24 of the Most Unique Things to Do in Boston According to Local Experts

Those taking a trip to Boston for the first time are likely planning to visit some of the most popular attractions. For example, we know you’re looking forward to walking on the Freedom Trail, visiting the Museum of Fine Arts, and other fan-favorite places when exploring Boston for the first time. However, don’t forget there are also many unique things to do in Boston!

If you have more time on your hands or you’ve already been to the top attractions in Boston, you’re probably looking to get off the beaten path.

We have you covered! Immerse yourself in off-the-wall sights and experiences on your next Boston trip. Follow along as we share the most unique things to do in Boston.

1. Stop by the Brattle Book Shop

Whether you’re a bookworm or just a curious traveler, you’ve got to see one of the oldest used bookstores in the United States. The Brattle Book Shop has served the Cornhill section of Boston since 1825.

As one of the nation’s oldest and most expansive used bookshops, the shop carries over 250,000 books, maps, prints, and postcards.

In addition, visitors can find first editions, collectibles, and fine leather bindings. With three floors of books of all genres as well as an outside lot, this acclaimed establishment will please any book lover. You can find the store in downtown Boston at 9 West Street.

2. Admire Art at the Isabella Stewart Gardner Museum

Travel back in time at this museum! Millionaire and fine art collector Isabella Stewart Gardner opened this iconic museum in late 1901, acquiring works and arranging the installations in the museum until her passing.

Serving as one of the finest art collections in the nation, Gardner’s compilation features more than 7,500 paintings, 1,500 rare books, and 7,000 archival objects from around the world, among other things.

As per her will, nothing in the museum has changed since her passing. Guests can roam the premises as patrons did at the turn of the 20th century.

3. Tour the Boston Tea Party Ships and Museum

If you’re looking for unique experiences in Boston, why not relive a historical event that started a revolution?

Located on the same body of water where the Boston Tea Party took place centuries ago, the Boston Tea Party Ships and Museum is a unique experience that everyone will enjoy.

Interact with live actors, lose yourself in the exhibits, admire the centuries-old artifacts, and relive the political protest that changed the course of U.S. history. And yes, visitors will get to board two ships throughout the tour guided by costumed interpreters!

4. Dine in Caffè Vittoria

The oldest Italian cafe in Boston, Caffè Vittoria, is still around and thriving! In fact, it is a beloved local hangout spot in the Boston area. Caffè Vittoria was established in 1929 and served as the first Italian cafe in Boston.

Located in the North End, the cafe serves traditional Italian and Italian American coffee and pastries like cannoli and tiramisu, in addition to gelato. You can also check out the cafe’s antique brew technology!

Moreover, Caffè Vittoria’s hot chocolate or “Cioccolatto Caldo” served with whipped cream has been praised for decades. In addition, the basement of the cafe houses Stanza Dei Sigari, a cigar-smoking lounge ready when you need one.

5. Explore Boston Athenaeum

Looking for artsy things to do in Boston? The Boston Athenaeum is one of the oldest and most prestigious independent libraries and cultural establishments in the nation.

Formed in 1805, the Athenaeum has informed the masses on works of literature, the arts, history, and the sciences for many years. It now contains over half a million volumes.

In addition, the institution houses an impressive art gallery and presents exhibitions as well as sponsors concerts, lectures, and community discussions. As one of the most unique things to do in Boston, you’ll want to check out this historic institution.

Further, guests can find the infamous human skin book in the first-floor reading room. Included in the admission fee, you’ll find the memoir of criminal James Allen (aka George Walton), which is bound in his skin.

6. Visit Historic Burial Grounds

Because Boston is almost 400 years old, the city’s graveyards boast fascinating characters and historical significance around every corner. With three active graveyards and sixteen historic burying grounds, those interested in the macabre won’t be bored.

You can also grab tickets to the Boston Ghosts and Gravestones Tour, which takes guests on a frightful yet fun trip around Boston to explore the city’s frightening past and sinister characters. Along the way, view Boston’s most haunted hotel and learn about the Boston Strangler, serial killer Jolly Jane, and much more.

7. Attend Biweekly Concerts at the Boston Public Library

Looking for fun things to do in Boston? The Boston Public Library isn’t just for silent reading or casual perusing. Once in a while, the place also comes alive with live music by local artists and up-and-coming bands. The entire concert series is sponsored by the Boston Public Library Foundation.

So, when do you need to go to attend the biweekly concerts at the Boston Public Library? The Central Library’s courtyard hosts free, one-hour concerts throughout the summer.

Ranging from jazz to classical and from world to folk, guests can enjoy beautiful music at one of the city’s most lovely spaces in Copley Square. Add this to your list of Boston things to do today!

