2 Days in Historic Boston: A History Lover’s Guide to Exploring Beantown

As one of America’s oldest cities, Boston is a premiere historical destination and a history lover’s dream. If you’re looking to explore Boston history, you’ve come to the right place! As a former Bostonian, I’ve had the chance to explore the city’s best historical spots and today, we’re going to cover them in this 2 Day guide to historic Boston!

Jam packed with historical pathways, monuments and buildings, Boston’s “Freedom Trail” tells the tales of the nation’s earliest beginnings with sites for you to visit all throughout the city!

While there are many historically relevant places in Boston, most likely, you are under time constraints. So, I’m highlighting the places I recommend the most. At the very least, I’ll make sure you get to walk the Freedom Trail on the same path that America’s Founding Fathers with stops at major sites along the way. After, you’ll enjoy a stay at the America’s oldest hotel and dine at the oldest restaurant. Here we go!

In this blog, I’ll share…

• Where to explore history in Boston and snap the best pics
• Where to eat in Boston
• Where to stay in Boston

Boston, a History Lover’s Dream

If Boston is known for anything, it’s history. I’m not talking about the kind that can surely be discovered in any small town or city around the US. Oh no. We’re talking about the birthplace of the American Revolution, which forever changed the course of history as we know it today. It all started on what is now known as “The Freedom Trail“, a walkable 2.5 mile path connecting the sites where some of the country’s most historical events took place.

When I was 13, I experienced Boston for the first time. Coming from California, it may as well have been a different country. I’d never visited a place where the neighborhoods had cobblestone streets, old brick exterior and gaslight posts. I immediately fell in love with the city which forever changed my idea of what “charming” and “quaint” means.

Little did I know that I’d get to be a Bostonian myself one day which was a dream for a history lover like myself.

Historical Boston

Founded in 1630, Boston is one of the US’ oldest cities. When the Puritans first settled in Massachusetts in the area now known as “Boston”, there wasn’t as much land to stand on as we have today. You might even say the city was once an island, having been built on Shawmut Peninsula.

Boston has expanded tremendously since then, but what I find most amazing about the city is that although it’s grown and evolved so much over the years, somehow the city’s conservational efforts have managed to keep the quintessential charm of Boston and many of its historical sites, buildings and monuments intact many centuries later.

What history is there to explore in Boston?

What if I told you that you can visit the church where Paul Revere warned that the British were coming, stroll through America’s first public park, see the resting place of famous groundbreakers like John Hancock and Samuel Adams, eat Boston Cream Pie from the restaurant that first created it and stay at America’s oldest (and arguably Boston’s most haunted) hotel… all in one city?

Well you can! And it’s all right here in “Beantown”.

Today, we’re going to focus specifically on The Freedom Trail. Don’t be surprised if you see tour guides dressed in 18^th century costumes reenacting The American Revolution.

For the next 2 days, you’ll be walking and standing a lot, so leave those heels at home ladies and opt for something comfier instead. Before we get into your Boston history 2 day itinerary, let’s go over some of the basics…

What is The Freedom Trail?

If you want to experience Boston’s history in a nutshell, look no further than The Freedom Trail, a walkable 2 ½ mile historical trail that snakes through the city, highlighting 16 of Boston’s most historically significant sites, 11 of which are relevant to the American Revolution.

You will literally step back in time, walking the same paths that America’s Founding Fathers did when they changed the course of history! I don’t know about you, but I always dork out pretending like I’m one of the Founding Fathers strutting down the cobblestone walkways in their buckle shoes. 😊

How long does The Freedom Trail take to complete?

Depending on how long you spend at each site, it could take you between 90 minutes and 2 days to complete The Freedom Trail.

A lot of the sites are a short walking distance from one another and easily accessible on foot. You’ll know you’re on the right track when you’re walking on brick with a line embedded in the walkway like this…

Self guided walking tour vs. Guided walking tour

You’ll find many companies offering guided walking tours in Boston which can be nice. However, working on someone else’s schedule may not always be ideal if you’re pressed for time.

