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.
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.
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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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1 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, octopus, fish tacos, and crab cakes.
Not into seafood? Wanna Empanada (238 North Highland Ave, 914.330.8374), located right down the street, is a new storefront in the town. The family-owned and -operated business started out as a food truck with the trio hailing from Ossining. The 2023 Best of Westchester winner for empanadas serve a rotation of over 70 savory and sweet fillings. From classic beef and jerk chicken to buffalo cauliflower and raspberry cheesecake, there’s no shortage of options.
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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. Hudson Valley Books for Humanity (677 Central Ave, 914.847.0773) is located in the historic Olive Opera House and features new, pre-loved, and rare books. If you’re into music, stop by the Den of Wax (175 Main St). This record store boasts every genre you can imagine and records ranging across various prices. Each album pairs with a unique design, creating a cohesive piece of art.
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 gorgeous maple trees. Remember to take photos aplenty on your stroll.
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7 p.m. – Treat yourself to Latin cuisine at Richie’s Kitchen
Head back into town for standout Latin dishes from Richie’s Kitchen on Main Street (157 Main St, 914.600.8688). From pollo guisado, or braised chicken served with rice and beans, to mofongo, a.k.a. mashed fried plantains with your choice of skirt steak, chicken, shredded beef, or shrimp and a choice of garlic or sweet chili sauce, there are dozens of traditional bites from which to choose. In the warmer months, the restaurant boasts outdoor seating.
8:30 p.m. – Sip on local brews at Sing Sing Kill Brewery
A short five-minute drive from Richie’s is Sing Sing Kill Brewery (75 Spring St, 914.502.0577) a taproom dedicated to brewing craft beer using sustainable practices. The taproom has seven house brews on tap, two guest taps, and numerous local wines and distilled spirits. Be on the lookout for weekend DJs, dance parties, and karaoke nights on the brewery’s Instagram page.
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10 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, indoor pool, and fitness center.
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Related: This Ossining Home Won a National Housing Innovation Award
