Ossining Day Trip: How to Spend 24 Hours in Town

Westchester, NY, USA: A rail bridge spans an inlet on the Hudson River, with St. Augustine’s Roman Catholic Church, Ossining, NY, in the background. Adobe Stock/ Linda Harms

A must-visit in Westchester County, the historic North County town of Ossining is full of quaint shops and delicious grub.

By Samantha Garbarini and Anthony Tornatore, with additional reporting by Ryan Noel

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. With so much to do in the area, Ossining is the perfect place to plan a day trip in Westchester.

P.S. If you go, don’t forget to tag us on Instagram! We may just regram you.

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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. Be sure to grab a gingerbread scone during the holiday season.

11 a.m. – Tour Ossining’s historic weir

Go back in time and learn about the town’s original brick water tunnel built in 1842. The free tour meets at the Joseph G. Caputo Community Center (95 Broadway; 914.941.3189). The easy, two-hour tour goes into the 20-foot-long, 10-foot-wide, and 30-foot-high weir that was constructed underground for the waste-water conduit.


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12 p.m. – Enjoy seafood at Brothers Fish & Chips in Ossining

Brothers Fish & Chips (172 N. Highland Ave.; 914.488.5141) is the place to be if you consider yourself a seafood connoisseur. Order takeout for lunch (but be sure to bookmark the chef’s tasting menu for dinner another night) to sample specialties like fish ceviche, tipsy mussels, fried calamari, and crab cake sandwiches.

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Not into seafood? The Tasty Table (21 Campwoods Rd.; 914.762.4000), located right nearby, is a go-to for brunch-style dishes and Americana salads and sandwiches. Go for the chicken salad if you want a lighter bite, or dig into the chicken caprese panini if you’re all about that fresh mozzarella life.

1:30 p.m. – Find unique toys for the little ones 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, DIY crafts, and development-oriented toys. It’s an ideal spot to visit if you’re in search of that perfect present for the kiddos in your life.


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3 p.m. – Shop on Ossining’s Main Street

Take home a souvenir of Ossining’s Portuguese community while shopping along Main Street. 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. After that, stroll a little down Main Street to Here Coffee and Beer (20 Main St.,914.223.1189) to reward yourself with a caffeine boost. The store is also stocked with local beer and snacks.


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5 p.m. – Take a stroll 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 and walk among the bare, but still gorgeous maple trees. If you’re lucky, the lake and trees might be covered in snow, allowing you to explore what’s truly a winter wonderland. Be sure to dress warm and remember to take photos aplenty.


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7 p.m. – Treat yourself to Italian classics at Capri Pizza & Pasta

Grab a seat at Capri Pizza & Pasta in Ossining (228 S Highland Ave; 914.944.8000) for what’s bound to be an unforgettable meal. The pizzas are a signature here, and gluten-free and cauliflower crusts are available for diners with any intolerances. Keep an eye out for the specialty pies, which run the gamut from chicken marsala to broccoli rabe.


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9 p.m. – Recharge your batteries at the Sleepy Hollow Hotel

Take a short drive to the Sleepy Hollow Hotel (455 S Broadway, Tarrytown; 914.631.5700) when it’s time to wind down for the night. The hotel is about a 20-minute drive from Ossining and has everything for you to enjoy your stay, including a bar and lounge, an indoor pool, and a fitness center.

Related: Where to Go Ice Skating in and Around Westchester County

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