Whether you are a local looking to try something new or a visitor looking to get off the tourist trail, there are plenty of unique things to do in Boston to keep you occupied.
Boston is one of the most historic cities in the USA, with its fair share of freaky history and interesting traditions, and also has a geographic layout that makes it easy to spend time in nature while still being technically in the city.
So, whether you have been here once or 100 times, I’m betting you’ll find something on the list below that makes you want to get out and explore some of the more non-touristy things to do in Boston.
Before You Visit Boston
There are some important notes before you visit Boston. You may know them already since you are looking to do some ‘beyond the tourist trail’ things in Boston, but I’ll list them out just the same:
- Weather/Time of Year: It’s important to know what the weather will be like based on the time of year you visit Boston. This city gets COLD in the winters, and quite balmy in the summers. The outdoor activities on this list are doable on warmer days, and museums on cooler ones!
- History: Boston is one of, if not the most historic, place in the country! There are a couple spots below that are historic, but if you haven’t explored the history here, make sure to do so.
- Boston on a Layover: Many of these unique things to do in Boston are perfect for a short trip or a layover. Spend some time on an activity, and get some rest too – luckily there are plenty of hotels on dayuse.com that can rent you a room for periods of about 8 daytime hours for a much better price!
- Getting to Boston: Boston is quite an easy city to get to via land, air, or even sea! Thie airport is a big hub, and it’s connected to all of New England via roads and railroads too.
Charles River Esplanade: Walk, Sunbathe, Picnic
The Charles River Esplanade is definitely not the most popular or touristy waterfront in the city – and is more frequented by locals – which is why it made this list. It’s a truly lovely walk (or run) along the water with views and good vibes. But that’s not all you can do – there are plenty of shaded grassy areas perfect for picnics, docks for sunbathing, or benches to watch the world go by especially on a sunny day.
Feeling extra adventurous? Grab a kayak and get on the water! This is a unique way to spend a warm afternoon in Boston that gets you close to nature.
Brattle Book Shop
Shopping for used books isn’t on every list of unique things to do, but this bookshop is worth it – and I’ll tell you why. Brattle Bookshop is one of the oldest bookshops in the country, and one of the biggest too with three floors.
Find everything here from rare books to the sale section… books with a yellow sticker are only $5 and white stickers are $1, so grab a few to enjoy by the river!
Boston Harbor Islands National & State Park
Many people get caught up in the big city and don’t know that there are tons of beautiful, remote-feeling islands making up a national (and state) park just outside the city! Not many cities can boast that, and there are loads of unique things to do around the Boston Harbor Islands.
On various islands, you can go hiking, swimming, sailing, and picnicking, and many people love to do Lighthouse tours where you sail around learning about a few historic lighthouses on the islands (including America’s first). For a true Boston experience, head to Spectacle Island for a sunset lobster clambake. It’s a pretty special feeling to enjoy a classic New England meal while watching the sky change color over the city! Or, more nature enthusiasts, try camping at Peddocks Island – you’ll never forget it.
Trapology Boston Escape Room
Tired of touristy activities? Why not try an escape room? And not just any escape room… Trapology is definitely unique in its setup with multiple different rooms (that have hosted celebrities) and also team building activities right in downtown. It’s a perfect rainy day activity in Boston as well!
Be Amazed at the Architecture and Art at Boston Public Library
The Boston Public Library is basically Boston’s Cistine Chapel… if I were to HAVE to make a comparison. Nothing against Michelangelo, but you’ll see what I mean when you see it (or look at the photo above). This library is one of the most impressive places to see fine art and amazing architecture in the city, and it’s yet another ‘first…’ the first free urban library in the USA.
It has gone through a lot of changes in 150 years, and the history, murals, statues, and art reflect that. Check out the library points of interest here, head to Bates Hall to study or read, or sign up for a tour; they usually happen on Wednesdays.
Stargazing at Coit Observatory (Boston University)
This is one of those “if you know, you know” type activities that ends up being a really unique night out.
The Coit Observatory at Boston University offers free public viewing nights on Wednesdays, where you can look through telescopes and learn a bit about the night sky.