In this case, a self-guided walking tour is a great alternative. I prefer this option so I can go at my own pace. Audio tour options are available as well.

Don’t worry, The Freedom Trail is very self-explanatory with signs and markers. You can’t miss them! At the end of this blog, I’ve also included a map you can download to visit each historical site on The Freedom Trail.

If you do go with a guided tour, note that most tours do not cover the entire Freedom Trail.

Private Driving Tour

For those who are pressed for time or want to avoid walking, a private driving tour is a great option. This tour allows you to arrange to be picked up & dropped off at your hotel (select locations). Prices range from $280/PP for 2 people or $155/PP for 6 people.

Now, let’s get ready to explore Boston history!

Your 2 Day Guide to Exploring Historical Boston

Day 1: Downtown Boston

Start of Freedom Trail

• Boston Commons

The Freedom Trail kicks off at America’s oldest public park, Boston Commons which is filled with history. Built in the 1630s, the park started off as a cow pasture and was turned into what was called a “trayning field”, becoming an encampment for the Redcoats for 8 years during British occupation of Boston in 1775.

During this Revolutionary period, The Commons was also a gathering place for historical Boston victories. John Hancock held a celebration for the Stamp Act’s repeal in 1765 and George Washington, General Lafeyette and John Adams celebrated America’s freedom from British rule. Today, you’ll find locals lounging, ice skating, running and strolling or, dancing like me. 😉

• Paul Revere House

The British are coming, the British are coming!

Well, I don’t think it’s just the British… It seems like everyone comes to see this landmark. The name pretty much sums it up, Paul Revere House is the home of Silversmith turned American hero, Paul Revere, and is totally worth a stop if your schedule allows. Paul Revere House still has some of the original architecture and furnishings owned by the Revere family.

Book a Paul Revere House tour here.

• Boston Massacre Site, Old State House

Outside of the Old State House, you’ll find the site of the “Boston Massacre” where 5 Boston civilians were shot and killed just a few yards away by British soldiers during Britain’s occupation of Boston in 1770. Every year on March 5, a reenactment takes places by the Bostonian Society to honor the anniversary.

• The Old South Meeting House

In 1773, this “back up space” to the Faneuil Hall meeting place was used to hold meetings that put the infamous motion into play by Sam Adams that started the Boston Tea Party.

Book an Old South Meeting House tour here.

Speaking of Tea Party… Let’s experience how it all happened!

• Boston Tea Party Museum

If you have time to take any tour, I highly recommend the one at the Boston Tea Party Museum. Here, you’ll relive the historical events as the Sons of Liberty did.

During the interactive tour, you’ll take part in a reenactment of the meeting held at the mock Old South Meeting House replica they have on site as well as “Destruction of the Tea” aboard a realistic 18^th c. ship, where you’ll dump tea into the river.

Up close, you’ll even get to see The Robinson Tea Chest, which is the only known surviving chest from 1776.

I personally love this museum and most notably Abigail’s Tea Room, a great place for afternoon tea. It’s a place to check out any time of year but specifically during the month of February when they offer a special evening of historical romance featuring themed actors reading the love letters between Abigail and John Adams.

Book Boston Tea Party Museum here.

By now, you’ve probably worked up an appetite. Don’t worry, I’ve got your belly covered. 😉

Where to eat in Downtown Boston

Along the trail, you will be walking to an area near Faneuil Hall where you’ll find several dining options to choose from. However, since this is a history buff’s itinerary, let’s explore a historical restaurant, shall we?                                                                  

• Union Oyster House

Head off the Freedom Trail for a 2 minute walk to America oldest restaurant, Union Oyster House, where notables like Daniel Webster and The Kennedy Family were among its frequent customers. It’s the perfect place to enjoy a meal while getting a taste of history, (corny but true! 😉) 

Situated in a building that predates the Revolutionary War, you’ll be looking at the decor while imagining the urgent historical discussions that happened in this very spot. Head upstairs to the 2nd floor where in 1796, Louis Philippe, king of France lived on the 2^nd floor in exile from 1830 to 1848.

