The worst thing you can do if you’re from Massachusetts is say you’re from Boston if you’re not.
If you’re friends with someone who is actually from Boston, they’ll draw up a map for you. It’s instinctual. It’s like scratching when you have an itch. You just do it.
You’re not from Boston if you’re from Springfield, OK?
But I digress.
In the travel world, where living like a local and doing as the locals do has long been regarded as the gold standard of travel – a sort of self-awarded Gold Star for all of your travel troubles.
Here’s the problem with that, though. You wouldn’t want to carry out your entire trip as a locals’ trip, because, well, you’d probably have an experience that straddled the lines between boring and bad.
Because when I was a local in Boston for the first eighteen years of my life, I can tell you that no one wanted to be waiting for the morning bus at 6:30 in the morning before the sun had cast its first rays on chapped skin and when the snow was 2 feet deep. I assure you that “living like a local” meant scarfing Burger King in between piano lessons near Symphony Hall on Saturdays. Or lying to your parents about why you were home late (I know now the “the train was just really late is the worst of flimsy excuses). I went to the Prudential Mall to buy things for my boyfriend and to CVS to fuel my eyeliner addiction (which began at age 12).
That’s living like a local. I didn’t notice any of the nice stuff around me, because it just wasn’t relevant. I knew that Boston was vaguely important and there were some really old buildings around, but all of that knowledge had been peppered into my hazy memory from primary school field trips. Pathetically, I’ve learned more about my hometown from Googling “Top Things to Do in Boston” than I did for the first 21 years of my life.
But Boston – where do I start with you? Iconic city of the Northeast, the biggest city in New England, academic center, college town, the home of the American Revolution and bastion of sports fanatics.
I’ve taken countless trips abroad, have made disgustingly disorganized itineraries, and have traveled enough to know what I like, and what I don’t like.
So here are my top things to do in Boston – as someone from Boston. Here’s what I would do if I were you, visiting Boston for the first time. I would gladly do any of the things on this list, happily, because they remind me of my home and I did them as a child. If you’re reading this and I went to 3rd, or 5th, or 11th grade with you, and you think this post is totally off, I’m sorry (kind of).
True to form, I haven’t included Fenway Park, because I’m not into sports. Sitting and watching male bodies flex their quads like sumo wrestlers, followed by the longest gameplay ever known to man is not my idea of a good time. You can get me to go if you buy me beer.
Let me rephrase. Here are my top things to do in Boston, when you don’t have unlimited time to spend. Here are my top things to do in Boston if you like to do a fair amount of sightseeing by walking, and you want to see the most iconic parts of the city.
1. The Boston Public Library at Copley
The most visited building of this list of my entire childhood takes on additional special meaning, because my father has been working here for nearly 20 years. I’d been visiting the library long before that, and when he began his job here, I was stoked. I thought I was the coolest kid in class.
Although the children’s room and the young adults’ room of yore has long disappeared and have now evolved into cooler renditions of their 90s and 2000s beings, the Boston Public Library is a beautiful representation of Boston and belongs on any Top Things to Do in Boston list.
Established in 1848, the Boston Public Library was the first large free municipal library in the United States. The library is made up of two parts – the McKim Building (the significantly older and more stately building), and the more modern Johnson Building. The Johnson Building has the full circulation part of the library – computers, desks, chairs, every fiction and non-fiction book you can think of, music archives. It looks a hell of a lot cooler than it did when I was five, which makes me sad, nostalgic, and happy at the same time.
If you take a wander across the somber cloisters and head towards the McKim building, you’ll come across the beautiful courtyard, a staple of my own summers in Boston, where I’d make a careful selection of 5 or 6 books, plant myself at one of the black iron chairs, and munch on sandwiches with my dad in the noontime breeze.
Then you’ll enter the McKim building, the glorious product of architectural wonder with influences from libraries in Paris, palazzos in Rome, and vaults in Valencia. Murals from the holy Grail legend can be found upstairs, as well as inscriptions similar to those in basilicas and monuments in ancient Rome. This area is also home to the stunningly somber yet warm Bates Hall, with its giant wooden research desks and luminescent green lamps.
Make a short stop here (no more than an hour is needed!) for a beautiful biblio-influenced tour of Boston’s offerings.
Perfect for: Lovers of architecture, book freaks, and Europe fanatics. Also good for people in a rush, because there are almost awesome historical exhibits on, so you can make a quick free stop here if you don’t have time to visit a museum.
Address and Hours:
700 Boylston Street, Boston, MA 0116
Monday – Thursday 9:00am – 9:00pm; Friday – Saturday 9:00am-5pm; Sunday 1:00pm-5:00pm
2. Shop on Newbury Street
A single parallel street away from the Boston Public Library at Copley is famous Newbury Street, the long shopping street (1.6 km) known for both independent and chain boutiques as well as outrageously expensive designer brands (think Chanel, Ted Baker, Diane von Furstenberg). But no matter the price point, they’re all housed in the adorable rust brick brownstone so common in Boston.
