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Neighborhood Guides

Three Boston Neighborhood Days Built for the Cold

Boston walking guides assume October. Three routes for the five months that follow, built around covered markets, short exposures and somewhere warm every fifteen minutes.

·3 min read
Three Boston Neighborhood Days Built for the Cold

Boston is a walking city for about seven months a year. For the other five it is a city of short dashes between warm rooms, and a route that ignores that fact is a route nobody finishes.

Three winter days built the other way around.

The South End: market, then brownstones

Start at the SoWa Winter Festival at the SoWa Power Station, which runs fifteen days across four weekends in November and December with opening night on November 20. Indoors, $10 admission, and full of small South End businesses selling handmade work. It is the anchor because it is warm and because it takes as long as you want it to.

From there, the South End's brownstone grid is the best cold-weather architecture walk in the city: Union Park, the Tremont Street stretch, the alley blocks between Shawmut and Washington. Fifteen minutes of exposure at a time, with a restaurant at the end of each one. The neighborhood has the highest density of rooms in Boston that will let you sit for two hours in February.

Back Bay station or the Orange Line at Tufts Medical Center.

Beacon Hill and the Common: lightings and ice

Beacon Hill in December is the postcard, and unlike most postcards it holds up. Gas lamps, Acorn Street, Charles Street shops that are open and warm.

The Common is the other half. The Frog Pond has ice from mid-November into March with cheap admission and rental skates. The Boston Common Tree Lighting and the State House and Copley Square ceremonies all land in the first week of December, all free, all within a twenty-minute walk of each other. On December 31, First Night Boston fills the same ground with ice sculpture, performances and midnight fireworks, free since 1976.

Park Street or Charles/MGH.

Jamaica Plain: studios and the long green stretch

Jamaica Plain is the least obvious winter neighborhood and the most rewarding. JP Holiday Open Studios takes a December weekend, from the Brewery Complex out along Green Street: free, self-guided, and the best low-cost gift shopping in the city.

Centre Street handles the eating. The Arboretum is open, free and nearly empty all winter, which is the best argument for it, and a thirty-minute loop there is about the right amount of outdoors for a January afternoon.

Orange Line at Stony Brook or Green Street.

The indoor fallback

Some days none of the above is tolerable. The short list of places that absorb a whole afternoon without going outside: the MFA and the Gardner in the Fenway, the Boston Public Library's McKim building in Copley, and the Central Library reading room, which is free and one of the best rooms in the city.

The North End works as a cold-weather evening for the same reason it works as a summer one: the blocks are short, the restaurants are close together, and the longest walk between two warm rooms is about ninety seconds.

Compliance, quickly

  • 21+ only at every dispensary and for every purchase
  • Verify licensed status via the Massachusetts Cannabis Control Commission at masscannabiscontrol.com
  • Massachusetts state law prohibits cannabis consumption in public spaces, which covers the Common, the Arboretum, the South End streets and every route above
  • Start low, go slow with edibles; cold weather makes the read on how you are doing harder, and a long outdoor stretch is the wrong place to find the onset window
  • Never drive after consuming; every route above is built on the T for exactly that reason

More of what is running this season is on the events hub.

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