34 Fun & Interesting Things to Do in Westchester 

Westchester County is unlike any other county in the state. It’s less than an hour from Manhattan, with some of the most popular cities New York State–yet, there are areas of the county where all you can see are woods, farmland, and picturesque nature views. Diving into the arts, culture, and history of the area is one of the best things to do in Westchester. Here are some of our favorite spots. 

Understanding Westchester County 

Westchester County is a unique area that enjoys proximity to New York City, Long Island Sound, and the natural wonders in the heart of the Hudson Valley. It’s home to some of the region’s oldest historic buildings and properties. Residents and visitors enjoy the blend of cities in villages, making for a perfect mix when planning day trips from NYC

Westchester attractions are easy to reach by train, with the most popular cities right off the Metro North Hudson Line. Amtrak also has service stops in Westchester, and you can easily get around by car, taxi, bus, and ride-sharing service. Most towns also have walkable streets and riverwalks. 

As one of the original twelve counties in NY, Westchester has deep roots that are fun to explore. The original inhabitants were the Wappinger Indians before the Dutch settlers. The county originally thrived as a trading post from both the Hudson River and Long Island Sound, making it a hub for travelers and settlers. It also played a major role in the American Revolution, with remnants of the period scattered across the region. 

Places to Visit & Things to Do in Westchester 

This list will be divided by types of places to visit and things to do in Westchester. That means: arts + culture, museums, outdoors + hiking trails, breweries, cute towns, and restaurants. So keep scrolling to your preferred sections!

I. Outdoor Things in Westchester + Hiking Trails 

1. Teatown Lake Reservation ★

The trails at Teatown Lake Reservation are open year-round from dawn to dusk. There are nearly 15 miles of trails to enjoy, popular among hikers, joggers, cross-country skiers, and snowshoers. Hikers will pass a diverse terrain, including wide-open fields, swamp lands, laurel groves, mixed hardwood forests, lakes, streams, and more. Choose from nine hiking trails categorized from easy to strenuous. The Teatown trail connects to the Croton Aqueduct Trail and the Briarcliff Peekskill Trailway for even more options. 

2. Croton Gorge Park and the New Croton Dam 

Located in Cortlandt, Croton Gorge Park is home to some of the largest hand-hewn structures in the world! The 97-acre park at the base of the Croton Dam grants visitors fantastic views of the water rushing down the spillway. You have direct trail access to the Old Croton Aqueduct. Park in the parking lot and take the pedestrian foot trails to get to the top of the bridge. This is less of a hike and more of a walk you can fit in between other activities.  

  • Difficulty: Easy
  • Length: 0.5 miles 
  • Route: Out and Back 

3. Cranberry Lake Preserve Hike ★ 

Cranberry Lake Preserve is a protected forest and quarry on 190 acres that was part of a former farm and mining operation. It’s a safe haven for local wildlife and plants, especially native birds, dragonflies, and turtles. You can explore a variety of habitats in the forest, lake, pond, and along the cliffs of the park. This is a great hike to do from November through April, but not in the summer because of the bugs. Bring food and drinks to stop along the way and have a picnic. 

4. Anthony’s Nose Hike ★ 

Anthony’s Nose is one of the most popular hikes in the Hudson Highlands (and part of the Appalachian Trail). It’s a short hike, only 1.9 miles, but the steepness of the trail makes it more moderately difficult. From the top are stunning views of Bear Mountain State Park. This hike is technically in the Hudson Valley, but it’s just 5 miles north of Peekskill (which is in Westchester)! Because of its popularity, the trail can get crowded, and parking is limited. 

  • Difficulty: Moderate
  • Length: 1.9 miles 
  • Route: Out and Back 

5. Bike or Walk the Tappan Zee Bridge (Governor Mario M. Cuomo Bridge)

There’s a path located on the northern side of the new Tappan Zee Bridge where pedestrians and cyclists can travel over the Hudson River. You catch amazing views of Rockland and Westchester counties and can even see the skyline of NYC in the distance. The path is not super wide, so be cautious if you are biking. Visitors have access to digital kiosks, restrooms, shuttle service, and sculptures scattered along the way. The path is open 6 am to 10 pm every day. 