My personal association with this area is shameful and yet relateable – I spent $600 in a few hours here when I was 18 years old with two friends from Tufts. I don’t know what induced me to believe that this was a healthy financial decision for an 18 year old (please believe me that I did not have that kind of financial independence). But I still wear the same Marc Jacobs rainboots even now, so….what can I say? It be like that sometimes.
Take a quick walk along the length of the street. Stop and have a coffee. Come away with some new bags in your hands. Or not. Up to you.
My favorites (for the thin of wallet and limited in funds)?
Trident Booksellers & Café, an adorable indie bookstore with enormous breakfast portions and a just-right eclectic selection of books.
Johnny Cupcakes, a bewildering store that has nothing to do with actual cupcakes (I found this out during high school and was deflated by this fact), but sells high-end (read: expensive) T-shirts, houses secret entrances, and other awesome locally designed products.
Perfect for: Hipsters and label whores, people with money to throw away
3. Boston Common and the Boston Public Gardens
As a Bostonian, I refer to these adjacent parks as the Common. Together. It was only when I entered my late teen years that I realized the Public Gardens were separate things.
Built in 1634, it is the oldest city park in the United States and an iconic marker of city greenery. Once a cow pasture (and by once, I mean in the 1630s), it then morphed into a camp used by the British during the American Revolution, and then used for public hangings. It emerged as a true park sometime around 1830, and remains as such today. Since then, it has been the site of various protests (Vietnam War) as well as speeches (Martin Luther King, Jr. Pope John Paul II). Judy Garland gave her largest concert ever here.
It lacks the size and stateliness of Manhattan’s Central Park (you can walk the entire length of the Common and the Gardens within 30 minutes at a slow pace, probably), but like all comparisons with New York, the Boston version has its ineffable charms.
Regardless, I’ve spent more afternoons here than I can count. From November to March, I ice skated at Frog Pond with my little brother or with my friends, going around and around and around until our cheeks turned pink and our ears numb, clutching paper cups of hot chocolate in gloved hands.
In the warmer months, you can hop on one of the iconic swan boats – which only seem to be open 3% of the year.
(Can anyone from Boston verify that it feels like the things are never running? Are we allowed to call them iconic if they’re never in service? I have questions.)
I’ve just looked. They’re open from April 18th to September 7th.
But having a ride on one is a beautifully lovely experience to have when they are – drifting calmly around the still pond by an enthusiastic pedaller helming the boat behind a couple of swans. My little brother also fell into the pond one time, which was a delightfully hilarious moment for 10-year-old me. The water came up to only his knees, which verifies my longtime-held assumption that the pond is less than a foot deep.
Around May, it’s prom season and the Boston Common is a prime photo location for prom photos. I won’t show you mine because my eyebrow game was stab-me-horrific back then and I wore a silver dress. Silver!!! I’ll spare you.
Instead, here’s a much more up-to-date photo of me on the bridge at the Public Gardens.
Perfect for: A Midday Stroll, picnickers (depending on the weather), families with kids, photographers.
4. Photograph and Walk Around Beacon Hill
The Beacon Hill aesthetic is the Boston aesthetic. The architecture is a throwback to the Federal era, that style of uniquely colonial American construction that really reminds you that you’re here.
I photographed one of my most popular Instagram shots of all time here: Acorn Street, commonly regarded as one of the most photographed streets in the United States.
Wikipedia touts its Federal-style rowhouses and gaslit lamps as flanking one of the most desirable and expensive street in Boston. A few blocks away, you’ll also find the golden-domed Massachusetts State House – flickering and gleaming on a sunny day (although I advise you not to look too long if you want to keep your eyesight).
It look quietly old money. Like the great-great-great-grandchildren of the richest original colonists live here. I’m probably not too far off. Have you seen some of these chandeliers from even the outside? And those pianos? Like, damn. If you’ve never experienced real estate envy, you’ll feel it here.
Even though the area is mostly residential, on Charles Street, you’ll be able to walk past upmarket Italian restaurants, cute cafes, and local antique shops. It really is pretty as hell. It reminds me of period miniseries and smells like fall.
Perfect for: Short walks, photographers, rich home buyers
5. Have a Meal (Or Three) at the North End a.k.a. Little Italy
Whoever decided to put two rival pastry shops within 100 meters of each other and among literally hundreds of Italian restaurants was either a fucking genius or the worst type of sociopath, because I can’t imagine a better way to totally destroy your keto/low-carb/whatever diet-of-the-day goals.
My own memories of trawling the North End amount to a vivid Valentine’s Day, when my at-the-time college boyfriend and I visited La Famliglia Georgio’s, a restaurant touting itself as serving “Roman Classics” (I didn’t know any better) and with a proudly solid 4.0 rating on Yelp.
