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night time picture of trolley in front of Boston skyline and holiday lights
nighttime picture of a trellis with Christmas lights in Boston
Nighttime picture of Faneuil Hall in Boston during Christmas with various trees decorated in holiday lights

Experience the Magic of Boston's Holiday Sights & Festive Nights Trolley Tour!

Greetings and welcome to Boston, where history meets the holidays! As we embark on our winter adventure, let’s journey through Boston’s past, present, and future during this festive season. Join our costumed character guides who will regale you with stories of yesteryears and the modern festivities that have made Boston a holiday haven.

Old Town Trolley’s Holiday Sights & Festive Nights Tour: A Great Way to Celebrate the Holiday Season!

Tour Highlights

close up picture of a Christmas tree with holiday lights and a bell ornament
Learn about the Christmas tree tradition
Educational Storytelling
Nighttime Boston picture of holiday decorations including holly leaves and pinecones and a full moon and Faneuil Hall in the background
Learn about the history of the Holidays in Boston.
Seasonal Stories
glass container wrapped in a ribbon and holding candy canes; in the background are holiday lights
All guests will receive a small gift during the Boston Holiday Tour.
Festive Gifts
nighttime picture of a trellis with Christmas lights in Boston
Make this your new annual tradition with friends and family!
Boston Holiday tour
Designed especially for the New England winters, our festive trolleys will give you more than just a warm welcome.
Heated Trolleys

A Dickensian Adventure on the Holiday Sights & Festive Nights Trolley Tour:

Our journey begins with a “Dickens of an adventure.” As we traverse the city, you’ll learn about Christmas in the time of the Colonists and even Charles Dickens’ stay at the Omni Parker House. See how contemporary Boston celebrates the festive season.

Boston Common:
Make a stop at the Boston Common, where the magic of the holidays comes to life. You’ll witness our famous ice-skating rink and discover the fascinating history behind Boston’s annual Christmas tree from Halifax, Nova Scotia. This is a fantastic opportunity for a family photo that captures the holiday spirit.

Charles Street:
Relax as we take you down Charles Street, one of Boston’s most historic thoroughfares. Let its elegant decorations transport you to holidays of the past. Learn about the renowned writers and artists who called this street home and even the Royal family’s Christmas stroll in the winter of 2022.

Tickets & Schedule


Trolley Stop 1:
The Marriott Long Wharf, 200 Atlantic Ave.


December 1-30, 2023.*
Check the reservations calendar for departure times.


Approximately 90 minutes.
Reservations are required.

price tag


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2023 Holiday Events

November 21
Boston’s Official Holiday Tree Arrival
Public Garden
11 am

November 30
Boston Common Tree Lighting
139 Tremont Street
6 pm – 8 pm

November 30
Holiday Music in the Courtyard
Isabella Stewart Gardner Museum
6 pm

December 1-24
Holiday Pops Symphony Hall
301 Massachusetts Ave.
3 pm – 7:30 pm

December 9
Jr. League of Boston Holiday Market
District Hall, 75 Northern Ave.
11 am – 4 pm

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