Ultimate Guide to Visiting Hudson Valley and Catskills New York in the Fall
I’m sharing two beautiful regions of upstate New York you should definitely visit this fall: Hudson Valley and the Catskills.
When the crisp air rolls in and the trees burst into an explosion of fiery autumnal hues, these New York gems become the ultimate destinations for all things fall. From adventurous outdoor hikes and stunning foliage views, to drool-worthy food spots and fun fall festivities, I’ve packed it all into this ultimate guide.
So grab your chunky sweaters and slip on your cutest boots, because we’re diving into the best things to do, places to eat, and where to stay in Hudson Valley and Catskills New York during the fall!
Note: I’ve merged the the two regions into this guide because they share a lot of the same fall activities. And while there are tons of cute small towns to choose from in between, I’m sharing my favorites that are well worth a visit!
Credit: moriahaslan
The Catskills
The Catskills region, located in southeastern New York, is a picturesque and enchanting destination that captures the essence of natural beauty. With its rolling mountains, lush forests, and cascading waterfalls, the Catskills offer outdoor enthusiasts a playground for activities like hiking, fishing, skiing, and more, while also serving as a peaceful retreat for those seeking solace in nature.
Where to stay in the Catskills region
The Catskills region of New York encompasses a collection of picturesque towns that offer a blend of artistic flair, outdoor exploration, and rural tranquility. Some notable towns include: Woodstock, Saugerties, Catskill, Hunter, Windham, Phoenicia, Margaretville, and Tannersville. They each contribute their own unique charm to the area. I’m sharing my favorites that you should check out this fall!
Credit: solepsizm/Shutterstock
Woodstock
Nestled in the heart of the Catskills, Woodstock is a haven for artists, nature lovers, and free spirits alike. Known for its rich cultural heritage, vibrant arts scene, and the iconic 1969 music festival that shares its name, Woodstock exudes a bohemian charm with its eclectic shops, galleries, and picturesque surroundings.
Best places to stay in Woodstock:
The Woodstock Inn on the Millstream
Best places to eat and drink in Woodstock:
Bread Alone Bakery
Cafe Espresso
Little Apple Café
The Mud Club
Pearl Moon
Good Night
The Bear Café
Credit: reid_buchanan
Saugerties
Located on the banks of the Hudson River, Saugerties is a charming New York town that seamlessly blends history, nature, and small-town charm. With its quaint Main Street lined with boutique shops, cozy cafes, and antique stores, as well as its proximity to scenic hiking trails and the stunning Saugerties Lighthouse, this riverside gem offers a delightful blend of relaxation and exploration for visitors.
Best places to stay in Saugerties:
Renwick Clifton House B&B (We stayed here back in 2018 and we loved the cozy feel, the home-cooked breakfasts on the second story balcony overlooking the Hudson, and the grounds were so beautiful to explore)
Holiday Inn Express & Suites Saugerties
Best places to eat and drink in Saugerties:
Miss Lucy's Kitchen
The Kitchen at Salt & Fire
The Dutch
Violet’s Bakery
Tivoli General
Inquiring Mind Bookstore & Cafe
If you prefer a more remote experience, I definitely recommend Catskill or Hunter! There are lots of little Airbnb style cabins surrounded by lush woods, like Getaway house!
Credit: claybanks
Hudson Valley
The Hudson Valley region, stretching along the Hudson River in New York, is a captivating and diverse area that combines stunning landscapes with rich history and cultural heritage. From charming towns and vineyards to grand historic estates and scenic river views, the Hudson Valley offers a delightful mix of outdoor adventures, artistic pursuits, and culinary delights, making it an ideal destination for exploring, indulging, and immersing oneself in its unique charm.
Where to stay in the Hudson Valley
The Hudson Valley in New York encompasses a variety of towns that contribute to the region's rich history, natural beauty, and vibrant culture. Some notable towns include: Sleepy Hollow, Tarrytown, Beacon, Croton-On-Hudson, New Paltz, Cold Spring, and New Windsor. They each add their own distinct charm to the valley. I’m sharing my favorites that you should check out this fall!
Credit: Jason Rosenberg/Google
Hudson
Hudson, NY, is a vibrant and eclectic town nestled in the heart of the Hudson Valley. Known for its thriving arts scene, antique shops, and exquisite dining options, Hudson exudes a charming mix of historic architecture and contemporary flair, making it a must-visit destination for those seeking a blend of culture, creativity, and small-town charm.
Best places to stay in Hudson:
Best places to eat and drink in Hudson:
Isaan Thai Star
Wunderbar Bistro
BackBar
The Maker Cafe
Tanzy’s
MOTO Coffee/Machine (this coffee shop is also a motorcycle shop!)
Supernatural Coffee + Bakery
Verdigris Tea & Chocolate Bar
Credit: Margaret Fox Photography
Sleepy Hollow / Tarrytown
Although Sleepy Hollow and Tarrytown are two separate towns, they are right next to each other and you can easily walk between the two without realizing it. In fact, they both share equal parts of Patriots Park where they host Farmer’s Markets every Saturday. Sleepy Hollow is renowned for its historic charm and haunting tales including the legendary Headless Horseman. Needless to say, these towns come alive in the fall for all of the spooky Halloween festivities. But aside eerie and mysterious vibes, they have lots of cute small town charm and delicious local restaurants!
