Week of Events
Monday, October 13, 2025
No events on this day.
Tuesday, October 14, 2025
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October 14, 2025 -Tuesdays at 10 October Speaker: Mark Mulvoy, American sports journalist and writer.
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October 14, 2025 -’25 Rye City Council Candidate Form – League of Women Voters
Tuesdays at 10 October Speaker: Mark Mulvoy, American sports journalist and writer.
Come to Whitby Castle at 10:00 a.m. on October 14 to hear Mark Mulvoy, former sports writer for The Boston Globe and Sports Illustrated where he covered baseball and became a ghostwriter for Jack Nicklaus's golf column. Mark is a great storyteller that you won't want to miss.
’25 Rye City Council Candidate Form – League of Women Voters
'25 Rye City Council Candidate Form League of Women Voters of Rye, Rye Brook & Port Chester Note: a separate mayoral candidate form will be held on Monday, October 20, 2025 at 7:30pm. Read all our MyRye.com candidate interviews: GOP Slate – Henderson / All in for Rye Q&A with Mayoral Candidate Bill Henderson Q&A […]
Wednesday, October 15, 2025
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October 15, 2025 -“Sound Shore Songwriter Series” at Rye Arts Center
“Sound Shore Songwriter Series” at Rye Arts Center
Inspired by Nashville's Bluebird Cafe, the Sound Shore Songwriter Series is an exciting new showcase for local singer-songwriters to perform original music and share stories behind the songs. Hosted by Rye-based singer-songwriter Paul Jensen, the kickoff October 15 showcase will feature artists Drew Angus, Charlotte Morris and Paul Guzzone. Known for his soul-stirring vocal talents […]
Thursday, October 16, 2025
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October 16, 2025 -Rye Rec Food Truck Thursdays
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October 16, 2025 -Moonlight & Mysteries: A Tarot Circle with Beth Leas
Rye Rec Food Truck Thursdays
Rye Rec Food Trucks are back! (Food Trucks Subject to Change) April 10-June 19, 5:30 PM to 8:15 PM. Down by the basketball courts at Rye Rec 4/17 - Arthur […]
Moonlight & Mysteries: A Tarot Circle with Beth Leas
Step into the enchantment of the season with Moonlight & Mysteries: A Tarot Circle with Beth Leas. In this intimate gathering, guests will come together in a soulful circle to […]
Friday, October 17, 2025
No events on this day.
Saturday, October 18, 2025
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October 18, 2025 -Hike River Trail at Ward Pound Ridge Reservation with State Senators Shelley Mayer and Pete Harckham
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October 18, 2025 -Osborn Scare Fair
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October 18, 2025 -Rockridge Fall Fest 2025
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October 18, 2025 -Rye Historical Society’s Fall Food and Whiskey Bash
Hike River Trail at Ward Pound Ridge Reservation with State Senators Shelley Mayer and Pete Harckham
State Senators Shelley Mayer and Pete Harckham in partnership with Westchester County Parks Saturday, October 18, 9-11 a.m. The hike will launch from Meadow parking lot at 9 a.m. Parking […]
Osborn Scare Fair
Get ready witches and monsters, as the Osborn School Parent-Teacher Organization (PTO) is thrilled to announce the return of its annual “Scare Fair” Halloween Carnival supporting curriculum enriching programs and […]
Rockridge Fall Fest 2025
Rockridge Fall Fest 2025 $10.00 entry fee per child which gets you a pumpkin and 15% coupon to be used that same day bounce house cotton candy popcorn tractor display […]
Rye Historical Society’s Fall Food and Whiskey Bash
Don't miss our annual Fall party for great food and delicious drinks! In addition to our popular bourbon tasting, we will serve curated cocktails made with Square House Bourbon, plus […]
Sunday, October 19, 2025
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October 19, 2025 -Rye Farmers Market
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October 19, 2025 -Halloween Window Painting + Inaugural Pumpkin Parade on Purchase Street
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October 19, 2025 -Boots, Beats & Line Dancing
Rye Farmers Market
Down to Earth's Rye Farmers Market is held in the parking lot off Theo Fremd behind the Purchase Street stores every Sunday through November 23rd. Stop by for an abundance […]
Halloween Window Painting + Inaugural Pumpkin Parade on Purchase Street
Annual Halloween Window Painting featuring the Inaugural Pumpkin Parade on Purchase Presented in Partnership with the Women’s Club of Rye - Children’s Philanthropy Registration required for painting; attending / viewing […]
Boots, Beats & Line Dancing
It’s the last hoorah under the Wainwright tent for 2025, and we’re going out with a foot-stomping, smile-inducing line dancing party! Grab your boots, your friends, and your best moves—Adam Cherko of Cherko Line Dancing will guide you through an evening of two-stepping, spinning, and laughing with friends, neighbors, and fellow dance enthusiasts. We’ll kick […]
