Sooner or later, everyone who comes to Boston ends up wandering the red-brick side streets of the North End. The city's oldest residential community (since the 1630s, no less) is a perfectly walkable utopia for coffee-sippin' people-watchers, history-buffin' Freedom Trailers and lovers of the neighborhood's default cuisine: Italian.
Once you've identified and enjoyed all the usual suspects—the Paul Revere House; pizza at Ernesto's or Regina Pizzeria; the Skinny House; St. Stephen's Church (the last remaining church in Boston designed by Charles Bulfinch)—you'll be ready to mosey off the beaten path and discover some of the North End's less-obvious treasures. Here are some pointers.
Discover Your Cuisine Scene
The North End owns Italian-American dining the same way Martin Scorsese owns Italian-American movies, but there are alternatives: Neptune Oyster is a seafood aficionado magnet; Aragosta Bar + Bistro (down on the waterfront at the Battery Wharf Hotel) offers New England cuisine with a Mediterranean twist; and Tenoch takes the Mexican torta to delicious new heights.
Aragosta: 3 Battery Wharf, 617.994.9001; Neptune Oyster: 63 Salem St., 617.742.3474; Tenoch 3: Lewis St., 617.248.9537
Shop 'Til You Drop
The serendipity of a leisurely North End stroll is sure to reveal something unexpected. Go for a browse around Shake the Tree in search of global cookbooks, unique jewelry and the kinds of birthday gifts you're unlikely to find anywhere else; or investigate the truly unique William Carlton Workshop, where vintage-style caps are crafted on early 1900s machines.
Shake the Tree: 67 Salem St., 617.742.0484; William Carlton Workshop: 148A Salem St., 415.622.7534
Get Your Drink On
Immerse yourself in soccer culture over Italian espresso at Caffe Dello Sport, where habitual use of the greeting “signore” is encouraged and there's always a match on the TV. The Living Room hosts regular comedy and board game nights, and gastropub Ward 8 (frequented by the creative types who work at the nearby HQ for Converse sneakers) strikes a well-judged balance between drinks and dining.
Caffe Dello Sport: 308 Hanover St., 617.523.5063; The Living Room: 101 Atlantic Ave., 617.723.5101; Ward 8: 90 N. Washington St., 617.823.4478
Where to Find Everything Else
Harborwalk—Boston’s network of waterfront paths—is still growing, and the North End section is a lesser-known highlight. Here you'll find Exhale Spa, which offers a sunny-day yoga class in the open air, with water all around for that Age of Aquarius vibe. For more chucklesome pursuits, head back to Hanover Street and prepare to split your sides at Improv Asylum; and don't forget to unleash your inner artisan at North Bennet Street School, which offers classes in bookbinding, carpentry and violin making.
North Bennet Street School: 150 North St., 617.227.0155; Improv Asylum: 216 Hanover St., 617.263.6887; Exhale Spa: 2 Battery Wharf, 617.603.3100