Boston is one of my favorite cities for a short weekend trip, so much so I’ve been 3 times in the past year. Clusters of distinct neighborhoods are tied together by Boston’s ubiquitous red brick, each equally proud of their own unique charms and of being a part of what makes Boston great. This is a city with working class roots and Ivy League pedigree with restaurants that offer far more than lobster rolls and chowder (though those are certainly worth seeking out while you’re here). The city’s core is highly walkable and the T(Boston’s train system) will get you anywhere else you want to go making Boston the perfect city for a quick sojourn. Here are my recommendations to get a taste of Boston in just a few days.
Boston Common and the Public Garden
Boston Common and the Public Garden are a green retreat in the heart of Boston’s downtown. Founded in 1634, Boston Common is the oldest park in America. In Colonial times, it served as a pasture, military training field, and a meeting place for the people of Boston; and has also hosted everyone from George Washington to Reverend Dr. Martin Luther King and Pope John Paul II. As America’s first public botanical garden, Boston’s Public Garden is showier than the more laid back Common, with its bright blooms and iconic Swan Boats giving a touch of whimsy to Boston’s downtown. These parks are a great place to people watch; on any given day you’ll find young families enjoying the Frog Pond, well-heeled Bostonian’s from the tony Back Bay and Beacon Hill neighborhoods out for a stroll, Harvard students enjoying a run in between classes and visitors from around the world experiencing this peaceful oasis in downtown Boston.
The Freedom Trail
Truth be told, I’m kind of cheating with this one as Boston’s Freedom Trail is actually 16 of Boston’s most famous and historically significant sites. Starting at Boston Common the 2.5 mile red brick path winds through downtown, past Quincy Market, through the North End and over the Charlestown Bridge before ending at the USS Constitution. Get a glimpse of where modern lawmakers shape policy at the Massachusetts State House or explore where the seeds of revolution were planted at The Old State House. Stop by Faneuil Hall, where the phase “no taxation without representation” was born; or check out the Paul Revere House, where one of the Revolution’s most famous sons lived and worked. While most of the sites are free the Old South Meeting House, the Old State House, and the Paul Revere House do charge admission. There are a number of books and apps to help you explore the Freedom Trail on your own or you can go on one of the many guided tours available.
The North End
The North End, originally established in 1630, is Boston’s oldest residential community and today is best known as a vibrant Italian-American neighborhood (aka Boston’s Little Italy). This is one of my favorite neighborhoods to visit; not only for the numerous Italian restaurants and cafes,this is a tightly knit community that cherishes its traditions and where something is always going on. I’ll never forget leaving my favorite North End restaurant, Panza, at 7 o’clock on a Thursday evening last August to find a parade going down the street. Turns out I stumbled upon the Festival of Saint Agrippina, a Catholic celebration with several blocks of festivities, processions,music and food. While who makes the better cannoli, Mike’s Pastry vs. Modern Pastry Shop, is a hotly contested topic of debate; I prefer to get my Italian pastry fix a few doors down at the unassumingly charming Cafe dello Sport. This cafe/bakery meets sports bar always has the latest soccer game, pulls a mean espresso and makes locals and visitors feel like family.
Museum of Fine Arts
I’m picky when it comes to art museums, too many are limited in their offerings or their collections seem haphazard. Boston’s Museum of Fine Arts has one of the most comprehensive collections of art in the U.S. and is a museum I’d happily spend the better part of an afternoon. From ancient Egyptian artifacts to modern artists creating tomorrow’s masterpieces and everything in between there is something here for every artistic taste. The Museum of Fine Arts offers much more than a chance to view its collections; studio art classes for children and adults, thought provoking lectures and independent film showings will leave surely leave you inspired.
TIP: If you plan to visit on a Wednesday admission is free after 4 pm.
Samuel Adams Brewery
A short train ride on the Orange Line to the Stony Brook T stop will deliver you to the Samuel Adams Brewery, which opens it’s doors for tours Monday-Saturday. Tours are free and last about an hour and you’ll learn about the brewing process from hops to glass. Then you’re whisked off to the tasting room where you can sample the delicious fruits of their labor. Aside from the popular Boston Lager and seasonal ales you’ll have a chance to try limited edition brews only available at the brewery.