It’s obviously weather-dependent, but on a clear night, it’s a really cool and unexpected thing to do in the city. Definitely something a bit different from your typical Boston itinerary.
Isabella Stewart Gardner Museum
If you want something that feels a little different from your typical museum experience, the Isabella Stewart Gardner Museum is a must. It’s not just about what’s inside the museum… it’s the museum itself that’s the experience.
This place was designed to look like a Venetian palace, with a stunning courtyard in the center filled with plants, sculptures, and natural light pouring in from above. It honestly feels like you’ve stepped out of Boston and into Europe for a second… which is always a win.
The art collection itself is eclectic and a little bit random (in a good way), because it was all curated by Isabella Stewart Gardner herself. Nothing has been moved since her death, which makes it feel very intentional and personal… and also slightly eerie knowing it’s been preserved exactly as she left it.
Also, fun fact: this is the site of one of the biggest unsolved art heists in history. So if you like a little mystery with your culture, you’ll definitely appreciate this one.
Try Traditional Candlepin Bowling
You may think bowling is… just bowling. But not in Boston.
Candlepin bowling is actually a New England thing, and it’s quite different from the version you’re probably used to. The pins are tall and skinny (like candles… hence the name), and the balls are much smaller and don’t have finger holes. Sounds easy… it is not.
You get three rolls per frame instead of two, and even then, getting a strike feels like a minor miracle. It’s honestly way more fun than regular bowling because it’s a bit chaotic and unpredictable… and everyone is equally bad at it, which levels the playing field.
Flatbread Company and Sacco’s Bowl Haven are great spots to try it if you want something casual, social, and very Boston.
Coolidge Corner Theatre: Old Movies, Done Properly
If you’re into movies at all, this is such a fun switch-up from your standard cinema.
Coolidge Corner Theatre is an old-school, independent movie theater that shows a mix of classic films, indie releases, and themed screenings. It’s the kind of place where you might catch a Hitchcock film one night and a cult favorite the next.
The building itself has that vintage charm, and the whole experience just feels a bit more intentional than going to a big chain theater. It’s also a great rainy day activity in Boston if you want something low-key but still interesting.
Boston Spooky History: Cemeteries, Ghost Tours, and All That Good Stuff
Boston is old… like, older-than-the-country old. So naturally, there’s a decent amount of spooky history floating around.
One of the more unique things to do in Boston is actually to lean into that and visit some of the city’s historic cemeteries or go on a ghost tour.
Mount Auburn Cemetery and Forest Hills Cemetery are two of the most beautiful and peaceful spots, and they honestly feel more like parks than anything else. Wide paths, trees, ponds… it’s a very calm experience, despite the subject matter.
If you want something more central, there are also several old burying grounds right in the city that date back to the 1600s… which is kind of wild when you think about it. Walking through them feels like stepping straight into early American history.
And if you’re into ghost tours, Boston has plenty. Whether or not you believe in ghosts is beside the point… it’s a fun way to learn some of the darker stories of the city.
Continuing on the creepy vibe… the Boston Athenaeum Skin Book
Yes, this is exactly what it sounds like.
The Boston Athenaeum is a beautiful, historic library that’s worth visiting on its own, but it’s also home to one of the more unusual items you’ll find anywhere… a book bound in human skin.
It’s one of those things that you don’t need to see… but once you know it exists, you kind of want to. The Athenaeum itself is quiet, elegant, and full of history, which somehow makes this fact even more unsettling.
Boston Mapparium Globe
This is one of those random, super unique experiences that you probably wouldn’t find unless someone told you about it… so here I am telling you about it.
The Mapparium is a three-story stained glass globe that you can actually walk through. Yes… inside the globe.
You step into a glass bridge that cuts through the middle of it, and suddenly you’re surrounded by a 360-degree view of the world as it was mapped decades ago. The colors, the scale, the whole thing… it’s surprisingly immersive for something that sounds kind of niche.
Also, the acoustics inside are weirdly cool. Even a whisper can travel across the space, which makes it feel a bit like a science experiment and a travel experience at the same time.
