5 things to do on a weekend trip to Boston

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.

 5 things to do on a weekend trip to Boston

Boston Common and the Public GardenBoston Common and the Public Garden- one of 5 things to do on a weekend trip to Boston www.casualtravelist.com

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 TrailThe Freedom Trail- one of 5 things to do on a weekend trip to Boston www.casualtravelist.com

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 EndThe North End- one of 5 things to do on a weekend trip to Boston www.casualtravelist.com

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 ArtsMuseum of Fine Arts - one of 5 things to do on a weekend trip to Boston www.casualtravelist.com

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 BrewerySamuel Adams Brewery Tour- one of 5 things to do on a weekend trip to Boston www.casualtravelist.com

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. Do you have any Boston activities you’d add to the list?

63 Comments on “5 things to do on a weekend trip to Boston

    • Boston is one of my favorite cities in the US, I’m sure you’ll love it too.

  1. 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!

    • There may be a better Italian restaurant than Panza but I’ll never know, I love that place so much!

    • I have yet to have a bad meal in the North End, it has the best Italian food outside of Italy.

    • I love that many of the Freedom Trail attractions are free as well.

  2. 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.
    Tim recently posted…Kalahari’s New DayMy Profile

    • It’s always nice to see when such a serious city shows its fun side.

  3. 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!

    • As you mention my list just scratches the surface of all the great things you can do in Boston.

    • Well, that would certainly make it a different trip then wouldn’t it?

  4. 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!
    Arnie recently posted…What City Should You Actually Live In?My Profile

    • Harvard is such a beautiful campus with a lot of fun cafes and bars around Cambridge.

    • That’s amazing that you’re sister did the Boston Marathon- tell her she is awesome!

    • While there are big, sprawling metropolises there are a lot of charming cities in the US too.

  5. 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
    Kate recently posted…A Hindu Blessing in Pushkar, IndiaMy Profile

    • Thanks Kate, hoping you make it to Boston sooner rather than later!

  6. 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 !?!?!?

    • True on all accounts Dan! As a former sailor I definitely had to stop by Old Ironsides.

    • While there is plenty to do inside Boston is known for some brutal winters. Spring, summer and fall are all great times to go.

    • Truth be told I have yet to visit the Green Monster, looks like a perfect reason for me to head back to Boston!

  7. 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!
    Heather Cole recently posted…When it’s ok not to haggleMy Profile

    • Boston is one heck of a town, I can’t wait to return either.

  8. 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!
    Francesca @onegrloneworld recently posted…5 Alternative Stops on the California Highway 1My Profile

    • Boston is one of the iconic American cities, definitely on my recommended list for when you make it to the US.

    • Boston is a pretty compact town and great for a short break. Good luck on your interview!

  9. 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!
    The Adventure Ahead recently posted…Finding the Volio WaterfallMy Profile

  10. 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.
    Tami recently posted…Looking Up in Zion National ParkMy Profile

  11. 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 🙂
    Amber recently posted…Five Pros of Solo TravelMy Profile

    • Hopefully you can get back to Boston, it’s definitely one of my favorite cities in the US.

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