  • Difficulty: Easy to Moderate
  • Length: 3.6 miles 
  • Route: Out and Back 

6. Untermeyer Garden Lights 

This 43-acre public park in Yonkers is a magical wonderland of lights during the winter months. Untermeyer Garden displays more than 100,000 lights in the Walled Garden around the holidays, with festive music to match. The display attracts thousands of visitors every year. In the summer, Untermeyer Garden is a great place for a beautiful walk through horticultural gardens, waterfalls, and more. 

  • Entrance Cost: Free! 
  • Location: Yonkers

7. Ossining Waterfront Hike

So much of Ossining’s unique history is located on the waterfront. Visitors can walk along the water at Louis Engel Waterfront Park and Henry Gourdine Park in the Old Village neighborhood. The parks are so close you can easily visit both. You’ll have access to paved paths, benches, picnic tables, a playground, and a spray park at Louis Engel that opens in the summer. You’ll have plenty of views of the river and are minutes away from the shops and eateries on Main Street. 

8. New York Boat Co.

New York Boat Co. offers a variety of fun cruises departing from Peekskill starting in April. Popular choices include sunset cruises, brunch cruises, and sightseeing trips to West Point. Tours range from 1 to 2.5 hours. There’s a drink menu with a small selection of snacks, but no meals are served on these trips. You can book a private cruise for yourself and your friends through the private events page

  • Entrance Cost: Based on tour
  • Location: Peekskill 

9. Wolf Conservation Center 

You can make an appointment to see the wolves of Westchester at the Wolf Conservation Center! Explore the habitats of ambassador wolves, red wolves, and Mexican grey wolves. There are several programs to participate in, including photography sessions, educational tours, or even the opportunity to spend the night at the wolf center. Be prepared for a bit of walking, especially up the driveway. 

  • Entrance Cost: Based on program
  • Location: South Salem

10. Rockefeller Park State Preserve 

Rockefeller Park is the perfect place for quiet countryside walks, with a range of hiking trails through forests and valleys. Popular destinations here for walking are the 13 Bridges Loop Trail along Gory Brook and the short walk around Swan Lake. There’s a fern garden at the entrance and a tree peony garden next to the Rockefeller Art Gallery that blooms from April to May. The park is only 7 minutes away from Kykuit, the Rockefeller Estate, and Blue Hills at Stone Barns

  • Entrance Cost: $6 per vehicle 
  • Location: Pleasantville 

II. Museums in Westchester 

11. Hudson River Museum + Planetarium

Lose yourself in this cultural complex of science, art, and discovery in Yonkers! The Hudson River Museum is a premier cultural institution on the banks of the Hudson River only 30 minutes from Manhattan. A general admission ticket will grant you access to the permanent collection galleries, museum exhibitions, and the outdoor courtyard. Other add-ons include the planetarium and Glenview Historic Home, an 1877 Gilded Age residence featured on The Gilded Age or HBO. Outside of exploring, the Hudson River Museum is a wonderful place to bring a picnic, blanket, or yoga mat to spread out on the lawn on a nice day. 

  • Entrance Cost: General Admission $10
  • Location: Yonkers

12. Neuberger Museum of Art 

Neuberger Museum of Art is on the campus of Purchase College, across from the SUNY library. The gallery began with a massive donation of over 108 art pieces from Roy R. Neuberger and now houses over 6,000 pieces of contemporary, modern, and African Art. Visitors will have the chance to enjoy lectures, tours, and programs throughout the year with the goal or growing a more diverse art community. If you drive to the museum, you can access the building by parking at West 1 Parking Lot. Admission is currently free for all visitors! 

