From Boston’s secret jazz spot to the tea on Boston’s neighborhood, the city contains hidden gems even locals might not know about. Whether you’re renting a house in Boston, looking for a house to call home in the city , or searching for an apartment to rent in Boston, check out this Rent. article we were featured in for Unique Things to Do in Boston.
1. Wander through a palace
“For a unique Boston experience, explore the Isabella Stewart Gardner Museum, where art and architecture meet in a stunning Venetian-style palace with a mysterious unsolved art heist in its history,” recommends David, the world explorer behind the blog, My Travelation.
Founded by art collector and philanthropist Isabella Stewart Gardner in 1903, the museum not only houses world-class art but is also a work of art itself. Gardner herself arranged each piece according to her personal vision, and per her will, nothing in the museum can be moved or changed. This means you get a rare experience: seeing the collection exactly as she intended over a century ago. Each gallery within the museum holds pieces from Gardner’s collection, which includes paintings, sculptures, tapestries, and decorative arts from various eras and regions.
If you have time after exploring the museum, David has some recommendations on nearby attractions. “Take a stroll along the nearby Emerald Necklace, a series of serene parks designed by Frederick Law Olmsted, offering a peaceful escape from the city’s hustle.”
2. Try authentic Vietnamese coffee and bahn mi
The first wave of Vietnamese immigrants came to the U.S. in the 1970s, bringing Vietnamese coffee culture with them. In Boston, cafes started popping up everywhere, especially in neighborhoods like Dorchester and the South End, where the Vietnamese community flourished. The French also had a hand in influencing colonial Vietnamese cuisine, offering a fresh flavor experience.
One unique thing to do in Boston is experience the result of French and Vietnamese flavor blending, and you can do so at a lesser-known gem known as Phinista Cafe in the South End. The cafe’s name nods to the traditional Vietnamese “phin” coffee brewing method, which involves slowly dripping coffee through a metal filter, resulting in a rich, flavorful brew.
Try the signature phin coffee for a rich, authentic Vietnamese flavor. Pair it with a crispy baguette filled with pickled veggies and grilled meat, known as a bahn mi, for a fun and unique brunch combo in the culturally-rich South End neighborhood of Boston.
3. Find some of the best jazz music in Boston
While you’re in the South End area, a newer hidden gem to Boston is Long Live Roxbury – a brewery and taproom tucked away in an old brick warehouse that used to be a piano factory. Inside, however, you’ll be greeted with modern and fresh decor, and if you come on a Thursday night, the sweet sound of live jazz.
Located nearby to the infamous Berklee College of Music, Long Live is the perfect venue for past and present affiliates of the music school to share their talents with the local community while you sip on some of the best local beer around.
The welcoming atmosphere, fantastic brews, and focus on community-building events might just make Long Live one of the hottest new spots in town. Grab a 4-pack of beer to-go to keep cheersing to good times long after your visit.
4. Explore Boston’s history and innovation on self-guided tours
Boston’s rich history and creative energy come to life through its iconic tours, offering a unique way to explore the city. Stroll down cobblestone streets, uncovering stories of rebellion, or step into Boston’s buzzing tech hubs where innovation happens daily. These trails let you experience the best of Boston, where history and the modern-day blend into a journey through the city’s unique legacy.
The Freedom Trail
“Boston is an open air museum and the one thing you literally cannot miss is the iconic Freedom Trail,” says Michael Wenke, an operator at Boston’s Revolutionary Story Tour. The Boston Freedom Trail is a 2.5-mile red-brick path that weaves through downtown Boston, guiding visitors to 16 of the city’s most important historic sites.
“It’s completely free to explore on your own,” shares Wenke. “You can walk the whole thing, but there’s a water shuttle that takes you from Long Wharf to Charlestown Navy Yard, and for the price of a subway ride you can get in a mini harbor cruise.”
With many of the sites offering detailed exhibits and reenactments, you can engross yourself in the stories of early American patriots and learn how Boston played a crucial role in sparking independence. To top it off, the Freedom Trail winds through some of Boston’s most charming neighborhoods, giving you a taste of the city’s unique character.
