Freedom Trail and Best of the North End (Boston, MA)
Boston is one of the most walkable cities in North America and its downtown core is teeming with historical sights. Exploring the main points downtown is made easy by following the Freedom Trail, a red brick path that connects 16 important sites that led to the founding of the United States. While this tour centres on Boston’s North End (one of the best Little Italy’s in North America), to soak up additional history you can start at the beginning of the Freedom Trail in Boston Common. For more details on the Freedom Trail stops, you can pick up a National Park Service map or take a Free Tours by Foot self-guided or group walking tour.
Boston is located on the traditional territory of the Massachusett, Pawtucket, and their neighbors the Wampanoag, and Nipmuc Peoples.
Tour Map
The Historic Prelude
The golden dome of the Massachusetts State House from beautiful Boston Common (October 2018)Start at the Park Street Station on the green and red line of Boston’s T (Subway), the oldest subway system in the country, built in 1897.
Here is a brief rundown of the sites en route to Quincy Market and the North End. Follow the Freedom Trail along the sidewalk.
Boston Common – a 50 acre central park that is the oldest city park in the United States (1634)
Massachusetts State House –state capitol and seat of government; oldest continually-running state capital building in the U.S.(1798)
Park Street Church – historic and still active church with a prominent location near Boston Common (1804)
Granary Burying Ground – burial place of many Revolutionary-war figures including Sam Adams, Paul Revere, and John Hancock (1660)
King’s Chapel and Burying Ground –one of the best example of Georgian architecture in the U.S. (1754). The graveyard outside predates the church by more than a century and is the oldest in the city (1630).
First School Site – oldest public school in the U.S. (1635) and the site of Old Boston City Hall.
Old Corner Bookstore – one of the city’s oldest brick buildings (1718) that operated as a bookstore for decades and was a meeting place for the likes of Charles Dickens and Ralph Waldo Emerson (it’s now a Chipotle).
Old South Meeting House – meeting house and church (1729); most famous for being the organizing point for the Boston Tea Party in 1773. From here, revolutionaries marched to the waterfront dumping 242 chests of tea into the harbor to protest British duties.
Old State House – one of the oldest public buildings in the U.S. (1713); and the centre of civil life in Colonial Boston; currently operates as a museum.
Boston Massacre Site – historical marker located outside the Old State House highlighting a confrontation that became a pivotal moment for American independence (1770).
For a history buff, downtown Boston is hard to beat. The Old North Church is just one of many historic sights (October 2021)Historic Quincy Market
The enhanced ‘food-centred’ extension of the Freedom Trail begins at the Faneuil Hall/Quincy Market complex. Built in 1743, Faneuil Hall was the first town hall in the U.S. and the building operates in much the same way it did in the 18th century. The ground floor is a marketplace and the Great Hall on the top floor has been the site of many historic speeches. Behind Faneuil Hall, Quincy Market, built in 1824-1826, is a food court with more than 30 vendors, centred around a large dome in the seating area. The area around the market features numerous shops, street vendors, and performers.
Boston Chowda
Inside Quincy Market
10am-7pm, until 8pm on Friday and Saturday
There are many options to grab a bite to eat in Quincy Market although no trip to Boston would be complete without tasting some clam chowder. Boston Chowda has been serving this quintessential Boston soup along with lobster rolls and more for the past 30 years.
The Boston Chipyard
Outside Quincy Market
9am-10pm, until midnight on Friday and Saturday
Located in the covered area between the Quincy Market and North Market buildings, the Boston Chipyard, started by two teenagers in the 1970s serves some delicious cookies to power you through to the next few stops on our tour.
Follow the Freedom Trail by continuing along Union Street.
On the right side of Union Street, you’ll see some of Boston’s most famous restaurants including Union Oyster House, the city’s oldest restaurant and favourite of JFK (you can visit his booth). You’ll also pass the Bell in Hand, the oldest tavern in the United States, which began pouring beer in 1795.
On the left side of Union Street, you will see the New England Holocaust Memorial. Completed in 1995, the six glass towers etched with numbers are dedicated to the memory of the six million Jews murdered in the Holocaust.
The North End - A Taste of Italy
Make a right onto Hanover Street. You’ll cross the Rose Kennedy Greenway before entering The North End. If it’s a Friday or Saturday you’ll also pass the market (Haymarket), one of the oldest open air markets in the U.S., selling fresh produce and more since 1820. The nearby Boston Public Market (indoors) runs seven days a week.
The 1.5 mile (2.4 km) long park and public space known as the Rose Kennedy Greenway was formerly the site of a much maligned Interstate Highway that separated the North End from the rest of the city. The infamous “Big Dig,” saw the burying of this highway underground, creating very welcome green space in the heart of the city. However, the project took 15 years to complete (1991-2006) and was vastly over budget. While it was estimated to cost $7 billion (in 2020 dollars), it ended up costing nearly $22 billion, making it the most expensive highway project in U.S. history.
