Picture Hudson Valley attractions of the 1600s: Grand schooners sailing the swift currents and Canadian fur trappers paddling the river. Times have changed, but intrepid families from Brooklyn to Connecticut, Pennsylvania and beyond have discovered many hidden gems in the Hudson River Valley.
It’s easy to plan an eco-friendly historic Hudson Valley getaway thanks to frequent service from the Amtrak and Metro North train lines. Enjoy historic mansion tours and the lush forests and riverfront scenery coveted during the Gilded Age.
Even better, you don’t need to go as far as pricey Rhinebeck, Cold Spring or hipster Beacon for things to do. Smart shops, galleries, pocket parks and good dining are all part of a Westchester County heritage weekend. That means within 35 miles of Times Square, you’ll find historic Hudson Valley attractions to thrill all ages.
Our Family’s Favorite Places in the Hudson Valley
Our family loves the Westchester County towns of Sleepy Hollow, Tarrytown, Croton on Hudson and Peekskill. After our first immersion in the region’s fascinating 19th-century history, we were hooked. Why would any New Yorker look further than the Hudson Valley to uncover unique attractions close to home?
Fortunately, non-profit groups like Historic Hudson Valley and the Hudson River Valley National Heritage Area have conserved many of the region’s highlights. Any time of year something is happening, so Hudson Valley tourism is usually pretty busy.
Discover Hudson Valley Attractions throughout the year
Apple blossoms and magnolias kick off the spring season as the weather warms up. In summer, families are kayaking the Hudson and mountain biking the shoreline. Thanksgiving to mid-January is when cultural institutions go all out with period décor, holiday theming and sparkling holiday lights. Note that many attractions made famous by their Halloween celebrations (more later) undress and refresh after Thanksgiving.
Here are 16 Hudson Valley surprises you wouldn’t expect in Westchester.
1. Explore Hudson Valley winter attractions such as holiday lights.
Few civic displays compete with ERDAJT. The illuminated private home in Lagrangeville has won two Guinness World Records for most lights on a residential property. If you’re going that far, by all means get tickets and pause for hot cocoa by the campfire at Lumina, the drive-through holiday lights extravaganza in North Salem.
2. Revisit “A Christmas Carol” and the Scrooge legend.
One of the Hudson Valley’s top holiday attractions is the live reading of Charles Dicken’s “A Christmas Carol.” Notable storyteller Jonathan Kruk — a favorite of children — and musician Jim Keyes breathe life into the Ghosts of Christmas Past, Present, and Future. Performances take place Saturday and Sunday in December in the Old Dutch Church.
3. Explore Kykuit and Life in another era.
John D. Rockefeller, founder of Standard Oil and grandfather to New York’s future governor, built Kykuit in 1913 Families will be intrigued by the Rockefeller’s lifestyle and lavish holiday decorations. Don’t miss the family’s collection of Asian ceramics, underground gallery of art and tapestries, and beautiful gardens. Ask the kids to hunt for the Matisse and Picasso sculptures in the garden.
4. The Union Church glow is among the top Hudson Valley attractions.
When John D. Rockefeller commissioned Union Church of Pocantico Hills in 1921, he turned to the very best artists of his day to design the stained-glass windows. His foresight preserved a Rose Window by Henri Matisse and several colorful windows by Marc Chagall for future generations.
5. The Headless Horseman is Sleepy Hollow’s Signature Family Attraction.
Author Washington Irving was born and raised in Sleepy Hollow. During his long stint working in England, Irving famously wrote “The Legend of Sleepy Hollow” and other short stories about the region. Once called North Tarrytown, Irving’s hometown decided to embrace his better-known fictional name. Try to spot stuffed animals, dolls, flags, chalk drawings, cookies and shadow puppets depicting the Headless Horseman. Even Sleepy Hollow street signs and ambulances have the eerie figure painted on them.
6. Hudson Valley fall foliage peeks in the weeks leads to Halloween.
After mid-September, apple picking becomes a favorite among Hudson Valley things to do. Head to Poughkeepsie and bike or walk across Walkway Over the Hudson for Hudson Valley foliage spotting. Or, cross the Tappan Zee Bridge to Bear Mountain, which is a 5,000-acre State Park with a lot of lakes and hiking trails.
7. Visit the Washington Irving Estate, Hudson Valley ‘s literary attraction.
The Hudson Highlands nurtured the young Washington Irving, who bought a cottage there for his family in 1865 and developed what would become Sunnyside. Landscaped gardens and play areas attract local families year-round. If you’re interested in the house interior, there’s an hour-long tour that may engage older kids. Over the September to November Halloween holiday, look for a Sleepy Hollow scavenger hunt and a little photo selfie area. Hudson Valley winter activities include an estate tour to see it dressed in its period Christmas finery.