On this most romantic day, what arrived was a veritably bathtub of fettucine swimming in cream, studded with big chunks of broccoli and white chicken meat. You may think I am exaggerating, but I am not. Also, no shade, because there’s nothing like digging into a mountain of pasta. Nothing. Even though now I know that chicken and broccoli alfredo is decidedly an un-Roman dish (ask any Italian), remembering it as authentically Italian when I was 19 years old brings me more pleasure than it should.
And the food here is only the beginning. The North End, also known as Boston’s Little Italy, is the city’s oldest residential community, and a delightful homage to the Italian and Italian American community of the city. The entire neighbourhood is pending an approval to become a Boston Landmark, and with hundreds of restaurants literally within footsteps of each other, you can’t miss this iconic dining spot.
My favorites are Neptune Oyster, Giacomo’s, and although I’m a savory-over-sweet girl, I visit Mike’s Pastry and Modern Pastry every time. Something about the chaos of these two shops makes me feel right at home. Grab a coveted cannolo (or an entire box) and continue on your journey.
But food isn’t all that this area has to offer. Stop by the Old North Church, Paul Revere’s House (former home of American Patriot Paul Revere and the oldest house in downtown Boston), and Copp’s Hill Burying Ground for a dose of your Boston history.
Perfect for: Italian food lovers, pastry lovers, people who have a pulse
6. Follow the Freedom Trail
Look. You don’t need to walk the entire Freedom Trail (something that I personally admit I’ve never done). It’s 2.5 miles (4 km) long! But make sure that it’s on your radar and that you notice the red brick trail at your feet.
What exactly is it? It’s a pedestrian trail marked discreetly by red brick (it looks like this), showcasing landmarks that were key sites during the American Revolution during the nation’s founding. It always reminded me of Oz’s yellow brick road, and one of my favorite things to do is to do a little skip along it whenever I see it. It passes through 16 sites – the full list of which you’ll find here, and includes some of the sites I’ve written about in this top 10 things to do in Boston list (like Boston Common, the Paul Revere House, Copp’s Hill Burying Ground, and the USS Constitution). Checking out at least 2 or 3 of these sites, even in passing, will give you a taste of what Boston’s all about.
As a kid, doing this trail was something like a rite of passage – it fell in between losing recess as you got older and also taking home your first bad test grade.
But the reason it’s on this list of top 10 things to do in Boston is because this trail brings visitors around to the best of Boston’s Really Old Shit – and if you’re a history wonk like me, this kind of stuff will just delight the hell out of you.
Perfect for: The bodily able, people who love long walks, and people who have been charmed by the Federal-era architecture on Beacon Hill.
7. The Boston Tea Party Ships and Museum
In order to avoid this entire post becoming one big history lesson (we’ve all had enough of that), I’ll just give you a quick one-two liner.
In 1773, the American colonists completely destroyed a shipment of tea sent by the East India Company, which was commissioned to sell tea from China in the colonies without paying taxes. Why was this so important? It became a flagship event for what would eventually become the American Revolution, and the beginning of what we know now as the United States of America.
Where did this happen? In our dear old Boston.
The Boston Tea Party Museums are the perfect amount of historical kitsch (hello, colonist costumes and British Army jackets) and genuine storytelling clout. If you have children, even better. General admission is $30 (so for me, personally, a little steep), but live actors, exhibits, and the real U.S.S. Constitution ship (the world’s oldest commission naval vessel still afloat) make it a worthwhile experience if you’ve got extra cash in your wallet.
Perfect for: Costume nerds, families. People who consumed way too many naval wartime book or movie series (Horatio Hornblower, anyone?)
306 Congress Street, Boston, MA
Open Daily – 10:00am-4:00pm
Entrance Fee: $21-$30
8. See the Collections at the Museum of Fine Arts (MFA)
The Museum of Fine Arts is the best museum in Boston. Young children might not be able to appreciate the museum for what it is, but with its Roman columns and stately halls, the museum itself a spectacle to behold. It’s also the fifth largest museum in the United States, and in number of paintings, is second only to the Met in New York.
It houses beautiful original American artworks (many of which appear in textbooks today), depicting the likes of George Washington and Paul Revere. It also has a formidable collection of original Monets and Renoirs.
On another note, though, can anyone tell me why the world “Oriental” still exists in museum lingo and various other academic realms (I’m looking at you, UK)?
It costs $25 to get into, but if you flash a student ID, you can get in on some discount action. I’m not exactly proud of this fact, but I’ve been using my ID from my first year at Tufts (nearly 10 years ago now), and no one’s blinked an eye.
A visit here for the average museum goer (like yours truly) will likely take 2-3 hours. Art fanatics will take longer. Those with children will have their patience tested, as tends to be the case with museums. You have been warned.
Perfect for: Art lovers (duh), people with too much time to spend in Boston, individuals with 3 hours to kill
465 Huntington Ave, Boston, MA
Saturday – Tuesday: 10:00am- 5:00pm
Wednesday – Friday: 10:00am – 10:00pm
If you liked this post, please share it on social media!