Boston’s Freedom Trail is a 2.5 mile pathway that links together a unique collection of museums, churches, parks, cemeteries, landmarks, and historic sites that tell the story of the revolution that gave birth to America. It’s also full of hidden gems that make Boston such a unique place to visit. Starting in the shadow of Boston Common (America’s oldest park) and ending at the Bunker Hill Monument, the Freedom Trail is one of the most popular tourist destinations in New England – 4 million folks take this stroll each year. Walking the trail is free, pet-friendly, and worth every second.
Whether you are new to the Trail or a seasoned veteran – here are the best kept secrets spots along the trail (and some not so secret) that you shouldn’t miss on your journey through American history!
The Great Elm
First, you have to start exploring at the Boston Common. Dating back to 1634, the Common is America’s oldest park and was originally used as a common space to graze your cattle, this area also has a more sinister past. In the center of the park, you will find a plaque on the ground marking the former spot of the Great Elm until it fell in a storm in 1876 as the estimated age of 250+ years old. It stood 65 feet tall and was once considered Boston’s “oldest inhabitant”. In the mid-1600’s the Common was also the site of public executions – all done by hanging; many on the Great Elm.
State Street Hopscotch
As you follow the trail down State Street, keep your eyes on the sidewalk to find this ornate hopscotch court that marks the site of the first public school in the English-speaking Americas – Boston Latin. Established in 1635, Boston Latin is still in operation today at its new, more modern location. Famous graduates of the original include Sam Adams, John Hancock, Ralph Waldo Emerson, and Cotton Mather.
Donkey Kong
Continue past the statue of Benjamin Franklin and the former site of Boston Latin, you will find one of the best hidden gems and unique statues on the Freedom trail – a donkey. Many think this statue is a political statement paying homage to Boston’s liberal history and famous Democratic leaders. Nope? This donkey belongs to Roger Webb, the developer who saved this historic area from demolition. he bought the now-famous Boston Burro during a trip to Italy and wanted to find a place to put it. He decided to stick the donkey in his courtyard just off the Freedom Trail. It is now one of the most photographed spots on the entire Trail. Say cheese!
Sam Adam’s Tap House
Do you have a cousin from Boston? If so, you have probably sampled some Sam Adams – the official beer of the Red Sox and Boston! As you approach historic Faneuil Hall, you will see the towering statue of Mr. Adams – a Founding Father and Boston legend. Take a break from your tour and grab a beer at the new Sam Adam’s Boston Taproom. It doesn’t hurt to drink in a little history! Interested in learning more about Boston AND visiting a few more famous bars and pubs along the way? Check out Brews & Clues’ Freedom Trail pub crawl / scavenger hunt – a self-guided walking/drinking through downtown Boston’s best spots.
Eat Your Way Through Quincy Market
The Freedom Trail will guide you just past Quincy Market – an indoor/outdoor food bonanza. Step off the trail and walk down the main concourse and take in all the local smells, tastes, and sounds. Grab a cup of New England Clam Chowda! Have a slice of pizza at Regina’s! And, what’s a trip to Boston without some baked beans and brown bread. There’s literally something for everyone in Quincy Market.
Rose Kennedy Greenway
As the Freedom Trail crosses over the John Fitzgerald Expressway towards the North End, you will pass through a dynamic and beautiful new green space nestled between the busy highway. The Rose Kennedy Greenway is a linear park named after the matriarch of the Kennedy family (Rose is JFK’s and Ted Kennedy’s mother). These 17-acres were converted into an urban oasis as part of Boston’s controversial “Big Dig” construction project in the early 2000’s. The Greenway stretches over 1 mile from the North End through the Waterfront and ending in Chinatown. The park is full of sculptures, pop-up vendors, gardens, seating areas, and places to lounge in the grass and take in some rays.
Mike’s and Modern
Which is better – Mike’s or Modern? As you follow the Freedom Trail through the North End – Boston’s Italian Neighborhood – you need to make a decision? Will you grab a cannoli from Mike’s or Modern? We say – try both! The North End’s “cannoli wars” have raged for 50+ years, and – honesty – you can’t wrong at either place. If you like variety, go to Mike’s – they have over 18 flavors of cannoli to choose from. If you are looking for authenticity – the OG cannoli – head to Modern. Just like to eat? Grab a box from both – you won’t regret it. And, you’ve been walking all day. You can afford the calories!
Bunker Hill Monument
Most people don’t make it all the way to the “Terminus of the Trail”, but we think it’s a walk worth taking. The monument marks the location of the Battle of Bunker Hill – the first of many battles between the Patriots and the British that sparked the American Revolution. The obelisk is actually one of the first ever monuments in the US. An interesting piece of Boston trivia – the Bunker Hill Monument is actually not on Bunker Hill. It sits atop Breed’s Hill. Want some more trivia? Just in front of the monument is a statue of Col. William Prescott who is believed to have coined the famous phrase, “Don’t fire until you see the whites of their eyes”.
Like trivia? You can walk the Freedom Trail using Go Trivia as your guide. You’ll explore all these spots while answering some trivia questions and learning a little about Boston – then and now!
