Head of the Charles regatta Archives - MyRye.com

(PHOTO: The RowAmerica Rye Men's U17 A boat from a victory at the Head of the Charles regatta in October 2026. Contributed.)

RowAmerica Rye Youth Wins First Place at World-Renowned Head of the Charles Regatta

by Charlie Morris, Staff Writer October 19, 2026October 19, 2026

RowAmerica Rye delivered a signature performance at the famous Head of the Charles regatta from October 16-18, 2026, as they clinched first place in the team competition by earning the […]

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			2 events 1 2 events, 1 6:00 pm - 9:00 pm SPRYE Annual Benefit Dinner October 1 @ 6:00 pm - 9:00 pm SPRYE Annual Benefit Dinner You are cordially invited to join SPRYE as we celebrate 15 years of service to seniors and their families. Cocktails & Sit Down Dinner Festive Attire RSVP by September 18, […] $175, 6:30 pm - 9:00 pm BYOB: Van Gogh Sunflowers October 1 @ 6:30 pm - 9:00 pm BYOB: Van Gogh Sunflowers Using bold colors, expressive brushstrokes, and simple step-by-step instruction, you'll create your own cheerful Van Gogh Inspired sunflower masterpiece. Bring your favorite bottle, unwind, and join us for an evenings […] $75	0 events 2 0 events, 2	2 events 3 2 events, 3 10:30 am - 11:00 am Little Historians Story Hour October 3 @ 10:30 am - 11:00 am Little Historians Story Hour Little Historians Story Time is a bi-monthly children’s program (Ages 6-10) designed to spark curiosity, imagination, and a love of history in young learners. This program encourages an exploration of […] Free, 6:30 pm - 9:30 pm Rye Historical Society’s Fall Celebration & Benefit featuring Crafted in America October 3 @ 6:30 pm - 9:30 pm Rye Historical Society’s Fall Celebration & Benefit featuring Crafted in America Don't miss RHS's Fall Celebration & Benefit featuring Crafted in America on Saturday, October 3rd. Tickets are available now for this fan favorite, festive annual event at the Historic Knapp […] $200	1 event 4 1 event, 4 8:30 am - 1:00 pm Weekly Rye Farmers Market October 4 @ 8:30 am - 1:00 pm Weekly Rye Farmers Market Down to Earth’s Rye Farmers Market is held in parking lot off Theodore Fremd behind the Purchase Street (Car Park 2) stores every Sunday through November 22, 2026. Support regional […]
0 events 5 0 events, 5	2 events 6 2 events, 6 12:30 pm - 1:30 pm Musical Segue: Music Therapy for Dementia October 6 @ 12:30 pm - 1:30 pm Musical Segue: Music Therapy for Dementia Musical Segue is a complimentary music therapy group for individuals with dementia designed to support cognitive function, emotional well-being, and self-expression through live music, singing, rhythm activities, and reminiscence. While […] FREE, 7:00 pm - 8:00 pm Mattering: The Secret to a Life of Deep Connection and Purpose with Jennifer Breheny Wallace October 6 @ 7:00 pm - 8:00 pm Mattering: The Secret to a Life of Deep Connection and Purpose with Jennifer Breheny Wallace Mattering: The Secret to a Life of Deep Connection and Purpose with Jennifer Breheny Wallace Jennifer Breheny Wallace is an award-winning journalist and bestselling author. Her first book, Never Enough: When Achievement Culture Becomes […] Free	0 events 7 0 events, 7	0 events 8 0 events, 8	0 events 9 0 events, 9	2 events 10 2 events, 10 9:30 am - 10:30 am Member Mornings October 10 @ 9:30 am - 10:30 am Member Mornings Calling all Rye