Boston's Best Bars For People-Watching
Picco
513 Tremont Street
Boston, MA 02116
(617) 927-0066
www.piccorestaurant.com
The P stands for pizza. The IC stands for ice cream. And while the Pizza and Ice Cream Company (PICCO) offers up a handful of other delicious menu items, their focus on creating delicious pizza and ice cream is reason number one that they're worth checking out. As for people-watching, it's on a busy corner for foot traffic at Tremont and Berkley in the South End. Picco also has a strong craft beer selection, which is highlighted on the dessert menu The Adult Ice Cream Soda (raspberry Belgian Lambic and vanilla ice cream) and the Cow Tipper Frappe (milk stout and vanilla ice cream) give you a reason to stick around even longer and enjoy the scenery.
The Landing
1 Long Wharf
Boston, MA
(617) 227-4321
www.bostonharborcruises.com/the-landing-at-long-wharf
This seasonal outdoor bar on Long Wharf has a very limited food menu, but the drinks and waterfront setting make it very worthy of this list. The Landing sits steps from the various harbor cruises that sail in and out of port throughout the day. Crowds flock to the wharf to enjoy the ocean breeze, which, perhaps not coincidentally is a beverage on the bar's drink menu. And for your friends who may not be into people watching, there's a lovely view of Boston Harbor that's equally as enjoyable.
Abe & Louie's
793 Boylston Street
Boston, MA 02116
(617) 536-6300
www.abeandlouies.com
Abe and Louie's combines prime people-watching real estate with prime cuts of meat. Don't show up to this steakhouse expecting a cheap meal (although, many of their delicious lunch sandwiches are under $15). Their steaks are quality, and that's what you're paying for. The view along Boylston Street is an added bonus, especially from out on the patio.
Game On
82 Lansdowne Street
Boston, MA 02215
617-351-7001
gameonboston.com
Game On has been a staple at Fenway Park since 2005. On game days, crowds pack in for a pre-game drink or a bite to eat. The outdoor patio and indoor open-air seating areas make for some of the best people-watching around. Enjoy a drink and some pretty decent bar food while you're there, and maybe enjoy a baseball game on TV when the crowds thin out.
Stephanie's on Newbury
190 Newbury St
Boston, MA 02116
(617) 236-0990
www.stephaniesonnewbury.com
Locals and tourists alike flock to Newbury Street for the shopping, and you can head there to watch. Stephanie's on Newbury is almost always hopping. People line up outside the establishment to dine al fresco, especially on the sandwiches, salads and snacks featured on the afternoon menu. You might have to wait a bit, but if you can get a seat, there's plenty of room to sit out on the porch and enjoy the view along this heavily pedestrian-populated stretch of Back Bay.