Once you pass Cross St., you’ve made it into the North End, one of Boston’s most famous neighbourhoods. The oldest residential community is the city, the North End has been known as the city’s Little Italy since the late 1800s. There is a huge variety of Italian eateries, shops, and cafes packed into just one square kilometre, and dining out in the neighbourhood is popular for locals and tourists alike. While we’re sticking to quick eats on this tour, you’ll also want to check out the dinner scene (centred on Hanover St. and Salem St.) sometime during your time in the city.
Continue up Hanover St.
Bricco Salumeria & Pasta Shop
111 Board Alley (behind 241 Hanover St.)
10am-10pm
Stop into the hidden-away Bricco Salumeria just off Hanover St (on Board Alley), one of the many salumerias in the area which specializes in Italian meats and cheeses. You may want to split a deli sandwich to save room for other delicacies of the North End.
For our next food stop, we’re going to make a short detour from Hanover St. to try a slice of Boston’s most famous and historic pizza.
Continue up Hanover Street
Turn left onto Richmond St.
Turn right on Salem St. and then the first left on Cooper St.
Turn right on N Margin St. (turns into Thacher St.)
Regina Pizzeria
11 ½ Thacher St.
11am-10pm
You’ve made it to Boston’s original pizzeria. Pizzeria Regina began at this location nearly 100 years ago (1926). While it now has more than a dozen locations in the region, the original location is where you want to go.
Continue up Thacher St.
Turn right on Prince St.
Turn right on Hanover St.
Mike’s Pastry
300 Hanover St.
8am-10pm
Modern Pastry
257 Hanover St.
7am-10pm, until midnight on Friday and Saturday
You have two choices for a mandatory item on any North End tour – cannoli. While wandering the North End, you may have seen people carrying boxes with creations from both Mike’s Pastry and Modern Pastry. Both these spots have been operating in the North End for decades. While Mike’s has a wider variety of flavours, and is most popular with tourists (you’ll likely see a line out the door), Modern is known as a more authentic spot, and favoured by locals. Pro tip: try them both!
Mike - the Cannoli king of Boston with the ubiquitous white box (September 2019)
Arguably the Boston local cannoli of choice: Modern (October 2021)Caffè Vittoria
290-296 Hanover St.
8am-midnight
If you’re looking for a coffee break, grab a seat and a cappuccino or espresso at Caffe Vittoria, the first Italian cafe in Boston, caffeinating the North End since 1929 and conveniently located between the two cannoli spots.
If you’re up for more walking at this point there are three more sites on the North End portion of the ‘official’ Freedom Trail tour - keep following the red brick line up Hanover St.
Paul Revere House – colonial home of the Revolutionary war figure (1680) Paul Revere from 1770 to 1800; currently a museum.
Old North Church – historic church (1723) where the signal was sent for Paul Revere’s midnight ride that led to the battle that launched the American Revolution
Copp’s Hill Burying Ground – the city’s second-oldest cemetery (1659).
From here, you can either head back to the starting point (the closest ‘T’ stations are North Station or Haymarket) or you could continue following the Freedom Trail across the river to Charlestown to see the USS Constitution and climb the 294 steps of the Bunker Hill Monument. Note, this section will add another 2.5 km/1.5 miles to the walk (one-way).
The Encore - historic sites in Charlestown
USS Constitution – world’s oldest commissioned naval vessel still afloat (1797)
Bunker Hill Monument – monument dedicated in 1843 to commemorate the Battle of Bunker Hill during the Revolutionary War (1775).
From Bunker Hill, your closest stop on the T (subway) is Community College on the Orange Line. It is four stops from here to Downtown Crossing, in the heart of the city and a short walk back to the starting point.
Route Information
Tour Map
Start at the Park Street ‘T’ station (green and red line) and follow the Freedom Trail past many historic sites to Faneuil Hall/Quincy Market. Alternatively, start right at Faneuil Hall/Quincy Market (closest ‘T’ station is State on the orange and blue line).
Boston Chowda (inside Quincy Market)
The Boston Chipyard (covered area between Quincy Market and North Market)
Continue along Union St.
Turn right onto Hanover St.Bricco Salumeria & Pasta Shop (11 Board Alley, behind 241 Hanover St.)
Continue up Hanover Street
Turn left onto Richmond St.
Turn right on Salem St. and then the first left on Cooper St.
Turn right on N Margin St. (turns into Thacher St.)Regina Pizzeria (11 ½ Thacher St.)
Continue up Thacher St.
Turn right on Prince St.
Turn right on Hanover St.Mike’s Pastry (300 Hanover St.)
Modern Pastry (257 Hanover St.)
Caffè Vittoria (290-296 Hanover St.)
Either continue following the Freedom Trail further into the North End and/or Charlestown, return to the ‘T’ (closest station is Haymarket) or explore other nearby neighbourhoods such as Downtown, Waterfront, or Beacon Hill.