Orange County comes alive each autumn as crisp air sweeps through the valleys and hillsides glow in shades of scarlet, amber, and gold. Orchards brim with ripe heirloom fruit, craft beverage makers celebrate the harvest, and every walk outdoors feels as fresh and invigorating as biting into a just-picked apple.
Just 50 miles from New York City, the county’s orchards, farms, cideries, breweries, and wineries set the stage for a perfect fall escape. Chase peak foliage, sip fresh-pressed beverages, and savor the season’s best flavors. Grab your sweater and trade the city buzz for crisp air and countryside charm—autumn is in full swing.
Hit the Road for Scenic Drives
Take in a brilliant display of gold, copper, and fiery orange leaves along the iconic Hawk’s Nest Drive on Route 97 in Sparrowbush. This winding roadway hugs the Delaware River as it curves between Port Jervis and the historic village of Hancock. Named for the birds of prey that nest in the cliffs above, the drive rewards travelers with sweeping river valley views, towering autumn canopies, and dramatic twists and turns. Keep watch overhead, you may spot hawks, falcons, or even bald eagles soaring through the crisp fall skies.
Afterwards, savor the flavors of fall in Orange County with a stop at Fox N Hare Brewing Company, tucked at the bottom of the mountain in Port Jervis. Here, locally crafted beers pair perfectly with cozy pub favorites like burgers, wings, and soft pretzels—just the thing after a scenic autumn drive or hike. Together, these spots create a fall itinerary brimming with flavor, comfort, and plenty of Hudson Valley charm.
Or take in the vibrant colors of fall along the Shawangunk Mountain Scenic Byway in Pine Bush. This 88-mile state-designated route winds around the northern Shawangunk Mountains and through the Rondout and Wallkill valleys, offering sweeping views of forests, farms, and ridgelines painted in autumn’s brightest hues. It’s the perfect drive to soak in the season. At the gateway to the Shawangunk Mountain Scenic Byway in Crawford, you’ll find Christopher Jacobs Winery at Pennings Vineyard. This charming spot invites visitors to sip and savor with guided tastings at the bar, tours through the vineyard, or a laid-back picnic on the lawn. As the sun dips behind the Shawangunk ridge, the vineyard comes alive with golden light—making it the perfect place to pair local wine with the sweeping fall colors of the season.
Hike or Bike for Views
If your fall escape includes hiking or biking, Orange County has plenty to explore.
Schunnemunk State Park in New Windsor stretches across 3,300 acres with 25 miles of trails that shine in autumn. A climb to the summit rewards hikers with panoramic views of valleys brushed in rich scarlets, warm coppers, and burnished yellows. From above, the Hudson River winds gracefully through a quilt of farms and forests, each patch glowing with seasonal color.
From wild landscapes, the day shifts to artistic ones at Storm King Art Center, just a short drive away. Spread across 500 acres of rolling hills and wide meadows, this open-air museum becomes a natural gallery each fall, where world-renowned sculptures stand framed by russet leaves, golden light, and crisp blue skies. Pack a picnic or grab a treat from the outdoor café, then linger as art and nature blend into one unforgettable scene.
To round out the afternoon, head to nearby Brotherhood Winery in Washingtonville, the oldest winery in the country. Stroll the historic grounds, descend into hand-excavated 19th-century cellars, and sample a wide selection of vintages. If you visit before October 12, you can join one of their Instagram-worthy Grape Stomps, complete with rustic wooden barrels and a touch of friendly competition. Cap the visit with seasonal food and drinks at the 1839 Restaurant and Bar, raising a glass to the harvest season.
For another fall adventure, set out on the Walden–Wallkill Valley Rail Trail, a scenic six-mile stretch winding through farmland, woodlands, and charming small towns. Walk or bike beneath canopies brushed with scarlet, amber, and russet tones while breathing in the crisp autumn air. The trail’s gentle terrain makes it perfect for all ages to enjoy the season’s beauty at their own pace.
After your ride, continue to Angry Orchard in Walden. Stroll the orchards, take a guided tour, or sip seasonal ciders in the tasting room while admiring panoramic views of the Shawangunk Ridge glowing with fall color. Together, the trail and cidery create a fall experience that perfectly blends outdoor exploration with the flavors of the harvest—an iconic Hudson Valley day.
Relish the Bounty
Autumn vibes aren’t limited to trails. If your perfect fall day includes shopping, Orange County delivers.
For a perfect fall escape, begin in Sugar Loaf Arts and Crafts Village, where 18th- and 19th-century buildings now house more than 60 artists’ studios, galleries, and boutiques. It’s the ideal spot to browse one-of-a-kind creations while enjoying the village’s historic charm and the crisp feel of autumn in the air. From there, head to Tin Barn Brewing in nearby Chester, where sweeping views of technicolor foliage stretch from the sky deck. Settle in with a hazy IPA, catch some live music, and dig into playful pub fare like Buffalo Brussels Sprouts, Chicken Wing Pie, and Fried Pickles—all framed by the brilliant colors of the season.
Another day trip brings you to Warwick Village, a walkable downtown filled with cozy boutiques, antique shops, and galleries. As you explore, tree-lined streets glow in shades of red and gold, creating the perfect fall backdrop. Just outside the village, wrap up your visit at Demarest Hill Winery, where vineyards drape the countryside in autumn hues. Enjoy a relaxed tasting, soak in the sweeping views, and raise a glass to the season surrounded by the flavors and colors that define fall in the Hudson Valley.
One-Stop Wonders
Want to savor the season without the stress of hopping from town to town? In Orange County, you’ll find it all in one place—brilliant foliage, harvest flavors, and festive small-town charm wrapped into a single vibrant fall destination.
Kick off your fall adventure at Apple Dave’s Orchards & Distillery in Warwick, a longtime favorite for families and groups. Spend the day wandering the orchards, picking apples, listening to live music, and enjoying a seasonal menu paired with craft beers, wine, and cocktails made from farm-fresh ingredients. Even the family dog is welcome to join the fun. Just down the road, continue the experience at Applewood Winery, where tastings of award-winning wines are set against rolling orchards painted in autumn’s brightest colors. Together, the two destinations create a harvest day full of flavor and charm.
In New Hampton, Orchard Hill Cider Mill offers a more intimate way to savor the season. Their cozy tasting room pours award-winning hard ciders and pommeau that perfectly capture the crispness of fall afternoons. Right next door, Soons Orchard celebrates the bounty of the season with pick-your-own apples and a bustling farm store overflowing with fresh-pressed cider, warm cinnamon donuts, homemade pies, and just-picked produce. Whether you’re stocking up for the season or simply treating yourself, it’s a classic Hudson Valley fall experience.
Make the most of autumn at Pennings Orchard in Warwick, a family-run farm that’s been welcoming visitors for generations. Beyond apple picking and hayrides, the farm market is a highlight—stocked with local produce, cheeses, baked goods, and specialty items perfect for bringing the season’s flavors home. The on-site Pennings Farm Cidery adds to the experience, serving crisp ciders made from their own apples. Enjoy a glass on the lawn or patio with live music, food trucks, and sweeping views of orchards glowing in autumn color. With its blend of tradition and festive energy, Pennings captures the heart of fall in the Hudson Valley.
Visit pickocny.com or follow on Instagram @pickocny to plan your own autumn adventure in Orange County!
PHOTOS: Courtesy Orange County Tourism
Header Photo: Hawk’s Nest Drive
