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Touring Boston’s Strangest and Most Bizarre Sites

The city of Boston has long played a huge role in our nation’s history. From the time of its founding in the 1630s, the city has been central to a number of events that have dramatically shaped the country we know and love today. From its role in instigating the American Revolution to the violent acts that led to the infamous Boston Massacre, Boston certainly boasts some unique and strange history.

According to Boston USA, the Greater Boston Conventions and Visitors Bureau expects to welcome more than 21.8 million domestic and international visitors in 2017. Visitors flock to the city for its museums, gardens, sports events, historical reenactments, and much more. If you want to get off the beaten path and visit attractions that most Boston visitors have never even heard of, this article will help you optimize your time for touring Boston’s strangest and most bizarre sites.

Choose Transportation

Traveling with a large group in a city as busy as Boston must be carefully planned. It’s best to keep your group together as you travel from site to site, which is why a private Boston bus rental with a driver is the best way to see the city.


Renting a private bus with a driver has a number of benefits to your group. First, it eliminates the stress that often comes with navigating traffic in a new city. Your group can sit back and enjoy the sights and sounds of the city as you travel from attraction to attraction.

Next, a bus rental gives your group the ability to stay together as you tour the city. This eliminates the risk of certain group members getting lost and arriving to a destination or event late. It also facilitates opportunities to create lasting memories touring the city with the entire group.

The Big Ones

When you visit Boston, there are a few quintessentially bizarre sites that you HAVE to check out.

All Saints Way: A hidden alley tucked away off of Battery Street. When open, the ‘Way’ is home to hundreds of images, figurines, and tokens of saints arranged in an impromptu shrine-like space.

Urban Interactive: This immersive experience will challenge your group in a live action, role-playing game. In your role as the ‘agent’, you’ll have to uncover a series of clues placed throughout Harvard Square in order to track down a long lost and highly precious gemstone.

 Phineas Gage’s Skull: Phineas Gage was an American railroad foreman who dramatically survived a railroad accident in which an iron bar was sent clean through his skull. Remarkably, Gage remained conscious in the aftermath of the accident and lived a relatively normal life following the removal of the bar. His skull is now on display at the Warren Anatomical Museum.

 The Trolley of the Doomed: This nighttime adventure will take you to some of Boston’s most haunted sites. You’ll learn about Ephraim Littlefield’s black-market body trading operation and visit the site of Boston’s largest unmarked burial ground.

Museum of Bad Art: This strange Boston attraction contains no surprises. When you visit, you’ll find a whole lot of exactly what its name suggests: really crappy art! It was founded in 1993 and, to this day, is the only museum in the world “dedicated to bringing the worst of art to the widest of audiences.”

Map Choice Destinations

In addition to the sites we mentioned above, there are several map destinations where you can go to experience a lot of Boston’s unique culture in one concentrated area. These destinations include:

Downtown Waterfront: Bizarre attractions include John Joseph Moakley United States Courthouse (one of the most picturesque locations in the city), Legal Harborside (a 20,000-square foot seafood emporium), and The Boston Tea Party Ships and Museum.

 Beacon Hill: Unique sites include The State House (across from the Boston Common and built in 1978), Red Wagon (the best shop in Boston for indulging your inner child), and the Granary Burial Ground (where Paul Revere is buried!).

 Historic Downtown: Must-visits include The Orpheum Theatre (a Boston “insider’s secret”), historic taverns and pubs (The Black Rose and the Green Dragon Tavern, among others), and the Haymarket (Boston’s centuries-old outdoor market).

 Chinatown:  Bizarre attractions include the site of the Boston Massacre, the China Pearl (the best restaurant of more than 200 in Boston’s Chinatown), and Kam Man Foods (unique grocery specializing in Chinese foods, herbs, and much more).

Book Tours


In addition to simply visiting some of these sites, your group will love booking a few tours during your stay in Boston. Many locations will offer private tours that can accommodate the unique needs of your group, but you’ll have to book in advance and plan your arrival time accordingly to make the most of these opportunities.

Some of the more unique offerings in Boston include tours of Fenway Park and the Freedom Trail, cruises on the Boston Harbor, whale watching excursions, duck tours, and historical sightseeing tours in one of the city’s iconic trolleys.

Plan Distractions

As you travel from location to location, you’ll need more than just playlists and radio to keep you entertained. To keep your group engaged and having fun, plan some games as healthy distractions. Some examples of games to play on long bus rides include travel bingo, scavenger hunts, and location-specific trivia games.

The best games for your group will depend on how many people you have and how long you have to play. If you keep games relatively short, you can always play multiple rounds or multiple different games when traveling between destinations that are a bit further apart. It’s always better to pick shorter games so that you can finish them before you arrive at your next stop.

Enjoy Your Boston Tour!

 Boston offers so much for you group to see and do. Even if you pack your trip full of tours and locations, there’ll most likely be a good chunk of the city that you don’t get to see. But this only means you’ll have to bring your group back again in the future to see more of Boston’s strangest and most bizarre sites!

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