My husband Todd and I just got back from an epic Fall Foilage Roadtrip. Our trip was 10 days and we visited 8 different cities. Our first stop was Salem, MA which you can read all about HERE. The next stop on the trip was Boston, MA.
Why Visit?
Boston, Massachusetts may just be my favorite city I have ever been to! For such a large city, it feels rather small and homey. It’s definitely a “walking city” and the city’s architect and old buildings are absolutely stunning! Not to mention that Boston also has a rich history of early America (hello Boston Tea Party!).
Out of all of our stops I think Boston had the longest list of things I wanted to do (sadly we ran out of time to do it all, but now we just need to go back!)
Where to Stay?
Because of Boston’s pricey hotel/airbnb costs, we decided to stay out of the city and drive in. We decided to stay in an Airbnb in Salem.
If you have never used Airbnb, you really should give it a try! Often times I find it is cheaper to stay in a house than it is a one bedroom hotel room! Also, you often get to stay in the quaintest and coolest houses out there. If you would like to give Airbnb a try click on this link to get $40 dollars off your first booking!
While we stayed in Salem to go into Boston (and had a good experience), we also loved our Airbnb from Marblehead (about a 45 minute drive into Boston). The Airbnb we stayed at would be a great place to stay out of the city.
Where to Eat:
Tatte Bakery & Cafe: Tatte is a great place for breakfast, dessert, or a warm coffee. There are many locations so it should be easy to find one! Warning though, it was fairly crowded at breakfast time, but very delicious!
Quincy Market: This is a great stop to eat at because just about anyone can find something they would like in Quincy Market! There are many different vendors all from seafood to BBQ. We decided to try out mmMac n’ Cheese because you can customize and add whatever you want into their delicious Mac! We were definitely not disappointed.
Ernesto’s: If you want an affordable and delicious option, make your way to the North End of Boston, also known as Boston’s very own “Little Italy.” There we found the award winning, Ernesto’s pizzeria. One slice off the menu is actually two, and you can see from the pics that they are pretty big! Ernesto’s is also not a far walk from the second half of the Freedom Trail, so makes a great stop along the way!
Thinking Cup: If you need a quick break and a cup of joe on the Freedom Trail, Thinking cup is a great place to take a rest!
What to Do:
Freedom Trail: I feel like I have to start off with the most obvious/touristy thing to in all of Boston. The Freedom Trail. The Freedom Trail is a walk through the city that takes you through many of the historical sites that surrounded The American Revolution. You can pay for a guided tour, or you can do a self-guided tour by picking up a free map from the visitor’s center and following the red bricks throughout the city.
Hair Tie: Anthropologie (similar)
Jacket: H&M (similar)
Jeans: Old Navy (similar)
Shoes: Vince Camuto
Being a bit of history nerds, we very much enjoyed this. We really enjoyed Park Street Church and Granary Burial Ground. We ran out of time, but really wanted to take a tour of Paul Revere’s home (must pay to enter) as well as Old North Church. If you have extra time in Boston I would definitely recommend touring these sites.
We did a self-guided tour and used this site to read a little bit of information about each stop, which I found helpful. There are also some apps you can download (for a small fee) for more information as you walk the trail.
Acorn Street: Acorn Street is the most photographed street in America! Tucked away in a very prestigious area in Boston is this beautiful little street that still has its original cobbs. Take a quick stroll over to it (very pretty area and not far from Boston Commons). Make sure to snap a few pics in the area. Be warned though, no profession photography is allowed without a permit!
Eat a Canoli at Mike’s Pastry: Ya’ll this was a life changing experience….I thought I didn’t like canolis. Todd also thought he didn’t like canolis. We now not only like, but LOVE canolis (well if they are from Mike’s Pastry!) While you are in the North End, make sure you stop by this famous Pastry shop! It’s a quick pace environment so I recommend taking it to go! Also, I’m pretty sure they are all delicious, but we got the one with the chocolate chips on the end and it was perfect! This was the best dessert I had the whole trip!
Explore Boston Commons: Boston Commons is like the Central Park of Boston. Beautiful park with a ton of room to run around. There is also a carousel in the park. We parked in the Boston Commons parking garage, which I highly recommend if you are planning on driving into the city (warning it’s expensive parking be prepared to pay around $25 for just one day of parking).
Eat Boston Cream Pie at The Omni Parker House Hotel: You can’t go to Boston without eating Boston Cream Pie! And what better place than the place it originated from!? The Omni is a fancy hotel in the heart of Boston. If you go in it can be slightly confusing on where you can eat the Boston Cream Pie (it’s not the main dining room). So simply ask someone and they will direct you the right way!
Explore Boston’s Beauty: Seriously Boston is such a photographic town. Just walking around and finding beautiful areas to view/take pictures at was seriously so fun!
Leggings: Aerie
There was so much we didn’t get to do in Boston! Here are some other things that were on our list that we didn’t get to do!
Others Suggestion:
Fenway Park Tour
Pinocchio Pizza
Christopher Columbus Park
Gelato Amorino
Explore Harvard/Go on tour
Boston Cheers
Hammond Castle
Isabella Stewart Gardner Museum
Boston Duck Tour
Cranberry Farm Tour (Acushnet, MA)
Cafe Art Science
Tougas Family Farm
Boston Public Library
Boston Public Market
Check out the rest of our trip here!
Thanks for stopping by!
-Kasey
As you can tell we barely scratched the surface of what there is to do in Boston, MA! If you want further information on Boston, make sure to check out the resources I used to plan our trip on my Pinterest Fall Foilage Trip board!
Also, I have created a Google Map of our stops to help you plan!
Lastly, I created a Fall Playlist for our trip that was awesome to listen to during all the driving! You can check it out here.
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