Things To Do In Westchester County NY: Top 23 Most Unique Spots | Stanton House Inn
shopping is one of the most popular things to do in Westchester

On the hunt for fun things to do in Westchester this weekend? Whether you’re into:

  • Outdoor activities

  • Historic sites

  • Or live music of all kinds

Westchester County is a unique microcosm of America. Check out our handpicked list of top spots to make your visit unforgettable.

Ready to explore the best things to do in Westchester NY? Let’s get into it:

Quick Hits

  • Mix of Attractions: From grand estates like the Rockefeller State Park Preserve and Kykuit to scenic trails, live music, and family-friendly spots like Rye Playland.

  • Unique Outdoor Experiences: Hike the 13 Bridges Loop Trail at Rockefeller State Park Preserve, kayak with Hudson River Recreation tours, or wander through the landscaped Untermyer Gardens.

  • Rich Historical Sites: Explore Van Cortlandt Manor and Lyndhurst Mansion with interactive and guided tours that dive into Westchester’s history and architecture.

A Brief History of Westchester County

One of the landscaped parks welcoming visitors to Westchester County

Long before it became part of New York State, Westchester County was known as Lenapehoking, home to the Algonquian peoples. Tribes that lived or passed through here regularly included the:

  • Manhattans

  • Weckquaesgeek

  • And Siwanoy

And famous explorers Giovanni da Verrazzano and Henry Hudson popped by in the 1500s and 1600s while exploring the Hudson River Valley.

Fast forward to 1683, and Westchester County was one of the first twelve counties in the Province of New York. It even included what we now call the Bronx at the time. By 1775, it was the wealthiest and most populated county in the colony.

1800s

After the Revolutionary War, Westchester bounced back quickly. By 1798, it was divided into 20 towns with a population of 24,000. Two big changes in the 1800s really shaped the county: the Croton Dam and Aqueduct, finished in 1842, and the arrival of the railroad. These developments turned the county into a hub of activity and growth. It also shifted the population southwards.

Post-Civil War, the area saw a boom as wealthy entrepreneurs built grand estates, especially along the Hudson River. This also brought in manufacturing, with factories sprouting up along the waterways.

1900s

In the 20th century, Westchester evolved into the suburban county we know today. The Bronx River Parkway, completed in 1925, holds the distinction of being the first modern, multi-lane roadway in North America. This, along with the development of parks, helped support existing communities and sparked new ones.

So, whether you’re a history buff or just curious, Westchester’s story is a fascinating time machine ride through American history.

The Best Things to do in Westchester County NY

Sculpture in Kykuit, John D. Rockefeller's Home, with the Hudson River in the background

If you’re looking for some fun things to do in Westchester County this weekend, you’re in luck. There’s a little something for everyone here. Check out these activities:

  • Exploring grand estates

  • Hiking scenic trails

  • Enjoying live music

  • Visiting family-friendly attractions

Ready to dive in? Read on for some of the best activities to explore in Westchester County this weekend.

Explore Rockefeller State Park Preserve | Pleasantville

Hiking trail located in the bluffs above Sleepy Hollow and Tarrytown, New York

Nature lovers, this one’s for you. Rockefeller State Park Preserve is a slice of paradise. 45 miles of scenic carriage roads laid out by John D. Rockefeller Sr. and Jr., are perfect for a leisurely walk, jog, or even a horseback ride.

One trail you can’t miss is the 13 Bridges Loop. It’s a 1.9-mile journey that takes you over—you guessed it—13 charming bridges. And then there’s Swan Lake, home to all kinds of waterfowl. If you’re into bird-watching, you’ll be in heaven with 202 recorded bird species.

In winter, the trails become a cross-country skiing wonderland. With massive oak, tulip poplar, and maple trees, some over 200 years old, Rockefeller State Park Preserve is a year-round escape into nature.

Visit Historic Kykuit, The Rockefeller Estate | Sleepy Hollow

Main house at Kykuit: the Rockefeller Estate, one the National Register of Historic Places and home to four generations of Rockefellers

For history and art buffs, Kykuit: the Rockefeller Estate, is a must-see. This estate and historic site was home to four generations of the Rockefeller family and is packed with:

  • Fine and decorative art collections

  • Beautiful gardens and landscapes

  • Stunning architecture

  • Amazing views of the Hudson River

John D. Rockefeller Jr. and his wife, Abby Aldrich Rockefeller, gathered an incredible art collection. Featured works here ones by Picasso, Warhol, and more. The gardens, enhanced by Nelson Rockefeller, are adorned with modern sculptures by artists like Henry Moore.

