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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Thursday, October 29

Featured

Two Hildas Fly Into A Bar! Caroline Rhea & Lucy Davis

OCT

29

4:00 PM

The Cellar at Hotel Salem, 209 Essex St, Salem, MA

Double your pleasure and double your fun with an exclusive evening featuring two iconic Hildas, Caroline Rhea and Lucy Davis....

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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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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

  
  
• Rasa String Quartet: An American Patchwork 7:00 pm

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

  
  

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

  
  

Friday, October 30

• Night of the Living Comics 8:00 pm

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

  
  

Saturday, October 31

• Radio Musikola Halloween Bash 8:00 pm

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

  
  

Sunday, November 1

• Drop the Mic: Sunday Morning Poetry & Spoken Word 10:00 am

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

  
  
• 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

  
  

Friday, November 13

• Death By Design | Washington Street Players 9:00 am

  Holliston Town Hall, 703 Washington St, Holliston

  
  

Saturday, November 14

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

  Holliston Town Hall, 703 Washington St, Holliston