Top 10 UNIQUE Things to Do in Boston, Massachusetts 2024

If you have read my perfect weekend itinerary for Boston, Massachusetts, you know there are so many things to do, see, and eat in the city. A weekend doesn’t even scratch the surface for all the unique things there are in Boston! If you have more time to spare on your trip to Boston, check out these 10 unique things to do. From more historic landmarks to off-the-beaten-path attractions, you will discover the hidden gems and unique experiences that Boston has to offer. Whether you’re a local looking for new adventures or a visitor seeking unconventional experiences, Boston’s diverse and dynamic offerings are sure to captivate you.

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Let’s get started with 10 unique things to add to your perfect Boston itinerary:

1. Haunted Boston Booze and Boos Walking Tour

Boston has a rich and complex history from its start, including periods of bloody conflicts and bloodshed. Embark on a spine-chilling journey through Boston’s haunted past with a haunted pub crawl. Discover the city’s dark secrets and ghostly tales as you visit historic pubs with eerie histories. From the ghosts of colonial-era conflicts to haunted Revolutionary War sites, this spooky guided walking tour is a great alternative way to see the city and learn more about its history.

This guided experience is perfect for history lovers and beer lovers alike, with plenty of history and ghost stories shared while sipping on the perfect brew. You will begin your tour by passing by the King’s Chapel and its adjacent cemetery, the Granary Burying Ground, Beacon Hill, and finally, Old City Hall. Explore haunted alleys, hear chilling tales, and enjoy a drink or two in places where spirits are said to linger.

You can expect this tour to last 2 - 2 ½ hours and will be led by a costumed tour guide that is extremely knowledgeable on the history of the area and sights you will be passing. Please note that alcoholic beverages are not included in the price of the tour and are available for purchase at each of the planned stops. You will even get a commemorative can cooler to take home from your experience!

2. North End to Freedom Trail Food and History Tour

Another unique alternative for seeing the city on a walking tour is through this North End to Freedom Trail food and history tour. With the perfect blend of historical knowledge and a foodie’s paradise for trying the best Boston has to offer, everyone in your group will love this guided walking tour beginning in the North End neighborhood and ending at the Freedom Trail. Visit the historic Old North Church and learn about the oldest standing church building in Boston, dating back to 1723, and its role in the American Revolution. Enjoy beautiful views of Faneuil Hall and Quincy Market. You will also learn about the Sons of Liberty and see where the Boston Tea Party took place.

You will be guided by a local with expert knowledge on the history of the city, who will share facts and cultural significance about each of your stops. Included in the tour are three different food stops, where you will be able to sample a variety of fresh breads, pizza, meats, and cheese. There will also be a dedicated drink stop, where you will enjoy a hot Italian beverage and pastry. At the end of your tour, enjoy a surprise local treat that is also included in the cost of the tour.

3. Martha’s Vineyard Day Trip

Martha’s Vineyard is a unique and captivating destination for travelers with its natural beauty and rich island culture. It is home to several beautiful beaches, each with its own unique charm. The island is also dotted with iconic lighthouses that add to the maritime environment. You can make a whole trip out of Martha’s Vineyard on its own, but it is still worth it if you are only able to make it for a day. If you are short on time, this day trip is the perfect way to escape the hustle and bustle of city life and enjoy a peaceful retreat in this laid-back atmosphere.

You will enjoy an air-conditioned and hassle-free ride from Boston to Cape Cod, and then panoramic ocean views of the Nantucket Sound as you take the ferry over to Martha’s Vineyard. Once you arrive, you will be able to explore the island at your leisure, taking in all the beaches, shopping, and dining experiences it has to offer. Or you can upgrade to a narrated island tour, with stops in Edgartown and Gay Head Cliffs. Whether are choose to join the tour or explore on your own, there are so many incredible places to see on Martha’s Vineyard. Check out the Flying Horses Carousel in Oak Bluffs, marvel at the over 300 beautifully crafted gingerbread houses at Martha’s Vineyard Camp Meeting Association, or simply relax on one of the beautiful beaches. Regardless of what you choose, you are guaranteed to have a memorable experience visiting Martha’s Vineyard. This day trip concludes with transportation back to Boston in the evening, with optional hotel drop off if you are staying within range.

