Top Boston Pop Culture in 2026

Discover some of Boston’s deepest, darkest secrets that lots of tourists miss out on by joining this “frightseeing” tour aboard the Trolley of the Doomed, which roams around the haunted streets and burial grounds of Boston. Your costumed host provides illuminating insights into the history of the city's spookiest sights, such as Copp’s Hill Burying Ground.

Explore the best of Boston at your own pace on a hop-on hop-off trolley tour of the city. Choose from a 1- or 2-day pass and see Boston’s top attractions, including the USS Constitution, the original bar from TV show “Cheers,” and the Faneuil Hall Marketplace, to name a few. The pass includes discounted admission to the Boston Tea Party Ships and Museum, to enjoy during or after the tour.

Experience the best of New England’s marine wildlife on this guided whale-watching cruise around the Stellwagen Bank National Marine Sanctuary. Hop on a high-speed boat in Boston that gets to and from the whales in the least amount of time possible. Look out for humpback and fin whales, plus Atlantic white-sided dolphins, with the help of a naturalist guide. The on-board galley offers food and beverages for purchase during the trip.

Relive one of the most important events leading up to the American Revolution and learn about a side of the story most tourists miss on this guided tour of the Boston Tea Party Ships and Museum. Explore authentically restored tea ships with the help of a guide as you get their insights into this pivotal event, and throw some of your own tea into Boston Harbor. It's an ideal experience for American history buffs, tourists, and locals alike.

Explore the eerie side of Boston as you take a stroll through some of its most haunted locations with a local guide. Learn about Boston's rich history and the ghosts who inhabit its hallowed halls. Perfect for history buffs and thrill-seekers alike, this 1.5 mile, 90 minute walking tour offers a unique glimpse into the city's haunted past...and present. This is a small group tour, limited to 15 guests, so you are part of a conversation, not a lecture. - Visit some of Boston's most historic and haunted sites - Hear chilling tales of ghosts and supernatural events - Ideal for history lovers and those seeking a thrilling experience - Expert local guide provides insights into Boston's haunted history

History, haunts, and hops: that’s what you can expect during this guided walking tour of Boston’s pubs. If the stories are true, then you’ll visit watering holes where ghosts and ghouls roam. Boston’s bloody history is no tall tale: you’ll pass by sites like the King’s Chapel cemetery and Granary Burying Ground to learn about those who died fighting for American independence. This pub crawl is an intoxicatingly good time for history buffs desiring an alternative walking tour.

Combine two attractions Boston has to offer—delicious food and rich history—on this walking tour that starts in the popular North End and continues along the Freedom Trail. Taste fresh bread, pizza, and a classic Italian deli sandwich at local stops in this historic Italian neighborhood. Then, walk the Freedom Trail to learn about the American Revolution, all while enjoying scenic views of Boston Harbor and the Rose Kennedy Greenway. Explore the charming architecture of Beacon Hill and experience the city's blend of old and new.

Explore Boston after dark on a guided walking tour focused on true crime, urban legends, and lesser-known historical events. Led by a local guide, the experience emphasizes storytelling and discussion rather than scripted narration. The small-group format creates an engaging evening experience that presents a different perspective on the city’s past beyond standard daytime tours.

Travel back in time, to the early years of the United States of America, during this guided walking tour of Boston’s Freedom Trail and beyond. Relive the events of the American Revolution as you pass Faneuil Hall, see the Old and New State Houses, and visit the setting of the infamous Boston Massacre. Then head downtown past Boston Common and the modern John Hancock Tower, finishing in Copley Square.

Enjoy one of the simplest ways to discover Martha's Vineyard, and leave all the planning and logistics to someone else, on this hassle-free day trip from Boston. Following pickup directly from your centrally located hotel, take a short ferry ride to Martha's Vineyard. Upon arrival, enjoy free time to explore—or upgrade to add on an island tour that visits its highlights. Complimentary snacks, bottled water, and guidebooks are provided during the drive.

Discover Boston’s top attractions on this comprehensive guided bike tour around the city. See the unique character and charm of each community up close, like the beautiful brownstones in Back Bay and the South End. Visit Boston’s historic North End and pedal past Copley Square and Fenway Park. Cross the Freedom Trail, passing significant locations to United States history.

Discover some of Boston's most notable historic landmarks—and pair your sightseeing with a pizza crawl—on this time-saving, two-in-one walking tour. With just a guide and small group for company, stroll through the city’s oldest neighborhoods, including Little Italy on the North End. Walk along the Freedom Trail to sights including Paul Revere House and the USS Constitution, and head to local pizzerias for three full-size slices along the way.