  • Entrance Cost: Free!
  • Location: Purchase

13. Hudson Valley MOCA 

From the outside, the Hudson Valley MOCA doesn’t look like much–wait till you step inside. Located in Peekskill, this museum presents challenging contemporary art exhibits from local and internationally renowned artists. The museum is only open on Thursdays and Saturdays, with admission discounts for residents, veterans, seniors, students, and children. The location is easy to get to and has a ton of parking. You can pair your visit to Hudson Valley MOCA with the Peekskill Museum at the Herrick House, less than 5 minutes away. 

  • Entrance Cost: General Admission $30
  • Location: Peekskill 

14. Lincoln Depot Museum 

This small museum is worth the stop if you’re in Peekskill near Water Street. The Lincoln Depot Museum is built in the historic freight and passenger rail depot, where President-elect Abraham Lincoln greeted New Yorkers on his 1861 train ride to Washington DC. The museum offers exhibits celebrating the memorable stop and Lincoln’s connection to New York. Collections on display include artifacts, artwork, and statues commemorating Lincoln. Other things to do in Peekskill to pair with your visit are the Peekskill Brewery, Peekskill Landing Park, and Riverfront Park

  • Entrance Cost: Free!
  • Location: Peekskill 

15. Katonah Museum of Art 

Katonah Museum of Art is a unique museum known for promoting visual arts. It’s a non-collecting museum (no permanent collection to view), so everything is fresh. They host 10-12 diverse exhibits simultaneously in addition to films, lectures, and workshops. There’s an outdoor area with tables you can picnic at if you bring your own food. Katonah is a cute town with a lot of culture you can explore before or after your visit.  

  • Entrance Cost: $12 adults; $6 for seniors and children 
  • Location: Katonah

16. KinoSaito Arts Center

Nestled in the town of Verplanck, the KinoSaito Arts Center is a fantastic venue dedicated to promoting abstract art and artistic experimentation. It’s located in the former St. Patrick’s Catholic School and offers two galleries, a performance space, and a theatre. Exhibitions vary from sculptures to photographs to paintings and more. You can grab a drink at the coffee bar with free WIFI or relax in the garden on a nice day. For fellow artists, they also have two resident artists’ studios and offer workshops. 

  • Entrance Cost: Free!
  • Location: Verplanck

III. Arts & Culture + Historic Sites 

17. Lyndhurst Mansion 

This grand estate is one of the highlights of Tarrytown, offering tours of the beautiful architecture and historical grounds. Lyndhurst Mansion (also known as Jay Gould estate) sits on 67 groomed acres next to the Hudson River. It’s one of the finest Gothic Revival homes in the country, with a ton of art displayed indoors. You can tour the property to appreciate the unique historical decor and rooms, including a restored bowling alley! Guided tours run from April to October, or you can purchase a Daily Grounds Pass for a self-guided tour of the grounds. 

18. Bethany Arts Community 

Located in Ossining, the Bethany Art Community is an amazing organization and gallery supporting artists from all backgrounds. The vibe is welcoming and supportive, providing a variety of exhibits, performances, and events for visitors to enjoy. If you love plays, this is a great location to catch a show in a small, intimate theatre. Outdoors, you can explore the sculpture park with various contemporary art displays on a beautiful lawn. Some of the artists live on the campus and will stick around to talk to onlookers about their style and techniques! 

  • Entrance Cost: Self-guided tours free; contact for tour prices 
  • Location: Ossining 

19. Armour-Stiner Octagon House ★

Visit the only known octagonal residence in the country right in Irvington, NY! The Armor-Stiner Octagon House was built in 1860 and is a unique building on the National Register of Historic Places with a lot to explore. Book a one-hour tour of the home and landscape of the 19th Century grounds, Victorian accents, and an amazing greenhouse recently restored. Inside the home, there are displays of framed art pieces by local artist Julia Whitney Barnes and spectacular rooms restored to their former glory after the home was almost destroyed in 1978.  