4. Boston Seafood Lover’s Tour

A food tour is always a unique way to gain insight and perspective into a city’s culture, and the best way to do that in Boston is by sampling the freshest seafood the East Coast has to offer. Try local favorites like award-winning clam chowder, fresh oysters at a Raw Bar, and full-sized lobster roll. These tastings highlight the diversity and flavors of Boston’s seafood offerings. You will get the opportunity to visit local seafood restaurants and eateries known for their seafood specialties. Enjoy dishes prepared by talented chefs, complemented by regional flavors and ingredients.

A sample menu for this tour could include two starters, a main dish, and a dessert, each at different locations in Boston. This allows you to see different parts of the city while traveling between restaurants, passing by sites along the Freedom Trail and Long Wharf, the oldest commercial port in the city. Walk along the Boston Harbor for scenic waterfront views and stories of the area as told by your knowledgeable guide.

5. Fall Foliage White Mountains Day Trip

Fall in New England is a spectacular season characterized by vibrant foliage, crisp air, and a variety of seasonal activities. Discover the magical time of fall in New England filled with natural beauty, outdoor adventures, and cultural festivities with this seamless day trip to the White Mountains. Enjoy the beauty the region has to offer with no hassle and roundtrip transfer from Boston. You will be picked up in the morning from your hotel to make your way to New Hampshire, stopping along the Kancamagus Highway on your way to the White Mountains.

Enjoy lunch in the charming town of North Conway (not included in the tour price) before continuing your sightseeing journey to the historic Mount Washington Hotel. In the evening, you will return to your hotel in Boston after a long, memorable day. Please note that the tour begins at 6:30 am and you will not return to Boston until late in the evening to allow for the nearly three hour drive each way.

6. Browse the Brattle Bookshop

This beloved and iconic bookstore is known for its rich history, vast collection of books, and unique charm. It has a long and storied history, dating back to its founding in 1825. It is one of the oldest and largest antiquarian bookshops in the United States, with a fascinating legacy that spans generations.

The bookstore is housed in a three-story building in Boston’s historic Downtown Crossing neighborhoods. Each floor is filled with shelves upon shelves of books, ranging from rare and collectible editions to contemporary titles across various genres. One of the distinctive features of this bookshop is its outdoor book carts, located in the adjacent courtyard. These carts are brimming with affordable used books, making it a treasure trove for book lovers searching for hidden gems. It is also renowned for its collection of rare and collectible books, including first editions, signed copies, vintage publications, and unique literary treasures. The staff are passionate about books and literature, and will be happy to assist customers in finding specific titles, recommending reads, and sharing insights about specific literary history.

Overall, the Brattle Bookshop is a cherished destination for book lovers, history enthusiasts, and anyone seeking a unique and immersive bookstore experience in the heart of Boston. The store is open Monday-Saturday 9:00 am to 5:30 pm. Be sure to stop in during your trip for a unique experience!

7. Eat Dinner in a Grand Old Theater

The Empire Garden Restaurant is one of the most unique dining experiences you will find in Boston, known for its delicious Chinese cuisine and inviting atmosphere. Choose from a wide range of dishes that appeal to different tastes and preferences, including traditional favorites like dim sum and fried rice, to specialty items like Peking duck and Cantonese seafood. This restaurant offers a diverse menu showcasing the flavors of China.

Located in the heart of Boston’s Chinatown district, Empire Garden Restaurant is convenient and easily accessible to both locals and visitors. It was built in an abandoned old-fashioned movie theater that dates back to 1903. The building hosted vaudeville shows for decades, until it was transformed into a movie theater in 1947. Today, the restaurant can get extremely busy, particularly between the hours of 11:00 am and 2:00pm. The secret is to arrive exactly at 2:00 pm to be seated almost immediately! The storied past and stunning architecture of the vaulted ceilings of the old theater make the Empire Garden Restaurant a unique place to try exceptional dim sum.

