking tours available for the Freedom Trail, and most of them give you great background on each stop. Personally, I like to explore at my own pace, so I usually skip the official group tours. But if that’s your thing, you can grab tickets at the Boston Common gift shop, which is also where the trail officially begins. They also sell self-guided audio tours for around $10.
But here’s my little tip: download the National Park Service app and search for the Freedom Trail—there’s a completely free self-guided audio tour in there! We didn’t find it until our last day in Boston. The weather was finally nice (unlike the freezing cold, wind, and rain we had on our first day), so we decided to walk the trail again before heading to the airport—this time with the audio tour. It made a huge difference. Each section is only about 2–5 minutes long and plays at the different stops along the trail. After doing it once just by reading signs and then again with the audio, I can honestly say the second time was way better. It really brought the history to life.
Check the weather
Boston can be chilly, especially with the wind, and it can rain out of nowhere. I’m all for looking cute in photos, but honestly, comfort matters more when you’re out walking for hours. Dress for the weather—layers are key! I wore water-resistant boots, a raincoat, brought an umbrella, and threw on a beanie. I was so glad I did. Cold and soggy isn’t fun when you’re trying to enjoy the sights.
Know what time things close
Some stops along the trail, like churches, monuments, and state buildings, actually have closing hours—so if you want to go inside, keep an eye on the time (and the season, because hours can vary). For example, we reached the Bunker Hill Monument around 5:30 p.m., and while we could still walk around outside, the inside was closed for the day. On the other hand, outdoor landmarks and statues can be seen anytime.
Bring water and snacks
I never go anywhere without my water bottle—whether I’m at home or traveling. Even if the weather’s cold, you’re still moving a lot and using energy, so staying hydrated is super important. The last thing you want is to feel sluggish or dehydrated in the middle of the day. Same goes for snacks—when you’re walking more than usual, a quick bite can make all the difference. Toss a few granola bars or something easy in your bag to keep your energy up and avoid getting hangry halfway through the trail.
Exploring Inside
As a huge history buff, I absolutely loved walking the Freedom Trail—both with and without the audio tour. It was such a memorable experience. Even the others in my group, who aren’t as into history as I am, still had a great time and found the trail interesting. If you’re wondering which stops are worth stepping inside for, here are a few of my favorites from the trail.
Bunker Hill Monument
Even though it was closed when we first got there, I ended up going back another day by myself to check it out—and it was totally worth it. You can actually climb all 294 steps to the top (yep, it’s a workout—tight spiral stairs the whole way). The view from the top is amazing and gives you such a cool perspective of the city. Plus, seeing the inside gave me a better appreciation for the architecture and what went into building the monument. Best part? Entry is completely free.
Funny side note: I had music playing in one ear to keep me motivated while climbing, and on the way down, “So Long, London” came on—which made me smile because it felt oddly perfect. This monument honors those who fought in the Battle of Bunker Hill, part of the bigger story of America saying goodbye to Britain. Kind of poetic, right?
Paul Revere’s House
Most Americans know the name Paul Revere thanks to the iconic phrase, “The British are coming, the British are coming.” Men like Paul played such a key role in making the revolution happen. His house, built in 1680, has since been transformed into a living museum. For an entry fee of around $6 per person (we used our Go City pass for this, which you can read more about here), you get to tour this historic three-story home. The foundation has done a great job preserving the house to be as historically accurate as possible. It was pretty wild to see how the Revere family raised 16 children in such a small space—definitely a learning experience! On the day I visited, there was extra buzz around the house since it was just before the 250th anniversary of Paul’s famous ride. It’s definitely worth a quick stop to check out this piece of history.
USS Constitution Museum and Ship
The USS Constitution, the world’s oldest commissioned warship still afloat, was launched in 1797 with the purpose of helping build the new nation’s navy. It played a significant role in the early years of the United States, especially during the War of 1812. The ship is often referred to as “Old Ironsides” because of its ability to withstand enemy cannonballs, earning a legendary reputation in naval history.
The museum dedicated to the ship offers a fascinating look at the life of sailors during the Revolutionary War era, as well as the history of the ship itself. It tells the story of how the Constitution was nearly scrapped multiple times throughout its history, only to be saved by its symbolic importance as a beacon of hope and pride for the American people
After exploring the museum, we were able to board the actual ship itself, which was an incredible experience. Standing on the deck, I couldn’t help but feel for the sailors who lived and worked there—the space was incredibly cramped! It’s hard to imagine how they managed, but the experience really brought history to life in a way that’s hard to describe.
I had such a great time on the Freedom Trail and learned so much along the way! The mix of history, stunning landmarks, and stories behind each site made it a truly memorable experience. Whether you’re a history lover or just looking to explore Boston, I’d definitely recommend walking the Freedom Trail. It’s a perfect way to dive into the past while enjoying everything the city has to offer.
Stay Safe and Start Exploring!