Massachusetts
Sightseeing Walking Tours

Enter your dates to find available activities

Our most recommended Massachusetts Sightseeing Walking Tours

Boston Fenway Park: 1-Hour Guided Walking Tour

1. Boston Fenway Park: 1-Hour Guided Walking Tour

Explore the historic grounds of Fenway Park, a true Boston icon since 1906. Visit the home of the Boston Red Sox. Become enchanted by the charm of this 109-year-old Boston monument. Be led by a guide on a 1-hour walking tour of Fenway Park. This authentic gem is home to celebrated baseball World Champions from 1903, 1912, 1915, 1916, 1918, 2004, 2007, 2013, and 2018. On the public guided tour, view the stadium and baseball field where Red Sox legends Williams, Yaz, Fisk, and Rice made their mark on Red Sox Nation. See Pesky's Pole and sit atop the world-famous Green Monster, which stands 37 feet 2 inches high overlooking left field. Take in the magnificent sights and breathtaking views of Boston atop the Roof Deck overlooking right field. Finish your tour at the Fenway Park Living Museum collection, which engages fans of all ages by showcasing the vast collection of Red Sox baseball memorabilia. Fenway Park is not only a local favorite but also an international tourist destination visited by fans from over 93 different countries. Upgrade your experience to a private tour that takes you through the same places as the public tour, but also gives you the opportunity to visit exclusive locations (subject to availability). Your guide will let you know what is available that day once you check-in for the tour. With the upgrade, you can cover the Red Seat, Visiting Team Clubhouse, Visiting Team Batting Cage, Red Sox Hall of Fame, Red Sox Front Office and Trophy Case, Batting Titles & Golden Glove Awards Display, State Street Pavilion Club, Warning Track, and Green Monster Scoreboard. 

Harvard: 70-Minute Harvard Tour

2. Harvard: 70-Minute Harvard Tour

What better way to see Harvard than through the eyes of a student! This tour is a 70-minute student-led walking tour of America's oldest university, designed to be a funny and educational journey through Harvard's campus. Beginning in the heart of Harvard Square, you'll be led into historic Harvard Yard by an enthusiastic Harvard student. Enjoy the sights while your guide entertains and inspires with tales of Harvard history and personal experience at the university they call home. You'll get an up-close look at major Harvard landmarks including Johnston Gate, the John Harvard Statue, Memorial Hall, and Widener Library. You'll even become privy to a few Harvard secrets along the way! Whether you're a student visiting colleges or a family on vacation, the Hahvahd Tour is undoubtedly the top way to see Harvard.

Salem: Haunt and History Guided Night Tour

3. Salem: Haunt and History Guided Night Tour

Take a 1 hour and 20-minute walk through Downtown Salem's most historic and haunted outdoor areas. Although every tour is slightly different, each tour visits about 10 locations. See 2 cemeteries, the Witch Trials Memorial, the location where an accused witch was tortured to death, filming locations from the movie Hocus Pocus, the Old Salem Jail, the site of the Salem Witch Dungeon, among others. Start the tour at 127 Essex Street in Downtown Salem where you will join a local historian and paranormal investigator who will lead the experiece. Embark on a casual walk through Salem's beautiful, historic and haunted downtown. Take the time to stop and hear stories about Salem's haunted, dark, and surprisingly inspiring history.

Salem: 1-Hour Haunted Ghost Tour

4. Salem: 1-Hour Haunted Ghost Tour

Meet your tour guide and venture through 8-12 different sites around the city, each one spookier than the last, starting with the historical Salem Old Town Hall. Continue down the eerie streets to explore the Old Burying Point Cemetery, a preserved burial ground that was established in 1637 where some prominent pilgrims and town officials were buried. This haunted tour takes you to different sites and reveals their true stories so that you can feel connected to the history that took place there. Experiencing these stories while at the sites where they occurred is a truly unique experience that can’t be recreated by simply reading about their history.  During your tour, find out how Salem became the center for all haunted happenings. The phenomenon is partially explained by Salem’s rich history and the fact that many of its oldest structures and sites are preserved today, including the famed Witch House.  Salem’s commitment to preserving this history has made it a perfect spot for spirits to linger and for visitors to experience a connection with the past.

Salem: 1692 Witchcraft Trials Walk

5. Salem: 1692 Witchcraft Trials Walk

Explore this history of the infamous 1692 Salem Witchcraft Trials on a 1.5-hour walking tour of the city. Listen to tales of the fear, political turmoil, and family rivalries all help fuel the hysteria that pitted neighbor against neighbor and family members against each other. Starting from the local partner's office, visit the jails where suspected witches were held, the court house, and homes of the judges and accused. Discover how two girls having fits transformed into a frantic quest to expel the Devil, leading to the deaths of 25 innocent people. 

