Boston’s Freedom Trail

The Freedom Trail is 2.5 miles of brick-paved history. On the plus side it’s a lovely stroll, and will equip you with a few bits of early American knowledge for trivia night. On the minus side it can be packed with map-touting tourists, over stimulated kids and sub-par restaurants. Here are recommendations on where to snack and sip some drinks along the trail like a local. And yes, there are scores of restaurants in the area, especially Italian red sauce joints in the North End, but that’s an entirely different subject.

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  • Ernestos, 69 Salem Street (a tiny hole-in the wall to grab a slice)
  • Galleria Umberto, 289 Hanover St (thicker, Sicilian style crust)
  • Regina, 11 1/2 Thacher Street (the original location makes for a crispy, slightly charred crust)

Belgian Treats
In college I spent a semester in the Netherlands, right on the border of Belgium, and used this time to become, among other things, a french fry aficionado and fan of Liege style waffles. Both of these can be found at Saus (33 Union Street), along with a large selection of snacks, sandwiches and imported beers.



From cannoli to giant lobstertails and cream puffs or tiramisu, the North End is full of choices. Mike’s has the longest lines, while Bova’s is tucked away [mostly] out of the tourist trail.

  • Bova’s (134 Salem St.)
  • Maria’s Pastry (46 Cross St.)
  • Mike’s Pastry (300 Hanover St.)
  • Modern Pastry (257 Hanover St.)
  • Parziale’s Bakery (80 Prince St.)


After a long day of walking sometimes a bar stool is the best reward. These options offer plenty of craft cocktails and beer.

North End

  • Ward 8 (90 N. Washington St.)

Heading back to the Park Street T stop? Here’s what’s nearby for drinks:

  • JM Curley (21 Temple Pl.)
  • The Merchant ( 60 Franklin St.)
  • Silvertone (69 Bromfield St.)