The Innovation Trail
Boston’s Innovation Trail is a self-guided journey through the city’s legacy of creativity and forward-thinking, showing how it’s grown from a revolutionary hotspot into a global leader in science, technology, and entrepreneurship.
“Enter the gates of Harvard Yard to see where the nation’s elite have been educated for four centuries,” reveals Daniel Berger-Jones from the historical tour group Boston History Company. “But don’t miss Kendall Square, where robotics, AI, Biotech and the space industry are being invented daily on the Innovation Trail.”
The trail is an inspiring walk for anyone interested in how ideas are transformed into life-changing solutions, and why Boston remains at the forefront of innovation and progress.
5. Find Boston’s secret, hottest sneaker store
“Tucked away in a random corner store near The Newbury Hotel, Bodega hides its true vibes behind a vintage Snapple machine that doubles as a secret door,” reveals Michelle McCormack, founder of the media service and hotspot finder Secret Boston.
A “secret” store cleverly disguised as an ordinary convenience shop, you can find Bodega in the Back Bay area. From the outside, you’ll see just another small neighborhood shop, complete with drink coolers, snacks, and everyday essentials. But once you step inside and slide open the soda machine door, you’re transported into a sleek, high-end boutique offering rare sneakers, streetwear, and unique designer pieces.
“This isn’t just shopping; it’s an experience, a peek into Boston’s underground culture, where DJs are spinning the latest beat while you shop for the hottest trends in sneaker culture,” emphasizes McCormack. Whether you’re a sneakerhead or just love finding cool spots, finding Bodega is a must for a fun, unique thing to do in Boston.
6. Brush up on your sports history
Located within Boston’s iconic TD Garden, the Sports Museum offers a truly unique experience. Sanjay, a writer for TD Garden Venue, highlights it as a top spot to delve into the city’s rich sports legacy and local history.“Here,” he says, “you can explore the rich history of Boston’s legendary sports teams and iconic moments. The hidden gem inside TD Garden offers an up-close look at the city’s sports culture, memorabilia, and exhibits that fans and history buffs alike will appreciate.” To top it off, you can feel the thrill of experiencing the arena completely empty.
Just a short walk away from the TD Gardens is the Pennyweight Hotel, a central hub to some of the city’s most iconic attractions. Whether you’re searching for a meal as you begin your day or seeking the ideal spot to relax after exploring the city, the hotel’s built-in bar, 155 on Portland, is the perfect place to enjoy elevated American fare. Grab brunch in the deco-inspired dining room, or wind down with craft cocktails on the cozy outdoor patio. With its stylish design and unbeatable location, the Pennyweight Hotel is the perfect place to stay if you’re traveling in the area, or a central location to rest and relax if you’re nearby.
7. Explore Boston’s unique Italian charm
“To really complete your trip to Boston I would be sure to carve out time to organically explore the old Italian charm that lives throughout the North End,” recommends Kayla Crugnale, owner of the North End-based Pia Boutique.
“In the North End, you will find many residents from some of the original families that created such a great neighborhood. There are many mom and pop shops (many around for generations) throughout the two main streets of Hanover and Salem, as well as throughout the crossing streets,” explains Crugnale.
As a business owner in the area of an elevated women’s fashion store, Curgnale knows Boston’s “Little Italy” well. “I would recommend grabbing a pistachio iced coffee from Cafe Dello Sport, a baked treat from Bova’s or a delicious dish from Florentine Cafe,” she shares. “Wander down to the Christopher Columbus Park to take in some water views and fall foliage, if it’s the season.”
Whether you’re doing some local shopping, sampling the extensive Italian fare in the area, or just wandering the narrow, winding streets, you won’t be able to miss the extensive Italian influence while checking out the North End.
8. Sample one of Boston’s famous lobster rolls
“Boston is just the most stunning city,” shares Stefanie Finocchio-Durham, founder of Boston-based acupuncture, massage, and healing space Root + Sky Wellness. “Fully walkable, beaming with history, eclectic, on the water, surrounded by nature, seriously—what else can you ask for? Anyone visiting the city, I tell them they must go to the North End and put their name in at Neptune Oyster.”
