The Perfect Hudson Valley Getaway for Every Type of New Yorker

Whether you prefer “a charming art oasis” or a small town with a city-quality cocktail culture, we’ve got the destination for you

October 22, 2021 11:56 am
A car drives north through the Hudson Valley in Upstate New York
Go north.
Clay Banks/Unsplash

Traveling to the Hudson Valley for a fall weekend away should be a no-brainer for any New Yorker. Most destinations within the region take under just two hours to reach, and the journey itself is almost the best part, as larger highways eventually turn into winding, scenic roads flanked on either side by colorful foliage and charming homes that will have you typing Zillow into your search bar quicker than you can say “A-frame cabin.” 

The Hudson Valley is a fantastic place to visit year-round, but autumn is when the region really sings. The once-hot and humid air turns crisp and breezy, buzzing mosquitoes begin to retreat to the hell holes from whence they came, and an autumnal pick-your-own harvest beckons with overpriced apples and pumpkins that will provide the perfect Instagram backdrop. Hard cider options abound, and the return of spooky season gives all those estate and mansion tours a different edge.

Just as each NYC neighborhood becomes known for a respective draw, though, so do the charming towns and hamlets within the Hudson Valley. We wouldn’t want you to drive up to the vast region without a plan in place for an optimal fall escape, and this list will help you with just that. So whether your idea of outdoorsy includes fishing, hiking and camping or just a cold cider on a patio, we’ve got you covered. 

Opus 40 in Woodstock
Opus 40 in Woodstock
Getty Images

If you’re seeking a charming art oasis … 

The small, charming town of Woodstock has come a long way since that one time when it didn’t actually host a certain infamous 1969 music festival. While mentioning Woodstock might conjure up stereotypical images of peace signs and tie dye, the real vibe is anything but one-note, the town having transformed into a modern hub for the arts.

Today, the art scene takes many forms in Woodstock, whether your intent is to purchase or just admire. A stroll down Tinker Street yields curated boutiques to explore, and spots like Pacama Handmade serve as a showroom for local artisans in a variety of mediums. During weekends there’s a flea market to take advantage of, there are plenty of galleries worth checking out (like the Elena Zang), and a Center for Photography offers an interesting roster of shows, speakers and programs. 

A must-see for any art enthusiast is Opus 40, a six-acre maze of bluestone, sculptures and pathways built over the course of 37 years by a retired art professor named Harvey Fite. Opus 40 is just one of the interesting attractions just outside of Woodstock, along with the trippy Kaatskill Kaleidoscope (known as the world’s largest) and the Karma Triyana Dharmachakra Tibetan Buddhist Monastery. Finally, a trip to Woodstock wouldn’t be complete without a visit to the Artists Cemetery — a preserved area with intricately designed grave markers commemorating the lives of the region’s artists. 

Lil' Deb's Oasis in Hudson.
Lil’ Deb’s Oasis in Hudson.
Lil’ Deb’s Oasis/Tomm Roesch

Your one-stop gateway to the Hudson Valley …

Once a sleepy albeit super charming town, Hudson is now a well-known, bustling enclave for New York City folk who have decided to escape the hustle and bustle. Luckily, as Hudson has continued to grow, its charm has decidedly remained. One trip there and it won’t be a mystery as to why Hudson’s population grew faster than any other metropolitan area in 2020. It’s the kind of place that hits the perfect balance between nature and industry, with more than 200 independent establishments to explore, beautifully restored historic homes and buildings — all surrounded by boundless nature. 

First timers must dedicate a good chunk of time to wandering Warren Street, the main drag of Hudson lined with boutiques, cafes, restaurants and more. Antique fanatics will have plenty to ogle within the ultra curated shops on Warren, but sticker shock is also something to expect. For more of a true treasure hunt, try diving into the massive Antique Warehouse, or Coxsackie Antique Center less than 30 minutes north. 

