Ossining Today: Hudson Plunge, Improv Night, and a Warm Place to Land

Icy plunge for a warm cause on the Hudson

Ossining kicks off the weekend with the Escape from Sing Sing Plunge at Louis Engel Park, where residents and teams are braving the Hudson at 10 a.m. to raise money for neighbors facing hardship across Westchester. The chilly charity jump supports ongoing efforts by organizers to provide emergency help and housing for local families.

Participants pay a registration fee and are encouraged to seek sponsors, with extra recognition and swag for top fundraisers. Prizes this year include costume awards and a recreation scholarship tied to the community that raises the most support, adding some friendly rivalry to a very local tradition.

Improv night at Hudson Valley Books for Humanity

Later tonight, Blind Tiger Improv brings its house teams to Hudson Valley Books for Humanity on Central Avenue for an 8 p.m. show. The performance is billed as fast-paced, PG-13 comedy from some of the troupe’s strongest ensembles, offering an easy night out within walking distance of downtown.

Tickets are modestly priced, and organizers emphasize keeping the space welcoming and inclusive for both seasoned improv fans and first-timers. With seats limited in the bookstore venue, early arrival is a good idea if you want to settle in with a chair and a cup of something warm.

Valentine’s concert nearby in Briarcliff

Just up the hill in Briarcliff Manor, the Westchester Harmony Chorus presents its “Heart & Hand” Valentine’s Day concert at 4 p.m. The free program features a cappella love songs spanning several eras, making it an easy add-on before or after time in the village.

The chorus, which recently adopted a new all-gender identity, has been a fixture in the county for decades. Today’s concert offers local residents a chance to hear tight harmonies without leaving the Rivertowns, and families may appreciate that the one-hour program wraps up before evening plans.

Village highlights warming center at Caputo

With winter hanging on, the village is again pointing residents toward the warming center at the Joseph G. Caputo Community Center this weekend. The reminder appears prominently on village webpages, underscoring that anyone who needs a safe, warm indoor space has a place to go.

Details on exact hours and services are posted by the village, so residents are encouraged to check official channels or call ahead before heading out. It is a small but important resource for people whose homes run cold or who simply need a break from the wind along the river.

Sources

• https://gullottahouse.org/2026-escape-from-sing-sing-plunge/
• https://riverjournalonline.com/event/escape-from-sing-sing-plunge/
• https://www.hvbooksforhumanity.com/events
• https://blindtigerimprov.com/
• https://riverjournalonline.com/event/heart-hand-a-valentines-day-concert/
• https://www.villageofossiningny.gov/village-clerk