Things to do in Boston on a rainy day

When it’s beautiful in Boston, there’s a plethora of things to do, places to walk, neighborhoods to explore. However, finding things to do in Boston on a rainy day can be a little trickier! If it’s not raining, it could potentially be snowing, sleeting, hailing, or you might have awful allergies that are keeping you indoors! But worry not, for fun still lurks beyond Boston’s unpredictable weather!

Luckily, it’s easy to find some not-so-well-kept secrets when it comes to fantastic Boston indoor activities! Read on below to see some of our personal favorites.

1. Play an escape room at Trapology Boston

177 Tremont St. 2nd floor Boston, MA 02111

Directions to Trapology Boston

Indoors? Check!
Easy to get to from an uber or a Lyft? Definitely. 177 Tremont St Boston, MA
Accessible from public T? 210 feet from the Boylston Green Line T, a 1 minute walk. Potentially cut that time and distance in a third if you don’t want to use the crosswalk. (However, safety first!)

Trapology Boston, Boston’s best escape the room, hosts six escape games of varying difficulty. Perfect for groups from 2-10, it’s a great way to spend an hour and a half of your day while you wait for the crazy rain to pass. Check here to look at available times!

“Trapology Boston was the perfect activity to bring my teenage children to. It’s hard to get them away from their phones and devices for a whole hour, and this was the perfect thing to do in Boston on a rainy day!”
– Shery

Always wanted to save yourselves from a sinking submarine haunted by a real angsty ghost? We have you covered.

Or maybe ever since Shawshank you’ve had a strange dream to stage an elaborate prison break. You know, minus the whole ‘going to prison for life’ thing. That dream isn’t strange to us, in fact we’ve dedicated a whole room to the pursuit of that dream.

Really, we’re just here to fulfill fantasies and make smiles happen.

Sure, we’re a little biased, but we’d love the opportunity to have you come in and play a game so we can show you why we’re so confident that a visit to us will be the highlight of your day in the city!

Rain or shine, we’re here and would be happy to challenge you, your family, and friends!

Check here to help you decide which one of our six games you want to play!

Click here to look at our game schedule and book your tickets!

Directions to Trapology Boston

2. Visit 95 year old Myrtle the turtle at the New England Aquarium

70 E India Row, Boston, MA 02110

The New England Aquarium just celebrated its 50th birthday in 2019! Over 20,000 animals live here. Most people spend about two hours wandering and looking at all of the exhibits. If you wanted to spend more time, you can get a stamp to return on the same day. There’s also an opportunity to catch an IMAX film in their gigantic theater!

All of this underwater excitement culminates in a massive four-story cylindrical Giant Ocean Tank that is simply awe-inspiring. In 1970, when it opened, it was the largest circular tank in the world.

If you hang at the top of the tank, you might be able to catch a feeding of Myrtle the Turtle. Fun fact, she’s between 90-95 years old!

Tips for visiting the New England Aquarium

Pro tip #1: If you plan early enough, you can get free New England Aquarium passes at the local library if you have a library card. Reserve it online, or give them a call!

Pro tip #2: Wear comfortable shoes and sleeves that can be rolled up so that you can interact in the Shark and Ray Touch Tank!

Pro tip #3: Boston is known for its seafood. Legal Seafood’s New England clam chowder is awesome and has been served at every presidential inauguration since Regan’s first in 1981. Another great seafood spot is James Hook & Co for their lobster rolls and The Daily Catch for their black pasta.

3. Have a good belly laugh at Improv Asylum

216 Hanover St, Boston, MA 02113

Image result for improv asylum

Maybe you’re all puzzled out, just came off a 6-month deep sea diving trip, and just want to sit back and cap off your Boston indoor activities extravaganza with some gut-busting laughs. Then look no further than Boston’s very own Improv Asylum! Boasting hysterical live improv shows 6 nights a week and nestled right in the heart of the North End, it’s a perfect spot to enjoy some good comedy.

After the show, maybe ask about one of their many improv classes that you can sign up for. Then you can prove once and for all to your friends that you are in fact funny and that you never knew what you were talking about, Chad!

Things you must not miss in Boston’s North End

Pro Tip: Since you’re so close, you’ll have to visit the three best bakeries in the North End – Modern Pastries, Mike’s Pastries, and Bova’s. Then, you’ll have to figure out which one you like more!