While this list is by no means extensive it will give you a taste of why Boston is a city I find myself returning to again and again(Discover these great packing tips for Boston to make your trip that much better). Also if you’ve got more time here are some great national parks near Boston. Do you have any Boston activities you’d add to the list?
I really liked exploring the North End – there were so many bakeries! Unfortunately I wasn’t able to make a return visit for dinner but I would have loved to – this looks like a place where people really know their salsa!
Boston is always so fun to visit. I love the markets and all the great seafood restaurants. Your post has some spots I have seen yet so I’ll need to get back soon.
Can’t wait to visit Boston when the weather is milder than it is when I’m there for the Seafood Show each March! I just loved the Library even when it was frigid out.
That was a great journey through some of Bostons highlights and I love the way you described Boston itself as a place with “working class roots and Ivy League pedigree”. The history of Boston is amazing and comes to life as you wander. I have been to Boston only once but the memory is a good one; especially the swans in the commons gave me a chuckle.
This list is a great start! I always encourage people to go to a game if they have the time (or if not, go to one of our great dive bars like the Cask’n’Flagon), and to try to check out some great live Irish music somewhere like the Black Rose or Mr. Dooley’s. There are also a lot of amazing nature spots like the Blue Hills or Castle Island where you can unwind while still in the city. Nice post, and I’m glad you enjoyed my town!
One of these days! I know it sounds weird, sometimes I feel as if Jo and I are not going to have time to see all that we want. There are so many new places, but we want to return to some of our favorites too! What a dilemma!
I really enjoyed the three days I spent in Boston. I cycled to Harvard which was pretty cool too. A cool Sam Adams goes down a treat, if I ever make it back I’ll be sure to try the brewery.
My sister just came back from running the Boston marathon and so I heard all about how awesome the city is! We want to go back together and while she’s busy racing I would love to do what you’ve pointed out here!! 😉
You really made me want to visit Boston! Thanks. As an European I sometimes have this impression that American cities are too big and unfriendly, but Boston looks so European and cozy. Probably I am wrong and most American cities are just wonderful.
I’ve never really considered going to Boston until now. I’ve heard some good things and this post reinforces how much there is to do/see and the great history Boston has at its roots. Beautiful photos as always. Thanks for the inspiration
Freedom Trail run is awesome! Goes to a ton of cool spots and ends with a boat ride across the harbor from the USS Constitution! Old Ironsides is a great take as well!! And how could any visit be complete without a tour of Fenway !?!?!?
I would love to visit Boston. The Museum of Fine Arts just sounds like a place I could spend a lot of time in. I wonder what time of year is the best time to visit.
We live just south of the city and these are all great ways to spend time in Boston! Of course, this time of year, you got to try and catch a Boston Red Sox game, or at least a tour of Fenway Park! It is a summertime tradition. Great suggestions.
I love finding out about places that aren’t perhaps always top of the tourist ‘to-do’ list! I’m sure I’d be a fan of Little Italy too…everywhere seems to have a Little Venice or similar and these areas always have bags of charm. Looks like it’s the same in Boston!
We visited Boston for a day from NYC a few years ago and fell in love it with. Really can’t wait to visit again as there is so much to do. We loved visiting Fenway park too as big baseball fans.
I HAD to read this one! I grew up in California with a grandma who was originally from Boston, and she was so proud! It’s a shame I haven’t been yet. I can see in this post why she loved it so much. Even though she wanted to escape the harsh winters, she could never forget this place. I can’t wait to visit! Thanks for sharing!
I must admit my knowledge of Boston is so half baked, but this entire itinerary sounds like so much fun! There’s really so much to keep you fascinated there, isn’t there?
I walked the Freedom Trail years ago in freezing January weather. I need to go back when I can do it without snow and when I can visit those beautiful gardens.
We have yet to visit Boston, but it has been on our list of must-travel-to places for years. It looks like such a beautiful city – I love the neighbourhood feel of it. We had some friends visit there a few years back, and they said they really enjoyed it. As we would only be able to make a short visit, we really like your weekend suggestions – a great way to get a taste of the area. Thanks for posting!
