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Freedom Trail Culinary & nightlife

Our most recommended Freedom Trail Culinary & nightlife

Boston: History Pub Crawl Tour Along the Freedom Trail

1. Boston: History Pub Crawl Tour Along the Freedom Trail

Enjoy drinks along the famous Freedom Trail with a local guide on this history tour and pub crawl in one. Uncover the stories left out of 8th-grade social studies while laughing with fellow travelers from around the globe. On this walking pub crawl tour, learn the unknown tales of Boston’s colonial and revolutionary history. Discover how beer played a major role in the founding of the nation, from the landing on Plymouth Rock to the Boston Massacre. Customize your experience by choosing from two different tour options. Pick the happy hour option to enjoy four draft beers of your choice, one at each pub. Go with the dry run tour if you want to buy your drinks as you go.

Boston: North End to Freedom Trail Food and History Tour

2. Boston: North End to Freedom Trail Food and History Tour

Learn about Boston's own Little Italy district of North End and its rich culinary scene. Also, learn about the significant role the city played during the American Revolution on a fascinating guided walking tour of Boston.  Make your way through to the heart of the North End, home to some of the city’s oldest buildings and renowned for its variety of food offerings. Try some fresh bread and Italian meats and cheeses at a hidden bakery. You will also indulge in some sweet local pastries. On the Freedom Trail, explore the Rose Kennedy Greenway, State Street, and the historic Custom House Tower. Then, head over to Old City Hall, which was the birthplace of public education in America. Don’t forget to get a picture of the bronzed Donkey outside the entrance Your tour will finish at the Boston Public Garden. Enjoy the rest of your day relaxing in the park and its beautiful surroundings. 

Boston: North End Pizza Tour with 3 Slices and Cannoli

3. Boston: North End Pizza Tour with 3 Slices and Cannoli

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.

Classic Bites of Boston Tour & Optional Beer Tasting

4. Classic Bites of Boston Tour & Optional Beer Tasting

Boston’s downtown is packed with revolutionary history, but along the Freedom Trail, you’ll also find some of the best examples of the iconic dishes Boston has to offer. Over the course of this 3-hour urban adventure, take a one-of-a-kind stroll through Downtown Boston. Taste classic dishes including Boston Baked Beans and Brown Bread, Clam Chowder, a fresh Lobster Roll and Boston Cream Pie. Plus, you’ll hear about the history of these foods and their rise to popularity in Boston. While this is not your typical Freedom Trail tour, you will visit sites of food-related historical significance along the way. End this tour feeling both full and fulfilled, after experiencing a great introduction to Boston through the lens of local foods. Upgrade your tour to the option which includes a beer tasting. Pair the iconic Boston foods with a local craft beer tasting at 2 of Boston's most historic taverns.

Boston: Freedom Trail Bar Crawl Smartphone Audio Guide

5. Boston: Freedom Trail Bar Crawl Smartphone Audio Guide

On the Boston Bar Crawl and Freedom Trail Walking Tour you and your team will discover Boston’s revolutionary history as you walk the steps of Boston’s famous Freedom Trail. You’ll discover secret history, enjoy famous landmarks, and—of course—drink at the most interesting bars in Beantown. This 2 mile walking experience that takes 3-4 hours to complete. It starts near Boston Common, weaves on and off the Freedom Trail, and finishes in the North End neighborhood. Work together with your friends to solve trivia questions, discover hidden landmarks, and earn points while competing for the top spot on the Brews & Clues Leaderboard! What are you waiting for? Put a team together and get after it!

Other Sightseeing Options in Freedom Trail

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What people are saying about Freedom Trail

Tour guide was amazing. Can't remember his name. Pizza spots VERY GOOD! The best cannoli i ever had. The tour was just long enough but not too long it lost my teenage sons interest. Definitely worth the money.

A great tour and time. The guide was extremely knowledgeable and funny. We learned some much more history then taught in school. And all the pizza was great! Highly recommend.

Maz was an excellent guide. We really enjoyed all of the food tasted during the tour, and the interesting information given along the way. It was a 10 out of 10!

Our tour guide was Meg, she was warm, inviting and knowledgeable! Definitely enjoyed our tour and beer crawl.

Great guide! Exciting, delicious and we had a lot of fun!