Neptune Oyster is a much-loved seafood spot in Boston’s North End, and is known for its fresh, high-quality seafood and cozy, intimate atmosphere. This small but iconic restaurant draws crowds who line up to experience its acclaimed raw bar and famous lobster roll, which is served either warm with butter or cold with mayo. Neptune’s menu changes seasonally to feature the freshest seafood, with options like oysters from both East and West Coasts, daily specials, and creative dishes that showcase New England flavors.
“While you wait for the text for the world’s best lobster roll, go stroll Hanover Street and walk the public gardens, take the ferry to East Boston, and visit the coolest shop there: EBO Grocery and Co. There, you can literally find some of the best wine and coolest provisions,” discloses Finocchio-Durham.
9. Discover the North End off the beaten path
“Just about every visitor to Boston will end up in the North End at least once, but most will only experience the touristy parts of the neighborhood,” says Chris, a member of the popular tour company for off-the-beaten path finds Boston Hidden Gems.
While the neighborhood is known for its bustling Italian restaurants and historic sites, there are plenty of lesser-known spots and local favorites that offer a quieter, more intimate taste of this historic district, making it the perfect base for finding unique things to do in Boston.
“Take photos at the Paul Revere Mall, yes, but just a block away is Charter Street Park, a quiet oasis with a beautiful garden managed by students from an adjacent school,” Chris continues. “Don’t miss the Harborwalk, with gorgeous views across the water and many benches for relaxing.”
This historic neighborhood is home to some of the oldest Italian restaurants, bakeries, and markets in Boston, many of which have been family-owned for generations.
“Finish your day in the North End with an Italian dinner,” recommends Berger-Jones from the Boston History Company. “Chowder, lobster, beer, and some of the nation’s premier art museums are the cherry on the sundae for locals or tourists alike.”
10. Fly amongst the trees on a treetop adventure
Looking for an adrenaline-packed adventure just outside the city? A unique thing to do in the Boston area is TreeTop Adventures in Canton, the perfect escape for young and adult climbers alike. Open spring through fall, the park features a variety of courses and treetop obstacles, including zip lines, netting, tunnels, boardwalks, and auto-belay jumps. It’s an ideal destination for friend outings, birthday parties, a day with the family, or even work groups. No need to travel hours for a day of fun—this unique experience is just a short drive from Boston.
11. Get lost in a sea of purple lilacs
“Located in Boston’s Jamaica Plain neighborhood, Harvard University’s Arnold Arboretum is the oldest public arboretum in North America and a botanical research institution,” shares Boston foodie and blogger Sacha, the face and advice behind Sacha Eats.
The Arnold Arboretum offers 281 acres of landscaped gardens, hiking trails, and beautiful vistas, perfect for year-round exploration.
“Every Spring, you can check out the Arboretum’s collection of over 400 lilacs in bloom. The Arboretum has one of the premier lilac collections in North America, and they even have a day-long celebration called Lilac Sunday that has been ongoing since 1908.”
If you’re looking for cheap eats in the area to accompany your visit to the arboretum, Sacha, a foodie expert of Boston, recommends trying Pikalo for empanadas; or if you’re feeling adventurous, treat yourself to some classic Ethiopian fare at Blue Nile.
12. Wander one of Boston’s most historic neighborhoods
Beacon Hill is one of the oldest neighborhoods in Boston and is filled with classic, beautifully preserved Federal-style homes. The district is full of cozy cafes, unique boutiques, and small businesses, making it the perfect place to grab a coffee and wander around. With the best of Beacon Hill being within a one mile radius, exploring the neighborhood is a great way to spend a day in Boston.
“You must set aside some time to visit historic Beacon Hill,” rave Michael and MacKenzie Donovan, the couple behind the local insights at Stay New England. “Grab a coffee at Tatte Bakery, then head over to Acorn St. to get your picture taken – it’s the most photographed street in all of New England. When you’re done, pop in and out of all the shops that line Charles Street. Finish the day with a stroll through the Public Gardens.”