  • Entrance Cost: Tours $29 
  • Location: Irvington

20. Pelham Art Center ★ 

Pelham Art Center is a local cultural hub that promotes access to art study and appreciation. They welcome visitors to learn more about enhancing their own artistic skills and provide a number of events and programs to help you explore your potential. The space is small and intimate and allows for a deep exploration of running exhibitions. It’s a great place to visit when you need to clear your head and is close to several restaurants in Pelham to grab a bite before or after. 

  • Entrance Cost: $5 suggested donation 
  • Location: Pelham

21. Sleepy Hollow Cemetery & Old Dutch Church  ★ 

Tim Evanson

The churchyard cemetery on the grounds of the Old Dutch Church was the inspiration for The Legend of Sleepy Hollow and one of the most popular Westcher attractions. The church was founded back in 1685 with the option for visitors to take self-guided tours of the ground. Just be mindful that the church belongs to an active congregation that holds worship services. 

Sleepy Hollow Cemetery was founded in 1849 and is often confused as being the graveyard from the tail of Sleepy Hollow. While it didn’t inspire the famous story, the grounds of the cemetery are still stunning and are the resting place for many famous people, including Elizabeth Arden, Andrew Carnegie, and William Rockefeller. The cemetery offers a variety of walking tours (some at night), and all proceeds go to the site’s upkeep. 

22. Washington Irving’s Sunnyside  

Sunnyside is the former home of famous author Washington Irving. Best known for his short stories about Rip Van Winkle and The Legend of Sleepy Hollow,  visiting this gem feels like your stepping into the past of one of the most creative minds out of NY. Irving did extensive renovations to the Dutch-stone home, including making the grounds more lush and picturesque and adding stained glass and tutor-style chimneys. Guests can schedule a tour of the home and grounds, which features a pond and a stream with a waterfall.  

  • Entrance Cost: $10 adults; $8 student and children
  • Location: Tarrytown 

23. Philipsburg Manors ★ 

Jump back into the year of 1750 by visiting the Philipsburg Manor in the historic Sleepy Hollow. Back in the day, Philipsburg Manor was a trading and milling complex. It was also the former home to 23 enslaved African individuals whose journey you will learn all about on your visit. You can tour the property’s buildings and touch reproductions of artifacts to get a better idea of what it was like to live in this enslaved community. The manor is only open from Spring to Fall and is a great trip for the whole family to learn about the history of Westchester. 

  • Entrance Cost: 
  • Location: Sleepy Hollow

24. Kyuit Rockefeller Estate ★ 

The river views from the Kyuit Rockefeller Estate are breathtaking. It’s one of many historic sites in Sleep Hollow, with over 40 rooms you can tour, a garden, and an art collection. You can expect to spend at least 2.5 hours on each tour, with additional time spent if you wish to peruse the gift shop, grab a snack, or picnic on the grounds. No food is allowed in the home, but there are lockers you can store your belongings for when you’re ready. Kyuit is open to visitors from May to November. 

  • Entrance Cost: 
  • Location: Sleepy Hollow

25. MANITOGA/Russel Wright Design Center ★ 

While not technically in Westchester County, MANITOGA is only minutes away from Peekskill in the quaint town of Garrison. This now National Historic Landmark was the former estate of industrial designer Russel Wright, with over 75 acres of woods, a garden, and mid-century architecture to explore. Tours are by appointment only (no walk-ins) and last about 90 minutes. You can visit the estate from mid-May to mid-November. This attraction is close to some of the most popular hikes near New York City, like Anthony’s Nose and the trails at Bear Mountain State Park

  • Entrance Cost: Based on tour; $5 suggested donation for trail use
  • Location: Garrison 

IV. Visit Westchester’s Cute Towns 

26. Tarrytown, NY & Sleep Hallow, NY

These two historic towns are only 30 minutes from Manhattan and can easily take a day to explore. They participate in several events together, such as the TASH Farmers Market and the Tarrytown and Sleepy Hollow Winter Stroll.  

