acorn street boston walking tour
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What to do in Boston // 2-Day Walking Tour

With all that there is in Boston, you might be wondering what to do in Boston if you only have a few days. This 2 day Boston walking tour is for you!

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Boston is such a fun city! There is so much history and so many different cultures all in one place. It’s one of those places where you can spend anywhere from a few days to even a full week! Or more! With our first trip to Boston, we opted for a few days to test the waters. And because that’s as long as we could get away. Haha. We were not disappointed! We got to see so much there and we ate some delicious food! You can bet that we will be going back to see more! Here is our full Boston walking tour for the two days we were there and everything we did. If you want to see everything we ate, check out the blog post below!


This post has the easiest 2-Day Boston Walking Tour to follow! 

How to Get Around in Boston

Ok, let’s talk about transportation. Like with most cities, there are multiple ways to get around. Let’s talk about all of the different ways to get around in Boston and the benefits and downsides of each!


This blog post is a Boston walking tour, so I would be remiss if I didn’t mention this, right? Walking has been one of our favorite ways to experience different cities. Well, cities that are walkable and pedestrian-friendly, which Boston is. You can see a lot that you would just glance at in a car, and you can get some good exercise to help justify all of that yummy food you are going to try. 


Another favorite way to see a city is by riding a bike. Boston is no exception! They use Blue Bikes and have a great app that you can use to pay and see all of the stations along with the number of bikes available. Although, if you aren’t too comfortable riding bikes in traffic, then this one might not be for you. Also if you have short legs, the bikes aren’t too forgiving. Haha. We didn’t end up riding bikes in Boston, but we got around just fine!


Boston has a great train system called the T. It goes basically everywhere that you need it to go and once you get your bearings, it is pretty simple. Google Maps is also amazing when it comes to trains because it can show you the best route to take via train and its schedule. 

If you’re worried about buying tickets for the train, there is usually an employee by the ticketing machines to help you. When buying tickets, you want to decide how many times you will ride the train. If you are planning on riding the train more than a few times, I would recommend getting a day or multi-day pass. If you are just looking for a ride to a spot further out, then a single-use ticket will do the trick! For this walking tour, single-use tickets on the second day should work! And maybe a few single-use tickets for the first day to get you to the start or from the end of this Boston walking tour.

Trains are also nice because they can get you to places further out, like Salem or New York!


As convenient as a car may seem, especially to Western United States people, I would not recommend a car in Boston. There are a lot of lights, traffic, and not a lot of parking, so getting places will take you longer than just walking. If you want to venture outside of Boston though, a car can come in handy for sure! But if you don’t have a car, there are other ways to travel to different cities.

What to Do in Boston // 2-Day Boston Walking Tour

If you’ve been reading other posts on what to do in Boston, you’ve probably heard about the Freedom Trail. And you’re about to hear about it again! There is so much to do along the Freedom Trail, that your walking tour of Boston starts at the beginning of the Freedom Trail!

Day 1 our Boston walking tour will mostly be filled with the Freedom Trail sites and Day 2 will be filled with other sites that you can’t see while on the Freedom Trail. Basically, we are going off the beaten path. Or beaten trail. Get it? 

For the first day, everything will be pretty close together, so walking or even renting a bike will be a good mode of transportation!

Boston Walking Tour Day 1

Acorn Street

Ok, I lied a little. We are starting a little before the Freedom Trail with a few sites that you won’t want to miss! The first is Acorn Street. It is just about the cutest street in North America. It is a cobblestone road with the cutest homes on each side and original gas streetlights from when the city was built. But Acorn Street, although the most photographed in the area, is not the only thing to see! All of the homes in Beacon Hill are so cute and unique. It made me feel like I was back in London. 

When I said it was one of the most photographed places, I wasn’t kidding. Hopefully going there first will help with the crowds! I would recommend walking around and going from the top down so that you can get all of the good shots. And not be in too many people’s pictures.

Oh, there are people that live in the homes along Acorn Street, so don’t forget to just be kind!

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Boston Public Garden

Next up is the Boston Public Garden! This is a very beautiful place to walk around and, of course, catch some history. While you are in the Public Garden, don’t forget to see the George Washington Statue and the Make Way for the Ducklings statue. Both are so fun! 

Nearby Attractions

  • Fiedler Dock

Nearby Restaurants

  • Cheers Bar
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Boston Commons

Now let’s start the Freedom Trail! The Boston Commons is a pretty big park and we definitely walked around a little bit more than we should have to find the start. I blame the jetlag. Haha. The start of the Freedom Trail can be found by the pavilion on the east side of the park about halfway up. If in doubt, just look for the tour guides dressed like Revolutionaries. 

