The Best Hidden Destinations in Boston

While staples such as Quincy Market, the Freedom Trail, and Fenway Park are certainly worth the visit, Boston has its fair share of hidden gems for those looking to get off the beaten path. From shady bars to a bodega that sells designer sneakers, here are some of the city’s best-kept secrets.

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Backbar

Restaurant, Bar, American

Considering the entrance is an unmarked red door beside a dumpster in a dirty alleyway, Backbar serves up surprisingly high-end cocktails and hors d’oeuvres. To find it, head to Journeyman restaurant in Somerville’s Union Square—the entrance is just to the right of the restaurant.

Secret roof garden in Cambridge

Park

From the ground, the Cambridge City Parking garage in Kendall Square just looks like any other overpriced garage in the city. However, go inside through the Broadway entrance all the way to the top floor and you will be treated to a secret rooftop garden with a gorgeous view overlooking the city.

Bodega for sneakerheads

Store

This one is for the sneakerheads in your group. To find it, you have to enter a rundown bodega filled with dusty, outdated merchandise. The Snapple vending machine in the back is actually a door that leads into a designer sneaker shop.

The hidden Saloon

Bar, Restaurant, American

Though fairly well-known among local residents, this speakeasy-style bar in Davis Square, Somerville, has no sign and is located underground, keeping it out of the eye of tourists and college students. True to the bar’s prohibition-era vibe, the drinks at Saloon are strong and the meals are heavy.

All Saints Way

Shrine

This private alleyway in Boston’s North End neighborhood has been turned into a shrine to the Patron Saints of… pretty much everything you can think of. Even when the gate is locked, you can still get a decent look from the street.

Secret steakhouse

Restaurant, American

Hidden by a curtain behind the famous American restaurant JM Curley, is a high-end steakhouse called Bogie’s Place. The restaurant seats 20 people and its entrance is marked by a sign simply reading ‘Adults Only’. Cameras and phones aren’t allowed here, so you’ll have to see it for yourself.

The giant light-up globe you can explore from the inside

Library

Inside the Mary Baker Eddy Library is the Mapparium, a three-story, pre-WWII, stained glass globe that guests can enter from the outside. Once you’re in, there is music and a light show.

Miniature village in the cemetery

Cemetery, Forest

Deep inside the Forest Hills Cemetery in Jamaica Plain sits a miniature village that eerily resembles a dollhouse town square made of stone. Apparently it was added as an art exhibit over a decade ago, though now it mostly serves to creep out visitors.

Volcanic Iceland Epic Trip

meet our Local Insider

Hanna

HOW LONG HAVE YOU BEEN A GUIDE?

2 years.

WHAT DO YOU LOVE ABOUT YOUR JOB?

It's the personal contact, the personal experiences. I love meeting people from all over the world... I really like getting to know everyone and feeling like I'm traveling with a group of friends.

WHAT DESTINATION IS ON YOUR TRAVEL BUCKET-LIST?

I have so many places on my list, but I would really lobe to go to Africa. I consider myself an “adventure girl” and Africa feels like the ULTIMATE adventure!

Every CULTURE TRIP Small-group adventure is led by a Local Insider just like Hanna.

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Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

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