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Ossining

Ossining, NY, USA

Ossining

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Ossining

Welcome to Ossining, home of Sing Sing prison and breathtaking views of the Hudson River! Explore historic landmarks like the Victorian-era Teatown Lake Reservation or grab a bite at one of the many charming eateries in town. Don't miss the Ossining Farmers Market for local goodies! An underrated gem just a train ride away from NYC.

Recommendations

Outdoor4.8/5

Croton Gorge Park

Welcome to Croton Gorge Park, where nature hugs you tight and adventure awaits! With its stunning views of the 85-foot tall Croton Dam and cascading waterfalls, this park is a playground for thrill-seeking travelers. Go rock climbing, have a picnic by the Hudson River, or simply bask in the beauty of this tranquil oasis. Get ready to explore and create unforgettable memories!

Outdoor4.8/5

Teatown Lake Reservation

Come explore the peaceful Teatown Lake Reservation in Ossining, NY. With 15 miles of hiking trails, a nature center, and paddle boat rentals, there's something for everyone to enjoy. Be sure to keep an eye out for local wildlife like turtles, deer, and birds. Don't forget your camera for some great Instagram shots!

Landmark4.6/5

Sleepy Hollow Cemetery

Welcome to the eerie yet enchanting Sleepy Hollow Cemetery in NY! Home to the legendary Headless Horseman, this spooky resting place oozes Gothic vibes. Marvel at the 90-acre expanse filled with quirky tombstones and visit the famous graves of Washington Irving, Andrew Carnegie, and Elizabeth Arden. Hauntingly beautiful, this cemetery is a must-see for thrill-seeking travelers!

Culture4.5/5

Sing Sing Prison Museum

Discover the haunting history at Sing Sing Prison Museum, where visitors explore the storied past of one of America’s most infamous correctional facilities, featuring captivating exhibits on crime, punishment, and reform.

Landmark4.5/5

Down to Earth Ossining Farmers Market

At Down to Earth Ossining Farmers Market, you'll find a vibrant mix of local vendors selling fresh produce, baked goods, and artisan crafts. Located near the corner of Main & Spring St in Ossining, NY, this market is a must-visit for anyone craving a taste of the Hudson Valley's best offerings. Come taste the local flavor!

Eat4.6/5

Sing Sing Kill Brewery

Located in the historic town of Ossining, Sing Sing Kill Brewery is a lively spot to grab a cold beer. With a cozy atmosphere and a rotating selection of craft brews, this local favorite is the perfect place to unwind after a day of exploring the Hudson Valley. Cheers to good times at Sing Sing Kill Brewery!

Eat$4.3/5

Mariella's Restaurant & Bar

Indulge in a culinary adventure at Mariella's Restaurant & Bar in Haverstraw, NY. This cozy spot on New Main St offers a delicious menu of Italian classics and fresh seafood. Sip on craft cocktails while enjoying live music on weekends. A perfect stop for foodies looking for a taste of authentic eats in a vibrant atmosphere. Visit now!

Eat$$$4.5/5

Sweet Grass Grill

Located in the charming town of Tarrytown, Sweet Grass Grill is a foodie's haven on 24 Main Street. This lively eatery offers a mouthwatering farm-to-table menu, showcasing the freshest local ingredients in creative and delicious ways. With its vibrant atmosphere and friendly staff, Sweet Grass Grill is the perfect spot to refuel after exploring the historic sites of Tarrytown. Get ready to tantalize your taste buds!

Eat$$$4.3/5

Karma Lounge Restaurant

Nestled in charming Ossining, Karma Lounge Restaurant is a foodie haven! With a vibrant atmosphere and a menu bursting with flavor, you’ll find everything from zesty tacos to sumptuous curries. Sip on their creative cocktails while enjoying live music—perfect for a fun night out! Don’t miss this culinary gem at 175 Main St; your taste buds will thank you!

Eat$$3.7/5

Texas Fried Chicken & Gyro

Eat$$4.8/5

First Village Coffee

Stays

Stay4.25/5

Courtyard by Marriott Tarrytown Westchester County

Nestled in the scenic Hudson Valley, Courtyard by Marriott Tarrytown Westchester County offers modern comforts and easy access to historic sites, making it an ideal getaway for travelers seeking a blend of relaxation and adventure.

