Scenic Byways, Spooky Thrills, and a Cornucopia of Festivals

Fall in Ulster County is special. Between the gorgeous earth tones that blanket the Catskills, the cornucopia of U-pick farms and pumpkin patches spread across the county, and the rich, spooky legacy of Upstate New York (home to the legend of Sleepy Hollow), this little slice of paradise in the mid-Hudson Valley—just 90 miles north of New York City—is the perfect place to enjoy all the lovely/scary trappings of autumn. You’ll find scenic byways, chilling hayrides, thrilling haunted houses, pumpkin patches everywhere you turn (including on a train), and a plethora of fall festivals. Here are some highlights:

Scenic Byways and Waterways

Peep Ulster County’s fall foliage up close along the Shawangunk Mountains Scenic Byway, an 88-mile loop that cuts across Ulster County from Kerhonkson to Gardiner and includes numerous trails and country roads along the way where you can pull over, taste the fresh country air, and capture the kaleidoscope of colors on camera. Just remember to breathe as you take in the astounding beauty of rustic farmlands and mountain vistas. For maps and more information on the byway, visit mtnscenicbyway.org.

For a different vantage point, hop aboard the historic Rip Van Winkle riverboat and take a leisurely guided trip down the Hudson River, where you’ll witness some of the region’s most notable landmarks and learn about the fascinating history of the regional estates, picturesque lighthouses, quaint villages and gorgeous preservation sites along the winding coastline. For tickets and more info visit HudsonRiverCruises.com

Hayrides and Haunted Houses

You won’t find a scarier Halloween experience than Headless Horseman Hayrides and Haunted Houses. But don’t take our word for it—just ask MTV, USA Today, AOL News, New York Daily News, Fangoria, HauntWorld Magazine, or even The Weather Channel. All have recognized Headless Horseman in Ulster Park as one of the best, most frightening, most scream-inducing haunted attractions in the world. Spread over 65 creepy acres on a 250-year-old farm in Historic Haunted Hudson Valley, the immersive experience features a theatrical one-mile hayride, a corn maze, escape rooms, and eight haunted attractions. The chills happen every weekend from Sept. 21 to Nov. 2, and while we wouldn’t recommend bringing the little ones for the main event, they do feature a Children’s Day—appropriately dubbed “A Tiny Taste of Terror”—on the second and fourth Saturdays of October. Details and tickets can be found at HeadlessHorseman.com.

Pumpkin Patches and Rail Rides

The Great Pumpkin Tradition is alive and well in Ulster County, with numerous farms offering an array of sizes and shades for carving, cooking, and porch decor. Round up the family and find your nearest patch—there are plenty spread all over the county, such as DuBois Farms in Highland, Jenkins-Lueken Orchard in New Paltz, Boice’s Farm and Garden in Saugerties, Maynard Farms in Ulster Park, Tantillo’s Farm Market in Gardiner, Tremper Hill Farms in Mount Tremper, and so many more. For a complete list of pumpkin purveyors, visit UlsterCountyAlive.com/landing/farms.

For a different kind of pumpkin adventure, the Catskill Mountain Railroad will host the Pumpkin Express Oct. 19, 20, 26, and 27. This family-friendly train adventure takes you on a scenic journey through the Catskills as they learn about the fictional legend behind the Jack-O-Lantern. At the end of the ride, passengers get to select their very own pumpkin to take home for decoration. Halloween costumes are welcome. For details and tickets visit CatskillMountainRailroad.com.

Five Can’t-Miss October Festivals

18th-Century Autumn Festival

On Sat., Oct. 19, immerse in living history with the 18th-Century Autumn Festival at the Senate House State Historic Site in Uptown Kingston! This delightful annual tradition features local performers donning 18th Century garb, re-enacting history, and offering demonstrations of meat smoking and hearthside cooking. The festival also features numerous hands-on activities, like apple pressing for cider, candle dipping, and 18th-century toys and games. The event begins at 11 a.m. and runs to 3 p.m. For more information, call 845.338.2786.

13th Annual Heart of the Hudson Valley Bounty Festival

Taste and discover the bounty of the Hudson Valley on Oct. 5 at this annual showcase of the area’s best food, music, artists and businesses. The festival will include a local-harvest Farmers Market featuring produce, wineries, artisan cheese and breads, baked goods and specialty farm items; restaurants and food venues; handmade wares from local artisans; live music; a homemade goods contest; and kids activities including a bounce house. For more information visit HVBountyFestival.com.

10th Annual O+ Festival

Every year, the O+ Festival descends on Kingston and beautifies downtown with epic outdoor murals that promote social consciousness, along with concerts and wellness breakouts—the festival’s mission is to “empower communities to take control of their well-being through the exchange of art, music and wellness.” In addition to world-renowned muralists and art tours, this year’s festival, happening Oct. 11-13, will feature music headliners !!! (chk chk chk), Elvis Perkins, and The World Inferno Friendship Society, along with health-awareness events such as Narcan and CPR trainings, cycling, and classes in the healing arts. For tickets and details, visit OPositiveFestival.org/Kingston.

12th Annual Ulster Italian Festival

Fun fact: 35,000 Italian Americans populate Ulster County, or about 20% of the population—hence the high number of quality pizzerias, casual bistros and white tablecloth fine dining spots serving some of the best Italian food in the U.S. Every year, the Ulster County Italian American Foundation hosts the Ulster Italian Festival at Rondout Waterfront in Kingston, celebrating the county’s Italian heritage with a variety of Italian foods, beverages, music and family fun. This year’s festival happens Sunday, Oct. 13, 11 a.m. – 7 p.m. For more details, visit UCItalianAmericanFoundation.org.

Hurley Heritage Society Ghost Walk

For those who can’t wait for Halloween to experience spooky thrills and chills, head to Hurley on Friday, Oct. 25 for their famous Ghost Walk, where you’ll see and hear tales of area ghosts—tales based on actual historical events in Hurley taken from primary documents and oral accounts. Just be warned: the walk is not recommended for young children, and you’ll want to bring a flashlight and appropriate footwear for trail walking. For tickets and more info, call 845.338.7686.

Start planning your October escape today.