The Boston Public Garden was established in the 1800s, making it one of the oldest public botanical spaces in the country. Not only will you catch great views of the city skyline, but the path is dotted with distinguished buildings. Wherever you decide to go in Beacon Hill, you’ll be met with stunning architecture and quintessential New England charm.
13. Get a taste for Boston’s beer
Named “Boston’s Best Brewery” in 2023, Roundhead Brewing Company is a Latino-inspired brewpub focusing on small batch beers and creative food combinations from the in-built pizza kitchen.
Everything about Roundhead emphasizes community, from the water sourced nearby to hiring staff from the neighborhood to sourcing ingredients from local farmers. It’s no surprise that the brewing company is known for being welcoming to all ages and community forward—the owners, Luis Espinoza and Craig Panzer, met at their kids’ soccer game.
Espinoza grew up working in his family’s bakery in Peru, which eventually led to the inspiration behind the food and brews at Roundhead. “Making bread is not that different from brewing beer,” explains Espinoza. “When I explained the brewing process to my dad, he told me, ‘Ahora haces pan liquido’: Now, you make liquid bread.”
For a unique Boston beer experience, the heavily Peruvian influenced Roundhead Brewing Company also is home to a giant social room, an upper 21+ patio with a view, and some of the best “liquid bread” around.
14. Make your own Boston-inspired gourmet meal
For a unique thing to do in Boston, dive into the city’s active culinary scene with Selfup cooking classes. Whether you’re a beginner or a seasoned cook, you’ll learn from top chefs in hands-on workshops that celebrate local ingredients and global flavors.
From mastering traditional New England seafood dishes to exploring Italian, French, or fusion cuisine, Selfup offers a memorable way to immerse yourself in Boston’s food culture. Many classes include a communal dining aspect, allowing you to enjoy the fruits of your labor in a relaxed, social setting. Whether you’re looking to improve your cooking skills, learn new recipes, or simply have a great meal, a local Boston cooking class is a perfect activity for food lovers looking to create—and taste—their own gourmet meals.
15. Pay tribute to Boston’s first responders and naval history
The Vendome Hotel Fire Memorial in Boston honors the nine firefighters who lost their lives in one of the city’s most tragic and significant fires. In 1972, a fire broke out at the historic Hotel Vendome, a century-old building located in Boston’s Back Bay. Although the fire was initially contained, a section of the building suddenly collapsed, trapping and killing the firefighters as they worked to secure the area. This tragedy remains one of the deadliest fire fighting incidents in Boston’s history.
“Touch the sculpture of a fireman’s hat and give some gratitude to our first responders. It’ll make your day a bit more intentional,” nods Chris, one half of the nomadic couple behind the travel blog, Eat Walk Learn.
“Don’t miss the sunset gun at the USS Constitution,” adds Wenke from the Revolutionary Story Tour. “They shoot a cannon off the top deck every night as the sun goes down over the horizon.”
The sunset gun at the USS Constitution is a longstanding Navy tradition that takes place at the historic Charlestown Navy Yard in Boston. This ceremonial firing signals the end of the day, as well as the lowering of the American flag, marking the transition from day to night.
This daily ritual, which dates back to the ship’s early years, is both a tribute to naval history and can be a powerful experience. The firing is a reminder of the ship’s active status in the U.S. Navy as the oldest commissioned warship still afloat.
16. Catch a show at the Boston Opera House
“One of the best parts about Boston is its rich history and centuries old buildings,” shares Elizabeth Brosseau, Boston-based author of the travel blog Carry On Only. “Often overlooked among the list of historical sites to visit is the Boston Opera House, also known as Citizens Bank Opera House.”
The Boston Opera House is one of the city’s most breathtaking historic theaters, known for its grand architecture, stunning interior, and top-tier performances.
“Grab a late lunch or early dinner on Newbury Street,” suggests Brosseua. “I’d recommend Faccia a Faccia, La Voile, or the latest hotspot on top of the Newbury Hotel, Contessa. Then, stroll through the public garden and the common to the Boston Opera House for a show. The building’s opulence and elegance will take your breath away. If you’re visiting in December, seeing the Nutcracker at the Boston Opera House should be on your list of things to do in Boston.”