Stay3.85/5

Sheraton Tarrytown Hotel

Step into luxury at Sheraton Tarrytown Hotel! Nestled in historic Tarrytown, NY, this modern hotel offers spacious rooms, a fitness center, and a refreshing indoor pool. Conveniently located near major attractions like Sleepy Hollow and Westchester Mall, Sheraton Tarrytown is the perfect home away from home for any traveler looking to explore the Hudson Valley.

Things To Do
Provided byViator

4.7/5

Couple's Private Hudson Valley Fall Foliage Helicopter Tour from Westchester

Perfect for a romantic date, couples enjoy the beautiful Fall colors of Hudson Valley from the sky. Helicopters lift off from a quiet location at Westchester Airport and in just a few minutes you will find yourself soaring above historic and natural landmarks dressed in fall colors. All tours are personally narrated by friendly and experienced pilots. 30-minute tour includes: Castle-on-Hudson, Kykuit (Rockefeller Estate), Sleepy Hollow Lighthouse, Gov. Mario M. Cuomo Bridge, Indian Point Energy Center, Harriman State Park, Bear Mountain, US Military Academy at West Point* and the infamous Sing Sing Prison. Opt for the 45-minute tour to see Dick's Castle, Bannerman Castle and landmarks south of the Gov. Mario M. Cuomo Bridge: Lyndhurst Mansion and The Palisades. *West Point subject to temporary airspace restrictions

$995.00
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4/5

Hudson Valley Fall Foliage Helicopter Tour from Westchester (Shared)

New York State’s picturesque fall foliage season is not to be missed. Instead of crowded parks and trails marvel at the cascade of blazing reds, yellows and oranges of Hudson Valley fall foliage from the comfort of a helicopter. Helicopters lift off from a quiet location at Westchester Airport and in just a few minutes you will find yourself soaring above historic and natural landmarks dressed in fall colors. All tours are personally narrated by friendly and experienced pilots. 30-minute tour includes: Castle-on-Hudson, Kykuit (Rockefeller Estate), Sleepy Hollow Lighthouse, Gov. Mario M. Cuomo Bridge, Indian Point Energy Center, Harriman State Park, Bear Mountain, US Military Academy at West Point* and the infamous Sing Sing Prison. Opt for the 45-minute tour to see Dick's Castle, Bannerman Castle and landmarks south of the Gov. Mario M. Cuomo Bridge: Lyndhurst Mansion and The Palisades. *West Point subject to temporary airspace restrictions

$415.00
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3.7/5
8 h

Circle Line: 8-hr Bear Mountain Oktoberfest Cruise

Experience the ultimate autumn getaway on the water with a scenic 50 mile voyage through the Hudson River Valley straight to Bear Mountain State Park. Surrounding you are brilliant fall foliage colors combined with an authentic Bavarian festival atmosphere right on the deck. Traditional German Fare: Feast on classic comfort dishes including Pork Schnitzel, savory Bratwursts, and warm oversized Bavarian Pretzels. Craft Beer Selection: Sip premium pours from collectible souvenir mugs, featuring authentic German brews like Warsteiner and Spaten alongside seasonal Pumpkin Ales and Sam Adams Octoberfest. Live musical performances throughout the journey, while award winning local guides share fascinating history about the passing landscapes. Upon arrival, enjoy two full hours of free time to hike stunning forest trails, relax by the lake, or visit the local trailside zoo before embarking on the relaxed return trip to Manhattan.

$79.00
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3/5
6 h

Sleepy Hollow and Historic Hudson Valley Tour from NYC

This 6-hour private tour blends iconic history with small-town charm in the riverside towns of Sleepy Hollow and Tarrytown. Enjoy hotel pickup and drop-off in Manhattan with a professional, English-speaking driver. Start at Sleepy Hollow Cemetery, home to Washington Irving’s grave and the Old Dutch Church. Continue to Philipsburg Manor, a colonial-era manor and mill. Stroll Tarrytown Main Street for local shops and cafés before heading to Kykuit – The Rockefeller Estate, with sweeping views of the Hudson (interior tour requires tickets). Flexible timing and stops ensure a personalized experience.

