If you are planning a trip to this city for the very first time, you are probably perusing through the top 10 lists of best things to do in Boston, which consist of all the usual tourist attractions that are sort of a right of passage for anyone who is a Beantown virgin, and wondering when is the best time to visit Boston. From the Freedom Trail to Faneuil Hall and Fenway Park, Boston is home to some of the most historic and unique points of interest, and you should certainly check those out. Be that as it may, there are some incredible and unconventional things to explore beyond the travel guides that only the locals may know of.
Boston is not your run-of-the-mill city. While there are so many must-see spots that even old-school Bostonians frequently attend, my advice for Beantown newbies is to put down the guidebook and devote a day or two to discovering the hidden gems in this charming and eclectic city. Some are quirky, some are creepy, and some of them are just plain mind-boggling, but what they definitely are not is ordinary.
- 1. Find the Secret Speakeasies
- 2. Visit Some Mysterious Boston Museums
- 3. Munch on Extraordinary Eats
- 4. Wander Off to Offbeat Outings
- 5. Witness Strange Spectacles
- 6. Embark on Atypical Adventures
- 7. Discover Hidden Treasures
1. Find the Secret Speakeasies
6 Clearway St, Back Bay
This is not your average convenience store. While the shelves may be lined with snacks, cleaning products, and other expected household items, do not be fooled. Once you step in, head straight for the giant Snapple vending machine. You won’t be getting a refreshing beverage as it’s actually an entryway to a secret store selling the hottest high-end street and skatewear, from sneakers to jackets and hats. Even if you don’t plan on buying anything, the sleek and fresh atmosphere of this hidden retail shop makes it one of the coolest places to browse in Boston.
292 Massachusetts Ave, Cambridge
Is there any combination better than grilled cheese, pints, and Pacman? Stop for a bite at Roxy’s Grilled Cheese in Central Square, and once you’re nice and full, head through the swinging doors leading to the kitchen and enter Area Four’s arcade bar.
This speakeasy bar is strictly hush-hush, packed with the best arcade entertainment and some fantastic beverages. Sip on cocktails and try your hand at skeeball or pinball for an unexpected night of retro gaming and recreation.
2. Visit Some Mysterious Boston Museums
Museum of Bad Art
55 Davis Square, Somerville
While the beauty of art is entirely subjective, the collections housed in the Museum of Bad Art in Somerville are, you guessed it, just plain bad. If you consider yourself an enthusiast of artwork so laughable you can’t look away, you must visit the world’s only museum completely dedicated to sub-standard masterpieces.
Located in the basement of the Somerville Theater is where you’ll discover an exhibit of failed attempts at celebrity portraits, fantasy landscapes, and abstract anomalies. The best part? You don’t need to pay a single penny to check out these bizarre creations.
Warren Anatomical Museum
10 Shattuck St, Mission Hill
Founded by Dr. John Collins Warren in 1847, the Warren Anatomical Museum in the Countway Library of Medicine houses an exhibition of the curious and strange. With over 15,000 artifacts, this museum features collections of civil-war era tools, death masks, and skeletal oddities with a mission to further our education on the history of medicine.
If you dare to enter, be sure to check out their most famous piece, the skull of Phineas Gage, a railroad worker who survived an iron rod through the brain. While this attraction may be a quick visit, it definitely ranks as one of the creepiest places in Boston to explore.
3. Munch on Extraordinary Eats
650 E Kendall Street, Cambridge
For an unexpected change in your diet, dine in at Cafe ArtScience in Cambridge for some avant-garde culinary experiments. Founded by a Harvard engineer, this food lab explores the future of cuisine, incorporating creativity and art into every dish they serve. This is no ordinary dining experience, as you’ll be gorging on sea urchin pannacotta, foie gras cheeseburgers, and cocktails with clarified coconut and lotus flower. And while these tempting treats may look like a work of art, they’ll taste even better.
Chinatown Food Tour
Chinatown has some of the best food in Boston, so why decide on just one place to eat? Discover an in-depth guide to the best markets, dim sum delicacies, and herbalist shops with the Chinatown Experience Tour. For $75, you can join a three hour Chinatown expedition to learn about the history and culture of this significant Boston neighborhood. You will sample street cart dumplings, try some exotic produce, and learn about the tips and tricks to mastering this delicious cuisine as you explore the hidden gems that can’t be found in a typical guidebook.
4. Wander Off to Offbeat Outings
A Trip to Hyannis
You don’t necessarily have to stay within the lines of Boston to explore the cool and unusual. Opt for a day to stray from your normal itinerary and take a bus to Hyannis for a quick Cape Cod vacation and one of the coolest things to do in Boston. In less than two hours you’ll be escaping the Boston crowds and relaxing by the beach or exploring the maritime museums in this sea coastal setting. For an adventurous addition to your detour, sign up for a whale watching boat ride and finish the day with a fresh and juicy lobster roll by the water before returning to Boston to continue your adventures around town.