Tarrytown has a bunch of shops and restaurants downtown and a scenic Riverwalk along the Hudson with views of the Tappan Zee. Lyndhurst Mansion and Sunnyside are popular historic landmarks here.  Sleepy Hollow is just up the river from Tarrytown and is considered one of the most haunted towns in the country. It’s famous for The Legend of Sleepy Hollow, with connected sites such as the Old Dutch Church, Sleepy Hollow Cemetery, and Philipsburg Manor. Around Halloween, the spectacular Annual Great Jack O’Lantern Blaze lights up the town with thousands of carved pumpkins!

27. Peekskill, NY

Peekskill is a quaint town in northwest Westchester with a gorgeous waterfront and walkable streets. The town is full of fun shops like Bruised Apple Books, an indie bookstore with an extensive collection of books and media treasures. Bucko! boutique offers quality clothing and homemade goods from sustainable sources. For a bite and a beer, the Peekskill Brewery serves beers crafted right in-house near Riverfront Green Park. Don’t forget to stop at the Peekskill Coffee House for a quirky experience and fun atmosphere to go with your espresso and coffee drinks. 

28. Bronxville, NY

Bronxille is a small affluent community in Westchester that offers a ton of affordable things to do for visitors. Start off your day by strolling along Bronxille Lake, a 1-mile loop with beautiful scenery. Toney Toni and the Gang on Pondfield Road has a great selection of chic clothing and accessories. Womrath Bookstore has been selling books for more than 80 years, or search for a mix of unique gifts from around the world at The Silk Road. For a bite to eat, travel back to the 50s at the Bronxville Diner to try some delicious crepes or try a packed sandwich at Lange’s

29. Purchase, NY 

If you’re looking for things to do near White Plains, Purchase is a cute town just to the east with a lot of art and culture. Visit the Neauberger Museum of Art in the heart of Purchase College for an extensive collection of art pieces or book a show at the Performing Arts Center. You can stroll around the beautiful gardens of the Donald M Kendall Sculptor Gardens at the PepsiCo Headquarters with impressive sculptures and gardens. Feeling adventurous? Climb the tree-top ropes courses at Boundless Adventures, with 137 obstacles and 23 ziplines across 11 routes. 

V. Breweries in Westchester 

  • Soul Brewing Company (Pleasantville) ★: An award-winning micro-brewery serving a huge variety of craft beers. They also offer live music, trivia nights, and other fun events. 
  • Wolf and Warrior (White Plains): This brewery is one of the best things to do in White Plains for a chill time with friends. Here, they brew delicious craft beers right on site and have great food to pair with their drinks.
  • Captain Lawrence Brewery (Elmsford & Mt. Kisco): Both locations have a wide variety of beers and delicious food. Elmsford has a huge outdoor beer garden and beer hall; Mt. Kisco is the newest location sporting a sleep industrial indoor beer hall. 
  • Decadent Ales (Mamaroneck): A fun open atmosphere to try local beer and unique combinations. Known for their burgers but they also offer Sunday Brunch. 

VI. Best Places to Eat in Westchester 

  • Hudson Fish & Farmer ★:  This New England-style seafood restaurant is a favorite eatery in Sleep Hollow located on the Riverwalk. They have awesome outdoor seating with views of the Tappan Zee Bridge and delicious fresh oysters, calamari salad, and more. 
  • Goosefeather ★: A popular Chinese eatery in Tarrytown specializing in Cantonese cuisine with modern twists, heavy in northern Chinese and Thai influences. The restaurant is set in a really cool 1840s mansion with natural sculptures surrounding it. 
  • Blue Hill at Stone Barns Farm: Located at the Stone Barns Center for Food & Agriculture in Pocantico Hills. Blue Hill is one of the best farms in Upstate NY, operating all year round and offering guests private dining overlooking the fields. 
  • The Cookery: Near Waterfront Park of Dobbs Ferry, The Cookery was voted Westchester’s Best Italian Restaurant serving inventive and modern Italian cuisine. They also have a brunch with a 3-course prefix perfect for a Sunday or weekend away. 

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