Photo Credit: Metropolitan Waterworks Museum

8. Visit the Metropolitan Waterworks Museum

Located in the Chestnut Hill Reservoir Pumping Station, this historic building that was part of Boston’s original supply system has been transformed into a museum showcasing the history and engineering of water supply in Boston. Explore exhibits highlighting the evolution of waterworks technology, including steam engines, pumps, and filtration systems. The museum’s collection includes large-scale machinery and interactive displays that demonstrate how water was sourced, treated, and distributed in the past. Apart from the fascinating exhibits, the building itself is an architectural gem, featuring grand arched windows, intricate brickwork, and industrial design elements typical of late 19th-century engineering structures. While you’re there, you can also stop by the Chestnut Hill Reservoir and walking trails to enjoy views of the water and surrounding landscape.

The museum is open Wednesday through Sunday from 11:00 am to 4:00 pm, and you can expect to spend 1-2 hours walking through the exhibits. Guided tours are available at 11:15 am, 12:30 pm and 2:00 pm, free of charge. Admission to the museum itself is also free, making it a great free activity to do while in Boston. For more behind the scenes experience, consider booking the special access tour for $18 per person. This experience requires a signed liability waiver for each participant, in order to go fully behind the scenes of the museum.

9. Learn How to Cook an Italian Dinner with Tiramisu

One of the best ways to soak in the culture of a place you are visiting is through the food. For an even more hands-on experience, consider taking a cooking class. Italian heritage has a significant and vibrant presence in Boston, shaping the city’s culture and cuisine. The North End neighborhood of Boston is often referred to as “Little Italy”, and has been a focal point of Italian culture and heritage for generations. Wander down the narrow streets lined with Italian restaurants, cafes, bakeries, and shops.

In this class, you will learn how to prepare traditional Italian dishes, from ravioli and tortellini, to tiramisu. At the end of the class, you will be able to enjoy everything you have made, along with wine and light snacks along the way. You will learn how to create four different types of pasta, along with various appetizers and desserts.

10. Have a Beer at Cheers

For fans of the show Cheers, you will not want to miss a stop at Cheers. Officially known as Cheers Beacon Hill, this bar and restaurant gained recognition and popularity due to its association with the show Cheers, which aired from 1982 to 1993. The bar in Boston is modeled after the fictional show, which was set in Boston and depicted the lives of the staff and regulars at the bar, creating a warm and friendly atmosphere that resonated with viewers.

The design of the interior replicates the bar as seen in the television series and includes elements such as the long wooden bar, bar stools, cozy booths, and memorabilia from the show. The nostalgic ambiance of the bar will make visitors feel like you’ve stepped into a piece of television history. The menu serves classic American pub fare, including burgers, sandwiches, soups, salads, and a selection of beverages, including cold beer on tap. The bar also has a gift shop where you can purchase Cheers-themed merchandise, souvenirs, and memorabilia to take home as a reminder of your visit. Stop in to enjoy this nostalgic dining and drinking experience in the heart of Boston’s Beacon Hill neighborhood.

As we wrap up this list of unique things to do in Boston, Massachusetts, it is evident that this city is a treasure trove of history, culture, and unique experiences. From exploring its revolutionary past at iconic sites like the Old North Church to indulging in the vibrant culinary scene with a seafood tour and haunted pub crawl, Boston offers a blend of the old and the new, the traditional and the unconventional. The exploration of Boston’s rich heritage from its bloody history to its literary gems like the Brattle Bookshop, has revealed the city’s depth and diversity. Whether strolling along the Freedom Trail, immersing yourself in the scenic beauty of the Charles River Esplanade, Boston captivates visitors with its charm and character.

What would you add to this list of 10 unique things to do in Boston?