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How to Spend an Ideal Saturday in Ossining

Penny & Tings in Ossining | Photo by Doug Schneider

Head ‘up the river’ this weekend and find the charm of living in this historic North County town full of quaint shops and delicious grub.

Residents may appreciate Ossining’s (relatively) affordable home prices and location on the Hudson River, but the charm of living in this North County town comes from the confluence of its retro Main Street, old-school businesses, Portuguese culture, and eclectic dining scene.

By Samantha Garbarini & Anthony Tornatore

10 a.m. – Start Your Morning with Coffee from First Village Coffee

Get a taste of what Ossining is all about at First Village Coffee (123 Main St.; 914.236.3765), a colorful community hub — note the constantly rotating art displayed on the walls — and coffee shop, serving trendy ’tados, turmeric lattes, and nitro-coffee-lemonades.

11 a.m. – Learn About the Town’s Most Famous Landmark

Learn about the town’s most famous landmark, Sing Sing Correctional Facility, at the Joseph G. Caputo Community Center (95 Broadway; 914.941.3189). A free exhibit lets you tour cells, check out a display of homemade weapons found at the prison, and see a replica of its euphemistically nicknamed electric chair, Old Sparky, while delving into the town’s history.


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12 p.m. – Enjoy Seafood at Brothers Fish & Chips

Brothers Fish & Chips (172 N. Highland Ave.; 914.488.5141) is your place to be if you consider yourself a seafood connoisseur. We recommend the Chef’s Tasting Menu, which is multiple courses crafted by their chef utilizing the best wild seafood available paired with seasonal & local farm produce. If you come on a Friday or Saturday night, enjoy Happy Hour with half-priced sangria and $5 beers.

1:30 p.m. – Buy Some Toys at Penny & Ting

Shop for your little ones at independent toy store Penny & Ting (133 Main St.; 914.373.2590), where owner Mary Howard curates a mix of classic children’s books, make-your-own-unicorn yarn kits, and development-oriented toys.


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3 p.m. – Shop on Main Street

Take home a souvenir of Ossining’s Portuguese community. At Melita’s Home (125 Main St.; 914.923.0351), owner Melita Silva sources colorful ceramics, linens, and decorative items from artisans in her native Portugal.

5 p.m. – Get Ready to Eat at Basta

Grab a seat in the tiny dining room at Basta (27 Campwoods Rd.; 914.236.3400). Chef and co-owner Roger Mason honed his craft in Italy and makes a killer carbonara with house-cured pancetta, and lots of light, crispy pizzas.

7 p.m. – Burn Off Those Calories at Teatown

You can’t do Ossining without a stop at Teatown (1600 Spring Valley Rd.; 914.762.2912). Traverse some of the thousand-acre preserve’s hiking trails in search of bald eagles, walk among the maple trees tapped for soon-to-be syrup, or later in the season, traipse through 230 species of native and endangered blooms on the preserve’s two-acre Wildflower Island sanctuary.


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9 p.m. – Recharge Your Battery at La Quinta Inn & Suites

Unfortunately, there are no inns or bed and breakfasts in the vicinity, however, enjoy your night at La Quinta Inn & Suites (540 Saw Mill River Rd.; 914.592.3300). This hotel is right off of I-287 and has everything for you to enjoy a bright stay including a free breakfast buffet, an indoor pool, and a fitness center.

Related: Bake Deliciously Gooey Gluten-Free Chocolate Chip Cookies With This Vegan Recipe


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