Boston's history takes a darker turn on this private walking tour, which traces crime stories across the Seaport District, North End, West End, and Faneuil Hall Marketplace. Hear about Italian mob history, the Brinks robbery, Boston Strangler history, political corruption, and the Boston Massacre as you visit related locations, including the South Boston Waterfront and Whitey's garage. A guide-led route gives true-crime-focused travelers a different way to see the city.

This is a self-guided exploration game where you'll be solving a paranormal case involving real people and their wandering ghosts. The file on Boston's North End is still open, and the ghost of Paul Revere walks it with you. You, with your detective and observational skills, and a little help from the Questo app, will try to close it in 2 hours. The route takes you from the waterfront through 13 of the North End's darkest addresses. Your job is to write down the names the history books left out. You'll discover dark stories like the five men killed in the Boston Massacre, the woman hanged as a witch four years before Salem, and the street that drowned in molasses in 1919. Each location involves inspecting a real-world object and solving a challenge. Best after dark with your phone torch on. About 1.6 miles of walking, with unlimited breaks. Hints and 24/7 support available if you get stuck. Perfect for Halloween or any night you're in the mood for creepy ghost stories.

With its centuries of history, it’s no surprise Boston is packed with haunted sights, though they aren’t always easy for visitors to find. On this nighttime ghost tour, follow a guide to some of the city’s most storied landmarks, such as the Granary Burying Ground, Bostom Common, and the Massachusetts State House, and discover the hidden history and spooky sightings associated with each.

Combine horror stories and booze on this haunted small-group pub crawl through Boston. Hear stories about spooky occasions and haunted history in Boston’s past from your guide and hop from pub to pub along the way. Take time to learn about Boston’s architecture and explore four different local bars in the city.

Explore Boston’s lesser-known history on an adults-only true crime walking tour. Led by a local guide, the experience connects real criminal cases to the city’s broader social and historical backdrop, helping you understand how these events influenced Boston’s development. With thoughtful storytelling and curated context, the tour offers a balanced perspective on crime, community, and legacy beyond sensational headlines.

See a different side of Boston on this unconventional walking tour that details the city’s notorious crime and mob history. Led by a local, you’ll stop at places like the South Boston waterfront, the Boston Massacre Site, and Rachel Revere Square, along with lesser-known locations that many locals don’t even know about. Listen to true stories about the mob and serial killers that bring the city’s crime-ridden past to life.

Discover the sweeter and spookier side of Boston on this haunted donut walking tour. Enjoy delicious donuts and sweet treats while exploring the city’s eerie history, ghost stories, and local legends. Visit historic Granary Burying Ground, where famous Bostonians including Paul Revere, Samuel Adams, and John Hancock are buried. Continue past iconic landmarks like Faneuil Hall and Quincy Market before enjoying more treats at Boston Public Market. From there, venture into the historic North End, where narrow streets and old brick buildings provide the perfect setting for mysterious tales. Pass Old North Church and hear stories from Boston’s darker past before finishing at Copp’s Hill Burying Ground. Come hungry and ready for a fun mix of sweets, history, and spooky stories.

This private ghost walking tour reveals Boston’s darker historical legacy. Evening shadows fall across streets shaped by centuries of change. At the Omni Parker House, stories reflect a refined past with mystery. In Granary Burying Ground, encounter resting places of early American figures. What secrets remain among these ancient stones? The Cathedral Church adds a solemn and spiritual presence. Boston Common recalls moments of public justice and transformation. Architectural landmarks stand silent as history unfolds in the night. Each step reveals a deeper layer of cultural memory. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.

Fans of Boston-based TV shows and movies will love this walking tour of Boston Common and Beacon Hill. Step inside the bar where ‘Cheers’ was made famous and see more than 30 filming locations for popular flicks such as ‘Good Will Hunting.’ A local actor serves as your guide and entertains with fun facts about Boston highlights.

Tour the Boston Common and Beacon Hill areas and visit more than 30 movie locations on this captivating private movie and TV walking tour! This tour is a must for film buffs, and is also a great way to explore Boston and its many attractions. On this Boston walking tour, your guide, a local actor, will provide a unique sightseeing tour with an entertaining twist!

Discover the spooky stories behind Boston’s historic places on a self-guided walking tour that lets you explore at your own pace. Turn-by-turn directions lead you through the streets of Boston, from the Boston Athenaeum to the Central Burying Ground, while a narrator shares theatrical tales from the city’s past. Choosing a self-guided tour means experiencing the city on your own terms, with more flexibility than a group excursion offers.