Don’t miss the Oceanus Fountain, a replica of Giambologna’s fountain from Florence. Tours run from May to early November, Thursdays through Sundays. You’ll get to explore art galleries, lush gardens, and even a collection of classic cars.

Enjoy Live Music at Capitol Theatre | Port Chester

If you haven’t been to the Capitol Theatre in Port Chester, you’re missing out. This place has historic charm and killer acoustics. Over the years, this historic site has hosted big names in rock, jazz, and even comedy. No matter your taste, you’ll find something to groove to.

Coming up, we’ve got John Mulaney, Joey Fatone & AJ McLean, and the Black Pumas. Plus, don’t miss the Westchester Reggae Festival with Etana, Big Youth, and Christopher Martin. And guess what? The Capitol Theatre is just a train ride away from NYC. So, grab your tickets and get ready for an unforgettable night of music!

Family Fun at Rye Playland | Rye

The Long Island Sound beach at Playland Park in the city of Rye, New York

Looking for a fun day out with the family? Head to Rye Playland! This Art-Deco amusement park has been a hit since 1928, blending old-school charm with modern thrills. With over 50 rides and attractions, there’s something for everyone.

Check out the show fountain at the entry plaza, paddle boats on the lake, and a zero-depth entry pool. Beach lovers will enjoy the park’s three beaches and 1.5 miles of boardwalk. And during the holidays, it transforms into a winter wonderland with lights, music, and free hot chocolate.

Whether you’re riding the historic Dragon Coaster or watching fireworks, Rye Playland promises a day full of fun and fond memories.

Hike Ward Pound Ridge Reservation | Pound Ridge

If you love the great outdoors, Ward Pound Ridge Reservation is the spot for you. As the largest park in Westchester County, it spans 4,315 acres and offers over 35 miles of trails for all skill levels.

But a hike isn’t the only thing on the menu. You can also try fly-fishing, picnicking, ice fishing, and cross-country skiing. The park is dedicated to conservation, with the Trailside Nature Museum offering seasonal programs.

Whether you’re trekking through diverse landscapes or enjoying outdoor activities, Ward Pound Ridge is a nature lover’s paradise.

Step Back in Time at Lyndhurst Mansion | Tarrytown

Lyndhurst Castle is one of the best things to do in westchester county, ny

History buffs, this one’s for you. Lyndhurst Mansion in Tarrytown is a Gothic Revival gem designed in 1838 by Alexander Jackson Davis. With rolling lawns, century-old Beech trees, and rose gardens, it’s a step back in time.

Choose from various guided tours:

  • The Classic Mansion tour covers the beautifully decorated first and second floors

  • Meanwhile, the Upstairs/Downstairs tour takes you to unique spots like the observation tower and kitchen

Don’t forget to wander the restored Civil War-era pathways and enjoy breathtaking views of the Hudson River from three viewing platforms.

Paddle Through the Hudson River

Kayaking through the Hudson Valley

Westchester County and the Hudson River is a paddler’s paradise. Hudson River Recreation offers kayak and stand-up paddleboard rentals, plus tours and lessons for newbies and seasoned paddlers alike. They’ve got top-notch gear and a friendly staff, ensuring you’ll have a safe and fun time on the water.

Check out these popular tours:

  • Sleepy Hollow Kayak Tour

  • Croton River Kayak Tour

  • Sunset Kayak Tour

  • Tarrytown Lakes Kayak Tour

  • Rye Beach Kayak Tour

Each tour gives you a unique adventure on the Hudson River. So, grab a paddle and get ready for an unforgettable experience!

Discover Art at Hudson River Museum | Yonkers

This place is a treasure trove of art, history, and science. The Hudson River Museum hosts an impressive collection of American art. Be on the lookout for stunning works from the Hudson River School, those 19th-century landscape artists who really knew how to paint a scene.

But wait, there’s more! The museum keeps things fresh with rotating exhibitions, so there’s always something new to feast your eyes on. And don’t miss the planetarium—it’s like a front-row seat to the wonders of the cosmos. Seriously, it’s out of this world.

Got kids? They’ll go wild for the Hudson Riverama, an interactive exhibit that dives into the ecology and history of the Hudson River. It’s fun and educational, a win-win for the whole family.

Discover History at Van Cortlandt Manor | Croton-on-Hudson

Step back in time at Van Cortlandt Manor, nestled in the beautiful Hudson River Valley. This historic site played a big role in American history, especially during the Federalist and Anti-Federalist debates. Explore the stone manor house, brick ferry house, and heritage gardens along the picturesque Croton River.

