Massachusetts
Sightseeing Walking Tours

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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. 

Salem: Haunt and History Guided Night Tour

2. 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.

Harvard: 70-Minute Harvard Tour

3. 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: 1692 Witchcraft Trials Walk

4. 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. 

Salem: Haunted Footsteps Ghost Tour

5. 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 Freedom Trail Walking Tour

6. Boston: 2.5-Hour Freedom Trail Walking Tour

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.

Boston: Historic Walking Tour of the Freedom Trail

7. 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.

Boston: Freedom Trail Tour

8. Boston: Freedom Trail Tour

Start the tour from the official Visitor's Center on America's first public park, The Boston Common. Meet your colonial-costumed historical interpreter and guide before embarking on a journey through Boston's colonial history. Spot lots of incredible historical sites along this short 1.2-mile stretch between The Boston Common and Faneuil Hall. Pass by the Granary Burial ground where American Fore Fathers are buried, and the site of the world-famous Boston Massacre. Also discover the Park Street Church, America's first public school, the site of The Boston Tea Party, the Old State House, and the Old South Meeting House. Finally contemplate Boston's most visited attraction, Faneuil Hall.

Boston: Italian Food Tour with Pizza, Meats, Cheese, & Bread

9. Boston: Italian Food Tour with Pizza, Meats, Cheese, & Bread

Your North End experience begins at the lifeblood of Boston, the Boston Harbor. Walk through a scenic waterfront park, with views of the harbor, East Boston and the historic wharfs lining Atlantic Ave. Make your way to the heart of the North End, with views of some of the most historic sites and properties in the neighborhood, some dating back to the late 1600s and early 1700s. Delicious food is never far away in the North End. Your guide will introduce you to a small, hidden Italian bakery serving up fresh bread daily. Break bread with your fellow travelers and let the carbs give you the energy to continue your adventure! A proper Italian salumeria is next, and you’ll have a chance to enjoy Italian meats and cheeses at their finest and freshest.  Next up, take in the energy of the North End’s busiest corridor, Hanover Street. It’s time for a mid-tour break with your guide at a traditional Italian café. Here, you will have a chance to enjoy your choice of a classic cappuccino, espresso, or tea. Let the caffeine kick in as you go back in time into North End history. You’ll hear stories about some of the most influential events that have happened in Boston, including Paul Revere’s midnight ride. Make your way to the Old North Church and step inside the hallowed walls. To this day, North Enders still attend this church, which is famous for its role in the Revolution.  After church, dive deeper into the local side of the North End. A taste of pizza awaits at a neighborhood favorite and the stories are endless. Cap off the North End food experience with samples of the best of the best Italian pastries along the backstreets of this delicious neighborhood. Hopefully, there will be a chance to meet and chat with the area’s top bakers if you catch them at a quiet moment.  After the tour, you’ll surely be ready to make a dinner reservation. Consult with your guide for the best recommendations and you will be set up for an amazing time in Boston.

Boston: Historic Taverns Tour

10. Boston: Historic Taverns Tour

This informative 3.5-hour walking tour visits some of New England’s most historic landmarks, as well as two of Boston's most historic taverns. The tour begins in Boston's oldest neighborhood, the North End. Board a public ferry for a round-trip ride to the Charlestown Navy Yard. Here, you'll see the USS Constitution aka "Old Ironsides", and Bunker Hill Monument. Walk through the Blackstone Block, and discover the true location of the "Boston Stone". See the Old State House, Faneuil Hall, and Quincy Market. The tour includes two tavern visits and one drink at each stop plus snacks.

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What people are saying about Massachusetts

Overall rating

4.7 / 5

based on 2,161 reviews

Julia (Jules) was a great guide - enthusiastic, passionate and knowledgeable about her history, she brought the tour to life with vivid details and stories of the subjects and events of the tour. I brought two 13 year olds and a 10 year old, each who had studied the American Revolution/Colonial America in school. This was a perfect supplement to their book studies. The kids were FULLY engaged the whole time, connecting things Julia said to the things they had learned in school. My youngest said at the end, "I didn't know history could be this interesting." Thank you, Julia, for lighting a spark, bringing the past to life for us, being charming and engaging, and an excellent guide for our day in Boston!

The tour was excellent. Our tour guide "Schmu" was great. He was very knowledgeable and had a good sense of humor. We learned so much history on tour. I would recommend the tour to anyone visiting Boston. Again, our tour guide was the best!

Scotty was a great tour guide. He had a great sense of humor & his historical info was informational but with a comedic side. Three pizza places were yummy & cannoli was delish! I enjoyed this tour.

Martin was an excellent guide! He made the tour informative and fun !

This was a fascinating tour. We really enjoyed ourselves.