4. Any of Boston’s Awesome Music Venues

Things to Do in Boston on a rainy day

Listen to some music at Boston’s House of Blues – Things to Do in Boston on a rainy day

If you’re a fan of music, then there’s no shortage of outlets for you to get your concert fix. From the popular House of Blues, to the intimate Brighton Music Hall, all the way to famous Fenway Park, the music is always bumping in Boston!

5. Self-guided Dunkie’s Tour

Things to Do in Boston on a rainy day

Eat a donut or get some iced coffee – Things to Do in Boston on a rainy day

If you’re not from the Northeast then you’ve definitely heard the mythical tale of a Dunkin’ Donuts on every corner. Well, it’s true! While not an official tour by any stretch of the imagination, I sincerely implore you to try your best to make it into the over 60 locations and write tales of what you discovered.

In terms of Things to Do in Boston on a rainy day, I’d rate this three strawberry frosted donuts out of a bacon, egg, and cheese on a croissant. I’ll let you figure out the conversion factor for that. What I will tell you is that tales of this adventure definitely reek of best-selling book potential – all it needs is an author!

6. Get your drink in at a brewery tour!


Boston is home to some of America’s earliest history. From the Boston Tea Party to the Midnight Ride of Paul Revere, Boston has had a lot to celebrate over the years. And celebrate we did! Enough so that craft breweries have become a growing staple of ol’ Beantown. Take a stroll over to Sam Adams, Harpoon, Trillium, or a host of other breweries in the area for a tour of how the appetizing ales (and lagers) get brought from barrel to glass to mouth to questionable decisions. All in the name of fun adult activities!

7. Visit some of Boston’s most unique bars on a Bar Crawl!

Things to Do in Boston on a rainy day

Bar crawl – Things to Do in Boston on a rainy day

Boston is host to a crazy amount of bar crawls all throughout the year, and is not just on a list of things to Do in Boston on a rainy day. It’s great on a sunny day, too!

From the always popular Santa Bar Crawl during the winter season to an “educational” crawl around Fenway, there’s literally* a bar crawl for everyone. So grab your Santa hats and your state issued I.D.s because we’re getting “crunk” kids!

Here are a few of our favorite bars in case you were going to self-guide a bar crawl:

  • Green Dragon Tavern – This historical bar on Union St in Boston’s North End was used as a tavern. Many historical secret groups used the basement as a meeting place. Historians consider this tavern as the “Headquarters of the Revolution”.
  • The Beantown Pub – Located across the street from the Granary Burying Ground is a unique spot where you can drink a Sam Adams beer while looking at a Sam Adams’ grave!
  • Yvonne’s – It’s an upscale speakeasy restaurant bar with our favorite architecture and interior decor.

Don’t worry, non-drinkers, there are plenty of mocktails and snacks that you will enjoy!

8. Eat grilled cheese at Roxy’s A4cade

Things to Do in Boston on a rainy day

Roxy’s A4cade – Things to Do in Boston on a rainy day

Do you like grilled cheeses? How about arcade games? Alcohol? Of course you do!

You can partake in all of these adult activities with a visit to the Roxy’s Grilled Cheese’s Central Square location. Tucked away in back is A4cade, a barcade with an array of arcade cabinets both new and old for customers to get greasy grilled cheese fingers all over!

9. Boston Grown-ups Museum

things to Do in Boston on a rainy day

Grown-Ups Museum – Things to Do in Boston on a rainy day

We’ve done a lot of talking regarding celebrating your status as an adult by acting like a dang child. There’s no better way to exercise this right than to take part in a night at the Boston Grown-ups Museum. For a few nights throughout the year, Boston Children’s Museum mystically converts itself into an adult’s only night of fun. And yes, this includes alcoholic beverages my dear friends. So keep an ear open for the next time one of these events comes around!

What ideas do you have for things to do in Boston on a rainy day? 

We’d love to hear from you and be constantly updating this list!

If you are looking for things to Do in Boston on a rainy day, we hope you’ve found something on this list!

If you do the Dunkie’s Tour and strike a publishing deal, we’re strongly expecting a mention in the back of that book somewhere. You can come over to Trapology at 177 Tremont Street to talk details. Until then, we hope you enjoy your time in the city!