Visiting Boston in the Winter

Posted bybeyondthemilestravelblogPosted inBoston, MATags:, , ,

The winters in Boston can be harsh, the temperatures can be pretty cold and there could be quite a bit of snow. I will be the first to admit that I prefer to visit cities when the weather is warmer and definitely when there is no snow. But visiting Boston in the winter is definitely not out of the question, maybe you are flying into Boston before heading up to northern New England to go skiing or maybe you want to visit the city when it’s less crowded and cheaper to visit.

There is still plenty to do in Boston during the winter and who knows if you prefer warmer weather, you could luck out, there have been quite a few times where the temperature gets up into the 50s and 60s in the middle of the winter in Boston.

If you aren’t a fan of the cold there are many things to do while staying warm:

  1. Take a Hop On & Off Trolley Tour – Still want to see all the sites of the city without having to brave the weather and walk outside. Get a ticket for the Old Town Trolley Tours. During the winter, they use fully enclosed trolleys which includes 18 stops at many of the famous sites, such as:
    • Faneuil Hall – A great stop to grab a bite to eat in the food hall or do some shopping
    • Cheers Restaurant – Definitely a must see if you are a fan of the hit tv show from the 80s.
    • North End – If you love italian food and bake goods, this is a must stop for a meal, also check out the Paul Revere Statue.
    • Boston Tea Party Museum – A must see historic museum and boat.
    • Boston Common and Public Garden – Two great parks to see even in the winter.
    • Beacon Hill – A historic and beautiful old neighborhood in Boston.
    • Copley Square – Shop at nearby Newbury Street, Copley Place Mall and Prudential Mall and check out the location of the Boston Marathon finish line.

And if you don’t want to get off at the stops, the tour is fully narrated and takes less than 2 hours for the full loop.

Faneuil Hall
Cheers
Boston Public Garden
Boston Tea Party Museum

2. Check out a museum – There are so many museums in Boston to choose from and a cold winter day is a great time to spend a day in a museum. Here is a list of some museums to check out in the city:

Boston Children’s Museum

3. Attend a Sporting Event – Winter is a great time to attend a hockey or basketball game. Both the Boston Bruins and Boston Celtics play at the TD Garden so chances are one of the teams would be playing in Boston while you’re in town.

4. Attend a Broadway Show – Boston has it’s own theater district and winter is a great time to end your day by checking out a show. Blue Man Group plays in Boston year round at the Charles Playhouse and most of the year, there are Broadway shows on tour visiting Boston.

5. Go shopping – What girl doesn’t love to shop? Did you know that Massachusetts does not charge sales tax on clothing purchases, this could help you save a little money shopping in Boston than if you were to shop at home. In Copley Square, there are two malls connected to each other by a skywalk, Copley Place which has some higher end stores and Prudential Mall which has some of the stores you would see in your malls at home.

If you don’t mind being outside, Fanieul Hall, Newbury Street and Downtown Crossing are great areas to get some shopping done.

6. Tour a local Brewery – Boston has got some great breweries and what better way to warm up from the cold weather than to take a tour of one of the breweries and then end the tour by tasting some samples of the local beer.

Both Sam Adams Brewery and Harpoon Brewery are located right in Boston and I can guarantee you will love the not just the beer but the tours as well.

Harpoon Brewery

7. Food, food, food! – Who doesn’t love to try the local food when traveling? Winter is the great time to indulge more than normal since you have some time before you need to work it off for swimsuit season! Boston definitely has some great food that you must try.

  • Seafood – Boston is known for it’s seafood and it’s top on people’s list of what they want to eat when visiting.
  • Italian Food – The North End of Boston has some of the best Italian food you will ever eat, outside of Italy.
  • Food Halls – Fanieul Hall and Time Out Market are two great food halls to check out for a variety of different types of food.
  • Boston Creme Pie – the Omni Parker House in Boston is the birthplace of the Boston Creme Pie.
Barking Crab Seafood Restaurant
Pizzeria Regina – North End Pizza
Cannoli from Mike’s Pastry in the North End

Even with the unpredictable cold weather, there is always something great to see and do in Boston. I hope this gives you some ideas if you are wanting to visit Boston in the winter.

26 thoughts on “Visiting Boston in the Winter”

  7. I visited Boston for the first time during winter. We did a lot of the things you suggested! And I definitely ate cannolis at Mikes!

    But at the same time I wish someone told me that a cute puffy jacket is not actually suitable for real winters 😭😭 I think in the next post you need to teach newbies how to stay warm in Boston in the winter 🥶

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    1. Yup you need a nice long down coat to try and stay warm, although I’m always still cold. Dealing with a pandemic and being stuck inside has been the first time I’ve been able to stay warm in the winter lol Guess there are some advantages to this crazy pandemic.

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  13. I have a feeling if we were planning a visit to Boston my number one priority would be the shopping and my other half would be eyeing up the brewery tours! There looks like there is so much to do! Also, that cannoli looks amazing! Thanks for the great guide!

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  16. I have loved my trips to Boston (not in winter!) but the cold would for sure have me beat!! I’d have to eat all the amazing food to stay warm 🙂

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  18. I haven’t been to Boston and was terrified at the idea of winter there (I mean, I’m Canadian but even I’ve heard Boston is coldddd). I think it may be bearable now though

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  22. I lived in Upstate NY for 2.5 years and had always planned to get to Boston. Still hoping to get there one day – and I think I’d be happy to visit during the winter. Sounds like there’s plenty to do 🙂

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  23. Boston is truly a great city to visit. I’ve been there more in the warmer months but winter would be nice too. I love going to the Parker House for their Boston Creme Pie. It’s a nice break for all the walking to see things.

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