If you only take one thing from this post, take this: If you're planning a winter weekend in Boston this year, do not forget to pack layers. Boston can be one freakin' cold city during the winter! 🥶
But if you're looking for more than the probably-obvious, I've got you, too. Because in this post, I am sharing with you exactly what to do during your winter weekend in Boston this year.
With loads of historical sites to see, shopping to do (RIP monthly budget 🪦), Christmas lights to admire, delicious food to eat, and more, Boston makes an absolutely incredible destination during the winter months –no matter how cold it can be.
This post is all about how to spend a winter weekend in Boston.
How To Spent a Winter Weekend in Boston, Massachusetts
Day 1 – North End, Downtown, and the Boston Common
The first day that you're in Boston, you'll want to knock out all of the "touristy" things to do, such as the Freedom Trail, downtown, and the more historic areas. Thankfully, Boston isn't that big of a city, so you can easily see and do all of these things in a single day – as long as you have an early start. In essence, you're taking time to explore the city today.
Morning – North End
I'd recommend starting your first morning off with some sightseeing. And when it comes to sightseeing in Boston, the best way to do so is to walk the Freedom Trail: a 2.5-mile path lined with historical landmarks that snakes through the northern part of the city.
The Trail technically runs south to north, but I actually recommend walking the Freedom Trail in reverse during the winter. This way, your day will end downtown – which is where you'll want to be anyway once the sun goes down.
In North End, here are some of the Freedom Trail landmarks you'll want to check out:
- Copps Hill Burial Ground
- Old North Church
- Paul Revere Statue House
- Paul Revere House
But if you aren't looking to brave the cold, there are a few indoor activities in North End, such as the New England Aquarium (buy tickets here – adults starting at $39). And thanks to Little Italy, the food scene in North End is great. So you could easily duck into cafes and eat your way across North End, if you'd prefer staying indoors.
Just make sure you visit Bova's Bakery (open 24/7!!!). The cannolis here were so good that I ended up ordering Bova's delivery every single day when I was in town. Cannot recommend this place enough.
Afternoon – Downtown
If you're choose to embrace the cold on your winter weekend in Boston, there's more Freedom Trail landmarks to see as you make your way downtown. Some of the cooler/must-see spots include...
- Faneuil Hall Marketplace
- Boston Massacre Site
- Granary Burying Ground
- Boston Common
- State House
But if you're looking for something warmer to do, you'll definitely want to pop into the Quincy Market, Boston's iconic shopping center and food hall. You can easily spend the afternoon bopping between shops and vendors. I recommend finding Boston Chowda Co. when you're there – their clam chowder was to die for.
Evening – Boston Common
Come nighttime, you'll need to make your way on over to the Boston Common to enjoy all the Christmas lights – even if you don't want to deal with the Boston cold. The park goes all out with Christmas decorations,...
And if you like ice skating, they even freeze over the pond and turn it into a skating rink ($10 admission fee and $15 rental skates).
Day 2 – Beacon Hill & Back Bay
On the second day - now that you've had a chance to check out the touristy things in Boston – we're going to head more south to visit the Back Bay area. It's time to spend some big $$$$ today.
Morning – Public Garden
On morning #2, you'll want to grab a cup of coffee/hot chocolate and make your way on over to the Boston Public Garden for a morning walk. The garden isn't very large, so it shouldn't take you more than 30 minutes or so to walk around it and see all the statues.
If the weather isn't unbearable, I'd also recommend taking a quick detour to walk around Beacon Hill, one of the most expensive neighborhoods in the United States. Beacon Hill is also where you'll find Acorn Street, which is one of the most Instagrammable spots in the city. Snap a few pics here, give it a witty caption – and I bet your post will get more likes than normal.
Afternoon – Back Bay
After your visit to the Public Garden, exit west and you'll find yourself entering the Back Bay neighborhood. And fun fact – the neighborhood is called "Back Bay" because it was literally part of the bay/underwater until the late 1800s.
Back Bay is known for its iconic brownstone buildings, but the main attraction here is Newbury Street. Nicknamed one of the most expensive streets in the world, you'll find tons of high-end, luxury boutiques lining either side of Newbury Street, including brands such as Chanel, Burberry, and Cartier, to name a few. (With armed guards stationed at the entries!)
But even if you aren't looking to spend Gucci-levels amount of money, you can still find something in your budget. (Here's to you, my fellow Zara- and Champion-budget peeps.) For this reason, Back Bay is the perfect place to get some last-minute Christmas shopping done. You can click here to access a map of Newbury Street – which not only includes a full list of places to shop, but also places to park and places to eat.
You could easily spend all day walking up and down Newbury Street as you pop in and out of shops. But if you've got time (and/or the energy), MIT is just a quick walk away. Cross over the Harvard Bridge at the western-most point of Back Bay, and you can be on MIT campus in minutes.
Evening – Christmas Lights Downtown
Once you've had your fun in Back Bay – and hopefully, your rent/mortgage money is still in tact – you'll want to make your way back to the downtown area. After sunset, you'll want to spend some more time admiring the Christmas lights.
If you enjoyed the light at the Boston Common last night, I'd suggest checking out Summer Street, the Faneuil Hall Marketplace, and/or the Quincy Market for night number two. The Christmas lights in each of these areas are phenomenal! (Plus, you can do more shopping... If your bank account isn't just absolutely hemorrhaging money at this point.)
Day 3 – Traveler's Pick (Here Are 5 Ideas)
How you want to spend the third day is really up to you, but I included some ideas below. If you're leaving early in the day, you may only be able to do one of these things. But if you're staying a little later, you may be able to do 2-3 things before heading out.
Explore South Boston
Aside from the piers and Convention Center, there isn't a ton to do in South Boston. But you'll find the Boston Tea Party Museum in this part of town (buy tickets here – adults starting at $35), as well as several bars and restaurants.
Visit Harvard University
Located 3-miles northeast of downtown Boston, you'll find Cambridge, Massachusetts, home of Harvard University. The walk isn't too bad (can speak from personal experience), but you can also hop on the T and get there pretty quickly.
Visit MIT's Campus
If you want to stay closer to downtown Boston but want to have that "elite university" experience, you'll find the Massachusetts Institute of Technology (MIT) just opposite the Charles River. From downtown, it's about a thirty-minute walk.
Check Out One of Boston's Many (50+) Museums
As one of America's oldest cities, there is no shortage of museums in Boston. For a complete list of museums, I'd recommend visiting Museums of Boston, a website dedicated to cataloguing all the museums in Boston and surrounding areas.
Revisit Your Favorite Spots
Surely, you pinpointed a favorite spot (or two) from your first two days in Boston. Before heading out of town, give some of your favorites a revisit.