The Ultimate Guide to Boston’s Freedom Trail

No visit to Boston is complete without walking the Freedom Trail. This 2.5-mile trek is a rite of passage for visitors and locals alike. It’s impossible to get lost as you follow the red brick or painted line through the city’s North End and past hundreds of years of history that saw the first stirrings of the American Revolution.

About 1.5 million people walk the Freedom Trail each year, and the route takes you through heavily populated areas of the city. To avoid the crowds and make the most of your day, plan your trek with these tips in mind.

Start Early and Go Backwards
Most people park in the underground lot at the Boston Common and begin their tour there. You can avoid the crowds by starting in Charlestown instead and walking the trail in the opposite direction. Park at the Nautica Parking Garage at 88 Constitution Road by 9 a.m., and you can begin your day at the family-friendly USS Constitution Museum (they’ll validate your parking, and you can Uber back to the lot at the end of the day). The USS Constitution is the country’s oldest commissioned ship and is well worth a tour. It opens at 10 a.m., but keep your eye on the line, which you can see from the museum. Getting here first thing in the morning will minimize your wait.

If boats aren’t your thing, you can skip the Navy Yard and follow the trail to the Bunker Hill Monument. If you’re up to the challenge, climb all 294 steps to the top for panoramic views of the city. There’s usually an ice cream truck near the park for a cold reward when you’re done. Many people who walk the trail the traditional way are out of steam by the end and never make it to the top, but a morning climb solves this problem.

Eat, Drink and Be Merry
Don’t turn the Freedom Trail into a forced march. It should be fun, and there are truly excellent restaurants to stop for refreshment as you make your way over the Charlestown Bridge and into the North End. This quaint neighborhood is Boston’s own Little Italy, and there are dozens of outstanding eateries to choose from. Pizzeria Regina is a local institution and a great choice for a quick meal; travelers with a more leisurely pace should sip a cappuccino and sample the tiramisu at cash-only Caffé Vittoria. For sweets on the run, there are several cannoli and gelato stands along Hanover Street.

Tailor the Trip to Your Interests
There’s no rule that says you have to stop at all 17 historic sites on the Freedom Trail. Pick and choose based on the length of the line when you get there, or plan ahead to hit the highlights you’re most interested in. Try these suggestions to get started:

For Nature Lovers: Climb the Bunker Hill Monument in the morning; then take your time strolling through the park-like setting of Copp’s Hill Burying Ground. Grab a sandwich in the North End and picnic on the Rose Kennedy Greenway for a break before walking to Boston Common, where you can make your way to the Swan Boats in the Public Garden.
For History Buffs: Taste the sweeter side of history at Captain Jackson’s Historic Chocolate, which is part of the Old North Church site. Don’t miss the Paul Revere House, which provides an excellent look at historic architecture and gives insight into what it was like to live in the 1700s. Grab a meal at Boston’s oldest restaurant, the Union Oyster House, before continuing past the Granary Burying Ground to the Common.
For Families: The USS Constitution Museum has fun, interactive exhibits to give kids an overview of the city and its revolutionary history. Once you’ve made it through the North End, the Rose Kennedy Greenway has splash pads to let kids cool off on a hot summer day. Dry off in the sun as you head toward Quincy Market, where the food court has something for everybody and there’s nearly always a crowd-pleasing street performer on the front steps. Finally, stop into the Old South Meeting House and ask to do the scavenger hunt — an excellent way to make learning fun while adults enjoy a break from the heat of the day.

Remember, there’s no right or wrong way to do the Freedom Trail. You can do as many or as few sites as you like. Even if you don’t enter a single building, the Freedom Trail allows you to soak up the sights and culture of Boston in the best possible way.