Top 10 Things to Do in Boston (Away from the Beaten Path)

If you’re planning a trip to Boston, you are in luck because there are a lot of tings that you can do and see there. But today I will take a slightly different approach and share with you my top 10 things to do in Boston that are away from the beaten path.

Among the most popular things to do in Boston are shopping and eating at Faneuil Hall and Quincy Market, witnessing the die-hard passion of Sox fans at Fenway, and experiencing the sites that shaped our American history — the Freedom Trail, North Church and Bunker Hill.

All these things give a glimpse into Boston and its heritage but after you’ve had your fill of Duck Tours and clam chowder, there’s so much more to explore! You will be surprised to find out that some attractions and things to do that are not usually mentioned in your “best of Boston” blogs and videos will actually be the most rewarding.

And this is what you’re going to learn today: which are some less touristy activities and things to see or try in Boston. Because following the herd is not always the best idea.

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So if you’re seeking a more unique Boston travel experience, then follow these steps for how not to be a tourist, but a hidden gem finder: top 10 things to do in Boston that are way off the beaten path, but still insanely enjoyable!

1. Head east for the best pizza

Though the North End is considered Boston’s Little Italy, it was East Boston where Italians first immigrated and it’s also home to Eastie staple Santarpio’s, a truly local pizza joint that’s been making pies since 1933.

This place is old school, family Italian in every way with a simple, short menu and no frills, except for the taste of the pizza — thin crusts crisped to perfection in brick ovens and topped with fresh ingredients. Great prices too!

It’s still incredibly popular so expect a line on weekends, but definitely worth the couple of stops on the T. Location: 111 Chelsea Street, East Boston

The pizza is really delicious!
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2. Drink coffee like a local

If you want to be a local, then skip Starbucks in favor of Dunkin’ Donuts. You would be skeptical to think that DD would taste better in the north, but I gave it a taste test.

Maybe because DD’s roots are in Massachusetts, I’m not sure, but Bostonians’ passionate claims that it’s superior to Starbucks are true. So at least give it a try!

3. Be creative with lunch

Walk right past Faneuil Hall and head to Haymarket, an open air market with every imaginable fruit and vegetable as well as bread and cheese at prices much cheaper than supermarkets (since it’s unsold overstock) — six Fuji’s for $2!! Grab some stuff and head to the Public Gardens for a picnic. Open Fridays and Saturdays.

4. Laze around Boston Common

Grab a blanket and your sweetie for a lazy afternoon enjoying the country’s oldest public park. Not only will you appreciate the park’s beauty, but this is people watching at its best and you’ll even be treated to some great local talent.

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Entertainment and relaxation don’t have to cost a fortune – so take advantage of the good weather and enjoy spending some time in the park. We sometimes just need to unwind and break away from all the concrete and technology around us and the Boston Common Park will be perfect for that.

5. Sink your teeth into Boston’s best cannoli

Apparently the joke among locals is that Mike’s Pastry is for tourists but locals know that the best Italian cannoli in the North End is at Modern Pastry because they’re fresh and “filled to order”.


So get a taste of the sweet life by experiencing the best cannoli you have ever had or indulge in any of the other sweets on display. There are a ton to choose from and you’ll have to test at least a few to find your winner.

6. Go off the beaten path in Beacon Hill

Cleverly dubbed for its proximity to the State House, The Fill-A-Buster is a local dive frequented by college students and Beacon Hill workers.

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Named best breakfast in Boston for their egg sandwiches, they’re also very friendly, very Boston, very cheap and very fun… you can check out the action before heading over on their live video stream if you want to.

7. Stroll the harborwalk

Explore the Boston Harbor on 40-miles of harborwalk trails and walkways that wind along the waterfront from Charlestown to Dorchester with great skyline views, sculpture, gardens, architecture, parks and restaurants along the way.

Of course, you don’t need to do the entire 40 miles to experience it. But have at least 30 – 45 minutes set for walking around and taking in all the beauty.

And if you happen to be just near the USS Constitution, the impressive wooden ship launched back in 1797, you owe it to yourself to just check it out. It’s a real piece of history and the museum itself is really cool too.

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8. Meet the locals

The best way to learn a city, the places and people is to meet the locals. Boston is filled with friendly and welcoming folks. I struck up a conversation at Santarpio’s and was invited into the kitchen for a tour and to meet the guys who make it all happen.

As long as you are open and sociable, you will be able to meet new people, possibly making new friends and learning about some things to see and do that truly just locals know about.

9. Play with a duck rather than ride one

Duck Tour or a soothing bath with a rubber duck bobbing on the bubbles? If your hotel is as luxurious as The Colonnade, then there’ll be a rubber duck waiting for you in your bathroom so you can skip the big metal tourist one.

10. Watch (don’t be one of) the tourists that ham it up in Copley Square

Tourists flock to Copley Square more in search of letting out their inner ham than actually taking pictures of the architecture that graces the square like Trinity Church and the Hancock Tower.

Or just enjoy the place yourself: in this case, it’s popular for a reason, so even though not completely away from the beaten path, it’s really enjoyable and a must see.

These would by my top 10 things to do in Boston that most tourists don’t. Did you manage to find any hidden gems during your visits to Boston? Let me know by leaving a comment below!

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