You can even try your hand at blacksmithing, brick making, and open-hearth cooking with their interactive experiences. And don’t miss the seasonal events like the Great Jack O’Lantern Blaze, featuring over 7,000 hand-carved, illuminated pumpkins. Van Cortlandt Manor is a perfect mix of education and enchantment, and one of the best things to do in Croton-on-Hudson, NY.

Wander Untermyer Gardens | Yonkers

Looking down a landscaped corridor to the Hudson River at Untermyer

Need a break from the hustle and bustle? Untermyer Gardens in Yonkers is the place to be. Spanning 43 acres, this beautifully landscaped park features the Walled Garden, inspired by ancient Indo-Persian gardens, with a long pool and an amphitheater.

In the summer, Untermyer Gardens comes alive with guided tours, yoga classes, and concerts. Just remember, no picnics are allowed, and the gardens close at dusk. Whether you’re taking a peaceful stroll or joining an event, Untermyer Gardens is a serene escape in Yonkers, NY.

Old Croton Aqueduct Trail

The Old Croton Aqueduct Trail passes right by the Croton free library, a top public library in the county

If you love history and the outdoors, the Old Croton Aqueduct Trail is calling your name. This scenic 41-mile path, built in 1837, once supplied water to New York City. Now, it’s a National Historic Landmark perfect for walking, jogging, and cycling.

Highlights of the trail include:

  • A winding path through urban centers and small communities

  • Numerous historic sites, preserves, and landmarks

  • Year-round recreational opportunities

Explore the Croton Dam and dive into Westchester County’s rich heritage and natural beauty. It’s a fantastic way to enjoy both history and the great outdoors!

PepsiCo Sculpture Gardens | Purchase

The PepsiCo Sculpture Gardens is where the magic happens. Wander through an outdoor gallery with over 45 sculptures by famous twentieth-century artists. Designed by the garden wizard Russell Page, this place turns corporate grounds into a serene arboretum.

Open to the public on weekends from March to November, it’s a perfect spot to enjoy modern art in a peaceful setting. So, grab a friend, take a stroll, and soak in the beauty!

Armour-Stiner Octagon House | Irvington

Ever seen an octagon house? No? Then you’ve got to visit the Armour-Stiner Octagon House in Irvington. This architectural gem from 1872 is a rare find and looks like something straight out of a Victorian fairy tale.

Take a guided tour to learn about its unique design, fascinating interiors, and rich history. It’s a must-see for anyone who loves quirky architecture and history.

Caramoor Center for Music & the Arts | Katonah

One of the musical performances at Caramoor in July

Music and arts fans, Caramoor Center in Katonah, NY, is calling your name! Set on a stunning 90-acre estate, this place offers a mix of concerts and events all year round. Whether you’re into classical, jazz, opera, or American roots music, Caramoor’s got you covered.

Here’s what you can enjoy at Caramoor:

  • Garden tours

  • Art exhibitions

  • Educational programs

  • Family-friendly events

Don’t miss the Venetian Theater for an intimate outdoor concert experience or the Rosen House, a Mediterranean-style villa filled with fine art and lovely gardens. Spend your weekend soaking up the culture!

Mianus River Gorge | Bedford

Nature enthusiasts, this one’s for you! Mianus River Gorge Preserve offers 755 acres of rich woodland and ancient forest. It’s a short drive from NYC and a mere 24 minutes from Stanton House Inn. The Preserve is a habitat for countless species of animals, fungi, and plants.

Take a walk and discover various trees, shrubs, vines, herbs, and ferns. It’s a perfect escape from city life, a chance to reconnect with nature, and one of the best things to do in Bedford, New York.

Cute Towns in Westchester County to Visit

Cute houses in Croton-on-Hudson against a blue sky

Westchester County is packed with charming towns that are perfect for a quick getaway. Here are some highlights:

  • Rye: This town is a blast from the past with historic sites and the delightful Rye Playland amusement park. It’s a mix of history and fun—kind of like a history book with a roller coaster in the middle.

  • Sleepy Hollow: If you’re into haunted legends, this is your spot. Visit the Rockefeller State Park Preserve and the historic Sleepy Hollow Cemetery. Just watch out for the Headless Horseman!

  • Tarrytown: Just a hop, skip, and a jump from Sleepy Hollow, Tarrytown boasts a quaint main street, diverse dining options, and scenic parks along the Hudson River. It’s like walking into a Norman Rockwell painting.