$358.59
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1 h

Private Hudson Valley Fall Foliage Helicopter Charter from Manhattan

Take in the autumn colors of the Hudson Valley on a fall foliage helicopter tour. Conveniently departing from the Midtown Manhattan heliport of your choice, this private 1-hour charter is narrated live by your pilot. After leaving New York City airspace you’ll fly above the historic Hudson River region. Ride in comfort and luxury in an Airbus AS350/H125 helicopter for 2-5 people or a twin-engine Airbus AS355. Landmarks include: Lyndhurst Mansion, Palisades, Castle-on-Hudson, Kykuit (Rockefeller Estate), Sleepy Hollow Lighthouse, Gov. Mario M. Cuomo Bridge, Indian Point Energy Center, Harriman State Park, Bear Mountain, US Military Academy at West Point* and the infamous Sing Sing Prison. *West Point subject to temporary airspace restrictions

$6,565.00
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Private Fall Foliage Helicopter Tour for 2-6 from Westchester

Perfect for couples, the whole family or group of friends, enjoy the beautiful Fall colors of Hudson Valley from the sky. Helicopters lift off from Westchester County Airport and in just a few minutes soar above historic and natural landmarks dressed in fall colors. All tours are personally narrated by friendly and experienced pilots. Ride in comfort and luxury in an Airbus AS350/H125 helicopter for 2-6 people or twin engine Airbus AS355 for 5 people. 30-minute tour includes: Castle-on-Hudson, Kykuit (Rockefeller Estate), Sleepy Hollow Lighthouse, Gov. Mario M. Cuomo Bridge, Indian Point Energy Center, Harriman State Park, Bear Mountain, US Military Academy at West Point* and the infamous Sing Sing Prison. Opt for the 45-minute tour to see Dick's Castle, Bannerman Castle and landmarks south of the Gov. Mario M. Cuomo Bridge: Lyndhurst Mansion and The Palisades. Options with transfer include roundtrip car service between Manhattan and Westchester County Airport.

$1,710.00
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5/5

Unmissable Cairo Tour: Pyramids, Mummies Museum,Citadel & Bazaars

Experience the wonders of ancient Egypt with our premium Giza Pyramids tour, National Egyptian Civilization Museum(NECM) , Citadel best Muslim building mosque of Mohamed Ali . Enjoy: - **Skip-the-line tickets** for the Pyramids and Sphinx (no waiting) - **Private Egyptologist guide** fluent in your language or your language . - **Authentic camel ride** through the Sahara desert **Why travelers choose us:** - Fully customizable private experience - Instant booking confirmation - 24/7 customer support - Best price guarantee **Recent traveler review:** "The guide's knowledge was incredible - he made the pyramids come alive! The Nile lunch was the perfect ending." - Sarah, USA (5-star rating) Book now for an unforgettable journey through ancient history with Egypt's top-rated tour operator. Limited availability - secure your spot today!

$25.00
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5/5

Private Helicopter Flight Lesson from Westchester

Experience the thrill of flying around the Hudson Valley with this helicopter flight lesson from Westchester Airport in White Plains, NY. Start with ground instruction to learn about basic flying technique and safety and then take to the air during an approximately 30- or 60-minute private lesson. One student will be allowed access to the controls under the supervision of a certified flight instructor. While airborne, you will enjoy breathtaking views and try your hand at basic maneuvers (turning, climbing, descending, etc.) In the Robinson R44 Raven II helicopter you have the option to invite an additional passenger/observer to ride along with you (subject to weight limitations). Please note: the observer does not fly the helicopter. Flying lessons are not permitted in NYC airspace. No prior flying experience needed.

$705.00
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5/5
7 h

NYC: Train Trip with Sleepy Hollow and Walkway Over Hudson

Our tour begins in the center of Midtown. From Grand Central we will take Metro North up to Tarrytown and Sleepy Hollow. There we will explore this historic area and you will learn about its most famous resident: Washington Irving. Trace the path of Ichabod Crane and the Headless Horseman. We will visit the Old Dutch Burial Ground and Church. After a brief coffee and pastry break, we will take a majestic train ride up to Poughkeepsie where you will be able to experience the new jewel of the river, the Walkway Over the Hudson. We will take a brief elevator ride to the top where you will get incredible views. From there, we will take the train back to the Hudson Highlands where we will visit the charming village of Cold Spring. You will experience views of West Point and the sheer cliffs of Storm King. The tour ends here, but your day need not end- spend the day here or go onto another town!

