Top 10 Things to Do in Boston (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. If you’re seeking a more unique Boston travel experience, then follow these steps for how not to be a tourist: 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. 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!

2. Drink coffee like a local: If you want to be a local, then skip Starbucks in favor of Dunkin’ Donuts. As a southerner, I was skeptical 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.

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 Friday and Saturday.

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.

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”.


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. 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.

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.

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.

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.

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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