If you’re looking to sit on the Green Monster at Fenway Park, enjoy some famous baked beans, or take a stroll on the harbor, the best time to travel to
will depend on your budget, interests, and weather preferences. Summer and fall are the most popular seasons to visit Boston, but you’ll get better deals during winter and spring months.
Beantown is an iconic American city to visit—but planning a trip there can feel like you’re navigating Fenway Park after a Red Sox win. Extreme travel costs and undesirable weather could put a damper on your vacation, so you’ll want to be careful in planning your trip.
knows planning your perfect trip can be hard—that’s why we’ve done the research for you. Jerry is here to help you find the best time to visit Boston for your wallet, weather preferences, and ideal crowd level.
To find the right time to visit Boston, you’ll need to ask yourself a few questions. If you want nicer weather with lots of things to do, you’ll need to go during the summer or fall time. But if you’re more focused on getting the best deals on travel, plan your trip for the winter or spring.
Peak season: June through October
The good: Nice weather, lots of events to attend
The bad: Most expensive time to visit, large tourist crowds, humid in the summer
The weather: 70s-80s in summer months, low 60s-70s in fall months
The height of tourism in Boston is in the summer and the fall. The summer months are the most popular months to visit Boston, due to athletics and outdoor events, but autumn is close behind.
Boston Harbor is a very popular spot for tourists. You can walk along the harbor, enjoy some time at the beach, or take a cruise at this historic spot.
The good: Fewer tourists, not as expensive as peak season, events to attend
The bad: Can still be cold and need to wear layers
The weather: 30s-60s
Boston’s “shoulder season,” or the period between low and high seasons, is in the spring. You’ll miss the major crowds and prices of the peak season if you visit during March, April, or May, but you’ll still get a taste of the true Boston experience.
Dine Out Boston happens again in March, so this is great news if you want to attend without the large tourist swarms. March also hosts Boston’s famous
happens in May. You’ll have lots to do in this shoulder season!
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The cheapest time to travel to Boston
If you’re wanting to visit Boston and save the most money possible, you’ll want to book your visit during the winter. The colder temperatures and wintry precipitation scare off most of the tourists during November, December, January, and February, so you’ll find cheaper hotels and better deals during these months.
However, a spring trip is another good option if winter isn’t your cup of tea. The months of March, April, and May still have plenty of fun events for you to attend. You’ll get to enjoy the beautiful springtime, avoid the major tourist crowds, and score some pretty good travel deals!
Ready to start planning your trip to Beantown? Check out this table to find the perfect time for your trip based on your interests and the activities you’re planning.
Activity
Best month to visit
Why?
Dine Out Boston
March or August
If you’re a foodie, you’ll want to attend this culinary event to sample the best Boston has to offer.
Boston Wine Festival
January-March
Relax, unwind, and enjoy some delicious wine selections during this festival.
Boston Harbor
Mainly summer events
Take a stroll, enjoy a cruise, or attend July’s [Boston Harborfest](https://www.bostonharborfest.com] and
Pro Tip Boston has great food and plenty of events to attend throughout the year, so plan your trip based on your budget and the weather if there aren’t any specific events you want to attend.
How to save on car and rental insurance
Whether you decide on driving to Beantown or renting a car when you land at the airport, it’s very important to make sure you have the right car insurance to cover you.
is here to help—as the #1 car insurance super app, Jerry is your new best friend for finding affordable policies in no time.
Just download the Jerry app, enter your information, and let Jerry compare quotes from 50+ trusted insurance companies to get you the best deals. It doesn’t stop there—Jerry provides end-to-end support to get you signed up and can even help you cancel your existing policy! The savings with Jerry are real: Jerry users save an average of $887 per year!
MORE:How to get a car rental discount code
“When I started shopping for insurance for my new car, the estimates I received were around $150.
Winter is considered to be the worst time to travel to Boston. The city gets significant winter weather consisting of slush, sleet, and snowbanks measuring a few feet tall!
What months make up the snowy season in Boston?
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Boston usually gets snow from December through February. It’s also been known to receive snow in November and sometimes all the way into May, so unfortunately you can never know what to expect.