Ready to hit the road and explore some of the coolest spots just outside NYC?
This Westchester County road trip is packed with everything—epic views, cute towns, hidden trails, historic mansions, and food that’ll totally ruin your diet (worth it).
Whether you’re looking for nature, spooky legends, or just an excuse to eat ice cream by the river, this itinerary has you covered.
You’ll find chill hikes, jaw-dropping buildings, and a few spots that’ll make your Instagram very happy.
1. Untermyer Gardens
Untermyer Gardens features fancy fountains, Greek-style columns, and feels like a secret garden, sitting right in Yonkers with epic views of the Hudson River.
It’s known for its dramatic Walled Garden, which looks like something out of an ancient myth, with Persian-inspired tiles and marble sphinxes too.
Fun fact: this spot used to be part of a 150-acre estate owned by a super-rich lawyer in the 1900s, and now it’s totally free to visit and perfect for pretending you’re in a movie.
2. Rye
Next up is Rye, a cozy coastal town that’s all about beachy boardwalks, salty breezes, and old-school charm.
You can ride the Dragon Coaster at Playland (yes, the same one from Big with Tom Hanks), chill at Rye Town Park Beach, or grab giant pretzels with a view at Barley Beach House.
It’s got serious summer energy, but even off-season, Rye’s cute downtown, historic mansions, and ocean views make it totally worth a stop.
Just a heads-up: Playland Park is usually closed during the winter and typically reopens from May until late September or early October.
3. Tarrytown & Sleepy Hollow
Then swing through Tarrytown and Sleepy Hollow, where spooky legends meet storybook streets and stunning river views.
You can tour the actual Old Dutch Church and cemetery where the Headless Horseman tale was born, then stroll over to the massive, fairy-tale-looking Lyndhurst Mansion.
Don’t miss Bridge View Tavern in Sleepy Hollow for burgers served with Hudson River views.
These two towns are absolutely stunning during fall, but honestly, they’re great fun at any time of year.
Please note that Old Dutch Church & Lyndhurst Mansion normally close during winter.
4. Kykuit, the Rockefeller Estate
Just a few minutes away is Kykuit, the super fancy former home of the Rockefeller family, and yeah—it’s as jaw-dropping as it sounds.
You’ll get guided through rooms filled with fine art, peek into the Coach Barn lined with classic cars and carriages, and wander gardens packed with sculptures that look straight out of a museum.
It’s part palace, part art gallery, part secret lair, and totally worth booking a tour ahead of time (they fill up fast!).
The Rockefeller Estate usually closes over winter and typically offers tours from May through November—be sure to check online before heading over!
5. Rockefeller State Park Preserve
If you’re craving fresh air after all that mansion magic, Rockefeller State Park Preserve is the perfect spot to stretch your legs.
It’s got over 45 miles of super chill carriage roads—think wide, flat paths made for lazy strolls, or pretending you’re in a Jane Austen movie.
Keep your eyes peeled for swans floating on Swan Lake, stone bridges tucked into the trees, and maybe even a deer or two popping out to say hi.
6. Pleasantville
Next stop: Pleasantville, a small town with big personality and the kind of main street that makes you want to move there on the spot.
You can catch an indie film at the Jacob Burns Film Center, sip a latte at Black Cow Coffee, and browse shelves at The Village Bookstore like you’ve got all the time in the world.
It’s the kind of place where everything feels a little slower, a little cozier, and a lot more charming—aka perfect for a chill afternoon break.
7. Teatown Lake Reservation
Right down the road is Teatown Lake Reservation, where hiking trails, wildflowers, and woodsy lake views totally steal the show.
There’s a loop around Teatown Lake that’s great for an easy walk, or you can hit the longer trails if you’re feeling extra adventurous, with nearly 15 miles of trails to explore.
Bonus: the nature center has turtles, owls, and other rescued wildlife.
8. Croton Gorge Park
From there, head over to Croton Gorge Park, where the main attraction is a massive stone dam with water cascading down like a real-life movie set.
You can picnic right at the base of the dam, or hike the trail up to the top for an unreal view of the waterfall and Croton River.
It’s loud, it’s dramatic, and honestly, it might be one of the coolest spots in all of Westchester for an “I can’t believe this is New York” moment.
9. Peekskill
Last but definitely not least is Peekskill, a funky little river town that’s got big artsy energy and some seriously good eats.
You can wander through the street murals downtown, check out the Hudson Valley MOCA, or grab a bite at Taco Dive Bar (yes, the tacos are that good).
Finish it off with a sunset stroll along the waterfront at Riverfront Green Park, where the views look like a postcard.
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