I loved Boston, especially the Freedom Trail. However, the highlight for my husband and I was taking time to read all the gravestones in the Granary Burying Grounds (next to the Park Street Church) where the victims of the Boston Massacre and other famous Boston-ites are buried. It gave us so much to think about.
I was recently in Massachusetts, but unfortunately due to the limitation of time, had to miss out on Boston this time around. Thanks for posting about it though, at least now I can see it through someone else’s eyes 🙂
Tanj from A Travelogue says
Boston has always been on my list but haven’t been there yet. Great guide! Thanks!
Brianna says
Boston is one of my favorite cities in the US, I’m sure you’ll love it too.
Vanessa says
I really liked exploring the North End – there were so many bakeries! Unfortunately I wasn’t able to make a return visit for dinner but I would have loved to – this looks like a place where people really know their salsa!
Brianna says
There may be a better Italian restaurant than Panza but I’ll never know, I love that place so much!
Carol Colborn says
Freedom Trail and Cheers, that’s what we did!
Brianna says
Where everybody knows your name 🙂
Andrea says
Aha love that the Freedom Trail covers such an expansive area with important sites around the city. Boston looks so classy and elegant!
Brianna says
Boston has something for everyone.
Sue Reddel says
Boston is always so fun to visit. I love the markets and all the great seafood restaurants. Your post has some spots I have seen yet so I’ll need to get back soon.
Brianna says
There is never a bad time to go back to Boston.
Elaine J. Masters says
Can’t wait to visit Boston when the weather is milder than it is when I’m there for the Seafood Show each March! I just loved the Library even when it was frigid out.
Brianna says
The library is just spectacular!
Karilyn Owen says
Boton has been on my list for ages. Great guide! I’ve bookmarked for when I actually make it there!
Brianna says
Hoping you make it there sooner rather than later!
Constance - Foreign Sanctuary says
I would love to check out the North End in Boston. I love the older buildings and I bet the Italian restaurants in the area are amazing!
Brianna says
I have yet to have a bad meal in the North End, it has the best Italian food outside of Italy.
Dave from Daves Travel Pages says
The Freedom Trail looks like a great way to take in some of the history.
Brianna says
I love that many of the Freedom Trail attractions are free as well.
Tim says
That was a great journey through some of Bostons highlights and I love the way you described Boston itself as a place with “working class roots and Ivy League pedigree”. The history of Boston is amazing and comes to life as you wander. I have been to Boston only once but the memory is a good one; especially the swans in the commons gave me a chuckle.
Brianna says
It’s always nice to see when such a serious city shows its fun side.
Delia says
This list is a great start! I always encourage people to go to a game if they have the time (or if not, go to one of our great dive bars like the Cask’n’Flagon), and to try to check out some great live Irish music somewhere like the Black Rose or Mr. Dooley’s. There are also a lot of amazing nature spots like the Blue Hills or Castle Island where you can unwind while still in the city. Nice post, and I’m glad you enjoyed my town!
Brianna says
As you mention my list just scratches the surface of all the great things you can do in Boston.
Peter Parkorr says
Sounds like a good itinerary! I’m wondering… brewery first maybe, do the rest drunk? Haha 😉
Brianna says
Well, that would certainly make it a different trip then wouldn’t it?
Arnie says
One of these days! I know it sounds weird, sometimes I feel as if Jo and I are not going to have time to see all that we want. There are so many new places, but we want to return to some of our favorites too! What a dilemma!
Brianna says
So many places, so little time!
Gemma Two Scots Abroad says
I really enjoyed the three days I spent in Boston. I cycled to Harvard which was pretty cool too. A cool Sam Adams goes down a treat, if I ever make it back I’ll be sure to try the brewery.
Brianna says
Harvard is such a beautiful campus with a lot of fun cafes and bars around Cambridge.
Alli says
My sister just came back from running the Boston marathon and so I heard all about how awesome the city is! We want to go back together and while she’s busy racing I would love to do what you’ve pointed out here!! 😉
Brianna says
That’s amazing that you’re sister did the Boston Marathon- tell her she is awesome!
Bente Vold Klausen says
You really made me want to visit Boston! Thanks. As an European I sometimes have this impression that American cities are too big and unfriendly, but Boston looks so European and cozy. Probably I am wrong and most American cities are just wonderful.
Brianna says
While there are big, sprawling metropolises there are a lot of charming cities in the US too.
