5 Weird Things To Do In Boston

boston sightseeing

Boston sightseeing because the city is full of attractions for everyone. From family-friendly places like the famous Faneuil Hall to adult-oriented places like the numerous historic bars, there’s always something to do. But what about those who are looking for something a little weirder? The places that the every-man or average tourist can’t find on TripAdvisor? Boston is home to a lot of weird places that make you scratch your head and ask, “Why is this here?”

When you’re in a city where duck-shaped trucks turn into boats and tour the city, the weird isn’t so far away. Here are some of the weirdest places in Boston that you can visit.


Hood Milk Bottle

boston sightseeing

courtesy of Boston Eater

308 Congress St, Boston, MA 02210

This 40-foot-tall Hood milk bottle has stood outside the Boston Children’s Museum for nearly four decades now. Originally built by Arthur Gagner in 1930, the wooden structure now doubles as an odd landmark of the city while also serving as an ice cream stand during the spring and summer.


All Saints Way

boston sightseeing

courtesy of Huffington Post

4 Battery St Boston, MA 02109

Peter Baldassari’s collection of trinkets and mementos depicting the saints is hidden in an alley off of Battery Street in the North End. Behind a black door is this shrine full of images, figurines, and tokens of saints. While it is private property, Baldassari is known to give quick tours. The collection is also visible from the street.


Jamaica Pond Bench

boston sightseeing

courtesy of Yelp

Jamaica Pond, Boston, MA 02130

This curious bench sits next to Jamaica Pond, in a string of Boston parks known as the Emerald Necklace. The parks were designed by famed architect Frederick Law Olmstead, who created this U-shaped bench as a joke. Olmstead snuck the bench in without the approval of the parks department, where it went unnoticed by the City of Boston for a whole week. Sitting down is next to impossible, but laying down is an option.


Boston Athenaeum and the Skin Book

boston sightseeing

courtesy of Patch

10 ½ Beacon St, Boston, MA 02108

The Boston Athenaeum is one of the city’s largest and oldest membership libraries. Not only is it stunning in its architecture but it contains one of the weirdest gems in Boston’s history, the Skin Book. The book titled, “A Narrative of the Life of James Allen: Alias George Walton, Alias Jonas Pierce, Alias James H. York, Alias Burley Grove, the Highwayman: Being his Death-Bed Confession, to the Warden of the Massachusetts State Prison,” details the life of famous highwayman and thief. Interestingly enough, the book is bound by his own skin. Allen had the book sent to one of his victims, post-mortem.


The Scarlett O’Hara houseboston sightseeing

courtesy of Unlimited Sir

Rollins Pl, Boston, MA 02114

This two-story Greek Revival “house” is tucked away on Boston’s Beacon Hill. Notice the quotation marks. This isn’t a house at all. Instead, it is a three-dimensional painting made to obscure a brick and concrete wall. The detail is exceptional, including the flowers under the  “porch” that are kept neat and beautiful year round.


So next time you’re searching for things to do beyond the usual Newbury Street walk or Faneuil Hall browsing, focus your efforts on something weirder. Think outside the box, veer off the Freedom Trail and explore some alleys. You never know what you may find.


Looking for more things to do in Boston? Check out the best outdoor bars in the city!

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