Historical Society members! Join us for coffee, conversation, and a closer look at history on the second Saturday of every month. We invite our members to arrive […] Free, 11:00 am - 2:00 pm Rockridge Fall Fest October 10 @ 11:00 am - 2:00 pm Rockridge Fall Fest Pumpkin decorating Face panting Jumping castle Pie tasting Tractor photo op Popcorn Free	1 event 11 1 event, 11 8:30 am - 1:00 pm Weekly Rye Farmers Market October 11 @ 8:30 am - 1:00 pm Weekly Rye Farmers Market Down to Earth’s Rye Farmers Market is held in parking lot off Theodore Fremd behind the Purchase Street (Car Park 2) stores every Sunday through November 22, 2026. Support regional […]
0 events 12 0 events, 12	2 events 13 2 events, 13 12:30 pm - 1:30 pm Musical Segue: Music Therapy for Dementia October 13 @ 12:30 pm - 1:30 pm Musical Segue: Music Therapy for Dementia Musical Segue is a complimentary music therapy group for individuals with dementia designed to support cognitive function, emotional well-being, and self-expression through live music, singing, rhythm activities, and reminiscence. While […] FREE, 6:30 pm - 8:00 pm Rye Arts Center: Create What’s Next: Talk & Workshop October 13 @ 6:30 pm - 8:00 pm Rye Arts Center: Create What’s Next: Talk & Workshop Interact, chat and play, while Naomi Vladeck helps you explore the forces that keep you stuck. She’ll introduce three tiny practices to stimulate our courage to create from a future […] $45	0 events 14 0 events, 14	2 events 15 2 events, 15 6:30 pm - 9:00 pm BYOB: Wolf Kahn Landscapes October 15 @ 6:30 pm - 9:00 pm BYOB: Wolf Kahn Landscapes Paint a breathtaking landscape bursting with rich, unexpected color inspired by renowned artist Wolf Kahn. Blending vibrant hues with expressive brushwork, Kahn transformed ordinary scenes into luminous works of art. […] $75, 7:00 pm - 8:30 pm Wainwright House – Don’t Make Me Laugh: A Pelvic Floor Panel October 15 @ 7:00 pm - 8:30 pm Wainwright House – Don’t Make Me Laugh: A Pelvic Floor Panel Don't Make Me Laugh is a conversation twenty years overdue. Guided by Fiona Jalinoos, this panel brings together three pelvic floor physiotherapists and a high-risk OB/GYN to talk honestly about […] $40 – $50	2 events 16 2 events, 16 5:30 pm - 7:00 pm Sail Through History: An evening with Eric Jay Dolin October 16 @ 5:30 pm - 7:00 pm Sail Through History: An evening with Eric Jay Dolin Join Rye Historical Society for a special evening with Eric Jay Dolin, critically acclaimed author of Rebels at Sea: Privateering in the American Revolution. Dolin will share fresh insight into […] $60, 6:00 pm - 9:30 pm Wainwright House: 2026 Diamond Benefit \| Honoring Legacy, Community & Leadership October 16 @ 6:00 pm - 9:30 pm Wainwright House: 2026 Diamond Benefit \| Honoring Legacy, Community & Leadership Set against the golden glow of Milton Harbor, this festive night gathers friends, neighbors, and changemakers to celebrate those who shape, serve, and sustain our shared spaces for a vibrant […] $150	5 events 17 5 events, 17 8:30 am - 1:00 pm Rye Historical Society: Sail Through History: A Special Tour of the Tall Ship Lynx October 17 @ 8:30 am - 1:00 pm Rye Historical Society: Sail Through History: A Special Tour of the Tall Ship Lynx Have you wondered what it would have been like aboard privateering ships? Explore the thrilling nautical history of privateers during the American Revolution