Nearby Attractions

  • Robert Gould Shaw and the 54th Regiment Memorial
  • Massachusetts State House

Nearby Restaurants

  • Tatte Bakery & Cafe
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Granary Burying Ground

If you want to see a pretty historically significant cemetery, this is the one for you! This is where John Hancock, Samuel Adams, Paul Revere, and the victims of the Boston Massacre are buried. Among others of course! This graveyard is the final resting place for more than 5,000 Bostonians!

Nearby Attractions

  • Park Street Church
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King’s Chapel

Next up on our 2 day Boston walking tour is the King’s Chapel! Kings Chapel is the oldest Anglican Church in America and the home to so much history of the original colonists and early America. The burying ground on the back of the church is the final resting place to many notable people including Mary Chilton, the first woman to step off of the Mayflower. It’s also the home to a pretty eerie tombstone. you’ll know when you see it! 

Nearby Attractions

  • King’s Chapel Burying Ground
  • Boston Latin School and Benjamin Franklin Statue
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Old South Meeting House

The Old South Meeting House is next! It used to be a church prior to becoming a meeting house and Ben Franklin was actually baptized here! After it became a meeting house, this is where colonists rallied each other prior to the Boston Tea Party.

Nearby Attractions

  • Boston Irish Famine Memorial

Nearby Restaurants

  • Chipotle in the Old Corner Bookstore
  • Shake Shack
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Boston Massacre Site

If you blink, you might miss this! The Boston Massacre site is actually just an emblem on the road next to a pretty busy intersection. Although it has been moved a couple of times so that it didn’t end up in an intersection, this spot is not one you want to miss. 

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Faneuil Hall

Faneuil Hall is our next stop! This area has been a commercial area and meeting house for most of its life. If you are hungry, head to Quincy Market to get some delicious foods ranging from pizza to seafood, to even some Greek food. 

Nearby Attractions

  • Quincy Market
  • New England Aquarium

Nearby Restaurants

  • Boston Chowda Co
  • Regina Pizzeria
  • North End Bakery
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Marshall Street

Although Marshall Street is not part of the Freedom Trail, you do walk through it to get to Paul Revere’s House and why not stop to take some pictures? This cute cobblestone street gave us some serious Diagon Alley vibes. We couldn’t stop taking pictures! 

Nearby Attractions

  • Boston Stone
  • Rose Kennedy Greenway

Nearby Restaurants

  • Union Oyster House
  • The Green Dragon Tavern
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Paul Revere House

Paul Revere’s House is in the North End and is a pretty cool site to see! There are also a ton of food places nearby, so be sure to take some time to try a few out! Bring cash with you though because a lot of places in the North End are cash-only.

Nearby Restaurants

  • Antico Forno
  • Mike’s Pastry
  • Giacomo’s Boston North End

Old North Church

Have you heard of “One if by land, two if by sea”? It’s how the revolutionaries planned to communicate with each other based on how the British were making their way over. And the Old North Church is where they were to hang those lanterns up! Paul Revere was actually one of several riders who were headed out in different directions to warn the colonists that the British were coming. It’s interesting to learn that he actually didn’t even finish his whole ride before getting caught by the British. It was actually Henry Wadsworth Longfellow who turned Paul Revere from just a mere participant in this part of history to an icon in his poem “Paul Revere’s Ride”. He wrote the poem to unify the northern and southern colonies before the Civil War. Pretty crazy, huh?

At the Old North Church, you can take tours of the church, the bell tower, and the crypts. It’s worth doing at least one of those! Although, we definitely recommend the church and the bell tower.

Nearby Attractions

  • Paul Revere Statue
  • Copp’s Hill Burying Ground

Nearby Restaurants

  • Bova’s Bakery
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Paul Revere Park

Just down the road and across the bridge from the Old North Church, you will find Paul Revere Park. Nestled right there next to the water, you can enjoy great views of the city and the harbor. It’s also a great place to relax after all of the walkings you have done! This is where you can end for the day, but if you still want more to do, check out the list of nearby attractions that are all in the area and amazing.

Nearby Attractions

  • Bunker Hill Monument
  • USS Constitution Museum
  • Constitution Museum
  • North Point Park
  • Museum of Science

Nearby Restaurants

Boston Walking Tour Day 2

On to the second day of our Boston walking tour! We are going to be straying from the Freedom Trail today and exploring some fun sites on the other side of Boston. There are not too many big attractions this day, so take your time and explore the Nearby Attractions! 


Depending on where you are staying, it may be a journey to get to the Franklin Zoo (our first stop of the day) and get home from Fenway Park (our last stop), so you may want to take a train to these! I’ve listed nearby train stations on this day so you can get around more easily.

