Christmas in Boston: Things to Do for a Festive Winter Getaway


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Though the northeast is filled with so many great cities to visit during the winter, not a single one is quite as magical as Christmas in Boston. This historic city has its own charm that truly comes alive around Christmastime.

Picture this: cobblestone streets, an enormous Christmas tree, ice skating rinks set against the backdrop of a beautiful city, all lightly dressed with powdered snow. What more could you want out of a winter city experience?

Since Winter is just around the corner and you’re about to begin planning where you should visit during the holiday, we want you to seriously consider adding Boston to your list. Here’s everything you need to know about visiting Boston during the holiday season!

Tips for Visiting Boston in Winter

Visiting Boston during the holiday season can be lots of fun, but there are some tips you should consider when planning your trip.

Pack lots of layers

Boston is known for being extremely chilly during the winter. Though more recent winter seasons haven’t seen as much snow during the holidays, the temperatures drop quite a bit. The average temperature around the holiday season is approximately 30°F; however, if you’re going in and out of a lot of shops, you’ll want to bring layers.

Grab a CharlieCard

When traveling around Boston, you’ll most likely be utilizing the T, the city’s subway system. Though it can be tempting to purchase many one-way single tickets, hop over to the nearest convenience store instead and grab yourself a free CharlieCard from customer service. All you have to do is start with a small amount of money on the card. We suggest adding at least $20 to start.

Don’t forget your winter boots.

New Englanders love their winter boots. In fact, they can be a bit of a fashion statement and are essential to staying warm and comfortable when the ground can get quite slick. If you have a pair, be sure to pack them in your bag, because you’re going to need them.

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5 Best Holiday Events in Boston

SantaCon Crawl & Ugly Sweater Pub Crawl

One of the best things to do in Boston around the holidays that aren’t necessarily family-friendly is to go on a pub crawl. There are many different types of pub crawls during this time, but SantaCon and the Ugly Sweater crawls are the most popular. 

For SantaCon, everyone dresses up in their best Santa suits and hops from pub to pub. The Ugly Sweater crawl is precisely what it sounds like: dig out your ugliest holiday sweater and put it on while visiting many pubs throughout the day!

Faneuil Hall Tree Lighting

Though there are many different tree lightings throughout Boston for the holiday, none is as impressive as the Faneuil Hall Tree Lighting. This iconic celebration normally happens at the very beginning of December on a weeknight. Everyone gathers in the tiny cobblestone streets around Quincy Market to brave the cold and see the tree finally light up!

This event is made even better because there are tons of fun celebratory performances from local bands and comedians up on stage. Be warned though: this event is very crowded. Try to get there earlier if you want to be closer to the tree and the entertainment. Luckily, the tree is so large that you can see it no matter where you end up!

Plus, did we mention this is the largest Christmas tree in New England? You absolutely must see it once!

A Christmas tree in Boston

Boston First Night

Boston First Night is an event that happens on New Year’s Eve in the city. This is essentially made up of a wide variety of different celebrations that occur in various locations! Throughout the day, you can find the city hosting a wide variety of fun activities such as performances, crafts, ice sculpture making, and more. Finish the night off with free fireworks over the water!

SoWa Winter Festival

SoWa stands for “South of Washington” and is the artsy and trendy neighborhood located in Boston’s Back Bay. It’s extremely up and coming and is frequented by art lovers often. The district hosts its own winter festival that is an opportunity for local artists to showcase their creations. There are also great food vendors and entertainment options during this festival.

 

Beacon Hill Holiday Stroll

Beacon Hill is home to some of the most beautiful and quaint buildings in all of Boston. It’s often seen as one of the most picturesque parts of the city, and for good reason. Cobblestone streets in this area are lined by beautiful brownstones that Boston is most well-known for.

During the Beacon Hill Holiday Stroll, visitors are welcome to walk through the neighborhood. Children can stop by and visit Santa, while adults will enjoy the refreshments and festive snack options. There are also carriage rides available which only adds to the ambiance at this time in the city!

7 Top Things to Do in Boston in Winter

If bigger events are not your cup of tea, no need to worry! Boston is filled with quite a few fun things in winter around the holiday season. Below, learn more about the 8 top things to do for your Christmas trip!

Walk through Boston Blink!

Boston Blink! is a free light show that occurs in Faneuil Hall. This area is generally very much in the holiday spirit, and everywhere you look is covered in bright lights. During the show, all of the lights blink to the festive holiday music!

This fun light show is held throughout December and January and happens on average about 12 times once the sun goes down. If you happen to be in the area, it’s a great way to spend 30 minutes of your time.

Watch the Boston Bruins play at TD Garden

Boston is a major sports city, which doesn’t change just because the holidays are around the corner. If you want to escape the frigidness of Boston winter, then pop on over to TD Garden (or the Warrior Ice Arena, depending on what time of winter you visit) to see the local Boston Bruins play. Seeing an ice hockey game is one of the best ways to immerse yourself in Boston’s sports culture. You’ll feel like a true Bostonian yelling in the stands!

See the reenactment of the Boston Tea Party

Every year, a group of locals put on a reenactment of the Boston Tea Party on December 16. The event occurred on the very same day but in 1773. Around 100 people help to reenact the event which is often watched by locals and tourists alike. This is a great way to learn more about Boston’s historical connections to America’s origins. One thing to note is that this does occur no matter the weather!

Go ice skating at Frog Pond

Adult couple hanging out in the city during Christmas time over lights city background and snow at night

There is no better way to experience the true Boston holiday spirit without ice skating on Frong Pond. This skating rink pops up right in the middle of the Boston Common and is the most popular skating rink in the city. If you’d prefer to visit another skating rink that isn’t as busy, check out the new skating rink at 401 Park in the Fenway area!

What makes ice skating at Frog Pond so great is that you’ll be skating against the backdrop of the city downtown. Afterwards, be sure to stop by one of the local cafes to grab a hot cocoa to warm yourself up.

Attend a Boston Pops concert

The Boston Pops perform at Symphony Hall throughout December. They have a memorable holiday performance that absolutely can’t be missed if you’re a music fan. By the end, you’ll truly be in the holiday spirit!

If you plan on attending a Boston Pops concert, make sure you purchase your tickets at least two weeks in advance. They’re known for selling out quickly!

See the Nutcracker performance

Every year, the Boston Ballet puts on performances of the Nutcracker right around the holiday season. This truly is an experience, even if you aren’t a big ballet fan. This classic story dates back to the early 19th century, and the performance by the Boston Ballet has broken numerous box office records. Similar to the Boston Pops, you’ll want to purchase your tickets well in advance.

Sled in Boston Common

Boston common at winter sunset

Believe it or not, but people do actually sled in the Boston Common! There aren’t any hills here, but the second that the city sees some snow, you’ll see all of the locals (including the college kids) run straight to Boston Common. You don’t even need a super lovely sled – you could grab something as simple as a big trash bag to get pulled around on in the snow, and you’ll have just as much fun.

Be warned that oftentimes a huge snowball fight also occurs here. You might just get caught in the thick of it if you aren’t careful! However, it’s a super fun time to be in the common because you feel connected with so many people just having fun out in the snow. The feeling is very festive!

The best place to spend the holiday season is in Boston!

Now you know all the essentials for spending part of your holiday season in the most magical city in New England. Hopefully you’ll add Boston to your travel list this upcoming winter; you won’t regret it!


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