Events and Things to Do in Highland, NY

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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Friday, August 28

• Vet2Vet of Ulster County- Veteran Coffee Hour (Highland NY)

  10:00 am

  Highland Public Library, 14 Elting Pl, Highland

  
  

Saturday, September 12

• Kaal Rock Park Concert Series 4:00 pm

  Kaal Rock Park, Poughkeepsie

  
  

Saturday, September 19

• Jay Medal Soirée 5:30 pm

  Jay Estate, 210 Boston Post Rd, Rye

  
  
• Giant Hudson Valley Moon Festival: Free Admission! 11:00 am

  517 Neversink Dr, Port Jervis

  
  
• Kaal Rock Park Concerts 4:00 pm

  Kaal Rock Park, Poughkeepsie

  
  
• Judi Silvano's Garden Winds

  8:00 pm

  Cunneen-Hackett Arts Center, 9 Vassar St, Poughkeepsie

  
  

Sunday, September 20

• Walkway Connections: Three Centuries, Three Cultures on Historic Huguenot Street

  2:00 pm

  Walkway Over the Hudson State Historic Park, 87 Haviland Rd, Highland

  
  

Saturday, September 26

• Kaal Rock Park Concerts 4:00 pm

  Kaal Rock Park, Poughkeepsie

  
  
• Defensive Driving Course – Ulster County, NY

  10:00 am

  Highland Public Library, 14 Elting Pl, Highland

  
  
• Out on the Farm 2026: An All-Ages Upstate NY Queer Fall Festival

  2:00 pm

  Bad Seed Cider Taproom, 43 Baileys Gap Rd, Highland

  
  

Sunday, September 27

• Out of the Darkness Community Walk

  9:00 am

  Walkway Over the Hudson State Historic Park, 87 Haviland Rd, Highland

  
  

Friday, October 2

• Vet2Vet of Ulster County- Veteran Coffee Hour (Highland NY)

  10:00 am

  Highland Public Library, 14 Elting Pl, Highland

  
  

Tuesday, October 6

• The Sound of Nashville in the Hudson Valley Queen City

  6:00 pm

  Bardavon, 35 Market St, Poughkeepsie