17. Check out the Charlestown neighborhood
Whether you’re a history buff or just love waterfront walking, Boston’s Charlestown neighborhood holds some of the city’s greatest historical moments and monuments as well as beautiful places to relax or recreate along the water.
However, if you’re looking for a more unique thing to do in Boston’s Charlestown area, stop by one of the city’s most friendly neighborhood dispensaries, known as The Heritage Club. “‘Weed’ love to see you,” the dispensary jokes.
The one-stop-shop emphasizes top-tier quality and outstanding customer service, to make this an experience you won’t soon forget. Known as Boston’s first black woman-owned dispensary, The Heritage Club focuses heavily on community initiatives, frequently hosting pop ups, local artists, and supporting other nearby and BIPOC businesses with fun collaborations.
18. Escape the city for an adventurous nature experience
Just a two hour drive west of Boston lies the heart of Sunderland, a rural area that is the center point of many outdoor adventures in Massachusetts. If you’re looking for a unique thing to do in the Boston area that is nature-centered, make sure you check out Adventure East. The adventure company offers outdoor experiences throughout Massachusetts, focusing on the scenic landscapes of the Pioneer Valley and beyond.
From guided hikes in the Berkshire Mountains to kayaking on the Connecticut River, Adventure East provides a range of activities that let people of all skill levels connect with nature in a hands-on way. The experiences are designed to offer immersive journeys through some of Massachusetts’ most beautiful locations, highlighting the area’s natural beauty and abundant wildlife.
With experiences tailored for all seasons, the outdoor experience company offers everything from fall foliage hikes and winter snowshoeing to summer paddling and mountain biking. They also host specialized outings, including birdwatching tours, wellness retreats, and more.
19. Discover Boston’s spooky past on a haunted ghost tour
Boston’s ghost tours give you a unique and thrilling way to explore the city’s rich, and often spooky, history after dark. These guided tours take you through some of Boston’s oldest neighborhoods, weaving stories of colonial-era hauntings, Revolutionary War spirits, and strange happenings in historic landmarks.
Dan Seeger, manager of Boston’s longest-running Haunted Boston Ghost Tours, gives you a taste of what you might experience if you dare to embark on the paranormal adventure.
“Haunted Boston has guided brave souls on spine-chilling adventures through Boston’s historic streets. As night falls, expert storytellers lead you through historic crime scenes, mass graves, and haunted sites, sharing true and eerie tales of restless spirits, unsolved mysteries, and tragic pasts. It’s an unforgettable experience that will leave you questioning what lurks in the shadows,” exclaims Seeger.
20. Visit a holiday market
The Snowport Holiday Market in Boston is a festive, European-style holiday market that transforms the Seaport District into a winter wonderland each holiday season. Set against the waterfront, this popular outdoor experience features over 100 local vendors and artisans offering everything from handmade gifts and crafts to gourmet foods and seasonal treats. With twinkling lights, holiday music, and cozy outdoor seating, Snowport provides a perfect place to get in the holiday spirit.
One stall you must visit at the market is Lizzie’s Bakery, which specializes in decadent cakes and desserts. The marketing professional turned baker has become renowned for her innovative sweets, ranging from classic vanilla with edible gold leaf cakes to a more adventurous fruity pebble themed dessert. Voted Boston’s Best for wedding cakes since 2021 and featured on the Food Network, the pop-up serves world-class cupcakes, cookies, cake jars, cakesicles, and even make-your-own cake tasting boxes – a perfect holiday treat for you or your loved ones.
Unique things to do in Boston to get to know your city
If you’re looking for something off the beaten path, there are plenty of unique things to do in Boston. From quirky activities to hidden local hangouts, Boston contains endless opportunities to experience something new. Part of the fun is uncovering all the little things that make the city so much more than what Boston is known for. Whether it’s your first visit to Beantown, you’re thinking of moving to the city, or you’ve been a local for years, hopefully this list has sparked something new for you to discover in Boston.
20 Unique Things to Do in Boston, MA: The Insider’s Guide to the Best of the City| Rent.