  • Croton-on-Hudson: Best known for the historic Cortlandt Manor and the Great Jack O’Lantern Blaze, this town shines in the fall. Imagine thousands of glowing pumpkins lighting up the night.

  • Mamaroneck: Once a filmmaking hub, now it’s famous for its historic villages and waterfront parks. Don’t miss the charming village of Larchmont for a bit of everything.

  • Pound Ridge: Famous for its rolling hills and celebrity residents, it offers excellent hiking trails and fine dining at the Inn at Pound Ridge. It’s a great place to stretch your legs and fill your belly.

Shopping in Westchester County NY

Downtown of the village of Ossining, New York

Westchester County is a shopper’s paradise with a mix of upscale malls, charming village shops, and unique boutiques. Here’s a quick rundown of the best spots:

  • Upscale Malls: Check out The Westchester in White Plains for luxury brands and designer stores.

  • Village Shops: Explore Bronxville and Katonah for one-of-a-kind boutiques and specialty stores.

  • High-End Shopping Centers: Ridge Hill in Yonkers has a town-square vibe, and Cross County Shopping Center combines historic charm with modern amenities.

  • Farmers’ Markets & Artisan Fairs: Discover local produce, crafts, and unique gifts.

Whether you’re after luxury brands or local treasures, Westchester’s got something for everyone.

Restaurants in Westchester County, New York

Downtown Scarsdale, New York

Foodies, bring your forks! Westchester County is a culinary hotspot with something to satisfy every craving. Here are some must-visit spots:

  • Blue Hill at Stone Barns: For a farm-to-table experience with locally-sourced ingredients.

  • Walter’s Hot Dog Stand: Serving iconic hot dogs since 1919—an absolute must-visit.

  • Goosefeather: Enjoy a unique dining experience in a historic manor house.

  • The Cookery in Dobbs Ferry: Rustic yet sophisticated, with inventive pastas that will knock your socks off.

  • Burrata: Artisanal pizzas that are simply divine.

With top NYC chefs bringing their talents to Westchester, the dining scene here is sure to impress.

Fairs & Festivals in Westchester County

Thousands of illuminated pumpkins take over one of the best historic places in Westchester each October

Westchester County is buzzing with fairs and festivals all year round. Here are some highlights you won’t want to miss:

  • Sheep Shearing Fest at Stone Barns Center: Held in April, this family-friendly event features traditional sheep shearing and farm activities. It’s a great way to welcome spring!

  • Fireworks at Rye Playland: Every Friday night in July and August, enjoy a spectacular fireworks display to cap off a day of fun at the amusement park.

  • Sleepy Hollow Halloween Festivities: October in Sleepy Hollow is a spooky treat with haunted hayrides, lantern tours, and appearances by the Headless Horseman.

  • The Great Jack O’Lantern Blaze at Croton-on-Hudson: From late September through November, marvel at over 7,000 hand-carved, illuminated pumpkins set against the historic Van Cortlandt Manor.

Directions to Westchester County

The double arched bridges of Ossining, one way to get here from the Big Apple

Ready to head to Westchester County? It’s super easy, whether you’re coming from Greenwich, CT, or bustling New York City. Here’s the scoop on how to get here:

  • Bus

  • Train

  • Taxi

  • Car

From Greenwich, CT

Traveling from Greenwich to Westchester is a breeze. You’ve got options:

  • Bus: Hop on at Westchester Ave @ E Broadway to Bedford Rd @ Broadway via N Broadway @ Main St and Ej Conroy Dr @ Main St. It takes about 1 hour and 38 minutes.

  • Train: Take a train from Greenwich to the western part of the county via 125th Street – Harlem, about 1 hour and 55 minutes. Each of the Westchester towns along the Long Island Sound are even closer

  • Car: Drive any direction but east to get to somewhere in Westchester County via I-95 N, the Merritt Parkway, or local roads.

  • Taxi: A taxi ride covers the same distance, obviously.

From New York City

And getting from NYC to Westchester is a snap:

  • Train: Metro-North Railroad’s Hudson, Harlem, or New Haven lines get you from midtown Manhattan to White Plains in just 35 minutes. These towns all make fantastic Metro-North day trips.

  • Car: Driving takes around 30 to 45 minutes via I-87 N from the Big Apple.

  • Amtrak: Stops at Yonkers, New Rochelle, and Croton-on-Hudson.

  • Bus: The Bee-Line Bus System offers routes from NYC to Westchester.

