Events and Things to Do in Head of the Harbor, NY

Saturday, September 12

Featured

Caroline Episcopal Church’s Annual Country Fair

SEP

12

10:00 AM

Caroline Episcopal Church, 1 Dyke Rd, Setauket- East Setauket, NY

Our famous Annual Country Fair returns this year Saturday, September 12th, 2026! Every year, this massive community event...

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Saturday, September 19

Featured

Jay Medal Soirée

SEP

19

5:30 PM

Jay Estate, 210 Boston Post Rd, Rye, NY

The Jay Heritage Center in Rye, New York will celebrate America at 250 with a toast to Jay Medal honorees Pulitzer...

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Saturday, October 3

Featured

“Paw-ktoberfest: Heroes, Hops & Paws” Benefiting Paws of War

OCT

3

1:00 PM

The Stone Goat Restaurant & Brewery, 552 N Country Rd, St James, NY

Join Jet Direct Mortgage, The Stone Goat, and Paws of War for an afternoon of food, music, friends, pups, and fun, all for a...

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Saturday, September 12

• Caroline Episcopal Church’s Annual Country Fair 10:00 am

  Caroline Episcopal Church, 1 Dyke Rd, Setauket- East Setauket

  
  

Thursday, September 17

• Long Island and the Legacy of Eugenics with author Mark Torres | FREE 3:00 pm

  The Long Island Museum, 1200 NY-25A, Stony Brook

  
  
• NASS Open House Pre-K/K 6pm; Gr. 1/2 6:30pm; Gr. 3/4 7pm; Gr. 5 7:30pm 6:00 pm

  Three Village Csd, Stony Brook

  
  
• MINNE Open House Pre-K/K 6pm; Gr. 1/2 6:30pm; Gr. 3/4 7pm; Gr. 5 7:30pm 6:00 pm

  Three Village Csd, Stony Brook

  
  

Friday, September 18

• Stitch & Chit-Ch(at) - FREE! 2:00 pm

  The Long Island Museum, 1200 NY-25A, Stony Brook

  
  

Saturday, September 19

• Jay Medal Soirée 5:30 pm

  Jay Estate, 210 Boston Post Rd, Rye

  
  
• (mostly) True Things Stories about Best Laid Plans 7:00 pm

  The Performing Arts Studio 224 E. Main St. Port Jefferson, NY 11777

  
  

Monday, September 21

• Caroline Episcopal Church’s 3rd Annual “Holy Smoke” Golf Tourney 9:00 am

  Port Jefferson Country Club (44 Fairway Drive, Port Jefferson, NY)

  
  

Wednesday, September 23

• Free Baton Twirling Class w/ TNT Twirlers 6:45 pm

  290 Norwood Ave, Port Jefferson Station

  
  

Saturday, October 3

• “Paw-ktoberfest: Heroes, Hops & Paws” Benefiting Paws of War 1:00 pm

  The Stone Goat Restaurant & Brewery, 552 N Country Rd, St James