Kate says
I’ve never really considered going to Boston until now. I’ve heard some good things and this post reinforces how much there is to do/see and the great history Boston has at its roots. Beautiful photos as always. Thanks for the inspiration
Brianna says
Thanks Kate, hoping you make it to Boston sooner rather than later!
Dan says
Freedom Trail run is awesome! Goes to a ton of cool spots and ends with a boat ride across the harbor from the USS Constitution! Old Ironsides is a great take as well!! And how could any visit be complete without a tour of Fenway !?!?!?
Brianna says
True on all accounts Dan! As a former sailor I definitely had to stop by Old Ironsides.
Terumi says
I would love to visit Boston. The Museum of Fine Arts just sounds like a place I could spend a lot of time in. I wonder what time of year is the best time to visit.
Brianna says
While there is plenty to do inside Boston is known for some brutal winters. Spring, summer and fall are all great times to go.
Don says
We live just south of the city and these are all great ways to spend time in Boston! Of course, this time of year, you got to try and catch a Boston Red Sox game, or at least a tour of Fenway Park! It is a summertime tradition. Great suggestions.
Brianna says
Truth be told I have yet to visit the Green Monster, looks like a perfect reason for me to head back to Boston!
Heather Cole says
I love finding out about places that aren’t perhaps always top of the tourist ‘to-do’ list! I’m sure I’d be a fan of Little Italy too…everywhere seems to have a Little Venice or similar and these areas always have bags of charm. Looks like it’s the same in Boston!
Nic from Roaming Renegades says
We visited Boston for a day from NYC a few years ago and fell in love it with. Really can’t wait to visit again as there is so much to do. We loved visiting Fenway park too as big baseball fans.
Brianna says
Boston is one heck of a town, I can’t wait to return either.
Charles McCool says
All great places to visit in Boston. I love Santarpios pizza near the airport but, truth, pizza anywhere in Boston is fantastic.
Brianna says
You can’t go wrong with any Italian in Boston
Francesca @onegrloneworld says
I HAD to read this one! I grew up in California with a grandma who was originally from Boston, and she was so proud! It’s a shame I haven’t been yet. I can see in this post why she loved it so much. Even though she wanted to escape the harsh winters, she could never forget this place. I can’t wait to visit! Thanks for sharing!
Brianna says
You’ll have a great time for sure!
Revati Victor says
I must admit my knowledge of Boston is so half baked, but this entire itinerary sounds like so much fun! There’s really so much to keep you fascinated there, isn’t there?
Brianna says
Boston is one of the iconic American cities, definitely on my recommended list for when you make it to the US.
Mags says
Great Recommendations. I’ve not been to Boston yet, but it’s been on my list for a while. I’ll have to make a quick trip of it.
Brianna says
There is so much to do, it is a great town.
Connie Reed says
I walked the Freedom Trail years ago in freezing January weather. I need to go back when I can do it without snow and when I can visit those beautiful gardens.
Jennifer @ Made all the Difference Travel Blog says
Great List of things to do in Boston. Hopefully, I will have time to do one or two when I go up for a interview.
Brianna says
Boston is a pretty compact town and great for a short break. Good luck on your interview!
The Adventure Ahead says
We have yet to visit Boston, but it has been on our list of must-travel-to places for years. It looks like such a beautiful city – I love the neighbourhood feel of it. We had some friends visit there a few years back, and they said they really enjoyed it. As we would only be able to make a short visit, we really like your weekend suggestions – a great way to get a taste of the area. Thanks for posting!
Sanjana @ Green Global Travel says
I’ll have to keep these in mind for when I visit Boston this summer! Thanks for sharing!
Tami says
I loved Boston, especially the Freedom Trail. However, the highlight for my husband and I was taking time to read all the gravestones in the Granary Burying Grounds (next to the Park Street Church) where the victims of the Boston Massacre and other famous Boston-ites are buried. It gave us so much to think about.
Amber says
I was recently in Massachusetts, but unfortunately due to the limitation of time, had to miss out on Boston this time around. Thanks for posting about it though, at least now I can see it through someone else’s eyes 🙂
Brianna says
Hopefully you can get back to Boston, it’s definitely one of my favorite cities in the US.