Events and Things to Do in Holliston-Hopkinton, MA

Saturday, October 24

Featured

Chop's Diner: Dine on the Dark Side

OCT

24

7:30 PM

MetroWest YMCA Family Outdoor Center, 45 East St, Hopkinton, MA

Join us at "Chop’s Diner" - for a Halloween-themed dinner theater experience that benefits the MetroWest YMCA!. Deep in the...

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Monday, November 16

Featured

Home For The Holidays

NOV

16

6:00 PM

Hoboken Citizens Club, 252 Central St, Milford, MA

Join the Greenleaf Garden Club of Milford for a festive creative demonstration by floral designer Patrice Iacovelli. Attendees...

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Thursday, October 22

• MOON MAN Movie Premier 7:30 pm

  98 Hayden Rowe St, Hopkinton

  
  

Friday, October 23

• Create & Sip at the Center: Duck Pastels 6:30 pm

  98 Hayden Rowe St, Hopkinton

  
  

Saturday, October 24

• Milford Annual Pumpkin Stroll 5:30 pm

  23 Pine St, Milford

  
  
• Chop's Diner: Dine on the Dark Side 7:30 pm

  MetroWest YMCA Family Outdoor Center, 45 East St, Hopkinton

  
  

Sunday, October 25

• Wee Wicked Dash 9:45 am

  Hopkinton Center for the Arts, 98 Hayden Rowe St, Hopkinton

  
  
• HCA Wicked 5K 2026 10:00 am

  Hopkinton Center for the Arts, 98 Hayden Rowe St, Hopkinton

  
  
• HNN Great Pumpkin Trail Walk Fundraiser 10:00 am

  Blair Square, Upper Charles Rail Trail (Holliston), Holliston

  
  

Thursday, October 29

• Two Hildas Fly Into A Bar! Caroline Rhea & Lucy Davis 4:00 pm

  The Cellar at Hotel Salem, 209 Essex St, Salem

  
  

Sunday, November 1

• The Butterfly Garden Reunion 4:00 pm

  Our Lady of Fatima Shrine, 101 Summer St, Holliston

  
  

Friday, November 6

• Death By Design | Washington Street Players 7:00 pm

  Holliston Town Hall, 703 Washington St, Holliston

  
  

Saturday, November 7

• Holliston Mill Open Studios 11:00 am

  Holliston Mill, 24 Water St, Holliston

  
  
• Mah Jongg & More 7:00 pm

  The (Senior) Center, 150 Goulding St, Holliston, MA, 01746

  
  
• Death By Design | Washington Street Players 7:00 pm

  Holliston Town Hall, 703 Washington St, Holliston

  
  

Sunday, November 8

• Handweaving Workshop 10:00 am

  Hopkinton Center for the Arts, 98 Hayden Rowe St, Hopkinton

  
  
• Forum: Spiritual Foundations of Political Resistance 3:00 pm

  Framingham Friends Meeting, 841 Edmands Rd, Framingham

  
  
• Death By Design | Washington Street Players 4:30 pm

  Holliston Town Hall, 703 Washington St, Holliston

  
  

Monday, November 16

• Home For The Holidays 6:00 pm

  Hoboken Citizens Club, 252 Central St, Milford

  
  

Friday, November 20

• Creative Mornings for Little Artists 10:00 am

  Hopkinton Center for the Arts, 98 Hayden Rowe St, Hopkinton

  
  

Sunday, December 6

• Santa's Workshop 11:00 am

  ConnectEd & Inspired Art Studio, 138 S Main St, Milford

  
  

Friday, December 18

• Creative Mornings for Little Artists 10:00 am

  Hopkinton Center for the Arts, 98 Hayden Rowe St, Hopkinton