$135.00
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5/5
40 mins

New York City Sunset Helicopter Tour from New Jersey

Experience New York City at its most breathtaking moments - from the sky at sunset. As the sun dips below the horizon, the city glows in a golden light, reflecting off the Hudson River and simmering glass towers of Manhattan. Your helicopter lifts off for an unforgettable journey over the city’s most famous landmarks - from the Statue of Liberty and the One World Trade Center to the Empire State Building, Central Park, and the Chrysler Building. You’ll take in both the West Side skyline along the Hudson and the East Side views overlooking the United Nations, the East River bridges, and the iconic cityscape of Midtown and Lower Manhattan. As day turns to night, the lights of New York begin to sparkle beneath you, transforming the skyline into a sea of color and brilliance. It’s a breathtaking perspective — romantic, peaceful, and utterly mesmerizing.

$444.00
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5/5
4 h

Event at New York City with DJ Music, Photography & Music Video

The New York city tour starts from Manhattan City Walking Tour, Brooklyn Bridge, and Pear 36 New York!! Meet at Bleecker St; Manhattan is the perfect place for capture some Photography and videography. You not only learning but also creating memories with Photography and videography. So our NYC Tour Guide & Photographer will wait for you there. You will get all the Photography shots and videography videos. Camera: Sony a7r5 & Lense

$380.00
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5/5
45 mins

New York Fall Foliage Helicopter Tour from New Jersey

This Fall Foliage flight allows you to take in the spectacular views of New York during the seasonal change in color from the bright greens of summer to the brilliant hues of autumn. As you fly towards the Manhattan skyline, above the Hudson River to the tip of Manhattan you will be able to see New York City landmarks like The Empire State Building, The Chrysler Building, Central Park, and the George Washington Bridge as well as newer attractions like the Vessel and Summit One Vanderbilt. Continue on to the breathtaking NJ Palisade Cliffs while you approach the famous Tappan Zee Bridge on the border of Westchester County, and Sleepy Hollow, the home of the notorious Headless Horseman. Available seasonally from September 21st – November 30th *HeliNY is Wingman/TOPS certified!

$440.53
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5/5

Walkway Over the Hudson & Wineries- Private Transport

The Walkway Over the Hudson is the longest and highest elevated pedestrian bridge in the world! Benmarl Winery is America's oldest Vineyard! When you accompany two of those facts with a company that will bring you to and from your locations with professionalism, reliability and friendliness, you can't go wrong! Don't feel guilty indulging one bit at your wineries because you got some exercise in during your amazing time at the Walkway Over the Hudson! Optional bike rentals are available upon request for the Walkway Over the Hudson. Please let us know ahead of time. *Hotel accommodations are available upon request. Simply send us an email and we will be happy to assist you. *Depending on winery availability at the time of your booking, it may be necessary to visit different comparable local wineries than listed. *the Walkway Over the Hudson is a flat paved walkway that is 1.30 miles long. You will get picked up on the other side.

$235.00
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5/5
3 h

Nyack 2-Hour Guided Food Tour with lunch included

Explore and tour the Village of Nyack, Art and Soul on the Hudson Valley with your local tour guide and food enthusiast, Joey G. Your tour guide will start at the Historic St. George Hotel, right on the Hudson River. Joey G will take you on and off the beaten path of the quaint, eclectic, and artistic Hudson Valley Village of Nyack. You will meet and greet with local chefs, creatives, and food experts along your tour. Additionally we will get to explore portions of the Nyack neighborhoods and learn about what makes it such a special place.