Best places to stay in the Sleepy Hollow / Tarrytown area:
Best places to eat and drink in Sleepy Hollow / Tarrytown:
The Taco Project
Bella’s Restaurant
Grassroots Kitchen
Eatarry
Muddy Water Coffee
The best things to do and see in the Catskills and Hudson Valley New York area in the fall
Aside from exploring the small but lively, foliage-filled towns, there is so much to do and see in the Catskills and Hudson Valley areas — especially in the fall!
Credit: Sam Smith/Google
Five State lookout
The Five State Lookout is a scenic overlook located in the Hudson Valley region of New York. Situated atop the Shawangunk Ridge, it offers breathtaking panoramic views of five states: New York, New Jersey, Connecticut, Massachusetts, and Pennsylvania. It’s the perfect spot to enjoy the colorful foliage and some amazing views!
Minnewaska State Park
Minnewaska State Park, nestled within the Shawangunk Mountains of New York, is a nature lover's paradise! With its rugged cliffs, pristine lakes, and picturesque waterfalls, this expansive park offers an array of outdoor activities such as hiking, biking, swimming, and rock climbing, providing visitors with endless opportunities to immerse themselves in the region's natural beauty. In the fall the colors explode into a sea of autumal colors. Best spots to visit: Kaaterskill Falls (hike both upper and lower levels — it’s worth it!), Awosting Falls, Gertrude’s Nose, and Sam's Point.
Credit: claybanks
Bear Mountain State Park
Bear Mountain State Park, located on the west bank of the Hudson River, is a natural gem offering a perfect blend of outdoor recreation and breathtaking scenery. Not only does the park provide ample opportunities for outdoor activities and stunning panoramic views of the Hudson Valley, but they also have a carousel, zoo, swimming pool, museum, and even an ice rink in the winter! Best spots to visit: Anthony’s Nose, Bear Mountain Bridge, and Bear Mountain Loop Trail.
Harriman State Park
Harriman State Park is located just north of Bear Mountain State Park. Spanning over 47,500 acres, it’s the New York State’s largest park. With its extensive trail network, pristine lakes, and rugged woodlands, Harriman State Park offers endless opportunities for hiking, camping, fishing, and wildlife watching, making it a haven for outdoor enthusiasts seeking a retreat into nature. Best spots to visit: Reeves Brook Loop Trail, Appalachian Trail, Diamond Mountain Trail, and I personally love Lake Welch for its cove of foliage surrounding the water.
Credit: Irene Serrano/Google
Overlook Mountain & The Fire Tower
At over 3,000 feet Overlook Mountain is a tiring hike, but it comes with a great reward — a stunning view of the Catskills! If you’re not satisfied and have a bit more energy, climb up the 60 foot Fire Tower for an even higher overlook! It’s also home to the ruins of a historic hotel that is said to be haunted.
Rail Explorers
Immerse yourself in a sea of fall foliage with Rail Explorers! Their foot-pedaled vehicle offers you a unique way to explore the autumnal colors of the Catskills along the old train tracks. This 2.5 hour experience is very popular during the fall season so make sure to book in advance!
Credit: Hunter Mountain Resort
Hunter Mountain Skyride
Hunter Mountain Skyride offers an unforgettable experience to witness the captivating beauty of the Catskills in the fall. As you ascend to the scenic summit in the chairlift, you'll be greeted by a panoramic display of foliage across the Catskill Mountains. And if you’re lucky, you might even get to see the Berkshire Mountains of Massachusetts and the Green Mountains of Vermont!
Hudson River Foliage Cruise
If you’re looking for something a bit more chill, and possibly romantic, take a foliage cruise along the Hudson! Snuggle up and sip on some hot cider as you sail blissfully down a river of autumnal colors. The crisp autumn air and the serene ambiance create a truly magical fall experience!
Credit: Catskill Mountain Railroad Co.
Catskill Fall Adventure Trains
Another great way to see the stunning foliage is to take a train ride! Catskill Mountain Railroad offers an hour long ride through a sea of fall colors and offers some beautiful scenic views of nature.
The Great Jack O’Lantern Blaze
One of my favorite Halloween attractions is The Great Jack O'Lantern Blaze! This fun immersive fall festival features thousands of illuminated and intricately carved pumpkins, larger-than-life art installations, synchronized lighting, and a spooky soundtrack to really get you in the mood. From a pumpkin portal to a spinning carousel, The Great Jack O'Lantern Blaze is a must-see experience that captures the spirit of Halloween and the wonder of the fall season!
Apple and pumpkin picking
It wouldn’t be fall without a trip to the farm for some classic apple and pumpkin picking! Luckily for you, there are tons of places to check this activity off your fall bucket list. Here’s a few noteworthy spots:
Story Farms - Catskills, NY
Harvest Moon - North Salem, NY
DuBois Farms - Highland, NY
Fishkill Farms - Hopewell Junction, NY
Kelder's Farm - Kerhonkson, NY
Fall festivals & parades
The Hudson Valley region is renowned for its vibrant festivals and parades that capture the essence of the fall season. Whether you're looking to explore a festive fair or watch a Halloween parade, the Hudson Valley offers an abundance of festivities that showcase the region's rich history, creativity, and love for all things fall! Here’s a few to check out:
New York Cider Week - Multiple locations across the state
Fall Antiques Fair - Rhinebeck, NY
Pumpkin Festival - Beacon, NY
Tarrytown Halloween Parade - Tarrytown, NY
Festival of Witches - Sleepy Hollow, NY
Hudson Valley Wine & Food Fest - Rhinebeck, NY
Hudson Halloween Parade - Hudson, NY
Hunter Mountain Oktoberfest - Hunter, NY
Headless Horseman Hayrides - Ulster Park