In addition to all the glorious history you’ll be served up, the food here is outstanding. I’ve dined here several times and am always super happy with the oysters and lobster (my go to selections). Don’t worry if you’re not into seafood. They also have other options.

Insider Tip:

I prefer sitting in booths, HOWEVER, the ones here are incredibly tight and narrow. I’m very petite by most people’s standards and it was a tight fit even for me. On my last visit with my mom, she had to squeeze in uncomfortably, until the sweet waitress offered a table alternative. Save yourself the squeeze and opt for a table with chairs if you are in the front dining area.

If you are in the mood for a more casual vibe, there are plenty of other dining options adjacent to Faneuil Hall Market Place which is very walking friendly.

Day 2: Charlestown, Boston

End of Freedom Trail

Yesterday was all about Boston’s historical Downtown. Today, you’ll head to the end of The Freedom Trail in Boston’s oldest neighborhood, Charlestown, which sits between the Mystic River and the Charles River. This is where you’ll find some of America’s most significant Revolutionary history.

For me, this area easily takes a day to explore.

Your next stop on the Freedom Trail is Bunker Hill Monument. Get ready to bring your sneakers and energy for this one.

• Bunker Hill Monument

While you can enjoy the monument from the ground, you may also want to take the vertical hike up to the top. Just shy of 300 stairs, the Bunker Hill Monument is not for the out of shape or faint of heart. It’s a trek.

If you are not up for the climb, there is a nice green area to sit at or a visitor/education museum on the grounds to view while you wait for the stair climbers in your party.

Once your knees stop shaking from the climb, it’s time to get your sea legs on and head over to Charlestown Navy Yard.

• USS Constitution

You’ll want to make time to visit the USS Constitution, affectionately known as “Old Ironsides” from its time during the War of 1812. Today, it stands as the world’s oldest commissioned warship.

Having never been defeated in battle, this remaining treasure is a piece of American history you don’t want to miss out on. You can also head into the USS Constitution Museum to learn more about the ship.

At this point, your belly is probably hungry…

Where to eat in Charlestown, Boston

And because this is a historical tour of Boston, dine where America’s war heros dined… at Warren Tavern which hosted the likes of George Washington and Paul Revere.

As the first tavern in Massachusetts, this tavern was also one of the first places that was rebuilt after the British destroyed most of the area. It’s named after General Joseph Warren who was taken in the Battle of Bunker Hill.

Here, you can find typical American classics like fried chicken, burgers and steak tips as well as seafood and salads.

Where to Stay, Hotels in Boston

Why not enjoy a little piece of history during your hotel stay? I recommend staying at Omni Parker House which I’ve stayed at before.

• Omni Parker House | Downtown Boston

“The Grand Dame of Boston Hotels” is America’s longest, continuously operating hotel, Omni Parker House, which has a lot of history since opening in 1855. Many famous people stayed here, probably most notably is JFK, who was a frequent guest, announcing his bid for Congress here and also, proposing to Jackie in the hotel’s restaurant at table #40.

It was nice to have breakfast at the hotel’s restaurant and taste the original Boston Cream Pie which was invented here in 1856. If you love it so much, they’ll ship a pie home!

While the hotel is not for those looking for an ultra-luxurious stay, I found the rooms comfortable with modern amenities. You also can’t beat being in the heart of Downtown Boston right on The Freedom Trail… literally. You can get a room with a view of King’s Chapel and Old City Hall, which is what I did.

That’s a Wrap!

I hope you enjoyed this 2 Day guide to Boston’s history! If you found it useful, share it with your friends! For more blogs like this, subscribe to the blog. I promise not to spam you. 😉

Are you a history lover? How would you explore history in Boston? Comment below!

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Thank you so much for your continued love and support! I wouldn’t be here if it weren’t for you.

Until next time… keep it real.

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