Unique Hotels, Inns, and Places to Stay in and near Westchester County

Croton dam in the spring

Looking for a place to rest your head? Westchester County has some fantastic options:

  • Stanton House Inn, Greenwich: A charming bed and breakfast with beautiful rooms and a peaceful garden.

  • Castle Hotel & Spa, Tarrytown: Luxurious accommodations, a world-class spa, and fine dining.

  • The Abbey Inn & Spa, Peekskill: Set in a converted 19th-century convent with stunning Hudson River views.

  • Tarrytown House Estate on the Hudson: Historic charm, modern amenities, and extensive gardens in Tarrytown.

  • The Opus, White Plains: Offers luxury accommodations.

  • Crabtree’s Kittle House, Chappaqua: Rustic charm with a cozy vibe.

  • The Ritz-Carlton New York, Westchester in White Plains: Elegant rooms, a rooftop pool, and a prime location for exploring.

More Nearby Cities and Towns to Explore Near Westchester County

Stone artwork at Kykuit

Westchester County is a great hub, but its proximity to other charming spots makes it an ideal base for more exploring. Here are a few nearby places worth checking out:

Hudson Valley

The streets of Hudson, NY

The Hudson Valley is like a picture-perfect postcard come to life, filled with quaint towns and outdoor adventures. Here are some highlights:

  • Cold Spring: Great for antique shops and galleries. Perfect for a lazy day trip.

  • Breakneck Ridge: A hiker’s dream with stunning views of the Hudson River.

  • Dia: Beacon: An art museum in a former factory, showcasing top-notch contemporary art.

For a unique outdoor art experience, visit Storm King Art Center in Mountainville. Stroll along the Walkway Over the Hudson in Highland, NY, a historic bridge turned pedestrian park with breathtaking views. History buffs, don’t miss the Vanderbilt Mansion and the Franklin D. Roosevelt Presidential Library in Hyde Park, or the West Point Military Academy.

In Tarrytown, Main Street looks straight out of a Norman Rockwell painting and offers a diverse dining scene. Sleepy Hollow, famous for Washington Irving’s “The Legend of Sleepy Hollow,” has the Rockefeller State Park Preserve and a historic cemetery where folks like Andrew Carnegie are buried. The Hudson Valley is a trove of culture, history, and natural beauty. It’s a must-visit!

Fairfield County, Connecticut

South Norwalk, a great spot to explore one weekend

Just a hop, skip, and a jump from Westchester, Fairfield County, Connecticut, has its own set of gems:

For family fun, the Maritime Aquarium in Norwalk has engaging marine life exhibits. Theater lovers should catch a show at the Westport Country Playhouse, known for its top-notch productions. Greenwich also has attractions like Greenwich Avenue and the romantic Stanton House Inn, a charming bed and breakfast.

Tl;dr

Westchester County is a lively spot brimming with activities for every kind of traveler. Dive into history at Kykuit or Van Cortlandt Manor, and soak up the natural beauty at Rockefeller State Park Preserve and Ward Pound Ridge Reservation. The county’s mix of attractions, shopping, and dining makes it a perfect weekend escape.

Explore the scenic Hudson Valley, enjoy the arts in Fairfield County, or pamper yourself in Westchester’s luxurious accommodations. Each visit exploring things to do in Westchester will leave you with plenty of nostalgia. So, pack your bags and set off to discover Westchester County and its nearby gems. Adventure is calling!

Frequently Asked Questions

What are some must-visit historical sites in Westchester County?

You have to check out Kykuit, The Rockefeller Estate, Van Cortlandt Manor, and Lyndhurst Mansion for a taste of Westchester’s rich history.

What outdoor activities can I enjoy in Westchester County?

Hike through Rockefeller State Park Preserve, kayak at Paddler’s Paradise, or walk the Old Croton Aqueduct Trail. There’s something for every skill level.

Are there family-friendly attractions in Westchester County?

Absolutely! Rye Playland is a family favorite with over 50 rides, a show fountain, paddle boats, and a public boardwalk. Fun for all ages, year-round.

Where can I find unique accommodations in Westchester County?

Stay at the Castle Hotel & Spa in Tarrytown, The Abbey Inn & Spa in Peekskill, or the Tarrytown House Estate on the Hudson. Each offers a unique and luxurious experience.

How can I travel to Westchester County from New York City?

Hop on the Metro-North Railroad’s Hudson, Harlem, or New Haven lines for a quick 35-minute ride. Driving takes about 30 to 45 minutes via I-87 N. You can also take Amtrak or the Bee-Line Bus System.

 

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