Unique Boston: 10 Reasons NOT to Follow the Crowd

On a recent business trip to Boston, I had some time to do some sightseeing. It was my first time here, and I was excited to explore the city. But I didn’t necessarily want to visit the most popular attractions…like Fenway Park, the Cheers bar, Boston Common and the Aquarium at Boston Harbor. While those places are all well and good, I wanted to discover lesser known spots, and in Boston there are plenty of them. After all, it is one of America’s oldest cities, so the history here dazzles the imagination. I talked to locals who gave me some great ideas on where to go. My top 10 are below. While I didn’t get to visit all of them, you can bet I’ll finish what I started the next time I’m in Beantown.

  1. Self-guided walking tours.

I’m all for DIY tours, so when I came across www.freetoursbyfoot.com I had to do at least one of them. I chose the Beacon Hill Walking Tour, and it did not disappoint. The tour takes you through some of Boston’s oldest streets, complete with boot scrapers at doorsteps and 300-year-old gas street lamps that are still in use! You will see the residences of the poet Robert Frost and Louise May-Alcott, many notable figures of government, and the famous Acorn Street. The tour also showcases Boston’s unique architecture.




The site of the beginning of my Beacon Hill tour.

  1. Curious George store in Harvard Square.

Who in their 40’s and above didn’t grow up with this magnanimous character? This is the world’s only store dedicated to the precocious monkey. As of this writing, the building that houses the iconic Harvard Square location is slated to be redeveloped, and there is a petition by the store owner to stop that (I’m betting he’ll succeed). What’s more, if you were a fan of NPR’s Car Talk, the Dewey, Cheetham & Howe window one the third floor above the store’s entrance will also be no more.



  1. Warren Anatomical Museum

If you have any penchant for oddities and are not squimmish, head to the fifth floor of the Countway Library of Medicine. Dr. Warren practiced medicine in the 1800’s and collected thousands of anatomical specimens to help in his studies. Upon his retirement, he left them to Harvard University. Among the more well-known items is the skull of Phineas Gage, a railroad worker who suffered an accident where a tamping iron penetrated his skull and he lived to tell the tale.

Phineus Gage's skull.

Phineus Gage’s skull.

  1. Caffe Vittoria

Coffee lovers unite! In Boston’s North End is Little Italy. Here’s where you’ll find the city’s oldest Italian café, since 1929. Don’t want to caffeinate? Try the shoppe’s famous martini, or savor their well-made cannoli.  Whilst sipping your espresso, peruse the wonderful display of coffee paraphernalia, from posters and unique coffee mugs to vintage espresso makers.


Have a cuppa love.

  1. Take a Ghost Tour

Every major city has a ghost tour or two, but Boston rises above the fray with Haunted Boston Ghost Tours. Step through the shadows and discover the chilling and ghastly tails of murder, revenge, lust and heartache. This city is ripe with folklore, and the ghost tours lend a macabre twist to centuries-old stories.


6. Escape the Room

This was the most fun I’ve had in a while. They put you in a LOCKED room, and you have exactly one hour to find various clues and hidden objects in order to “escape the room.” This is a group activity, but don’t fret if you come alone (as I did). You will be teamed with others; it’s a great way to make new friends for an afternoon.


Strangers turn into friends quickly when you’re locked in a room!

7. Tea Party at the Boston Public Library

America’s best answer to the Monarchy’s High Tea! For $35 dollars you and a friend can enjoy fancy tea, sandwiches and sweets at the library’s Courtyard restaurant, every day except Sunday, from 11:30 am – 3:30pm. Jolly good!


Petite heaven!

  1. Hysterical, Historical Tour of Harvard.

If you MUST take a guided tour, do this one. A knowledgeable guide in period costume will lead you on this entertaining tour covering nearly 400 years of Harvard history: Little-known facts about the Titanic, the bizarreness of the nation’s oldest higher-learning institution. And just why is John’s Harvard’s foot yellowish?


  1. Get your Culture on at Coolidge Corner Theater

You won’t see blockbusters here. Located in Brookline, just south of Cambridge, this non-profit, independent movie theatre screens a healthy variety of old and new flicks. In any one day you can catch 3-4 different films. In 1906 the building started as a Universalist Church, then converted to an art deco-style theatre in 1933.


  1. Kayak on the Charles River

This is another one I missed, but was mentioned a couple of times in my conversations with locals. Paddle Boston offers both river and harbor tours, even moonlight canoe tours! Whether by canoe or kayak, experienced or beginner (yes, they even have a paddling school), this is a unique outdoor urban adventure.

No Excuses

Without a doubt, Boston is brimming with wonderful experiences for anyone, if you’re willing to look a little deeper and get off of the beaten path. I found that it is a very walkable city…if you’re in halfway decent shape, you can get around just about anywhere on foot, and their public transportation system isn’t bad, either. So there’s no excuse not to get out and explore the lessor-known (and WAY more interesting) spots in Boston.


Taking a few moments of chill time at the Boston Harbor.

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