Quality farm-to-table cuisine is a given in Hudson, like at Swoon Kitchenbar and the acclaimed WM. Farmer and Sons, which was founded by NYC expats. For those seeking something a little different, Hudson’s recent boom has helped bring more options to the table, like tiki joint Lil Deb’s Oasis. If luxury is your thing, book a stay at the Maker before grabbing a fireside cocktail at the hotel’s lounge, which is tucked inside a restored 19th-century carriage house.

Sleepy Hollow
Sleepy Hollow
Getty Images

If you want to get spooked
Sleepy Hollow

The site of classic horror movie The Legend of Sleepy Hollow, this area was called North Tarrytown until 1996, when it officially changed its name. Many New Yorkers visit Sleepy Hollow during Halloween, but the entire autumn season is a great time to plan a stay. There are tons of landmarks around town that nod to the movie, like the Sleepy Hollow Cemetery where Washington Irving is buried, the Dutch Reform Church that has been in continuous operation since the late 1600s or the Headless Horseman Bridge. 

Those who arrived at Spooky Hollow by car should venture about two miles away to Lyndhurst Castle, situated within its own 67-acre park beside the Hudson River. The enormous mansion is one of the most renowned examples of Gothic Revival architecture, and offers tours of the estate and grounds. On only three days of the year at the end of October, after-dark tours lead guests through the candlelit halls as guides regale you with Victorian lore. 

Leaf peepers can head to Rockefeller Park Preserve, with 55 miles of trails bursting with the colors of fall that can be explored by foot or even on horseback. After working up a thirst, head to the beer garden at Bridge View Tavern for a cold Allagash, or The Tapp for a craft cocktail. 

Breakneck Ridge
Breakneck Ridge
Robi J/Getty Images

For one-of-a-kind design by both man and nature … 
Cold Spring

Would you believe us if we told you that within around an hour you could get from drinking your morning coffee in Manhattan to climbing a mountain? Well believe it, because the Hudson Line on the Metro North dumps you mere steps from the trailhead for Breakneck Ridge. Be warned, though, because despite its popularity, this trail is actually really hard. In fact, it has a 10/10 difficulty rating. Those willing to attempt it, though, will be rewarded by gorgeous views of the Hudson Valley. 

If you prefer a feast for the eyes that you don’t need to scramble up rocks for, check out the former home and studio of famed designer Russel Wright. Wright designed the home, called Manitoga, to live in creative harmony with nature, and fittingly the property includes 75 acres of woodland garden to explore. Manitoga’s woodland trails are open to the public during daytime hours with a small suggested donation, and tours of the home and studio can be booked on their site. 

After your outdoor adventures, take the Hudson Line back down to the main Cold Spring stop, where you can fuel up at a local cafe and do some shopping on Main Street. As its name suggests, this is the main street in Cold Spring, which is uber charming and full of places to antique and peruse curated vintage wares. 

Twin Star Orchards
Twin Star Orchards
Twin Star Orchards/Lily Brown

Wineries, cideries and cocktail bars, oh my!
New Paltz

There’s way more to the town of New Paltz than its namesake SUNY campus, but it’s partially thanks to many of the school’s alumni that the scene there has become as vibrant as it has, with many of them opening restaurants or adding to the buzzy art and music scene. As one might expect from a college town, New Paltz is home to some quality bar hopping; skip from the fire pit at cocktail bar Huckleberry to Fuschia for tiki drinks. 

A short drive will bring you to more picturesque locations to imbibe within, like the dog-friendly Adair Vineyards, with ten acres of land and delicious yet affordable wines. Robibero Family Vineyards is also a great choice, located a few miles away from the town center, and is just one of 15 wineries nestled within the Shawangunk Wine Trail, between the Shawangunk Mountains and the Hudson River. If cider is more your thing, you can head to Twin Star Orchards, the Upstate sister location to Bushwick’s Brooklyn Cider House. There you can pick your own “ugly” apples, sip on cider, and munch on homemade doughnuts. 


Join America's Fastest Growing Spirits Newsletter THE SPILL. Unlock all the reviews, recipes and revelry — and get 15% off award-winning La Tierra de Acre Mezcal.