Things to Do in Ossining NY: Top 15 Most Unique Spots

Sing Sing Prison is the most well-known feature of Ossining, a historic North County town in Westchester County. It’s also famous for being the homebase of Don and Betty Draper from Mad Men. That said, its charming mix of:

retro Main Street
old-school businesses
Portuguese culture
and eclectic dining scene

Is a far more enticing draw. Ossining, on the Hudson River, offers a variety of activities, attractions, and events for both visitors and locals. The town is an ideal destination for Westchester day trips. Discover hidden gems, savor delectable cuisine, and relax in the welcoming atmosphere of Ossining, New York.

Without further ado, let’s dive into some of the best things to do in Ossining NY!

Quick hits

Explore the unique blend of history, culture & outdoor activities in Ossining NY
Check out events & festivals like farmers markets or Annual Celebrations for a real taste of local life.
Discover nearby towns Croton-on Hudson, Briarcliff Manor & Sleepy Hollow for even more adventure!

A Brief History of Ossining, New York

Ossining, NY, has a rich history dating back to 1685. Originally inhabited by the Sint Sinck Indians, the town started as part of a manor. The State of New York confiscated the manor, as the last owner was a Loyalist during the Revolution and fled to England. The town flourished as a major port for the Hudson River.

Ossining’s history has a notorious aspect: the opening of Sing Sing Prison in 1826. Today, it still stands as one of America’s oldest maximum-security prisons. Ossining has since become quite unique, famous for beautiful architecture and diverse populace.

In 1845, a new town was carved out from the northern part of the Town of Mount Pleasant by the New York State Legislature. A local indigenous authority proposed the name Ossinsing, a variant of the name Sing Sing. The following year, they dropped the last “s” for easier pronunciation. And in 1901, to avoid mix-ups between local products and items made in Sing Sing prison, the village name was officially changed to Ossining.

Today, Ossining is a popular destination for escaping the bustling city life of nearby New York City. Ossining has a special mix of history, culture, and outdoor activities. It’s a great place to visit for a day trip.

Top Things to do in Ossining, NY

Ossining, NY, is filled with a variety of attractions and activities to suit diverse interests. If you’re ready to discover the best things to do in town, your search ends here! From exploring Sing Sing Prison’s storied past to hiking the serene trails of Sunny Ridge Preserve, Ossining has plenty to offer.

Sing Sing Prison

Also known as Sing Sing Correctional Facility, Sing Sing Prison is a significant historical site. It’s among the oldest prisons in the United States, with its history dating back to 1824. Located in Ossining, the maximum-security prison impacted the town’s history and development.

Visiting the historical site offers a unique opportunity to learn about the prison’s past and its role in shaping the community. Sing Sing Prison, with its intriguing history and notorious reputation, is a must-visit attraction. Its famous inmates and the role it played within the community make it a thought-provoking site.

Sing Sing Kill Greenway

For a breath of fresh air and a lovely riverside walk, head to the Sing Sing Kill Greenway. This picturesque walking path follows the river.

Wandering along the greenway is an opportunity to appreciate the surrounding nature and see local wildlife. No matter if you’re an experienced hiker or just someone who enjoys a leisurely walk, the Sing Sing Kill Greenway is a great choice. It offers a peaceful and enjoyable experience for people of all ages.

Sunny Ridge Preserve

Sunny Ridge Preserve in Ossining, NY, is a paradise for nature lovers. This 65-acre nature reserve offers a variety of hiking trails. Before setting out on your adventure, don’t forget the preserve is open from dawn to dusk, and pets are not allowed. With well-maintained trails and lovely scenery, Sunny Ridge Preserve is a destination for outdoorsy types.

Hiking Trails: Old Croton Aqueduct and North County Trailway

With trails accommodating all experience levels, Ossining is a paradise for hiking enthusiasts. The Old Croton Aqueduct and North County Trailway are two popular trails that you can access from Spring St.

The Old Croton Aqueduct, built between 1837 and 1842, once provided water to New York City. It now serves as a scenic 26-mile trail perfect for exploring the area’s natural beauty.

