From its vibrant Main Street to its iconic past - there's so much to explore in Ossining

From its vibrant Main Street to its iconic past, there is much to explore on a "Road Trip Close to Home."

Nikita Ramos

Feb 27, 2025, 12:43 PM

Updated 4 hr ago

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The Village of Ossining brims with rich history and culture.
From its vibrant Main Street to its iconic past, there is much to explore on a "Road Trip Close to Home."
Start your day with a brisk walk along the Sing Sing Kill Greenway at the Joseph G. Caputo Community Center.
It'll lead you to incredible views under the Broadway Bridge, below the historic Croton Aqueduct.
The area is known as the Double Arch Bridge, where two historic bridges span the Sing Sing Kill, one on top of the other.
It's a peaceful path that surrounds you with nature and history that dates back to the late 1830s.
After your walk, warm up indoors at First Village Coffee.
This local staple is a community hub for all things creative and caffeinated.
The walls of the coffee shop are adorned with constantly rotating work from local artists.
Also, try a taste of the fresh pastries all made in-house!
Bring your warm drink and snack with you down the road to the next stop, Hudson Valley Books for Humanity.
"This is more than a bookstore, this is a place of gathering," Owner Amy Hall said, "it's a very welcoming environment."
The shop sells an eclectic collection of good reads.
Most are donated, and some are new under the scope of social justice, the environment, diverse voices and more.
There's even a shelf of some banned books around the country!
"We want people to know that this is a place where they can find books that speak to them about some of the hard issues we're dealing with today," Hall said.
This bookstore also goes beyond the binding.
Browse a selection of everything from vinyl records and local pottery to home decor and gifts.
You'll find more than memories of Ossining to bring back with you from this "Road Trip Close to Home."
To learn more about First Village Coffee, click here.
For more on Hudson Valley Books for Humanity, click here.