Events and Things to Do in Winchester, MA

Friday, November 13

Featured

Winchester High School to Present Almost, Maine, November 13–15

NOV

13

7:00 PM

Winchester High School, 80 Skillings Rd, Winchester, MA

Winchester High School will present Almost, Maine, a romantic comedy by playwright John Cariani, with performances scheduled...

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Featured

Ripley Presents Lisa Bastoni with Sean Staples

NOV

13

7:30 PM

21 Church St, Winchester, MA

Americana. Thought-provoking. Joyful. From the heart. Friday, November 13, 7:30 p.m., From the stunning Ripley Chapel. Live in...

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Saturday, November 14

Featured

The Best Flippin' Card Show Monthly Mixer

NOV

14

8:30 AM

15 Middlesex Canal Park Dr, Woburn, MA

The best Saturday card show in the Boston area has fully expanded to 10,000+ sq. ft. to become the largest in the area. We are...

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Featured

2026 Holiday Faire

NOV

14

8:30 AM

Crawford Memorial United Methodist Church, 34 Dix St, Winchester, MA

Crawford’s Holiday Faire is coming back, Saturday, November 14!  8:30am-2:00pm.  Two floors of treasures to explore! MAIN...

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Featured

Arlington Greek Cuisine Fall Fest ♨(⋆‿⋆)♨ 3 DAYS ONLY Friday, Saturday & Sunday!! ♨(⋆‿⋆)♨

NOV

14

11:30 AM

Saint Athanasius The Great Greek Orthodox Church, 4 Appleton St, Arlington, MA

Experience authentic flavors at this indoor Greek cuisine festival held in the church auditorium. Join us for a weekend...

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Sunday, November 15

Featured

Celebrating 250 Years of Music in the United States

NOV

15

2:00 PM

Winchester Unitarian Society, 478 Main St, Winchester, MA

All are welcome to this free concert! The venue is handicapped accessible and street parking is available.

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Saturday, November 21

Featured

Super Saturday: 4th Annual Black Entrepreneurs Holiday Showcase & Sale

NOV

21

12:00 PM

West Medford Community Center, 111 Arlington St, Medford, MA

🎉🛍️ THE COUNTDOWN IS ON UNTIL SUPER SATURDAY! 🛍️🎉 WMCC's 4th Annual Black Entrepreneurs Holiday Showcase & Sale is back and...

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Sunday, December 6

Featured

Commonwealth School Virtual Open House

DEC

6

3:00 PM

Boston, MA

You may not expect a community so deeply academic to be so warm and welcoming, but Commonwealth contains multitudes—just like...

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Friday, November 13

• Winchester High School to Present Almost, Maine, November 13–15 7:00 pm

  Winchester High School, 80 Skillings Rd, Winchester

  
  
• Ripley Presents Lisa Bastoni with Sean Staples 7:30 pm

  21 Church St, Winchester

  
  

Saturday, November 14

• 2026 Holiday Faire 8:30 am

  Crawford Memorial United Methodist Church, 34 Dix St, Winchester

  
  
• The Best Flippin' Card Show Monthly Mixer 8:30 am

  15 Middlesex Canal Park Dr, Woburn

  
  
• Arlington Greek Cuisine Fall Fest ♨(⋆‿⋆)♨ 3 DAYS ONLY Friday, Saturday & Sunday!! ♨(⋆‿⋆)♨ 11:30 am

  Saint Athanasius The Great Greek Orthodox Church, 4 Appleton St, Arlington

  
  
• Fairy Garden Party 10:00 am

  studio on the

  
  
• Youth Rock Jam 3:00 pm

  Winchester Community Music School, 407 Highland Ave, Winchester

  
  

Sunday, November 15

• Celebrating 250 Years of Music in the United States 2:00 pm

  Winchester Unitarian Society, 478 Main St, Winchester

  
  

Tuesday, November 17

• Good Food, Good for the Earth: Eating Local, Seasonal & Whole 7:00 pm

  Wright-Locke Farm, 82 Ridge St, Winchester

  
  
• “Common Time” Concert: The Zahra Lux & Chris Gardino Duo 7:00 pm

  Griffin Museum-Photography, 67 Shore Rd, Winchester

  
  

Friday, November 20

• Boston International Kids Film Festival 9:00 am

  The Dorothy and Charles Mosesian Center for the Arts, 321 Arsenal St, Watertown

  
  

Saturday, November 21

• Super Saturday: 4th Annual Black Entrepreneurs Holiday Showcase & Sale 12:00 pm

  West Medford Community Center, 111 Arlington St, Medford

  
  
• Christmas Fair 9:30 am

  Parish of the Epiphany, 70 Church St, Winchester

  
  
• Winchester's 4th Annual Open Studios 10:00 am

  Multiple

  
  

Tuesday, November 24

• “Common Time” Concert: The Blues Chasers 7:00 pm

  Griffin Museum-Photography, 67 Shore Rd, Winchester

  
  

Wednesday, November 25

• Early Release Day - YAY ART! (Ages 5-8) 11:30 am

  Studio on the Common, 22 Church St, Winchester

  
  

Thursday, November 26

• En Ka Society Turkey Trot 2026 8:00 am

  Winchester Town Hall, 71 Mt Vernon St, Winchester

  
  

Monday, November 30

• Midnight-ish Madness! 10:00 am

  22 Church St, Winchester

  
  

Tuesday, December 1

• “Common Time” Concert: Miles Blackwood & Friends 7:00 pm

  Griffin Museum-Photography, 67 Shore Rd, Winchester

  
  

Wednesday, December 2

• Karma Winchester Hosts Exclusive IWA 5 Sake Masterclass 6:00 pm

  Karma in Winchester, 16 Thompson St, Winchester