Acclaimed author Washington Irving, writer of “The Legend of Sleepy Hollow” and “Rip Van Winkle”, lived close to the aqueduct. So close, in fact, that he could hear the construction. In a letter to a confidante, he claimed the young Irish workers building the aqueduct were convinced that goblins lived in the nearby woods.

The North County Trailway stretches a remarkable 22 miles. It’s an excellent opportunity for a long walk or jog through the picturesque surroundings. Put on your hiking boots and prepare for an adventure along these stunning trails. It’s a unique blend of history and nature.

Waterfront Parks: Henry Gourdine Park and Louis Engel Waterfront Park

Ossining’s waterfront parks, Henry Gourdine Park and Louis Engel Waterfront Park, are perfect if you’re seeking stunning Hudson River views. These parks offer picturesque settings for picnics, leisurely strolls, or simply soaking in the beauty of the river.

Both parks, Henry Gourdine Park and Louis Engel Park, offer fun activities for families. At Henry Gourdine Park, you can enjoy Jazz Forum Arts events. Louis Engel Park features a playground and a paved path suitable for bikes and scooters. Don’t forget to grab some sandwiches or ready-made meals from nearby delis for a delicious picnic by the water.

Teatown Lake Reservation

Teatown Lake Reservation is a must-visit attraction in Ossining, covering a vast area of 1,000 acres. It’s a haven for nature enthusiasts, offering a variety of trails to explore and a beautiful lake to admire. The nature center on site offers information about local wildlife and even the chance to view rescued animals. Regardless of whether you’re a seasoned hiker or just someone seeking a tranquil retreat, Teatown Lake Reservation is the place to be.

Ossining Public Library

The Ossining Public Library is more than just a place to borrow books. It’s a modern facility offering an extensive range of resources, programs, and events for all ages. Conveniently located near the Ossining train station, the library features:

A children’s zone
A teen zone
An art gallery
A theater

The Ossining Public Library is an excellent destination for families and individuals. Whether you’re:

looking for a quiet space to read
eager to attend an engaging event
or interested in participating in a free class

The library has got you covered with a variety of offerings. Plus, members have the added benefit of scoring free passes to some fantastic area museums.

Ossining Events and Festivals

Throughout the year, Ossining hosts a variety of events and festivals that cater to all interests and ages. There’s always something happening in this quirky town.

Annual Celebrations

Ossining has many yearly celebrations that unite the community and entertain families. Events such as the:

Eggstravaganza egg hunt
the Ossining Annual Health and Wellness Fair
and various cultural festivals with live music

Showcase the town’s diversity and spirit.

Don’t miss the Tree Lighting Ceremony, a popular event that kicks off the holiday season with music, food, and activities for everyone to enjoy.

Ossining Farmers Market

The Ossining Farmers Market is a beloved weekly event held every Saturday from 8am to 1pm in the parking lot of the Ossining Public Library. Offering a wide variety of:

fresh produce
baked goods
and other local products

This market is a fantastic way to support local farmers and enjoy the freshest seasonal offerings.

Aside from buying groceries, you can meet farmers, join activities, and listen to music at the market.

Ossining boasts a sizable Central American community. One of the highlights is the Xquisite Coffee Plantation. A charming Guatemalan-American family manages this delightful coffee stand. It’s worth stopping by for a cup of their aromatic brew at the Farmer’s Market.

Restaurants in Ossining, NY

A highlight of Ossining, NY, is its dining scene. All that diversity that’s settled here over the centuries has made quite the mix. From international cuisines to local favorites, Ossining’s culinary scene is sure to delight and satisfy your taste buds.

Main Street Eateries

Ossining’s Main Street, also known as Main St, is home to a variety of eateries offering international cuisines that cater to a wide range of tastes. Whether you’re craving Italian, Peruvian, or Jamaican flavors, you’ll find something to satisfy for breakfast, lunch, or dinner.

