Quirky Museums and Activities in Boston

Anyone who has visited Boston knows to stroll through Harvard Yard, glimpse American history along the Freedom Trail, take in a Red Sox game, and spend an afternoon in the Museum of Fine Arts or Isabella Stewart Gardner Museum.

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Anyone who has visited Boston knows to stroll through Harvard Yard, glimpse American history along the Freedom Trail, take in a Red Sox game, and spend an afternoon in the Museum of Fine Arts or Isabella Stewart Gardner Museum. But what if you’re a fan of attractions that offer something a little different? Boston still has you covered. Simply veer off the traditional sightseeing route, and check out these quirky and fun things to see.

Light ‘Em Up

Located in a dark basement in a North End former speakeasy, Stanza dei Sigari is the ultimate classic cigar bar. Grab the smoke of your choice, and try to snag a spot in a leather-clad booth (the place fills up quickly in the evenings). Relax and browse the interesting cigar-related memorabilia onsite, including a collection of antique humidors.

Like a Hole in the Head

Into medical oddities? The Warren Anatomical Museum houses a free collection of interesting skulls, fetal skeletons, implants, and medical artifacts tucked away inside the Harvard Countway Library of Medicine. Of special note is the skull of Phineas Gage, a man from the 1800s who survived the impalement of a metal rod through his skull, instigating medical curiosity regarding the connection of the brain and personality.

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Get Steamy

The Metropolitan Waterworks Museum located on Beacon Street is another small, free museum that’s perfect for those curious about engineering. To learn about the first water system in a major city, stop in to listen to educated volunteers explain how engineers handled the demands of rapid population growth. This mix of history and infrastructure is culminated in the collection of three-story, steam-driven water pumps dating back to the 19th century.

So Bad It’s Good

Ever look at a piece of art in a museum and think, “I could do better”? Welcome to the Museum of Bad Art, located about five miles from downtown Boston in the basement of the Somerville Theatre. This collection honors works widely considered bad by art connoisseurs. Grasp the complexities of portraiture, landscapes, and still-life paintings with titles such as “Sunday on the Pot with George” and “Two Trees in Love.” Admission is free for the rotating exhibit of about 25 of the museum’s 250 eye-rolling “masterpieces.”

Rev Your Engine

Just a half-hour drive from Boston takes you to the estate grounds of Larz and Isabel Anderson, one of the wealthiest couples in the nation in the late 1800s. They owned an impressive collection of antique cars, which has since turned into the Larz Anderson Auto Museum. The carriage house is filled with cars that belonged to the Andersons and others, including an 1899 Winton, 1905 Electromobile, and a 1925 Renault Taxi. It’s distinguished as America’s oldest car collection.

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