with a once-in-a-lifetime experience inspired by this […] $80, 9:00 am - 11:00 am Town of Rye Community Cleanup 2026 October 17 @ 9:00 am - 11:00 am Town of Rye Community Cleanup 2026 It’s Fall 2026 – Let’s Meetup & Cleanup Our Beautiful Communities! Saturday, October 17th, 2026, from 9:00 am to 11:00 am Join us after for speakers, snacks, and prizes at […] Free, 10:30 am - 11:00 am Little Historians Story Hour October 17 @ 10:30 am - 11:00 am Little Historians Story Hour Little Historians Story Time is a bi-monthly children’s program (Ages 6-10) designed to spark curiosity, imagination, and a love of history in young learners. This program encourages an exploration of […] Free, 1:00 pm - 5:30 pm Spooktacular Oktoberfest at Edith G. Read Wildlife Sanctuary October 17 @ 1:00 pm - 5:30 pm Spooktacular Oktoberfest at Edith G. Read Wildlife Sanctuary The Spooktacular Oktoberfest comes to Edith G. Read Wildlife Sanctuary in Rye on Saturday and Sunday, October 17 and 18, 2026. This festive fall celebration will have something for everyone, […] $25, 4:00 pm - 6:00 pm Hand in Hand: Annual Benefit & Auction October 17 @ 4:00 pm - 6:00 pm Hand in Hand: Annual Benefit & Auction For nearly 70 years, Clay Art Center has been a living testament to the impact of art — nurturing artists, welcoming students, and anchoring a creative community that spans generations. […] $95	2 events 18 2 events, 18 8:30 am - 1:00 pm Weekly Rye Farmers Market October 18 @ 8:30 am - 1:00 pm Weekly Rye Farmers Market Down to Earth’s Rye Farmers Market is held in parking lot off Theodore Fremd behind the Purchase Street (Car Park 2) stores every Sunday through November 22, 2026. Support regional […], 1:00 pm - 5:30 pm Spooktacular Oktoberfest at Edith G. Read Wildlife Sanctuary October 18 @ 1:00 pm - 5:30 pm Spooktacular Oktoberfest at Edith G. Read Wildlife Sanctuary The Spooktacular Oktoberfest comes to Edith G. Read Wildlife Sanctuary in Rye on Saturday and Sunday, October 17 and 18, 2026. This festive fall celebration will have something for everyone, […] $25
0 events 19 0 events, 19	2 events 20 2 events, 20 10:00 am - 11:00 am Raising Resilience – Dealing with Defiance October 20 @ 10:00 am - 11:00 am Raising Resilience – Dealing with Defiance A Rye Youth Council parent workshop covering the topic of dealing with defiance. There are two sections open for registration, in-person on Tuesday, October 20th at Rye Presbyterian Church or […] $30.00, 12:30 pm - 1:30 pm Musical Segue: Music Therapy for Dementia October 20 @ 12:30 pm - 1:30 pm Musical Segue: Music Therapy for Dementia Musical Segue is a complimentary music therapy group for individuals with dementia designed to support cognitive function, emotional well-being, and self-expression through live music, singing, rhythm activities, and reminiscence. While […] FREE	1 event 21 1 event, 21 12:00 pm - 1:00 pm Raising Resilience – Dealing with Defiance October 21 @ 12:00 pm - 1:00 pm Raising Resilience – Dealing with Defiance A Rye Youth Council parent workshop covering the topic of dealing with defiance. There are two sections open for registration, in-person on Tuesday, October 20th at Rye Presbyterian Church or […] $30.00	1 event 22 1 event, 22 6:00 pm - 8:00 pm Rye Arts Center BYOB: Light Sculptures October 22 @ 6:00 pm - 8:00 pm Rye Arts Center BYOB: Light Sculptures Gather to create cozy light sculptures to