The Best Time of Year to Visit Boston – An Insider’s Guide!

I’ve spent a lot of years in Boston, and I have the fact that it’s a college town to thank for that. Thanks to the diverse schools here, I was able to find a small liberal arts school that fit me just right. All in all, I spent about eight years either living in Boston or spending a great deal of time there.

I’ve seen Boston in every season, and I get asked a lot about what my favorite season is to be in Boston. And, as you’ll likely be able to tell by this article, I have a lot of mixed feelings about every season, to the point that it was quite tricky to say what the absolute best season and month to visit Boston is. 

But hopefully, my conclusion can help you out when planning your Boston trip. Let’s dive into the best time to visit Boston!

What’s the Best Time of Year to Visit Boston?

Before we start talking about why the best time to visit Boston is late spring and early summer, I want to add a quick preface: Every time of year is a good time to visit Boston! 

Well, that’s a slight lie. When I lived in Boston, my least favorite months of the year were January and February due to the high probability of snowstorms and the way the city has to shut down due to inclement weather. 

And after the holiday season in December, snow just seems a little less magical. When the snow turns to gray slush on the roads, you’re not exactly as excited to see it as you are when it’s falling down from the skies illuminated by twinkling Christmas lights.

But aside from those two months, every time is a good time to visit Boston. The holiday season brings about festivities galore, with tons of cheer, hot cocoa around every corner, the changing of the Boston Common Frog Pond over to an ice skating ring, and Christmas tree lightings scattered throughout the city.

Meanwhile, spring is a time of reawakening, when the city emerges from its sleepy late winter slumber. The Duck Boats reline the streets, and the Swan Boats come out of hiding at the Boston Public Garden. College students are testing the weather, donning shorts and sundresses, likely a little prematurely, as winter can sometimes have a not-so-welcome return in March or even April.

Summer is a strangely quiet time for the city, with the main reason being that Boston is such a college town, and many students go home for the summer. While tourists are coming in, they never quite fully replace all the students who have fled. But at the same time, Boston’s outdoor activities are in full swing, with food festivals, art markets, and much more taking place each day as the warm weather greets you each morning. 

Meanwhile, fall is quite the opposite. Once you hit mid-to-late August and early September, school is back in session, with college students making their return to the city. A word of warning: If you plan a trip for early fall, keep an eye out for move-in days for the city’s biggest colleges, as you can guarantee the whole city will be congested with college kids and their families.

With all these notes in mind, the best time to visit Boston is late spring and early summer, when you’re waking up to hot days and outdoor activities are either reopened or, if they stayed open all year, no longer require heavy winter coats or dealing with the threat of snow. 

That said, July and August can be hot and muggy, so you may not want to be outside anyway. That’s why the best months to visit Boston are May and June, but keep in mind that rain does happen this time of year, so be sure to pack an umbrella and plan some rainy-day activities. It’s also worth noting that this time of year is college graduation season, so be mindful of the influx of families around graduation dates.

The Benefits of Going to Boston During the Off-Season

Remember how I said that college students are generally away for the summer? That typically starts around early May. However, summer does bring about more tourists, which means higher prices for accommodations. And as noted, college graduation season can cause similar levels of congestion as fall’s move-in days.

You won’t find much relief come early fall when it comes to prices or crowds. Summer might be considered peak season, but it’s not at the highest peak just yet. That price hike comes in the fall, as Boston is a prime destination for some “leaf-peeping.”

September and October are often very expensive, with October being considered the most expensive month to visit Boston in recent years. It’s a good time to visit Boston if you want to see some beautiful fall foliage and enjoy the crisp autumn air, but the high price tag may make you want to stay away.

The shoulder season typically runs from late November through March. If you’re looking for lower price levels, this time of year can be a prime time to visit, but I really would recommend staying away in January and February. You’ll likely find that many of the attractions you wanted to see are shut down due to the weather. 

And take it from someone who was stuck indoors for two whole weeks the first year she lived in Boston: Late Boston winters can be brutal. The last thing you want is to get to Boston and have your whole itinerary thrown out the window because of bad weather.

If you want to go during the shoulder season, stick to late November and December. Boston is underrated as a holiday destination, which means that you generally get to enjoy all the holiday celebrations with lower crowd levels and are more surrounded by locals than tourists. Despite the holiday fun, hotels and other accommodations typically won’t be as expensive as you’ll find in early fall or summer. 

There you have it! The best time to visit Boston. What do you think is the best time of year to visit? Let us know in the comments!