Cambridge: Harvard University and MIT Combo Walking Tour

6. Cambridge: Harvard University and MIT Combo Walking Tour

Get unique insights into life at Harvard and MIT on a student-led walking tour. Discover the secrets and traditions of each school from your guides, current students that were once visitors themselves, and understand what you want to see and learn.  Your tour begins with a visit to Harvard. Set out to explore the ivy league school, learning about its history, culture, and famous alumni. See sights like Harvard Square, Johnston Gate, Harvard Yard, the Science Center, Memorial Hall, the Harvard Lampoon, the John Harvard statue, and more.  Next, head to Kendall Square to begin your tour of MIT. Meet the students creating the science and technology of tomorrow and hear about the history of another of America's top institutions. Learn about MIT traditions and culture as well as famous inventions and the MIT alumni that came up with them. 

Salem: Haunted Footsteps Ghost Tour

7. Salem: Haunted Footsteps Ghost Tour

Get an introduction to the history of Salem and discover local ghost stories on a guided 1.5-hour walking tour. Visit at least one cemetery and several buildings known for paranormal activity. Listen to dark tales of accidental death and murder. Hear about a man who was murdered for his treasure by his heirs and a woman who died in a fire and continues to haunt the home. Learn about the various unexplained sightings in some of the older structures in the city. Your tour will end in the downtown area, where your guide will direct you to wherever you'd like to visit next.

Boston: 2.5-Hour Walking Tour of the Freedom Trail

8. Boston: 2.5-Hour Walking Tour of the Freedom Trail

See all 16 of Boston's Iconic Freedom Trail sites in a single 2.5-hour tour with an experienced guide. Learn about icons like Paul Revere and John Hancock, along with lesser-known stories of women, African Americans, and immigrant patriots and pioneers. Discover tales of rebels, gangs, and Midnight Riders, with a few cheap dad jokes for good measure. Gain an understanding of Boston's role in the American Revolution and how the city became a pioneer in the fields of abolition, American education, and immigration. Start your tour opposite the Massachusetts State House and finish in the North End with the best view of the Charlestown Freedom Trail sites. Along the way, experience the explosive events of the American Revolution like the Boston Tea Party and the Boston Massacre in the places they happened.

Plymouth: Ghost and History Night Tour

9. Plymouth: Ghost and History Night Tour

Meet your guide in downtown Plymouth and embark on an adventure through 400 years of history and hauntings. Start the tour at the beautiful haunted cemetery, where you will be encouraged to participate in the paranormal investigations with your guide. Continue on past Plymouth Harbor and into the historic streets of downtown Plymouth. Listen as your expert guide shares ghost stories and anecdotes about the darker history of the city. The entire tour is completed on foot for approximately 1.5 miles.

Boston: Historic Walking Tour of the Freedom Trail

10. Boston: Historic Walking Tour of the Freedom Trail

Learn about the tumultuous 15-year period that culminated in the American Revolution on this small-group walking tour. As you walk through Boston, you’ll follow the footsteps of colonial Bostonians, all of whom grappled with the difficult question of loyalty or rebellion to crown and country. Start your walking tour on Boston Common, where the Freedom Trail originates. From there, you'll begin your walk along the historic Freedom Trail with your guide. Along the way, learn the significance of landmarks such as the Granary Burying Ground, the Old South Meeting House, the Boston Massacre Site, the Old State House, Faneuil Hall, and more. Your walking tour concludes at either Faneuil Hall (1.5-hour option) or Copp's Hill Terrace (2.5-hour option). The 1.5-hour tour visits 11 of 16 official Freedom Trail landmarks and the 2.5-hour tour includes views of all 16 official landmarks.

Frequently asked questions about Massachusetts Sightseeing Walking Tours

What are other things to do than Sightseeing Walking Tours that are worth visiting in Massachusetts?

The other unmissable things to do in Massachusetts are:

Which Massachusetts Sightseeing Walking Tours are taking additional COVID-19 precautions?

Other Sightseeing Options in Massachusetts

Want to discover all there is to do in Massachusetts? Click here for a full list.

What people are saying about Massachusetts

Overall rating

4.7 / 5

based on 2,161 reviews

I had a wonderful time with Deniss! She was warm, energetic and took the initiative to ask me about the areas I wanted to explore beforehand. She showed me around some of the more unique landmarks in seaport and brought me to a lovely tea house! She even shared pieces of Boston’s history and some travel tips with me which was a huge bonus! At the end of the tour, she was even kind enough to show me the way back to my student accommodation as it was my first time taking the T. A great experience!

Our tour guide, Mark, was very knowledgeable, informative, encouraging, and entertaining. He brought an engaging perspective to the varied sites we visited! A great tour for those who enjoy history!

A great tour. Highly recommended for all sports, stadium and history fans.

Great tour! Informative and fun. Our guide, Caitlin, was excellent

A very beautiful place with a lot of history. I love it