The Hudson Valley is full of small towns that will make you wonder why you haven’t taken this road trip sooner.
One minute, you’re exploring a historic riverfront village with cozy cafés and antique shops, and the next, you’re deep in the mountains, hiking to a waterfall or floating down a creek.
Some towns are artsy and full of music, some feel straight out of a history book, and some are all about outdoor adventure.
So grab some snacks, queue up your road trip playlist, and get ready to explore the best small towns that the Hudson Valley has to offer!
1. Tarrytown
Tarrytown is a charming riverfront town, located about 25 miles north of Manhattan, renowned for its history, cute shops, and historic mansions.
It’s best known for its connection to The Legend of Sleepy Hollow—yes, the one with the Headless Horseman—since the actual village of Sleepy Hollow is right next door.
You can visit Lyndhurst Mansion, a huge Gothic Revival estate, or walk across the Mario M. Cuomo Bridge for stunning views of the Hudson River.
Downtown, you’ll find plenty of great spots to eat, from Sweet Grass Grill’s farm-to-table dishes to cozy coffee shops on Main Street.
2. Nyack
Just across the Hudson from Tarrytown, Nyack has a totally different vibe—artsy, laid-back, and full of cool spots to explore.
This riverside town is known for its vibrant arts scene, with tons of galleries, street murals and even live music.
It’s also the birthplace of famous painter Edward Hopper and you can actually tour his childhood home.
If you’re into the outdoors, head to Hook Mountain State Park for scenic hikes along the cliffs, or rent a kayak and paddle right on the Hudson itself.
3. Warwick
Heading farther into the Hudson Valley, Warwick feels like you’re deep in the countryside, with rolling farmland, orchards, and some of the best apple cider donuts around.
This town is famous for its wineries and apple picking, especially in the fall when places like Ochs Orchard and Apple Dave’s draw weekend crowds for fresh fruit and homemade cider.
If you’re into wine then Warwick Valley Winery & Distillery is a must-stop, not just for tastings but also for wood-fired pizza, and live music on the lawn.
The downtown area is small yet full of character and is home to cozy cafés, antique shops, and gift stores like Frazzleberries.
4. Cold Spring
Cold Spring is the kind of place that makes you want to park the car, put down your phone, and just wander.
Right on the Hudson River, this small town is known for its antique shops, waterfront views, and easy access to some of the best hiking in the Hudson Valley, including the popular Breakneck Ridge trail.
If climbing mountains isn’t your thing, you can take a relaxing stroll along the riverfront at Dockside Park.
With its mix of small-town beauty and outdoor adventure, Cold Spring is the perfect spot to slow down, grab a coffee, and just enjoy the view.
5. Beacon
Just up the river from Cold Spring, Beacon feels completely different with its artsy, creative energy.
It’s home to DIA:Beacon, a massive contemporary art museum in a former factory, where you’ll find giant sculptures, light installations, and plenty of “wait, is this art?” moments.
Main Street is full of cool boutiques, vintage shops, and cafés, plus if you’re into books, Binnacle Books is a must-visit.
For the best views in town, hike up Mount Beacon—it’s a steep climb, but the view of the Hudson Valley at the top makes it totally worth the effort.
6. Ellenville
Leaving the Hudson River behind, Ellenville takes you further into the Catskills, where the mountains rise higher and the outdoor adventures become more thrilling.
This small town is known for epic hikes like the one to Sam’s Point, where you’ll find sweeping views, hidden ice caves, and even a waterfall if you catch it at the right time.
If you’re into more adrenaline-fueled fun, the nearby Mountain Wings Flight Park offers hang gliding—definitely not for the faint of heart.
And after all that adventure, you can refuel at Aroma Thyme Bistro which is surprisingly upscale for such a tiny town but totally worth the stop.
7. New Paltz
New Paltz has both college town energy and outdoor adventure, making it one of the most fun and relaxed spots in the Hudson Valley.
It’s home to the SUNY New Paltz university, which means you’ll find coffee shops, artsy boutiques, and casual places to grab a bite—P&G’s is a local favorite for burgers and a beer.
But the real highlight here is the Mohonk Preserve, where you can hike and rock climb.
For a more adventurous climb, the famous Labyrinth and Lemon Squeeze trail at the nearby Mohonk Mountain House, takes you through narrow rock crevices leading to a breathtaking view at the top.