carry light into the darker months of Autumn. Inspired by traditional Japanese paper-making techniques and the luminous work of artists like Isamu Noguchi, […] $65	2 events 23 2 events, 23 5:00 pm - 7:30 pm Slightly Spooky Square House October 23 @ 5:00 pm - 7:30 pm Slightly Spooky Square House Back by popular demand! Don't miss Rye Historical Society's annual favorite Halloween tradition when the Square House is completely transformed into the Spooky House! Skeletons, ghosts and other eerie creatures […] $25, 5:30 pm - 8:00 pm Halloween Festival at Crawford Park October 23 @ 5:30 pm - 8:00 pm Halloween Festival at Crawford Park On October 23rd, the Town of Rye at Crawford Park celebrates the spooky season with a family-friendly Halloween Festival! There will be a Trunk or Treat from 5:30pm – 6:30pm, […] Free	2 events 24 2 events, 24 11:00 am - 12:00 pm Architecture Tour of The Square House October 24 @ 11:00 am - 12:00 pm Architecture Tour of The Square House Join Rye Historical Society on the fourth Saturday of each month for an all-new Architecture Tour of the Square House! This fascinating tour begins in 1730, when the first structure […] $20, 5:00 pm - 7:30 pm Slightly Spooky Square House October 24 @ 5:00 pm - 7:30 pm Slightly Spooky Square House Back by popular demand! Don't miss Rye Historical Society's annual favorite Halloween tradition when the Square House is completely transformed into the Spooky House! Skeletons, ghosts and other eerie creatures […] $25	2 events 25 2 events, 25 8:30 am - 1:00 pm Weekly Rye Farmers Market October 25 @ 8:30 am - 1:00 pm Weekly Rye Farmers Market Down to Earth’s Rye Farmers Market is held in parking lot off Theodore Fremd behind the Purchase Street (Car Park 2) stores every Sunday through November 22, 2026. Support regional […], 12:00 pm - 1:30 pm Wainwright House The Labyrinth Within: A Journey Inward October 25 @ 12:00 pm - 1:30 pm Wainwright House The Labyrinth Within: A Journey Inward A guided labyrinth experience inspired by the changing light of September. Join Nadia Monosova for an experiential introduction to the labyrinth, a centuries-old contemplative practice of reflection, meditation, and self-discovery. […] $40 – $45
0 events 26 0 events, 26	1 event 27 1 event, 27 12:30 pm - 1:30 pm Musical Segue: Music Therapy for Dementia October 27 @ 12:30 pm - 1:30 pm Musical Segue: Music Therapy for Dementia Musical Segue is a complimentary music therapy group for individuals with dementia designed to support cognitive function, emotional well-being, and self-expression through live music, singing, rhythm activities, and reminiscence. While […] FREE	0 events 28 0 events, 28	1 event 29 1 event, 29 6:30 pm - 9:00 pm Rye Arts Center BYOB: Dotted Kusama Pumpkins October 29 @ 6:30 pm - 9:00 pm Rye Arts Center BYOB: Dotted Kusama Pumpkins Welcome fall with an evening of art and great sips! Inspired by the iconic Japanese artist Yayoi Kusama, you'll create a vibrant painting filled with her signature playful polka dots […] $75	0 events 30 0 events, 30	1 event 31 1 event, 31 10:30 am - 11:00 am Little Historians Story Hour October 31 @ 10:30 am - 11:00 am Little Historians Story Hour Little Historians Story Time is a bi-monthly children’s program (Ages 6-10) designed to spark curiosity, imagination, and a love of history in young learners. This program encourages an exploration of […] Free

