What are the Most Unique Things to Do in Boston?

November 20, 2019

With an abundance of fascinating history, cultures, architectural beauty, and green spaces, Boston showcases something for any visitor.

Those taking a trip to The Hub can see such significant markers like the USS Constitution, the Old North Church, and Faneuil Hall, as well as a myriad of world-class museums, theaters, restaurants, and beyond. But if you want to see more off-the-wall establishments and fixtures throughout the city, we have you covered. Read below to see the most unique things to do in Boston.

Unique Things to Do in Boston

Chris Ball / Flickr

1) Brattle Bookshop

The Brattle Bookshop has served the Cornhill section of Boston since 1825. One of the nation's oldest and most expansive used book shops, the shop carries over 250,000 books, maps, prints, postcards, and more. In addition, visitors can find first editions, collectibles, and fine leather bindings in its rare book room. With three floors of books of all genres as well as outside lot, this acclaimed establishment will please any book lover. You can find the store downtown at 9 West Street.

2) Isabella Stewart Gardner 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. One of the finest art collections in the nation, Gardner collected more than 7500 paintings, sculptures, furniture, textiles, silver, ceramics, 1500 rare books, and 7000 archival objects from around the world. As per her will, nothing in the museum has changed since her passing, and guests can roam the premises as  patrons did at the turn of the 20th century.

3) Caffe Vittoria

Established in 1929, Caffè Vittoria 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, tiramisu, and gelato. Moreover, their hot chocolate or "Cioccolatto Caldo" served with whip cream has been praised for decades. Additionally, the basement in the cafe houses Stanza Dei Sigari, a cigar smoking lounge. You can access their menu here.

4) Boston Athenaeum

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, sciences, and more, now containing over half a million volumes. In addition, the institution houses an impressive art gallery and presents exhibitions and sponsors concerts, lectures, and community discussions. 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 memoirs of criminal James Allen (aka George Walton), which are bound in his skin.

view of major thomas seward's gravestone in Copp's Hill Burying Ground in Boston Massachusetts

denisbin / Flickr

5) 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 burial grounds, those interested in the macabre won't be bored.

6) 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 in one of the city's most lovely spaces in Copley Square.

7) Top of the Hub

This upscale restaurant in the Prudential Tower resides 52 floors above the Back Bay area streets, providing extraordinary views and excellent dining. Guests can enjoy live music, fine dining, premium beverages, and fantastic service. Perfect for a night out with friends, colleagues, or your partner, you won't be disappointed by one of the most unique things to do in Boston.

8) 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. Please note that tickets are required to participate and that you must arrive early. Moreover, the Observatory holds Open Nights most Wednesday evenings throughout the year, weather permitting.

9) Skywalk Observatory

Open until 8 pm, the Skywalk Observatory gives fabulous 360-degree skyline views to visitors. Although daytime views provide better coverage, guests can still gain a fantastic bird’s eye view of Fenway Park, the Esplanade and Hatch Shell, the Hancock Tower, the Boston Common, MIT, Harvard University, and beyond. Also, guests can gain access to audio tour headsets relaying intriguing facts about the city. Of the best things to do in Boston at night, visitors should take advantage of an opportunity to see this 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 feel of the city, and Dreams of Freedom, a multimedia journey through time.

Bleacher Bar / Facebook

10) Red Sox Games at Bleacher Bar

For quality views of Red Sox games at Fenway Park, you can head to Bleacher Bar early before games 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. First come, first serve, you can't reserve seating, so we mean it when we say to arrive early if you want the best seats while you eat. Also, not only can you find traditional baseball food like fries and wings, but you can also order salads, hummus, chowder, and other menu items.

11) 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. This 70-feet aluminum boat promises fun on the water, and we recommend securing all loose items (or not bringing them). Open on select dates 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, hike, camp, fish, swim, and more. Further, Fort Warren on Goerges Island offers tours and fun, educational special events. A short car, ferry, and boat ride away from downtown, this is one of the most unique things to do in Boston.

Smart Destinations / Flickr

13) The Mapparium

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) 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) The Scarlett O'Hara House

A house or an optical illusion? The Scarlett O'Hara House has befuddled passing folks because it's not a Greek Revival-style home whatsoever. In fact, the brick wall showcasing the front porch design was painted in the 1980s to beautify the area between to historic brownstone homes. Located in the Beacon Hill neighborhood, you can find the space at 3 Rollins Place.

16) Captain Jackson's Historic 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. Also, note that the ingredients in the chocolate are the same used back in the 1700s.

Try Some of the Top Unique Things to Do in Boston

Now that you know some of the off-beat things to do throughout the city, where will you go to first? Let us know!

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