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Boston in September 2019: The Best Concerts, Comedy and Sports Events

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September really is the perfect time to be in Boston: Warm summer days give way to chilly nights, so there’s plenty of sunshine by which to explore the city and plenty of fireplaces to cozy up to after dinner. These events, concerts, games and shows offer endless entertainment around town.

Pro tip: Boston is easily walkable. Choose a hotel that’s in a central location, like The W in the Theatre District or The Godfrey Hotel by Boston Common, and you can rely on your feet and public transportation to get almost anywhere in the city.

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Watch A Movie Outdoors

The end of summer still has beautiful weather and plenty of outdoor events at which to enjoy it. Boston has free outdoor movie screenings throughout the month. See Avengers: Endgame at the Frog Pond during Mayor Walsh’s Movie Night on September 6, and Sunset Cinema at the MFA shows Us on September 12.

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Laugh Out Loud

Boston has enough comedy shows in September to keep you laughing all month long. Jen Kirkman appears on September 13, and Mr. King of Queens Kevin James tears it up on September 20. Janeane Garofalo and Dave Attell both perform on September 21, and Demetri Martin is in town on September 22 (hopefully with his drawing pad and guitar in hand). The always hilarious Jim Gaffigan appears on September 25.

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Appreciate Fine Art

Boston’s Isabella Stewart Gardner museum was once the site of the biggest art heist in American history when 13 works worth more than $500 million were stolen in 1990—but the museum has hundreds of other works on display. On their Third Thursday evenings, happening September 19, the museum stays open late and has performances and interactive art. Women Take The Floor, an exhibit displaying the works of overlooked female artists, opens at The Museum of Fine Art on September 13. The waterfront Institute of Contemporary Art, which has free admission on Thursday evenings, is hosting the first Yayoi Kusama exhibit in New England. Love is Calling, one of the interactive infinity rooms for which Kusama has become famous, opens September 24.

If you’re looking to stay near The Museum of Fine Art, book a night at the luxurious Sonder—Pierce Boston—or the retro-chic Verb Hotel where you can enjoy Japanese fare at Hojoko.

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Cheer For The Home Team

Unless you’ve been to a game in Boston, you can’t truly appreciate what it’s like to be a New England sports fan. September is an especially good time for sports because the baseball, football, soccer and hockey seasons all overlap. The Boston Red Sox have 14 games at Fenway Park in September. The New England Patriots play at Gillette Stadium on September 8 and September 22. The Boston Bruins, meanwhile, face off against rival teams at TD Garden on September 23, 25 and 28. And for soccer fans, the New England Revolution, which also calls Gillette home, has home games on September 21 and 29.

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See A Concert

Boston has major concert venues and a ton of theaters and smaller performance spaces. The Rockland Trust Bank Pavilion is a waterfront concert venue that hosts rock and country acts like Kacey Musgraves on September 12, and Bastille on September 17. Agganis Arena, part of Boston University, brings in Vampire Weekend on September 3 and Lizzo on September 17. The Who plays Fenway Park on September 13, and the Piano Man Billy Joel plays Fenway on September 14. For those who “ain’t ever getting older,” The Chainsmokers play TD Garden on September 27.

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