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.
If you are seeking a unique Boston travel experience, then follow these steps for how not to be a tourist. Here are my top 10 things to do in Boston that are way off the beaten path but still insanely enjoyable.
1. Eat Authentic Pizza at Santarpio’s in East Boston
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 is still incredibly popular so expect a line on weekends, but it is definitely worth the couple of stops on the T.
Address: 111 Chelsea Street, East Boston
Closest T Stop: Maverick Station (Blue Line)
Cost: $
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2. Find the Secret Door at Bodega
I always get a kick out of taking people here because they never believe me at first. From the outside, Bodega looks like a slightly rundown convenience store with dusty boxes of laundry detergent and old sodas in the window.
But if you walk to the back and slide open the fake Snapple machine, you walk right into a high-end streetwear and sneaker boutique!
It is a crazy contrast and easily one of the coolest retail experiences I have ever had. Even if you are not into expensive shoes, the novelty of the hidden entrance is completely worth the visit.
Address: 6 Clearway Street, Boston
Closest T Stop: Hynes Convention Center (Green Line)
Cost: Free to enter, $$$ to shop
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 mostly unsold overstock)!
Grab some fresh food and head over to the nearby Rose Kennedy Greenway for a picnic instead of eating at a crowded tourist trap. Just remember the market is only open on Fridays and Saturdays.
Address: 100 Hanover Street, Boston
Closest T Stop: Haymarket (Green or Orange Line)
Cost: $
Also read: Top 10 Most Affordable Cities in the US
4. Walk Inside a Giant Globe at The Mapparium
You will find this inside the Mary Baker Eddy Library and it is honestly mind-blowing. The Mapparium is a three-story stained-glass globe that you walk straight through via a glass bridge. Since the map was built in 1935, the country borders are completely frozen in time.
I feel that the best part is the acoustics, though, and you should pay close attention to it. Because of the spherical shape, you can stand at one end of the bridge and whisper, and a person at the exact opposite end will hear you perfectly.
Address: 200 Massachusetts Avenue, Boston
Closest T Stop: Symphony (Green Line)
Cost: $
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.
Address: 257 Hanover Street, Boston
Closest T Stop: Haymarket (Green or Orange Line)
Cost: $
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6. Grab a Local Breakfast at The Fill-A-Buster
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. They have been named best breakfast in Boston for their egg sandwiches.
They are very friendly, very Boston, very cheap, and very fun. You can even check out the action before heading over on their live video stream if you want to. It is the perfect unpretentious spot to grab a bite before exploring the historic Beacon Hill neighborhood.
Address: 142 Bowdoin Street, Boston
Closest T Stop: Bowdoin (Blue Line) or Park Street (Red or Green Line)
Cost: $
7. Browse the Outdoor Alley at Brattle Book Shop
If you love reading as much as I do, you will want to spend hours here. Brattle Book Shop is one of America’s oldest antiquarian bookstores. The inside is packed with rare finds, but some of the magic is outside.
They have an outdoor sale alley tucked right next to the main building. The alley is lined with discount book carts beneath giant murals of famous authors. It is a quiet oasis right in the middle of downtown Boston, and a great place to spend a few hours.
Address: 9 West Street, Boston
Closest T Stop: Downtown Crossing (Red or Orange Line)
Cost: $
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8. Stroll the Harborwalk
Explore the Boston Harbor on 40 miles of harborwalk trails and walkways that wind along the waterfront from Charlestown to Dorchester. You get great skyline views, public art, gardens, interesting architecture, parks, and restaurants along the way.
Of course you do not need to do the entire 40 miles to experience it (nor do I think it’s possible). But have at least 30 to 45 minutes set aside for walking around and taking in all the beauty.
I suggest starting near Fan Pier for the absolute best view of the downtown skyline.
Address: Start at Fan Pier Park, 1 Courthouse Square, Boston
Closest T Stop: Courthouse (Silver Line)
Cost: Free
9. Grab a Hot Dog and Plane Watch at Castle Island
Instead of lounging in the heavily trafficked public parks downtown, I love heading out to South Boston to visit Castle Island. You can walk the scenic loop around Fort Independence while catching a cool ocean breeze.
The best part is grabbing a cheap hot dog at Sullivan’s. It is a beloved local shack right on the island. You can eat your food while watching the massive airplanes take off and land right across the water at Logan Airport.
Address: 2010 Day Boulevard, South Boston
Closest T Stop: Broadway (Red Line) then take the #9 bus
Cost: $
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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 are my top 10 things to do in Boston that most tourists miss out on. I feel that mixing a few of these spots into your itinerary will give you a much richer understanding of what makes this city so great.
Did you manage to find any hidden gems during your own visits to Boston? Let me know by leaving a comment below!
