The shortlist

The coolest neighborhoods in Boston.

This site exists to give one answer per city, and for Boston that answer is Jamaica Plain. But the question was closer than the podium suggests. Three other neighborhoods pushed hard, each cool in a different way, and each missing one thing JP still has. Here is the shortlist, in order.

01

Jamaica Plain The pick

Jamaica Plain won because it still works for everyone who lives there. Not a food destination you visit, not a waterfront you photograph. A neighborhood that runs on its own residents. Papercuts Bookshop, 40 South Street Vintage, Drawdown Brewing, Third Cliff Bakery, all independent, all within a walk. Brassica Kitchen + Cafe does serious cooking without the scene. The others on this list are either fully gentrified or gentrifying at a speed that will break something. JP is holding the line, teachers next to techies, and the culture is still made by the people who show up on a Tuesday. That is the whole test. JP passes it.

Read the full case for Jamaica Plain →
02

Union Square, Somerville

The closest call on this list. Bow Market alone makes the argument, thirty-odd independents in a converted storage building, Remnant Brewing pouring in the courtyard, Rebel Rebel doing natural wine. The Neighborhood Restaurant still serves Portuguese breakfast, the farmers' market has run since 2005, and the Green Line finally showed up in 2022. The problem is what the train brought with it. Millions of square feet of development, and the immigrant-owned shops that built the place are the ones most at risk. If Union Square keeps its soul through the construction, it takes the crown.

03

South End

The most beautiful streets in Boston, block after block of intact Victorian rowhouses, and Tremont Street's Restaurant Row keeps producing. Coppa cures its own salumi. J.J. Foley's has held the corner since 1909. But the South End already finished the journey JP is still fighting. It is expensive and settled, and the turnover now is one chef-driven concept replacing another on Tremont, not a neighborhood arguing about its future. Polished is not the same as cool. Come here to eat well. Live somewhere that is still deciding what it is.

04

East Boston

The best geography in the city. Downtown skyline across the harbor, one Blue Line stop from town, a ferry if you want the view on the way in. The ICA Watershed puts serious contemporary art in an old copper pipe factory, and Democracy Brewing landed on Maverick Street. But Eastie's cool is landscape more than scene, and the gentrification here is the fastest and roughest in Boston. Dollar pupusas steps from million-dollar condos, harbor views walled off by new towers. If the neighborhood finds its balance before the developers finish, this pick gets rewritten.

No juries, no sponsors. How we pick explains the rules; Jamaica Plain is where they landed.

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