8. Attend the Observatory Public Nights

Located on the roof of the CAS building at Boston University, the Judson B. Coit Observatory features public open nights and observing projects of the Boston University Astronomical Society.

Judson B. Coit Observatory is open to the public most Wednesday nights. However, please note that tickets are required to participate and that you must arrive early.

Weather permitting, guests will be able to spend a free night stargazing in one of the best places in Boston to do so (and with the best stargazing equipment!).

9. Go Up to the Skywalk Observatory

Open until 8 p.m., the Skywalk Observatory gives fabulous 360-degree skyline views to visitors. Although daytime views provide further views, guests can still gain a fantastic bird’s eye view of Fenway Park, the Hancock Tower, Harvard University, and more at night.

Also, guests can use audio tour headsets relaying intriguing facts about the city. Of the best things to do in Boston at night, visitors should take advantage of this opportunity to see the gorgeous city after hours.

Furthermore, the Dreams of Freedom Museum in the Observatory celebrates the vital role immigrants have played in shaping Boston’s neighborhoods and culture. For instance, one out of every three residents has been born abroad and the city’s population speaks over 140 different languages.

In addition, visitors can enjoy two short films: Wings Over Boston, which gives an up-close-and-personal feel of the city, and Dreams of Freedom, a multimedia journey through time.

10. Attend a Red Sox Game at Bleacher Bar

For quality views of Red Sox games at Fenway Park, you can head to Bleacher Bar before the game and snag a spot by the viewing window.

Situated beneath the bleachers in the park’s centerfield a few feet away from the Ted Williams Red Seat, patrons can expect great views, atmosphere, and food. Spots are first come, first served. We mean it when we tell you to arrive early if you want the best seats while you eat!

Not only will you find traditional baseball food like fries and wings on the menu, but other dishes like salad, hummus, and chowder.

11. Try Out the Thrilling Codzilla

For a thrilling experience on the Boston Harbor, check out Codzilla! This high-speed boat tour goes 40 mph and makes 360-degree spins and hairpin tours.

The 70-foot aluminum boat promises plenty of fun on the water. We recommend securing all loose items (or not bringing them). Open on select dates from May through October, you’ll want to try one of the most unique things to do in Boston.

12. Check out the Boston Harbor Islands

The Boston Harbor Islands National Recreation Area presents 34 islands and peninsulas that enable visitors to see historic lighthouses, as well as hike, camp, fish, and swim.

Moreover, Fort Warren on Georges Island offers tours and fun, educational special events. A short car, ferry, or boat ride away from downtown is one of the most unique things to do in Boston.

13. See the Mapparium

As one of the most unique things to do in Boston, the Mapparium at the Mary Baker Eddy Library gives a three-dimensional perspective of the world of 1935.

Conceived by the Christian Science Publishing Society building architect, Chester Lindsay Churchill, this attraction has now been enhanced with a presentation of music, LED lights, and words. The presentation illustrates how ideas have spread and progressed around the world.

14. Find the Hidden Bodega Store

One of the city’s most popular fashion-wear shops is tucked behind the back of a corner store. To get to Bodega, which has been visited by various celebrities, you have to walk to the back of the store at 6 Clearway Street.

Customers need to slide open the old Snapple machine at the back of the store to visit the shop. Within Bodega, you can find upscale, trending clothes and shoes.

15. Admire the Scarlett O’Hara House

A house or an optical illusion? The Scarlett O’Hara House befuddles passing folks because it’s not a Greek Revival-style home. In fact, the brick wall showcasing the front porch design was painted in the 1980s to beautify the area between two historic brownstone homes.

Located in the Beacon Hill neighborhood, you can find the space at 3 Rollins Place.

16. Unwind at Captain Jackson’s Colonial Chocolate Shop

Named after Captain Newark Jackson, a mariner who operated a colonial chocolate shop in Boston’s North End in the 1740s, this themed chocolate shop brings a colonial atmosphere and culinary tradition to customers.

Located on the Old North Church & Historic Site, the staff dresses in period costumes and explains how chocolate was produced in colonial times.

Further, visitors can sample chocolate during the tour and purchase American Heritage Chocolate. Note that the ingredients in the chocolate are the same ones used in the 1700s.

17. Stop by the Historical Ether Dome

There are many theatres in Boston, but arguably none designed like the 19th-century operating theatre called the Ether Dome.

The Ether Dome is the place where the use of ether was first demonstrated. A Boston dentist made history at this location in the 1800s when he administered ether anesthetic to a patient just before the patient underwent surgery for tumor removal.