George’s Island Getaway
For a short-range getaway, George’s Island is just a ferry ride from the Boston Harbour. Take a break from the hustle and bustle of city life and enjoy a picnic or admire the view of the city from the fields. You can also find Fort Warren on the island. Tour this Civil War-era fort and admire the historic architecture that still stands today for an educational afternoon activity.
For a spookier side to things, keep a lookout for the Lady in Black. This island’s famous ghost was a Confederate prisoner’s wife who was later hanged for attempting to set him free. If you believe in the myth, you just might spot her.
5. Witness Strange Spectacles
The Donkey Show
2 Arrow St, Cambridge
The Donkey Show is quite possibly one of the most unique theatrical performances you’ll ever experience. This Tony Award-winning show is a disco party reenactment of A Midsummer Night’s Dream, put on every Saturday night at the Oberon. Prepare to be a part of the Shakespeare play-turned-fever dream as you’ll have actors and actresses dancing on your tables and rollerskating throughout the venue. While the plot isn’t necessary to follow, the dynamic showcase will make for a wildly entertaining night of drinks, jokes, songs, and lots of glitter.
Charles Playhouse, 74 Warrenton St, Boston Theater District
While the Charles Playhouse in Boston may be well known among tourists and long-time residents, the theater’s production of Shear Madness is a unique experience that should not be missed. Running for almost 40 years, Shear Madness takes you through a hair salon themed murder-mystery, where the first act of the show leads up to a murder, and the second act requires the audience to put together various clues from the performance and even question the characters. Because the audience takes control of the detective work, the actors improvise most of the show, meaning you could attend multiple times and still be shocked with a different ending.
6. Embark on Atypical Adventures
Adult Night at Legoland
598 Assembly Row, Somerville
When the kids are away the adults will play, with legos that is. Once a month, the Legoland Discovery Center in Somerville dedicates an entire Wednesday night strictly for adult attendance. With special themes like Carnival, Masquerade, and Witches and Wizards, this event makes for a unique date night or evening out with friends filled with games, competitions, and best of all, a fully stocked bar. As an extra special addition, attendees are encouraged to bring canned goods or donations for Legoland’s charity that helps children in need.
Sam Adams Brewery Tour
30 Germania St, Jamaica Plain
Bostonians are very loyal to Sam Adams beer, so what’s a better way to get to know Boston than to tour the very brewery of their favorite beverage? Located in Jamaica Plain, the Sam Adams brewery offers a free tour to guests every 30 minutes, complete with tastings and information about ingredients and the brewing process.
For a more in-depth tour of the barrel rooms paired with beer and cheese tastings, you’ll need to make a reservation, with tickets ranging from $10 to $50. If tours aren’t your thing, you can also explore their tap room for experimental tastings, beer flights, and Thursday night trivia!
They are given out on a first come, first serve basis.
Smoot’s Legacy on the Harvard Bridge
Massachusetts Ave Bridge & Storrow Dr, Cambridge
MIT Freshman Oliver Smoot had no idea that a pledge prank for his fraternity would become a 60-year legacy. In 1958, the Lambda Chi Alpha fraternity used Oliver Smoot’s 5 ft 7’ height to measure the exact length of the Harvard Bridge. Totaling 364.4 Smoots, the bridge boasts a new form of measurement for tourists to explore to this day. You can walk along the bridge that connects Back Bay to Cambridge and finds the painted markings of 10 Smoots, 20 Smoots, and so on for a unique afternoon activity.
The Ether Dome
Massachusetts General Hospital, Downtown Boston
While a visit to the hospital may not be high on your Boston itinerary, the Ether Dome certainly should be. Located in the Massachusetts General Hospital, this hidden surgical amphitheater is home to where the first successful public surgery using ether as an anesthetic was first held. With more than 8,000 live operations taking place from 1821 to 1868, the Ether Dome is a significant, yet somewhat spooky, destination that’s also free for the public to explore on weekdays. Be sure to check out the intricate architecture and surgical tools as well as a 2,500-year-old Egyptian mummy that was once operated on in this haunting yet fascinating 19th-century medical room.
Visiting a new city typically goes hand in hand with stopping by the most popular, tourist-approved destinations. And while there’s absolutely nothing wrong with exploring the must-see spots that make Boston so special, sometimes you need to check out the hidden gems to truly appreciate the unique and charming character of this city.
Whether your goal is to discover the extraordinary secrets of Boston or just escape the tourist-filled crowds, this list will guide you through the creepiest, most fascinating, and oh-so-delicious spots in the United State’s most historic city.