A Historical Guide through Boston

New Year, new travel plans! One of my goals (for every year it seems) is to get out and travel. We were able to go to a handful of new places last year, one of the highlights being Boston. I love History. It was always one of my favorite classes in school (along with literature class), so seeing it in real life was incredible. I mean, Independent America was basically born in Boston – the Boston Tea Party, patriots like Paul Revere and Samuel Adams, The American Revolutionary War…etc. Walking the same streets where some of America’s most important history took place was life changing for me. So, I thought I’d put together a Historical Guide through Boston for you guys.

The day we visited Boston, it was drizzly and cold – which actually turned out to be a blessing because the streets were pretty much empty. We were able to visit Jon’s family in Maine for Thanksgiving, and we figured, since we were on the East Coast anyways, we might as well take a side trip. Granted, we did have to leave the house at 5 am and drive for three hours, but it was completely worth it.

I love traveling in the shoulder seasons when everything is quieter, cheaper, and there’s a lot less hustle and bustle going on. Google Maps is my go-to necessity for every trip we go on. I have a horrible sense of direction (I get turned around in Target, OK), so whether I’m walking or driving, it’s nice to know that I can count on something to keep me on track.

That being said, I made a map of all the places we visited on our walking tour for you guys! Your own personal Historical Guide through Boston. This route is about 8 miles round trip, walking. For an all day adventure, that’s not too bad. I was already planning on eating every cannoli and pizza that came my way, so I wanted to be able to walk some of that off. I would suggest, definitely bring some comfy walking shoes or check out the bus system in the city (which I’ve heard is very affordable and user friendly). There’s a parking garage that we used right next door to Flour Bakery, which is where we started our adventure.

The map is split into 4 sections (Historical Sites + Buildings, Places to Eat, Shopping, and Instagrammable Locations), and I would highly recommend visiting all of these places on your visit!

So, without further ado, please read on it you’d like a quick recap of each stop on my Historical Guide through Boston.

A Historical Guide through Boston: Historical Sites + Buildings

The Paul Revere House:This is a great stop for some insider information about one of America’s most well known Patriots. The house museum is open daily year round and the admission is only $5.

Paul Revere Statue: A stunning work of art that lies in the shadows of the Old North Church. It took over 16 years to make and was unveiled in 1940.

Old North Church: The infamous church where Robert Newman lit two lanterns and hung them high in the church tower on the night of Paul Revere’s midnight ride.

Copp’s Hill Burying Ground: Here you will find the final resting place of Robert Newman, Phyllis Wheatley, and Prince Hall.

Old South Meeting House: Built in 1729, this place was the birthplace of the Boston Tea Party.

Granary Burying Ground: Take a walk among the tombstones, and you will find some of America’s greatest patriots, including Samuel Adams, Paul Revere, and John Hancock. They also have people dressed in period costumes that give you a tour of the graveyard.

Boston Public Library: Built in 1895, it is the third largest library in the world. Head to the second floor and visit the stunning Bates Hall. Afterwards, go back down to the main floor and treat yourself to afternoon tea in the Courtyard Restaurant.

The Bates Hall at The Boston Public Library.

A Historical Guide through Boston: Places to Eat

Flour Bakery: This was probably my favorite eating stop we made on the whole trip. If I was a local, I’d definitely be here for breakfast and lunch every day. It’s seriously that good. Flour Bakery has a warm and inviting atmosphere. They also have decadent pastries and all sorts of warm drinks – perfect for those drizzly Boston days. I also had the best sandwich of my life here – “smoked turkey with apple and dill slaw and cranberry chutney”. YUM! After our day was over, I slipped in here again and picked up four muffins. They were the discounted day old ones (which still tasted like they just popped out of the oven). The best $2 I have ever spent.

I’ll take one of everything, please.
The smoked turkey with an apple and dill slaw to die for.

Mike’s Pastry + Modern Pastry: There’s a debate between these two bakeries as to which one has the “best cannolis outside of Italy”. You’ll have to visit both and make up your mind as to which one truly is the best. Also, make sure you have some cash as they do not accept cards.

A traditional ricotta filled cannoli at Modern Pastry.

MAST’: Walking into MAST’, we didn’t think we were going to be able to afford much of a meal here. Think low lights, gilded mirrors, leather couches in the lounge, and a huge pizza oven in the loft type bar area. However, a whole pizza was only about $9. Score! We basically ate our weight in pizza, and I have zero regrets.

Margherita Pizza at MAST’

A Historical Guide through Boston: Shopping 

Boston Public Market: A spacious indoor market with fresh foods and local fare. I hear the Boston Cream pies here are delicious as well.

Brattle Book Shop: The day we visited Boston it was raining off and on all day. Because of this, the outdoor section of this book shop was closed. However, the inside was pretty magical in and of itself. Their third story is a collection of rare books (some even dating back to pre-1800s. So, of course I had to pick up a 1902 copy of a pocket Shakespeare book.

One of America’s oldest and largest antiquarian book shops.

A Historical Guide through Boston: Instagrammable Locations

Boston Public Garden: The Gardens are a great place for a stroll after lunch. They have the fattest squirrels I have ever seen, as well as a scenic lake with willow trees reaching down to the water and benches scattered around for you to sit on and enjoy the view.

Beacon Hill: This whole area is just darling. You can window shop at the stores and take a side street to walk past the prettiest little townhouses. There are some really expensive houses in this neighborhood.

Acorn Street: Otherwise known as “the most Instagrammed place in Boston”, Acorn Street is quintessential Old America with its brick buildings and cobblestone street. We were informed by a passerby that it’s normally very crowded here, but it was rainy that day so we had the place to ourselves. Yay for rainy day exploring!

Acorn Street: the prettiest little street in Boston.

And there you have it! Your own complete Historical Guide through Boston. Let me know if you guys have any suggestions or favorite places in Boston that I need to visit next time!

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