There are no events on this day.

September 29

September 29 @ 12:30 pm - 1:30 pm

Musical Segue: Music Therapy for Dementia

There are no events on this day.

October 1

October 1 @ 6:00 pm - 9:00 pm

SPRYE Annual Benefit Dinner

October 1 @ 6:30 pm - 9:00 pm

BYOB: Van Gogh Sunflowers

There are no events on this day.

October 3

October 3 @ 10:30 am - 11:00 am

Little Historians Story Hour

October 3 @ 6:30 pm - 9:30 pm

Rye Historical Society’s Fall Celebration & Benefit featuring Crafted in America

October 4

October 4 @ 8:30 am - 1:00 pm

Weekly Rye Farmers Market

There are no events on this day.

October 6

October 6 @ 12:30 pm - 1:30 pm

Musical Segue: Music Therapy for Dementia

October 6 @ 7:00 pm - 8:00 pm

Mattering: The Secret to a Life of Deep Connection and Purpose with Jennifer Breheny Wallace

There are no events on this day.

There are no events on this day.

There are no events on this day.

October 10

October 10 @ 9:30 am - 10:30 am

Member Mornings

October 10 @ 11:00 am - 2:00 pm

Rockridge Fall Fest

October 11

October 11 @ 8:30 am - 1:00 pm

Weekly Rye Farmers Market

There are no events on this day.

October 13

October 13 @ 12:30 pm - 1:30 pm

Musical Segue: Music Therapy for Dementia

October 13 @ 6:30 pm - 8:00 pm

Rye Arts Center: Create What’s Next: Talk & Workshop

There are no events on this day.

October 15

October 15 @ 6:30 pm - 9:00 pm

BYOB: Wolf Kahn Landscapes

October 15 @ 7:00 pm - 8:30 pm

Wainwright House – Don’t Make Me Laugh: A Pelvic Floor Panel

October 16

October 16 @ 5:30 pm - 7:00 pm

Sail Through History: An evening with Eric Jay Dolin

October 16 @ 6:00 pm - 9:30 pm

Wainwright House: 2026 Diamond Benefit | Honoring Legacy, Community & Leadership

October 17

October 17 @ 8:30 am - 1:00 pm

Rye Historical Society: Sail Through History: A Special Tour of the Tall Ship Lynx

October 17 @ 9:00 am - 11:00 am

Town of Rye Community Cleanup 2026

October 17 @ 10:30 am - 11:00 am

Little Historians Story Hour

October 17 @ 1:00 pm - 5:30 pm

Spooktacular Oktoberfest at Edith G. Read Wildlife Sanctuary

October 17 @ 4:00 pm - 6:00 pm

Hand in Hand: Annual Benefit & Auction

October 18

October 18 @ 8:30 am - 1:00 pm

Weekly Rye Farmers Market

October 18 @ 1:00 pm - 5:30 pm

Spooktacular Oktoberfest at Edith G. Read Wildlife Sanctuary

There are no events on this day.

October 20

October 20 @ 10:00 am - 11:00 am

Raising Resilience – Dealing with Defiance

October 20 @ 12:30 pm - 1:30 pm

Musical Segue: Music Therapy for Dementia

October 21

October 21 @ 12:00 pm - 1:00 pm

Raising Resilience – Dealing with Defiance

October 22

October 22 @ 6:00 pm - 8:00 pm

Rye Arts Center BYOB: Light Sculptures

October 23

October 23 @ 5:00 pm - 7:30 pm

Slightly Spooky Square House

October 21

October 21 @ 12:00 pm - 1:00 pm

Raising Resilience – Dealing with Defiance

October 22

October 22 @ 6:00 pm - 8:00 pm

Rye Arts Center BYOB: Light Sculptures

October 23

October 23 @ 5:00 pm - 7:30 pm

Slightly Spooky Square House

October 23 @ 5:30 pm - 8:00 pm

Halloween Festival at Crawford Park

October 24

October 24 @ 11:00 am - 12:00 pm

Architecture Tour of The Square House

October 24 @ 5:00 pm - 7:30 pm

Slightly Spooky Square House

October 25

October 25 @ 8:30 am - 1:00 pm

Weekly Rye Farmers Market

October 25 @ 12:00 pm - 1:30 pm

Wainwright House The Labyrinth Within: A Journey Inward

There are no events on this day.

October 27

October 27 @ 12:30 pm - 1:30 pm

Musical Segue: Music Therapy for Dementia

There are no events on this day.

October 29

October 29 @ 6:30 pm - 9:00 pm

Rye Arts Center BYOB: Dotted Kusama Pumpkins

There are no events on this day.

October 31

October 31 @ 10:30 am - 11:00 am

Little Historians Story Hour

November 1

November 1 @ 8:30 am - 1:00 pm

Weekly Rye Farmers Market

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