8. Discover Hudson Valley’s Black History at Phillipsburg Manor.
This historic home was one of the few active plantations near the Dutch enclave of New York City. Around 1750, 23 enslaved people worked for the Philipse family; some ground flour, others farmed. Kids will be fascinated watching the grist mill at work. The house tour – best for ages 10 and older — explores what slavery was like in the day.
9. Thrill to Van Cortlandt Manor’s Great Jack-o’-Lantern Blaze.
Another Hudson Valley mansion shines brightest at Halloween during the festival of carved pumpkins known as the Great Jack-o’-Lantern Blaze. Imagine a rambling pumpkin theme park. The manor’s extensive grounds morph into an immersive environment where illuminated, carved pumpkin sculptures, pumpkin animatronics and gourd-sourced artwork abound.
The individual pumpkins are all real. The same remarkable artisans create larger structures (think Statue of Liberty) out of synthetic material shaped like gourds. A team of pumpkin carvers works daily on-site during the eight-week run to refresh any gourds that decay. You’ll need to book ahead weeks in advance to get after-dark tickets (6pm or later during fall). Bundle up to enjoy watching your family experience a new world ruled by 7, 000 pumpkins.
10. Bury yourself in Hudson Valley history at the Sleepy Hollow Cemetery.
Don’t miss the Sleepy Hollow Cemetery, one of the top Hudson Valley attractions. Year-round, they do a gossipy daytime walking tour about the rich locals wrapped in shrouds and interred there. Around Halloween, book tickets ahead for evening walking tours by lantern light.
11. Spend a night at the Old Dutch Church.
Next door is the historic Old Dutch Church, where Washington Irving and his family are actually buried. Kids will enjoy discovering headstones with the family names that used in his “Legend of Sleepy Hollow” story. Book ahead for storytelling and dramatic readings during the Halloween and Christmas seasons.
12. Admire Hudson Valley architecture at the Abbey Inn & Spa.
The Abbey Inn is a boutique hotel on Fort Hill in Peekskill built within a former convent for the Sisters of Saint Mary. The ca. 1865 convent’s gabled roof and castle-like turrets are typical of Hudson Valley estates. One of the most romantic getaways in the Hudson Valley — weddings occur in the chapel — it’s appropriate for a family stay. Several of the 32 rooms and suites – each unique in layout – have sofabeds. Others have double queen beds. Contemporary artwork punctuates the spare décor and muted earth tones.
This part of Hudson Highlands, a promontory overlooking the river, is well known to hikers and rock climbers. Borrow one of the inn’s bikes or hike the trails of Fort Hill for views from the palisade to the sea level train tracks below. A small gym and seasonal outdoor pool are available to Abbey Inn guests.
13. Pamper yourselves on a Hudson Valley Wellness Break.
Be sure to plan a dining event at the inn’s gourmet Apropos Restaurant. It is very sophisticated, with fine dining and a fun bar. Go at Happy Hour for a chicken sandwich, veggie burger, duck tacos, coconut shrimp – their lighter fare is great for kids. Adults will appreciate that Apropos’ new American menu has been recognized in the Michelin guide for Westchester County. During the annual Westchester Restaurant Week in October, it’s also a bargain. Look for weekend specials year-round that combine a meal with a treatment at the Abbey Inn’s pretty spa. We can verify that their wellness practitioners are excellent.
14. Kids love this other culinary highlight in the Hudson Valley.
Another bite of interest is the Westchester Diner in Tarrytown. The typically huge diner menu features Greek salads, gyros, omelets, paninis, steaks and more. Ogle the wonderful glass dessert display filled with towering cakes, pies and strawberry-coated cheesecake. Note that Westchester Diner’s sister, the Stanford Diner in nearby Connecticut, was a favorite haunt of Anthony Bourdain.
15. March to the beat of West Point, another Hudson Valley family attraction.
The noted military academy, West Point, is on the other side of the Hudson River. Teens will enjoy their walking tours. Go birdwatching at Constitution Marsh, one of the local Audubon Center Wildlife sanctuaries. It’s easy to imagine how the Hudson River looked when Henry Hudson first sailed it in the 1600s looking for a path to the Pacific.
16. Return for an arts weekend getaway in the Hudson Valley.
You’ll need more than a weekend to enjoy the above and visit Cold Spring Harbor, a charming New England style town on the water. Or, train farther north to Beacon. This town has grown from a cluster of antique shops to a fashionable community packed with galleries. Book tickets for the fabulous private, contemporary art museum, Dia Beacon. It houses the DeMenil family’s collection and has many traveling shows. Another outing brings you to Storm King, an outdoor sculpture garden with towering works scattered among hundreds of rolling acres of grassland.
You’ve explored Hudson Valley attractions. Stop, reset, play again.
So, there really is a lot to see and a lot to do in Westchester County. And the Hudson River Valley extends for hundreds of more miles. We hope you’ll join us in revisiting the region regularly.
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