Hop aboard the city’s most enthralling Boston sightseeing excursion, Old Town Trolley Tours of Boston! The orange and green trolleys have been providing guests with Transportainment for more than 25 years. Old Town Trolley is the best way to relive history and see all our country’s Cradle of Liberty has to offer.

While on board Old Town Trolley Tours of Boston, you’ll feel as if you’ve journeyed back in time to the era of the first colonists. Imagine how Paul Revere felt when he made his historic “midnight ride”; hear tales of how he and other famous settlers fought for freedom. As the Old Town Trolley makes its way throughout the city, you’ll have the freedom to get off and back on as often as you wish; and there’s always another trolley coming along soon. Boston tours aboard the trolley is the best way to see the sights in the city.

See ancient burial grounds, national historic landmarks like the Old North Church and the Old State House and many of the moving monuments in Boston like Bunker Hill and the site of the Boston Massacre. Experience the magnitude of what our forefathers suffered through as you walk along the Freedom Trail. Boston’s critical place in the history of our country is evident in the many sights you’ll see on the Old Town Trolley Tour.

You can also hop off the trolley to visit chic shops, museums, fine restaurants and the famous pub that the TV show “Cheers” was fashioned after. There’s so much to do and see in Boston and we’ll help you discover it all in a comfortable, relaxing, informative tour. Our expert conductors make the ride even more enjoyable as they delight guests with humorous stories and historical facts about the many points of interest along the way.

One of the most important places in the USA’s past and present, Boston is steeped in history and culture, offering an array of exciting activities and intriguing attractions. And on board Old Town Trolley Tours, you’ll get an up close and in-depth look at it all. So when you’re ready to see everything from Faneuil Hall to Fenway Park, the Boston Harbor and everything in between, take your seat on one of our orange and green trolleys.

Here are just a few reasons why Old Town Trolley is the best sightseeing tour in town:

• 100% Money Back Guarantee (No Questions Asked)

Boston is home to the nation's first public park (The Boston Common 1634 ), the first public library (1653 ) and the first subway (1897 ).

• Boston’s Largest Trolley Fleet with the most frequent pickup service

• FREE Full-Color Boston Guidebook

• FREE Admission to the Old State House Museum

• FREE discount coupons to area attractions and restaurants ($50 value)

• Hop on and off ALL DAY

• More than 100 Points of Interest

In Season: April - November.
Come when there’s a cool breeze in the air or even during the dog days of summer, either way you’ll feel an eerie chill run up your spine. During Boston’s Ghosts & Gravestones Tour, you’ll be spooked by the supernatural and intrigued by the unusual—all a part of hundreds of years of conflict and war, turmoil, disease and strife. On board the Trolley of the Doomed, you’ll soon discover some of Boston’s deepest, darkest secrets and the stories of the tormented souls whom many believe still roam the streets and alleyways….

Walk slowly and cautiously through burial grounds that date back nearly 400 years; keep a close eye on your Gravedigger Guide, who’s likely just as scary as the stories he or she will be relating—each of our expert guides dresses and acts the part of one of our City’s most infamous characters. Learn why many Boston colonists feared being buried alive and be careful not to step too harshly on the many unmarked, unrecognizable gravestones under your feet.

Try to imagine how Bostonians felt when The Boston Strangler was still at large; discover why Jolly Jane was anything but jolly. Learn why and how the Boston Harbor was once a source of many deaths in the earliest days. Watch for signs of life from the other side as you pass by Boston’s most haunted hotel, the Omni Parker House, and listen to the tales of the resident spirits that have haunted certain rooms for decades.

Boston’s original Frightseeing Tour is an evening of phenomenon and fun, a chance to travel back in time to another era and see for yourself if ghosts really do exist. In season, the tour departs daily from the depot next to the Marriott Long Wharf Hotel and is 90 minutes in length. Come with an open mind and see what apparitions are revealed—it’s a ride on the dark side that you’ll always remember.

RESERVATIONS ARE REQUIRED!

There’s no better way to teach children history than to allow them to relive it. On the Old Town Trolley Educational Tour, middle-schoolers are able to do just that. Boston’s best three-hour historical field trip transports students back to the days of the American Revolution and introduces them to the Sons and Daughters of Liberty.

Their costumed guide will enlighten and entertain them as the tour takes the students to historic sites in Boston. Along the way, they’ll be engaged in a narrative that discusses the events that led to America’s independence. The students will see documents and artifacts, hear period music and speeches and be a part of various interactive presentations. They’ll have a chance to participate in fun onboard activities that help them learn more about how our country was born and the amazing tenacity of the Americans that came before them.

Old Town Trolley‘s Sons and Daughters of Liberty Tour adheres to and incorporates standards from the National Council for the Social Studies and offers both teachers and students a marvelous experience. Visiting sites that are significant to our past and discovering the real story behind the American Revolution, each student leaves with a deeper understanding of who they are and how our country became the nation it is today.

For a memorable and invaluable hands-on, educational experience, Old Town Trolley Tours has the ticket. Find out about our special discounts and promotions for teachers. The road to the revolution begins with a seat on board our orange and green trolleys.

50 to 60 "Sons of Liberty," disguised as Mohawks, protested the 3 cents per pound British tax on tea by dumping chests into the Boston Harbor on December 16, 1773. And the improper Bostonians repeated the performance on March 7, 1774.

In Season: Saturdays from January - April.
Ask yourself this question…is there anything more decadent that chocolate? If you answered no way, then Boston’s Original Chocolate Tour is just right for you. It’s an afternoon of palatable delight, featuring an array of chocolate treats that will tantalize every one of your taste buds.

Aboard Old Town Trolley Tours Original Boston Chocolate Tour, you’ll learn how many of your favorite chocolate desserts, like Tollhouse Cookies, originated right here in the Boston area. Your expert host will take you on a tour of three of the area’s most well-known establishments for some of the world’s most delicious chocolate experiences.

At the Top of the Hub in the Prudential Center, you’ll not only be treated to an unusual chocolate treasure - you never know what the featured dish is until you arrive; you’ll also catch a view of the city from more than 50 stories in the air!

You’ll also visit two other magnificent restaurants: the Omni Parker House Hotel—home to the very first Boston Cream Pie and the Langham Hotel! If your sweet tooth is bold enough, you’ll blissfully devour more scrumptious chocolate sensations. Along the way, some local chocolatiers have also provided a selection of chocolate creations for you to enjoy.

Ten percent of U.S. Recommended Daily Allowance of iron is found in one ounce of baking chocolate or cocoa.

Old Town Trolley’s Original Chocolate Tour is a sweet departure from the ordinary sightseeing tour. What a better way to spend the day!

RESERVATIONS ARE REQUIRED!