Whether you’re here for the trails, the history (don’t miss Historic Huguenot Street for a peek into the town’s colonial past), or just the great food, New Paltz is the kind of place that makes you want to stay a bit longer.
8. Kingston
Kingston is a mix of history, arts, and waterfront views, making it one of the most interesting small cities in the Hudson Valley.
As New York’s first capital, it’s filled with colonial-era sites like the Stockade District, where you can walk past 18th-century stone buildings and stop by local shops and cafés.
Down by the river, the Rondout Waterfront is filled with colorful historic buildings, boat tours, and some great seafood spots—Mariner’s Harbor is the go to for fresh oysters.
With old-school charm and a growing arts scene, Kingston feels like a city constantly reinventing itself, making it a fun and unexpected stop on a Hudson Valley road trip.
9. Red Hook
Heading north, Red Hook has a completely different feel—more rural, more laid-back, and all about farms and orchards.
You can spend the morning picking apples at Greig Farm, grab lunch at a local diner, and then end the day sipping craft spirits.
One of the top spots is Hudson Valley Distillers in nearby Clermont however it is temporarily closed as of early 2025.
If you’re into history, then the nearby Montgomery Place estate features beautiful gardens and walking trails with stunning views of the Hudson River.
Make sure to stop at Holy Cow, the local ice cream shop that has a cult following for its surprisingly cheap and delicious soft serve.
10. Hudson
Hudson feels like both a city and a small town, with historic charm, trendy shops, and a creative energy that draws artists, musicians, and chefs from all over.
Warren Street is the heart of it all and is lined with antique stores, stylish boutiques, and some of the best restaurants in the Hudson Valley.
When it comes to food, Swoon Kitchenbar is a top choice with delicious farm-to-table dishes, run by a husband/wife team.
If you’re into history, check out the beautifully restored Olana State Historic Site, the former home of landscape painter Frederic Church, where you’ll get stunning views of the river and Catskills.
11. Catskill
Crossing the river into Catskill, you’ll find a town that’s quieter than Hudson but just as packed with history and nature.
This is where famed painter Thomas Cole lived, and you can tour his home and studio to see where the Hudson River School art movement began.
If you’re more into the outdoors, Catskill has easy access to some of the best hiking in the region, including Kaaterskill Falls, a breathtaking two-tiered waterfall that’s been inspiring artists and adventurers for centuries.
After a day of exploring, head back to Main Street for a bite at Avalon Lounge, a spot with Korean food, live music, and an unexpectedly great vinyl selection.
12. Saugerties
Just south of Catskill, Saugerties has a lot of history to explore as well as tons of outdoor adventure, which makes it a standout spot.
One of its highlights is the Saugerties Lighthouse, a restored 19th-century lighthouse you can actually hike to, with stunning views of the Hudson River and even an option to stay overnight.
Downtown, the vibe is laid-back and fun, with indie shops, cafés, and spots like Inquiring Minds, a cozy bookstore where you can get lost in a good read.
And if you’re here in late summer, don’t miss the Hudson Valley Garlic Festival—a whole event dedicated to garlic, complete with garlic ice cream.
13. Woodstock
Woodstock might be best known for the legendary 1969 music festival (which actually happened miles away in Bethel), but this little Catskills town still holds onto its free-spirited atmosphere.
The streets are lined with colorful boutiques, crystal shops, and cafés. There’s also a good chance you’ll spot someone strumming a guitar on a street corner.
Head to Overlook Mountain, where a scenic and steep hike leads to an old hotel ruin and jaw-dropping views of the Hudson Valley.
Whether you’re here for the art, the music, or just to relax, Woodstock is the kind of place where you can’t help but slow down and enjoy the moment.
14. Phoenicia
Leaving Woodstock behind, Phoenicia feels like a true mountain escape, tucked deep in the Catskills.
This is the go-to spot for tubing down the Esopus Creek—on a hot summer day, you can float through the forest, passing over small rapids while taking in the mountain views.
If hiking is your thing, the Tanbark Trail is a great choice. It’s a short but steep climb that rewards you with a sweeping view over the town, or you can head to nearby Slide Mountain for a more challenging hike.
After all that, nothing beats a stop at the famous Phoenicia Diner—serving up next-level comfort food, like skillet pancakes and biscuits that will make you rethink every biscuit you’ve ever had.
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