Whenever Free Tours by Foot tour guide Brian is on a walking tour, people ask him: "Brian, where is the best place to get a sandwich for lunch in Boston". Since there are so many places around, here are tour guide Brian’s favorite sandwich shops along the Freedom Trail. Just stay the red brick trail and you can’t lost.
If you have time only for one place to get a sandwich, Sam Lagrassa's is the place and it is a must if you want a great sandwich. Located at 44 Providence Street, just off of School Street, on the Freedom Trail and sits a few steps from the first public school in American, the Boston Latin School (1635). They make everything on site and you will get a sandwich that is so big, it is a meal. They are only open weekdays (Monday through Friday) from 11:00am to 3:30pm. There is usually a long line between 12:00pm and 1:00pm, but the line moves quickly and well worth the short wait.
Another good place to get a sandwich on the Freedom Trail is Cheese Boys at 280 Washington St. Located on the Freedom Trail directly across from the Old Corner Book Store (now a chipotle), and in shadow of the Old South Meeting House (the Boston Tea Party left from there). If you prefer a light lunch, this place is for you. They make melted cheese sandwiches. Grilled cheese. They build their grilled cheese with turkey, vegetables, roast beef, or anything else you may want to try. A great concept, a great place and the folks who work there are very friendly.
Potbelly Sandwich Shop
Farther down the Freedom Trail Heading towards Faneuil Hall, you will see Potbelly Sandwich Shop at 263 Washington St. This place is good, quick and consistent. They always make a great sandwich, nothing huge but good. As an added bonus they have a street-facing counter to sit down and eat so you can do a bit of people watching while eating your lunch. Their sandwiches come on multi grain or regular bread and toasted just right. They also offer a great mushroom melt for the vegetarians.
The Prime Shoppe (inside Quincy Market)
Entering Quincy Market behind Faneuil Hall, there are many, many options, but one of my favorites for sandwiches inside Quincy Market is The Prime Shoppe. They sell ribs and barbecue, but make a mean turkey, stuffing, and cranberry sandwich. Kind of like Nana's on the day after Thanksgiving. You can take your turkey sandwich down to Christopher Columbus Park which is located on the waterfront (just a few minutes’ walk from Quincy Market) and eat under the trellis while watching the boats skip across the Boston Harbor or the planes landing at Logon International Airport.
Continuing on the Freedom Trail and into our Northend/ Little Italy Neighbor is Pauli's, located at 65 Salem Street. A great place. Not only do they have great Italian dishes like ravioli and tortellini, but they make one mean lobster roll; or like Bostonians say "lobstah” roll. They have two, the $15 one (prices are at market price) and the $30 one. If you get one, just spend the extra and order the large one. Chock full of lobster meat, it will feed two people or one very hungry one. There are many places in Boston to get a lobster roll, but this one near the Freedom Trail this is the best. Pauli's is a basic sandwich shop and not a sit down restaurant like many of the other places in our Northend/Little Italy neighborhood. Although they do have tables to sit down and eat, you order at the register, pick it up when it is ready and find a table. On a nice day, take it to go because from Pauli’s you are only a five minute walk to Christopher Columbus Park.
+++Did you know? There are many theories on when and who actually invented the sandwich. The one Brian likes the most, says it is named after an 18th century Aristocrat named John Montaqu, 4th Earl of Sandwich. It is said that he ordered his valet to bring him some meat tucked between two pieces of bread and that others present at the time said, "give me the same thing as Sandwich, give me a Sandwich!" Then the Duke of Boston said, "hey Sandwich this is wicked good, now I can play cribbage and eat without getting my cards all greasy (well ok, that part is made up, but he may have said that).+++