Looking for a quick but refreshing escape from NYC? Ossining, a historic Hudson River town just an hour away, offers the perfect mix of great coffee, scenic views, delicious food, and local charm. Nestled along the Hudson River, this small town boasts beautiful waterfront walks, unique local businesses, fantastic food, and a rich history—including the famous Sing Sing Prison, which you can spot from the train as you arrive.

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Whether you’re in the mood for good coffee, craft beer, a nature break, or just a slow-paced day away from the city, Ossining is the perfect place for an adventure.

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9:00 AM – Take the Scenic Hudson Line to Ossining 🚆

Kick off your journey by catching the Metro-North Hudson Line from Grand Central Terminal. The 50-minute train ride follows the Hudson River, offering some of the most breathtaking views in the region.

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How to Get here:

• Train: Metro-North Hudson Line ($11.75 off-peak, $15.50 peak one way)
• Depart: Grand Central Terminal
• Arrive: Ossining Station

Pro tips:

• Sit on the left side of the train for gorgeous Hudson River views.
• As you approach Ossining, look out for Sing Sing Prison on your right—one of the most famous prisons in the world, still in operation today!

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10:00 AM – Start with Coffee at Here Coffee & Beer ☕

Once you step off the train, fuel up at Here Coffee & Beer, a stylish, modern café serving top-notch espresso drinks and some of the best sandwiches in Westchester.

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Here Coffee & Beer
127 Main St, Ossining, NY

Why go?

• Cozy, minimalist space perfect for relaxing
• Insane breakfast sandwiches
• Great rotating selection of craft beer on tap

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10:45 AM – Visit the Ossining Farmers Market (Saturdays Only!) 🛍️

Since the Ossining Farmers Market closes at 1 PM, head there next to explore local vendors selling fresh produce, baked goods, cheeses, and handcrafted products.

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Ossining Farmers Market
Corner of Main St & Spring St
Open until 1 PM

Why stop by?

• Meet local farmers & artisans
• Grab a fresh-baked pastry or locally made honey
• Perfect way to support small businesses!

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11:30 AM – Walk Along the Hudson & Visit the Iconic Bridge Under the Bridge 🌊

Before heading downtown, take a leisurely stroll down to the river, just a few minutes from Main Street.

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Louis Engel Waterfront Park
Westerly Rd, Ossining, NY

Why go?

• Breathtaking Hudson River views
• Relaxing promenade walk
• Great spot to watch boats, see the sunset, or just take a break

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Bridge Under the Bridge – Ossining’s Iconic Landmark
As you walk, don’t miss Ossining’s famous “Bridge Under the Bridge”—a stunning layered structure that has become a symbol of the town. This unique architectural piece frames the train tracks beautifully, making it a fantastic photo spot!

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12:30 PM – Explore Downtown & Visit Hudson Valley Books for Humanity 📚

Ossining’s historic downtown is packed with independent shops, historic architecture, and community-driven businesses. One must-visit spot is Hudson Valley Books for Humanity, an independent bookstore with a fantastic selection of new & used books, social justice reads, and local authors.

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Hudson Valley Books for Humanity
67 Central Ave, Ossining, NY

Why visit?

• A welcoming, community-driven bookstore
• Focus on sustainability & diverse voices
• Great place to find something unique & local

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1:30 PM – Lunch at The Tasty Table 🍽️

Now that you’ve worked up an appetite, it’s time for lunch at The Tasty Table, one of Ossining’s most beloved spots for brunch and lunch.

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The Tasty Table
21 Campwoods Rd, Ossining, NY

Why it’s great?

• Generous portions & homemade flavors
• Outdoor seating available
• Great mix of comfort food & fresh, locally sourced ingredients

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2:30 PM – A Nature Break at Teatown Lake Reservation 🌿

Take a 10-minute Uber/Lyft ride to Teatown Lake Reservation, a serene nature preserve with easy walking trails and a gorgeous lake. A must for nature lovers!

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Teatown Lake Reservation
1600 Spring Valley Rd, Ossining, NY

Best trail: The Lakeside Loop—a peaceful, scenic 1.5-mile walk

Why go?

• Easy hiking with beautiful scenery
• Chance to see wildlife (turtles, hawks, and even otters!)
• Perfect way to recharge in nature

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4:30 PM – Afternoon Coffee at First Village Coffee ☕

After your nature adventure, head back to town and stop at First Village Coffee, a local favorite for specialty coffee and homemade pastries.

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First Village Coffee
123 Main St, Ossining, NY

Why visit?

• Locally roasted coffee & friendly vibes
• Great spot to unwind before dinner
• Beautiful, artsy space

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5:30 PM – Stroll Along Main Street & Discover Local Shops 🏙️

Before dinner, take a relaxed walk along Ossining’s Main Street. This charming stretch is lined with historic buildings, boutique shops, and hidden gems. Check out a few of the local businesses along the way:

• Melita’s Home – A delightful gift shop featuring handcrafted home goods and artisanal items
• Hudson Valley Arts & Collectibles – A small but intriguing shop with vintage finds and local art
• Bob’s Army & Navy – A quirky, old-school surplus store with everything from camping gear to local history books

Take your time to soak in the town’s atmosphere, pop into any interesting stores, and maybe even grab a small souvenir before heading to dinner.

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7:00 PM – Dinner at 3 Westerly (Waterfront Dining!) 🍷

End your day with a memorable dinner at 3 Westerly, an upscale waterfront restaurant with breathtaking Hudson River views, fresh seafood, and top-notch cocktails.

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3 Westerly Bar & Grill
3 Westerly Rd, Ossining, NY

Why it’s awesome?

• Gorgeous sunset views over the Hudson
• Extensive seafood & steak menu
• The perfect way to end your day in Ossining

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8:30 PM – Train Back to NYC 🚂

After a relaxing, adventure-filled Saturday, catch the Metro-North back to Grand Central, watching the Hudson River glow under the evening sky.

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As the train pulls away from Ossining, take a moment to reflect on the day. Whether it was the peaceful waterfront, the charming small businesses, or the cozy cafés, there’s something about this town that lingers with you. Maybe it’s the mix of history and modern energy, or just the perfect blend of adventure and relaxation. Either way, Ossining is always worth the visit—until next time.

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