Massachusetts
Off the beaten track

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Our most recommended Massachusetts Off the beaten track

Martha's Vineyard: 6 Town Island Group Tour

1. Martha's Vineyard: 6 Town Island Group Tour

Tour the 100 square mile island of Martha's Vineyard and hear the charming history of its 6 towns from a local guide. As you drive across the picturesque island, admire curiosities like America's oldest carousel and the cliffs of Aquinnah. Start in Oak Bluffs, known for its distinctive Victorian architecture with 300 colorful cottages designed to look like gingerbread houses. Turn a corner and see "The Flying Horse Carousel," America’s oldest carousel, operating since 1876. Continue to Edgartown, with its quaint harbor complete with an 80-year-old lighthouse. A former hub for the whaling industry, admire the stately Greek revival mansions built by ship captains. Travel along the idyllic countryside and small fishing villages before stopping for some clam chowder or lobster bisque in Menemsha. Next, arrive at the technicolor cliffs of Aquinnah before swinging by the bridge made famous in the movie Jaws.

Salem: 1692 Witchcraft Trials Walk

2. 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

3. 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.

Historic Pub Crawl Tour along the Freedom Trail

4. Historic Pub Crawl Tour along the Freedom Trail

Wander along the same cobblestone streets as Paul Revere once did, pass through bustling markets where Sam Adams peddled the idea of revolution. Visit historic bars that have been frequented by Bostonians for hundreds of years. Revisit the story of America's birth and raise a glass as you learn the importance of beer in the founding of America. This historic pub crawl reveals hidden history about the events leading up to the revolutionary war and takes you where it all started: taverns. The four historic taverns visited on the tour are in the Faneuil Hall area and provide a wonderful backdrop as expert guides tell stories about Boston's rebellious past that helped lead to America's independence. Each tavern dates back at least to the 1800's, several even further which includes America's oldest tavern! At each tavern your guide will recommend beer as unique as the history of the city. Most of the beers are exclusively served in Boston and several can only be found in the taverns visited on the tour!

Boston North End Pizza Tour

5. Boston North End Pizza Tour

Pizza is without a doubt America's favorite food. In all, there are over 61,000 restaurants serving pizza in the US, and Massachusetts alone boasts around 1,500 pizzerias. Enjoy a slice from Boston's oldest pizzeria that has a brick oven dating back to 1883, or a slice from a North End pizzeria voted Boston's Best Slice multiple times! Other stops may include a pizzeria named in the Top 25 Best in America, or from an eatery named one of the Top 10 Best Italian Restaurants in the World. Each tour features 3 different slices, all from top-rated Boston pizzerias. You’ll enjoy 2.5 hours of food, fun and history, and finish with a cannoli from a famous North End bakery.

Salem: Grave Matters Cemetery Tour

6. Salem: Grave Matters Cemetery Tour

Start the tour by entering through the main gate of the cemetery where you will be greeted by impressive chest tombs of some of the most prominent individuals of their time. Traversing the paths, see varying different carvings representing mortality, ascension, protection, and grief. Learn about how many of these hand made tombstones are incredibly unique and have stood the test of time, surviving some of the harshest of winters. Admire some of the extraordinarily beautiful stone carvings, many of which have symbolism and poetic remembrances. See the final resting places of some the Puritans who came to Salem and had a major impact on the United States and you will see many recognizable names. Discover how there are still 35 million descendants of these folks in the country so it is possible that may even see your own family name.

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What people are saying about Massachusetts

Overall rating

4.6 / 5

based on 51 reviews

Scotty was a great guide. He shared just the right amount of history to keep us interested and eager to learn more. In fact, we are getting one of the books he mentioned. The pizza and cannoli were delicious and made us want to return. I highly recommend this tour!

the tour was great. An incredible amount was explained which made everything a little more tangible. the lady who did the tour with us was just great. She explained everything so well. If she had done another tour today, we would have done another with her.

Scottie was an excellent tour guide! He was very funny and super knowledgeable. Learned a lot of really interesting history about Boston and the North End. Oh and the pizza was to die for! Excellent experience, would definitely recommend!

Gabby was an awesome guide. Lots of fun and casual. Smart too!!

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