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.
Get a taste of old and new Ossining. Start at First Village Coffee (123 Main St), 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. From there, it’s a short walk to Ossining Bakery (50 N Highland Ave). In business for decades, the old-fashioned bakery sells giant glazed doughnuts and plenty of the Portuguese egg tartlets pastel de nata.
Learn about the town’s most famous landmark, Sing Sing Correctional Facility, at the Joseph G. Caputo Community Center (95 Broadway). 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.
Behind the community center, find the entrance to the Sing Sing Kill Greenway, an elevated walkway through the Kill Brook ravine, passing under Ossining’s iconic Double Arch. Look familiar? The Greenway was a filming location for Spike Lee’s Oscar-nominated film BlacKkKlansman.
Shop for your little ones at independent toy store Penny & Ting (133 Main St), where owner Mary Howard curates a mix of classic children’s books, make-your-own-unicorn yarn kits, and development-oriented toys.
Churrasqueira Ribatejo (39 Spring St) is the place for a hearty lunch. The order here is the Portuguese rotisserie half-chicken with two sides — for just $12. If you’re in more of a seafood mood, it’s just a short drive to Brothers Fish & Chips (172 N Highland Ave), where they’re frying up three types of the pub-grub classic.
Take home a souvenir of Ossining’s Portuguese community. At Melita’s Home (125 Main St), owner Melita Silva sources colorful ceramics, linens, and decorative items from artisans in her native Portugal. Next door is Adega (127 Main St), a small wine store specializing in the country’s intense reds, crisp vinho verde, and syrupy ports.
You can’t do Ossining without a stop at Teatown (1600 Spring Valley Rd). 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.
There’s no shortage of places to grab a drink in town. If March goes out like a lamb, head to the stylish patio at 3 Westerly (3 Westerly Rd) for one of the county’s best views of sunset over the Hudson. Or, try one of the local brews — New England-style IPA, cream ale, or coconut porter, for example — at buzzy Sing Sing Kill Brewery (75-77 Spring St).
Grab a seat in the tiny dining room at Basta (27 Campwoods Rd). 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.