A Trail Through Downtown Boston's Neighborhoods, Churches, And Landmarks Is One Of America's Most Historic

Boston is a beloved American city filled with some of the nation's most historic sites, including the Old South Meeting House, where the infamous Boston Tea Party was said to originate, and the Old State House, the site of the Boston Massacre, which ignited movement toward the American Revolution. Unbeknownst to some visitors, and despite being a large, major city, Boston is actually quite walkable, and the most iconic trail in the area actually connects these storied, historic sites together in a long, city-spanning route called the Freedom Trail. 

The Freedom Trail stretches across 2.5 miles of Boston and the neighboring Charlestown, linking together 16 significant sites, including historic burial grounds, churches, seats of government, and the homes of the nation's most important players. Marked by a distinct red-brick or painted line through Boston's most bustling and exciting neighborhoods, the attractions along this trail are not to miss.

To some more cynical Bostonians, the Freedom Trail is often considered a bit of a tourist trap, with some locals reminding visitors that there are other places in the city worth exploring. For example, the route does not run through every neighborhood in the city, meaning you'll miss Back Bay, one of Boston's most coveted neighborhoods with the best upscale shopping and architecture, or Seaport, the lively, modern epicenter of young nightlife and entertainment. However, if you're a first-time visitor to Boston or a real history enthusiast, the Freedom Trail is a convenient and easy way to see the highlights of some of America's most prominent places. Furthermore, if you know where to look, there are some underrated and hidden gems to discover along the trail, in addition to the sites featured in guidebooks.

While you can pick up the famed red-brick line just about anywhere on the trail, to get the best overview of the iconic sites, start at the Visitors Center located on the Boston Common, America's oldest public park and the first site on the trail. It's possible to book a guided walking tour with a knowledgeable historian, often dressed in a period costume, leading the way. If you're braving it alone, you can still take in everything the trail has to offer via materials available at the visitors center or online with the Freedom Trail Foundation's virtual brochure.

You'll notice as you walk the trail that many sites along it are open to the public. Most of these sites are operated by non-profits who collaborate with the National Parks Service, so they require visitors to purchase a ticket. Of the sites that are worth the additional cost, make sure to check out King's Chapel (particularly their Crypt Tour), the Old State House (operated by Revolutionary Spaces, which also stewards the Old South Meeting House), and the Paul Revere House, the home of America's favorite messenger.

Sites with no admission fees that are also worth dedicating extra time to explore include the Old Granary Burying Ground to visit the tombs of Samuel Adams, Paul Revere, and Benjamin Franklin's family (note the kite-flying Founding Father himself is buried in Philadelphia). Other free entry spots you shouldn't miss out on include the U.S.S. Constitution Ship and Museum, which suggests a donation and is particularly child-friendly, with interactive exhibitions that you'll likely want to stay at for a while.

The trail doesn't highlight all of the history, and there are many spots you may not read about in brochures. For example, the Omni Parker House on the path of the Freedom Trail is where JFK announced his congressional run, the former president of North Vietnam, Ho Chi Minh, worked as a pastry chef, and the Boston Cream pie was invented. Today it's a beautiful historic hotel, well worth a stop for the famous dessert, but beware, it's known to be haunted.

Classic stops on the trail include Faneuil Hall and Quincy Marketplace, iconic food halls and shopping centers with many clam chowder and lobster roll offerings. You can also grab a local Sam Adams beer at the brewery's tap room located adjacent to the landmarks. However, for an underrated yet cheeky historic restaurant experience, try Carrie Nation Restaurant and Cocktail Club, located not too far off the trail. The restaurant pokes ironic fun at prohibition darling Carrie Nation, and if you wander towards the back of the restaurant, you'll find a tucked-away speakeasy bar. As a word to the wise, once you cross the bridge into Charlestown on the trail, food options get scarce, particularly those you can reach on foot, so it's recommended to eat on the Boston side. 

With some of these suggestions in mind, you can enjoy the iconic Freedom Trail. Perhaps this will inspire you to get off the beaten path to explore other sites around the city and the state. Extend your American Revolution sightseeing by heading up to Lexington, a Massachusetts town rich with its own history and iconic landmarks, or pop over to the Berkshires for the best leaf-peeping in the country. However, don't miss the many highlights in Boston's own backyard.