Let’s go!

Franklin Park Zoo

Let’s start this day by going to the zoo! The Franklin Park Zoo is such a beautiful zoo on the north end of Franklin Park. There are great exhibits and so many cool animals! It’s a great way to start your second day in Boston. If you’ve got littles, the Franklin Park Zoo is a great place to take them!

Close-by Train Station

  • Green Street on the Needham (Orange) Line – Use this station to go to the Boston Public Library
  • Four Corners/Geneva on the Franklin/Foxboro Line

Nearby Attractions

  • Franklin Park
  • Forest Hills Cemetary
  • Peters Hill

Nearby Restaurants

  • Evergreen Eatery & Cafe
  • Midway Cafe
  • Fiore’s Bakery

Boston Public Library

I know, you’re probably thinking to yourself “ a library?”  yes, you read that right. a library. But not just any library. The Boston Public Library is a pretty historic place and is very much worth visiting. Like most of their libraries, it is free to the public. Aside from it being a very beautiful building that makes you feel like you stepped into a building in Europe, the Boston Public Library also has a lot of historical significance and a lot of firsts. It was one of the first public libraries in America in general. It was also one of the first to lend out books and to have a children’s section. 

Close-by Train Station

  • Copley on the  Green Line E (use this station to go to the Museum of Fine Arts)
  • Back Bay on the Needham Line (Orange)

Nearby Attractions

  • Trinity Church
  • Copley Square
  • Newbury Street
  • Bodega – hidden shoe store!

Nearby Restaurants

  • Charlie’s Sandwich Shoppe

Museum of Fine Arts, Boston

The Museum of Fine Arts in Boston is A great place to visit while in Boston! there is so much history and so many things to learn that you could spend several hours there. Growing up and traveling, we went to a lot of museums. Josh on the other hand hadn’t been to a museum like this. it really made me appreciate it so much more to walk through it with him and see it through his eyes. we were also able to see the exhibit of the portraits of the president which was really neat. 

Close-by Train Station

  • Museum of Fine Arts on the Green Line E 

Nearby Restaurants

  • Boston Shawarma
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Isabella Stewart Gardner Museum

Now that we have done the Museum of Fine Arts, we are heading to another and more intimate museum. The Isabella Stewart Gardner Museum is a very beautiful museum that was founded by Isabella Stewart Gardner and her love of art. Aside from the beautiful paintings you will see, there are some empty frames that are a result of an art heist in 1990 that is still unsolved. To learn more, you can also watch the Netflix documentary called “This Is a Robbery: The World’s Biggest Art Heist.”

Close-by Train Station

  • Museum of Fine Arts on the Green Line E 

Nearby Attractions

  • Harvard Medical School

Nearby Restaurants

  • Laughing Monk Cafe

Back Bay Fens

For an out-of-stater like myself, when I heard about Back Bay Fens, I didn’t understand why people would want to see a fence in the Back Bay. However, that is so far from what it is. The Back Bay fence is essentially a large and beautiful park with different gardens and historical memorials throughout, along with several athletic fields. It is right there, in the middle of Boston and behind the Museum of Fine Arts. it is really such a beautiful park and area with so many different spots to relax and to take in nature, all the while never leaving the city. 

Close-by Train Stations

  • Museum of Fine Arts on the Green Line E 
  • Hynes Convention Center on Green Line B, C, D (north end access)

Nearby Attractions

  • James P Kelleher Rose Garden
  • World War II Memorial

Nearby Restaurants

  • Matcha Cafe Maiko

Fenway Park

If you don’t know much about baseball, you might be wondering why Fenway park. It’s worth it! Fenway Park is the oldest major league baseball stadium in America And a pretty unique stadium at that! It is home to the Boston Red Sox and has been since 1912. If you happen to go on a day when there is no baseball game, you may be able to take a tour of the stadium. Even though we haven’t been able to do that yet, we’ve heard such great things about it. even something about a garden on top? you guys will have to let me know! 

Although Fenway Park is the last stop on this Boston walking tour,  there is still a lot of Boston that you can see in this area. if you cross the bridge to Cambridge, you can head over to Harvard and see the beautiful campus!

Close-by Train Stations

  • Kenmore on the Green Line B, C, D
  • Blandford Street on Green Line B

Nearby Attractions

  • House of Blue
  • Harvard Bridge

Nearby Restaurants

  • Tasty Burger
  • Saloniki Greek
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There you have it! That is everything on our Boston walking tour! Boston is such a fun place to visit and there is so much to do here, but if you only have a couple of days, these are the spots I would recommend going to for sure!

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