Cravin Jamaican Cuisine

Cravin Jamaican Cuisine in Ossining is a must-try for Jamaican food lovers. Owned by local Peter Murdock, the restaurant offers a variety of dishes and homemade juices. Whether you’re adventurous enough to try oxtail or goat curry or prefer their chicken and vegetarian options, go for it. Don’t miss out on their sweet and spicy sorrel juice, it’s worth the temporary purple tongue!

Capri Pizza & Pasta

For lovers of Italian cuisine, Capri Pizza & Pasta on Main Street is a must-visit. Offering a variety of dishes like butternut squash ravioli and penne arrabiata, their pizzas are a standout, with options for gluten-free and cauliflower crusts. Specialty pies range from chicken marsala to broccoli rabe.

But personally, I go to Ossining, NY, for the Portuguese food. It’s that good.

Churrasqueira Ribatejo

This Portuguese family-run eatery is famed for its churrasco-style meats, grilled over an open flame. The star of the show at Churrasqueira Ribatejo is frango, chicken that comes with your choice of two sides. If you’re more of a beef person, try the bife a portuguesa, a meal that’s perfect any time of day. This traditional dish features a pan-seared steak topped with a fried egg and served alongside Portuguese chips and rice.

Doca’s Restaurant

Just a short walk from Churrasqueira Ribatejo, you’ll find Doca, my personal top pick. This place is a dream come true for lovers of codfish (or as the Portuguese call it, bacalhau). Doca’s menu is a tribute to Portugal’s favorite fish, with dishes that showcase it in all its glory – grilled, baked, boiled, you name it. But the star of the show here has to be the bolinhos de bacalhau, crispy fried balls of codfish that are downright addictive.

Having said all that, you’ll find all the typical Portuguese fare at Doca’s. It’s far more than just cod, promise.

Coffee and Dessert Spots

If you’re in the mood for a sweet treat or a cozy spot to unwind with a cup of coffee, Ossining has several charming cafes and dessert shops to choose from. Some options include:

First Village Coffee, which features a patio area with outdoor seating
Bigfoot Creamery
The Dessertist in nearby Croton-on-Hudson
The Blue Pig, also in Croton-on-Hudson

Each of these establishments offers a unique atmosphere, ranging from laid-back and cozy to bright and cheerful, making them perfect for a relaxing break or a catch-up with friends. So go ahead, treat yourself to a delicious dessert or a steaming cup of coffee in Ossining’s welcoming cafes and ice cream shops.

Shopping in Ossining, NY

Ossining, once known for its bustling Main Street shops, faced a decline in the 70s and 80s leading to many closures. That said, there’s been a new resurgence with new businesses, including shops and restaurants, sprouting up, adding to the list of attractions in Ossining, NY.

Melita’s Home

A recommendation for shopping in Ossining is Melita’s Home. This store offers a wide array of items, from home decor to jewelry and even baby clothes. Melita’s Home is a destination for a delightful selection of:

oil and vinegar cruets
and olive plates

All handcrafted in Portugal.

Penny & Ting

For a delightful shopping experience, drop by Penny & Ting, an independent toy store. Managed by Mary Howard, the store offers a charming selection of classic children’s books, do-it-yourself crafts, and toys that promote developmental learning. It’s the perfect place to hunt for the ultimate gift for the little ones in your life.

Hotels in Ossining, New York

I refer to Ossining as a day trip because there aren’t a ton of options for places to stay within Ossining itself.

Some hotels near Ossining, NY include:

Stanton House Inn, located just over the Connecticut border, is a family-owned inn offering comfortable rooms and suites, tranquil gardens, common areas, and a homemade breakfast. Our Greenwich, CT, bed and breakfast is about a 30-minute drive from Ossining, NY, making it a convenient place to stay during your visit.

The Edith Macy Conference Center is located on a 405-acre forested site in nearby Briarcliff Manor. This tranquil retreat and conference hotel features Arts & Crafts-inspired decor and offers woodland views. It boasts dining areas, a gym, walking trails, and a lake.