$65.00
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5/5
1 h 30 mins

5 Stops Central Park Pedicab Tour Customizable Landmarks

Explore Central Park in an immersive way with a customizable pedi-cab tour. This unique experience allows you to discover the park’s beauty and history at your own pace. Choose your preferred landmarks, from the iconic Bethesda Fountain to the serene Strawberry Fields, and enjoy insightful commentary along the way. Whether you want to capture the perfect photo or delve deeper into a specific site, this tour is designed for your interests. With a flexible duration of approximately one hour and three engaging pit stops, this tour is perfect for families, friends, or anyone seeking to enjoy Central Park like never before. - Customizable tour length with a standard duration of about one hour - Visit iconic landmarks like Bethesda Fountain and Bow Bridge - 8 stops for walking, photography, and deeper discussions - Educational insights into Central Park's history and hidden gems

$150.00
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5/5
8 h

Hudson Valley Craft Brewery Bike Tour

Enjoy a bike ride to one of the best craft breweries in the New York City Metro region on this full-day riding tour. Take the Hudson Valley's 'Old-Put' bike path to the Captain Lawrence Brewing Company in Elmsford. Just hop on the Metro-North train (with a bike), then travel down 35 miles of scenic, car-free rail trails. At the end of the ride, enjoy a tasting flight of locally famous beer. Transportation will be waiting to drive guests and bikes back to the train station afterwards. No car or driving is required and lunch and beer tasting are included. This tour is run once per month. Our 2025 dates are April 27, May 18, June 15, August 17, September 28, October 26 (All dates are Sundays)

$169.00
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4.8/5

Top Rated Luxury Private VIP Tour by vehicle, Select 3 or 5 hours

Instead of getting flustered with maps and subways, cruise along in a comfortable SUV on this private 3 or 5 hour tour of Lower Manhattan. Learn a great mix of history and fun facts from a personal navigator — a native New Yorker — who escorts you to top sights like Ground Zero, West Village, South Street Seaport, Chinatown and Little Italy. Upgrade to a 5-hour tour and explore Upper and Mid-Manhattan as well: Museum Mile, Rockefeller Center, Central Park and more. It’s the perfect way to bite into the Big Apple. Please note that this tour is also offered in Portuguese, French, and Spanish. If you would like to reserve a tour with a guide fluent in any of these languages, please be sure to select the Foreign Language Tour option during the booking process.

$697.50
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4.8/5

Private New York City Helicopter Tour for Couples from Westchester

Your private Robinson R44 helicopter will whisk you from Westchester County Airport to Manhattan and back at sunset, day or night. Dazzle your loved one with unforgettable aerial views of the iconic Manhattan Skyline from above while cozying up to one another. Helicopters take off from Westchester County Airport and reach NYC airspace within minutes. Our skilled pilots will take you on a 30-minute tour, showcasing bird's-eye views of Midtown Manhattan, Central Park, Empire State Building, Harlem, Yankee Stadium, and the George Washington Bridge. Please note: the 30-minute tour does not cover the Lower Manhattan/Statue of Liberty area. For a more extended tour, the 45-minute ride includes all the sights mentioned above, plus a visit to the Freedom Tower, Battery Park, Statue of Liberty and Ellis Island. If you choose the transfer option, we can provide roundtrip car service between Manhattan and Westchester County Airport for your convenience.

$995.00
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4.8/5

Manhattan Helicopter Tour from Westchester (Shared)

Soar above New York City and the picturesque Hudson Valley on a helicopter tour departing from Westchester Airport, just outside NYC. Choose between a 30-minute helicopter flight with aerial views of Central Park, Yankee Stadium and the East River bridges, and a 45-minute tour that continues downtown toward Freedom Tower, Battery Park, Ellis Island and the Statue of Liberty. Or plan a romantic date with an upgrade to a private couple’s flight.

$415.00
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4.8/5

NY Helicopter Tour: Manhattan & Brooklyn

Experience Manhattan from a breathtaking new perspective on a 25-30 minute NYC helicopter tour with HeliNY! Your helicopter ride will lift off from downtown Manhattan and fly past iconic New York City landmarks such as the Statue of Liberty, the Empire State Building, Times Square, and Central Park complete with live pilot narration. Fly high above the Verrazzano Bridge, pass by Staten Island and Brooklyn, then fly all the way to the Northern tip of Manhattan. HeliNY’s NYC helicopter tours are great for guests of all ages, making it the perfect addition to any New York City itinerary! Complete days worth of New York City sightseeing in just minutes, with the Manhattan skyline as your backdrop. Several departure times are available throughout the day to fit your schedule! *HeliNY is Wingman/TOPS certified!

$449.00
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