Aside from the interior architecture, which has received minimal changes throughout the decades, it’s pretty cool to visit a place where the historical demonstration of anesthesia first occurred. After all, this event helped transform the world’s medical practice as we know it today. Visiting this attraction is one of the most unusual things to do in Boston, but also the most interesting! So go ahead, add this to your list of “unique things to do Boston”!

18. Take a Trip to the Utopian Brook Farm

As you can see, there are tons of quirky things to do in Boston. Another one is to take a trip to Brook Farm, a not-so-ordinary farm located on Baker Street.

Brook Farm remains an authentic Boston attraction for history buffs who want to visit the place where the most famous Utopian commune supposedly started in the United States. In the 1800s, Brook Farm tried its best to equally distribute tasks of daily life while providing education to its people.

Although the intention looked good on the surface, the goal was challenging, and eventually, Brook Farm failed. Today, the Farm still stands as a reminder of their efforts.

19. Visit the Site of the Boston Massacre

The site of the Boston Massacre is right in front of the Old State House, but not a lot of visitors know what happened in the area.

On March 5, 1770, British soldiers fired on the crowd, killing multiple civilians. It was a horror story turned into reality, all because a mob of colonists protested taxes outside of the old State House.

Once a year, on the Saturday closest to the date of the Boston Massacre, reenactors re-create the events of this night. If you’re lucky, you’ll get to watch them relive the past. Otherwise, you’ll still be able to see the circular cobblestone design that honors where the fallen patriots lay.

20. Check out the World’s Largest Insulated Van de Graaff Generator

Nope, you’re not in Einstein’s futuristic lab, but it sure feels like it if you go inside the room where the world’s largest insular Van de Graaff generator is located.

The Boston Museum of Science contains many interesting exhibits, but an up-close look at energy in action is arguably one of the most fascinating. The Van de Graaff generator is a colossal contraption that contains an average of two million vaults that surge through the 40-foot-high machine. Seeing this with your two eyes is one of the coolest things to do in Boston this weekend.

You can spend hours just standing in awe of the cracking displays of indoor lightning, so it makes sense that this generator remains the star of the museum’s Theater of Electricity.

21. Tour the Metropolitan Waterworks Museum

Eager to see one of the country’s first metropolitan water systems? The Metropolitan Waterworks Museum holds remarkable steam-powered pumping engines that were used to pump water for Boston 24/7.

Some people don’t appreciate the importance of waterworks systems that we have today, but a visit to the Metropolitan Waterworks Museum teaches guests about its relevance to public health and safe water access.

For this reason, a trip to this unique museum is ideal for those who want to engage their curious minds, no matter their age. We agree it’s one of the most unique Boston experiences!

22. Behold the Mysteries of the First Spiritualist Temple

A visit to the First Spiritualist Temple qualifies as one of the most unique things to see in Boston, as well as arguably one of the most obscure things to do in Boston. Others call it weird things to do in Boston.

The First Spiritualist Temple is America’s original house of worship for Spiritualism. Basically, it’s a religious movement that believes in communing with the dead.

The exterior architecture of the building is intimidating, to say the least. You’ll find ghostly faces carved onto the corners of the building, which is just one of the few external clues to the building’s purpose.

23. Dine at the Union Oyster House

You won’t find a lot of nearly 200-year-old restaurants in Boston. However, the Union Oyster House has been serving guests since 1826. To this day, Union Oyster House still serves oysters, clams, and scallops among other seafood favorites.

The history embedded in this building goes way back, even before the restaurant opened its doors. The exiled Prince Philippe of France used to live on the second floor.

Before that, it was home to the Massachusetts Spy newspaper. With so much history in this place, dining in a centuries-old restaurant is just one of the treats!

24. Visit the Old North Church

Boston is full of natural historic landmarks, and the Old North Church is certainly one of them. Constructed in 1723, Old North Church is considered the oldest standing church building in Boston.

These days, it is an active Episcopal Church. However, during the 1700s, the building’s tall windows used to secretly shine signal lanterns as a discreet way to let the locals know which route was safer to go on.

One lit lantern meant that the British were using the land route, while two lit lanterns signaled that they’d taken the water route. This helped the locals avoid the British troops and go about their days unnoticed.

Explore Unique Things to Do in Boston Today!

The Boston area is one of the most historic places in the United States and has much to offer curious visitors willing to explore its depths.

Whether you’re keen to complete the Freedom Trail to see the historical sites located across the city or wish to do something more unique, there are tons of Boston vacation packages, tours, and ticket combos offered by Tripster. It all depends on the type of experience you’re looking for!

And for those who want to stay longer in Boston, book some of the best Boston hotels for every budget and type of traveler on Tripster. Happy trip planning!

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