Crabtree’s Kittle House is a historic inn and restaurant located in Chappaqua, NY. Its history dates back to 1790. It’s famous for its charming architecture, lush gardens, and an impressive wine cellar at the award-winning restaurant.

Directions to Ossining, NY

Whether by car or train reaching Ossining, NY, is both easy and convenient.

Greenwich, Connecticut to Ossining, NY, it’s a relatively straightforward drive that can take you up to 40 minutes.

From I-95 S , follow I-95 S and I-287 W to NY-100 N/Grasslands Rd in Greenburgh.
Take exit 4 from I-287 W.
Continue on NY-100 N.
Take NY-9A N to Ossining.

Here are the directions for driving from NYC:

Follow the Saw Mill River Parkway North.
Switch to the Taconic State Parkway North.
Take the Route 133/Ossining exit.
Follow Route 133 and you’ll arrive in Ossining in no time.

For traveling by train, Ossining is just 52 minutes from Manhattan. The Metro-North Hudson Line provides frequent service to Ossining.

More Towns to Explore Near Ossining, NY

Beyond the wealth of attractions and activities Ossining offers, it’s worth exploring neighboring towns like Croton-on-Hudson, Briarcliff Manor, and Sleepy Hollow. From picturesque parks to historical sites, these charming towns provide additional opportunities for discovery and adventure.

Venture beyond Ossining and uncover even more hidden gems in the surrounding areas.

Croton-on-Hudson

Located in New York’s Westchester County, the quaint village of Croton-on-Hudson offers a wealth of attractions and activities for visitors. Some of the top things to do in Croton-on-Hudson, NY include:

Croton Point Park
Croton Gorge Park
Croton River
New Croton Dam

These locations are perfect for outdoor enthusiasts looking to enjoy nature and explore the beauty of the Hudson Valley.

One of the highlights of Croton-on-Hudson is the Great Jack-O-Lantern Blaze, an annual event that transforms the historic Van Cortlandt Mansion into a carved pumpkin museum, attracting thousands of visitors each year. With its beautiful natural surroundings and unique events, Croton-on-Hudson is a must-visit destination.

Briarcliff Manor

Briarcliff Manor, a picturesque suburban village in Westchester County, invites visitors to explore its rich history and charming estates. The town is home to attractions such as the Rockefeller State Park Preserve, Scarborough Presbyterian Church, and the Old Croton Aqueduct Trail.

In addition to its historical sites, Briarcliff Manor also boasts a variety of restaurants, making it an ideal destination for a weekend getaway or an extended stay. Whether you’re a history buff or simply looking for a scenic escape, Briarcliff Manor offers a unique and enjoyable experience for all visitors.

Tl;dr

Ossining, NY, is a charming town that provides a wealth of attractions, activities, and events for visitors of all ages and interests. From exploring its rich history to immersing yourself in nature, Ossining offers a unique blend of experiences that will leave you with lasting memories. Whether you’re planning a weekend escape or a longer visit, Ossining is a destination that’s sure to captivate and inspire.

Frequently Asked Questions

What is Ossining NY famous for?

Ossining is famous for being the home of Sing Sing Correctional Facility, one of the most well-known prisons in America. It also boasts a crescent of 19th century architectural gems, as well as the worldwide Maryknoll Catholic missions and General Electric leadership training facility founded in 1956. It was home to both John Cheever and Don Draper from the TV series “Mad Men.”

Does Ossining have a downtown?

Yes, Ossining does have a downtown. The Downtown Ossining Historic District is full of unique facts and characteristics to explore.

Is Ossining walkable?

Ossining is a beautiful, historic, and walkable village with everything you need.

What are some must-see attractions in Ossining, NY?

If you’re visiting Ossining, NY, be sure to check out Sing Sing Prison, Sunny Ridge Preserve, and Teatown Lake Reservation – you won’t be disappointed!

Are there any annual events or festivals in Ossining?

Ossining has a number of annual events and festivals, such as the Tree Lighting Ceremony, Eggstravaganza egg hunt, and cultural festivals, giving you plenty of opportunities to get out and explore the town.