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Best Road Trip Destinations: Boston

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The Boston skyline at night

There’s no city more New England than Boston, so when you’re looking to get a taste of the East Coast, make sure this city is on your road trip destination list. Located on the Massachusetts Bay and considered one of America’s oldest cities, Boston is perfect for history buffs and bar hoppers alike, ensuring that every member of the family will find something fun to do.

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a historical postcard drawing from 1730 of Boston, Massachusetts
Boston in 1730
Photo: NYPL via Public Domain

Boston is among the most historically rich cities in America as the site of multiple key events of the Revolutionary War, including the Boston Massacre, the Boston Tea Party, the Battle of Bunker Hill, and the Siege of Boston. The city was officially established in 1629, though it wasn’t officially named Boston until 1630. In 1635, Boston opened America’s first public school (the Boston Latin School) making it a mecca for education, even today. Now, it is the location of some of the most renowned universities in the world, including Harvard and MIT, while also having multiple top-ranked hospitals.

What you’ll see

view of Boston, Massachusetts, from the water

History seeps through the pores of Boston, ensuring you won’t turn a corner without seeing something from the past. The city has an extremely diverse demographic, though it’s most known for the Irish culture that still exists today. Whether it’s a valet asking you if he could “pahk ya cah” or an older gentleman regaling you with stories of Boston’s past, there’s no denying you will receive a warm welcome.

Where to stop

A marker from the Boston Freedom Trail, surrounded by red bricks
Boston Freedom Trail marker
Photo: Jennifer Boyer via CC

When you first arrive in Boston, one of the most important sights to see is the Freedom Trail. A 2.5-mile redbrick trail that leads from Boston Common to Bunker Hill, this site will take you to some of the most important landmarks of the Revolutionary War. Along the way, you’ll see the Massachusetts State House, Granary Burying Ground, Old South Meeting House, the site of the Boston Massacre, and the Paul Revere House. The latter is the oldest remaining structure in downtown Boston.

Faneuil Hall Square in Boston, Massachusetts
Faneuil Hall Square
Photo: Robert Linsdell via CC

Along the Freedom Trail, you’ll even find another great place to be — Faneuil Hall Marketplace, the prime location of Quincy Market, South Market, and North Market, which offer a diverse collection of shops selling both food and consumer goods. Faneuil Hall is a great place to spend an afternoon, enjoying local fare and watching the world go by.

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Another good place to take a load off and relax is the waterfront. Here, you will find multiple cruise options, pedal-boat rentals, and even whale-watching tours. There are also plenty of pavement cafés where you can take a break while watching the boats come in and out of the harbor.

View of Boston from the waterfront
The waterfront in Boston
Photo: Marco Nürnberger via CC

Finally, for those of you who aren’t Yankees fans, Fenway Park is a must. There’s nothing better than taking in a game at America’s most loved baseball stadium.

Whether you’re a fan of history, culture, or just exploring new places, Boston is a must-see destination whenever you’re in the New England region.