Random Unique Smaller Points of Interest in Boston
There are a bunch of smaller, slightly random things around the city that are worth checking out if you’re nearby. Not necessarily something you’d plan your whole day around… but fun to stumble upon or add into your route.
- Edgar Allan Poe Square/Statue – A tribute to the writer with a slightly dramatic statue (very on-brand for Poe).
- Great Boston Molasses Flood Plaque – Yes, a real thing… a giant molasses tank exploded in 1919 and flooded the streets. Boston history is… something else.
- Skinny House (North End) – One of the narrowest houses in the city, built out of spite (long story, worth a quick Google).
- Acorn Street (Beacon Hill) – One of the most photographed streets in Boston, and once you see it, you’ll get why. Cobblestones, brick buildings, very aesthetic.
These are the kinds of things that make exploring Boston feel a bit like a treasure hunt.
Unique Foods to Try in Boston
Of all the unique things to do in Boston, eating your way through the city is… pretty important.
There are some classic dishes here that you kind of have to try at least once, plus a few local favorites that don’t show up everywhere else.
Boston Cream Pie
Despite the name, it’s actually a cake… but we’ll let that slide. Layers of sponge cake with cream filling and chocolate on top. It’s a Boston classic for a reason.
New England Clam Chowder
Thick, creamy, and honestly perfect on a cold day. You’ll find it everywhere, but some places definitely do it better than others.
North End Cannolis (and Italian Food)
The North End is Boston’s Little Italy, and you’ll have no shortage of options here. Mike’s Pastry and Modern Pastry are the big names for cannolis, but honestly… just follow the line.
North Shore Roast Beef Sandwich
This one is more local and a bit underrated. Thinly sliced roast beef piled high on a bun, often with cheese, sauce, and a bit of chaos trying to eat it.
Lobster Roll
Kind of obvious, but still worth mentioning. Go for one by the water if you can… it just hits better.
Other things worth trying
- Fried clams
- Oyster platters
- Fenway Frank (if you catch a game)
Basically… come hungry!
Ruins of Schoolmaster Hill
If you want a more unique way to experience Boston’s history without stepping into a museum, this is a cool one.
Located in Franklin Park, the ruins of Schoolmaster Hill are what remains of an old schoolhouse tied to early American history. It’s a bit off the radar, which makes it feel more like a discovery than a “stop.”
You can wander around the ruins, explore the surrounding park, and get a sense of history in a way that feels a bit more outdoorsy and less structured. It’s not a huge site, but it’s a nice change of pace from the usual historic landmarks.
Unique Dining Experiences in Boston
If you’re looking for something beyond just a good meal… Boston actually has a few fun, slightly different dining experiences worth checking out.
- Loretta’s Last Call – Dinner, drinks, and line dancing. It’s chaotic in the best way and a fun night out if you’re in the mood for something lively.
- Asta – A more conceptual tasting menu experience. Smaller, more curated, and very focused on the food itself.
- The Dinner Detective – A murder mystery dinner show where you’re part of the experience. Equal parts dinner and entertainment.
- Eataly Boston – Not exactly niche, but still a cool food hall experience where you can try a bunch of different Italian dishes in one place.
- Mariel – Cuban-inspired food with a really unique, almost theatrical interior design. Definitely more of a “vibe” dinner spot.
And that’s it for my list of unique, interesting, and different things to do in Boston! Let me know which one you try first!
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Passionate, full-time travel blogger with over 230k on social media and 150kMPV blog. Extraordinary photographer with two DSLR's + a drone with a love for capturing candid moments, epic drone shots, and magical compositions. I'm a natural-born content creator originally from California, but I've been on the road for 9 years living, working, traveling, blogging, and photographing my way around the world. I recommend the most amazingly adventurous and unique + boutique travel experiences/stays and helpful products to my audience and write comprehensive guides on my website that have helped millions of travelers so far. I love to inspire people to plan their dream trips, and many readers have given feedback as such. The reach on my platforms continues to soar, especially when combining cutting-edge social content with optimized articles on my high-authority website.