Jane's Walks Ossining, NY

05/03/2026

Explore Our Stories, On Every Street.

Celebrate Ossining 250 tomorrow, Sunday May 3 with an afternoon of Discovery & Community—right here in Ossining- kicking off in Westchester County's only national registered landmarked historic downtown.

Open to all and FREE- no cap on participants:

🕚 11:00 AM
Downtown Ossining: Past, Present, and Future
Led by Village Trustee & Former Village Historian Dana White
📍 Meet at 165 Main St (Ossining on Hudson sign by Open Door & Croton Aqueduct Trail)

🕐 1:00 PM
Dale Cemetery Heritage Trail: Special Edition
Led by Village Historian Joyce Sharrock Cole & Town Historian Caroline Curvan
📍 104 Havell Street

✨ Sparta Historic District Tour – FULLY BOOKED
The May 3 tour has reached capacity (20 participants) with a growing waitlist—but more dates are ahead:
🗓️ May 17 | June 14 | July 12 | August 16
Reserve at jugtavern.org

Free. Walkable. Community-driven.
This is what Jane’s Walk is all about.

05/02/2026

Tomorrow FREE Walking Tour in our beloved Ossining!!

05/02/2026

05/02/2026

What a start to Jane’s Walk Ossining!

We kicked off at Campwoods Grounds with 60+ participants—one of the largest walking tour turnouts there in recent memory. The crowd reflected exactly what this weekend is about: longtime Campwoods families, first-time visitors, and neighbors from across Ossining and surrounding communities coming together.

The energy was incredible—so much so that the group split into three tours, each filled with conversation, questions, and shared memories. One especially meaningful moment turned into an open dialogue led by someone who grew up there—people connecting, learning, and building on each other’s stories. That’s the heart of Jane’s Walk.

A big thank you to the Campwoods team for hosting and helping lead, and for creating a welcoming space for everyone to gather after.

This is what community looks like—connection, curiosity, and pride in place.

And we’re just getting started… join us Sunday!

05/02/2026

Thank you to everyone who joined the first Janes Walk at Campwoods Grounds- over 60 participants!

Please send me any pictures! Attached are some taken.

Which Janes Walk will you attend tomorrow?

SUNDAY, MAY 3, 11:00 AM

Downtown Ossining: Past, Present, and Future
With Village Trustee and Former Village Historian Dana White
Meet at 165 Main St, Ossining, NY 10562, by the Welcome to Ossining on Hudson sign, by Open Door and Croton Aqueduct Trail.

⸻

SUNDAY, MAY 3, 1:00 PM

Dale Cemetery Heritage Trail: Special Edition
Meet at Dale Cemetery, 104 Havell Street, Ossining
Ossining Historic Cemeteries Conservancy and Ossining 250
Tour led by esteemed Village Historian Joyce Sharrock Cole & acclaimed Town Historian Caroline Curvan.

⸻

SUNDAY, MAY 3, 1:00 PM

Sparta Historic District Tour
Meet at The Jug Tavern of Sparta, 74 Revolutionary Road
Tour led by Dr. Alan Stahl, Sparta resident and Curator of Numismatics at Princeton University

05/01/2026

River Journal article featuring Westchester's very first Jane's Walk in Ossining to celebrate Ossining 250 and America 250 in honor of Jane Jacobs!

04/28/2026

This must-join tour of Ossining's Dale Cemetary will be led by esteemed Village Historian Joyce Sharrock Cole & acclaimed Town Historian Caroline Curvan.

02/01/2026

So curious if anyone remembers the St. Paul Building?
See before & after of the corner of Spring Street & Saint Paul’s Place in Ossining.

Follow on Instagram to see more before & after pictures of our interesting & historic Village!

📍 50–62 Spring Street — Corner of Spring Street & Saint Paul’s Place, Ossining, NY

History:
In the early 1970s, the St. Paul Building housed local favorites like Meat Center Inc., White’s Restaurant, and Spring Street Pharmacy—a true neighborhood hub.

Spring Street remains the vital spine of Ossining’s historic downtown, connecting blocks in the Downtown Ossining Historic District and reflects our village’s journey, shaped by generations of families of all backgrounds who have called this place home and built its enduring spirit.

Then vs. Now:
🕰️ 1974: Bustling storefronts full of neighborhood life and daily commerce.

📸 1986: Buildings cleared for redevelopment (early plans eyed a municipal building here, per Westchester County Historical Society records).

📹 2026: Parking lot framed by tall pines grown into a mini urban forest over five decades.

For those new to Ossining or from multigenerational families here since the Sing Sing days — please comment below and share your favorite memory of Spring Street and the St. Paul Building! 👇



https://www.instagram.com/reel/DUF_vy8jSik/?igsh=a2h2OThvNXVpOTBn