Crisp mornings, golden afternoons, and the crunch of leaves underfoot! October in Westchester is pure magic. Whether you’re after apple orchards, spooky legends, artful evenings, or trails lined with fiery foliage, this season has something for everyone. Here’s your curated guide to the best of fall 2025 in Upper Westchester and beyond.
The Heart of Halloween
No county embraces Halloween like Westchester, birthplace of Washington Irving’s The Legend of Sleepy Hollow.
- The Great Jack O’Lantern Blaze once again transforms Van Cortlandt Manor with more than 7,000 glowing pumpkins arranged in whimsical, larger-than-life displays.
- SUP Witches of Sleepy Hollow Festival returns to Kingsland Point Park, where costumed paddlers take to the Hudson for a witchy paddle parade, while spectators enjoy live music, food, brews, vendors, and spooky views.
- Peek-a-Boo, River’s Edge Theatre Company’s provocative immersive haunt, is back at Bethany Arts Community after a sold-out 2024 run. Expect intimate encounters, voyeuristic thrills, and stories inspired by Hudson Valley’s hidden histories.
- The Sleepy Hollow Haunted Hayride delivers goosebumps as wagons rumble past the Old Dutch Church and into the dark woods where hoofbeats and shrieks echo through the night. A lively block party on Beekman Avenue, with live music and vendors, keeps spirits high.
- For those who prefer history with a hint of haunt, Lyndhurst After Dark invites visitors on candlelit tours exploring the mansion’s shadowy past, while the Gothic Harvest Market adds seasonal flair. Meanwhile, the Armour-Stiner Octagon House in Irvington offers eerie tours like Myths and Mysteries and the ghostly performance The Lady in White.
Arts, Culture & Big-Name Acts
October isn’t only about scares—it’s also packed with world-class performances and screenings.
- On October 24, Colbie Caillat and Shawn Colvin headline The Capitol Theatre in Port Chester for Pace Women’s Justice Center’s Raising the Bar Benefit Concert.
- Humorist David Sedaris brings his wit to The Performing Arts Center on October 4, while Steve Solomon, author and star of Broadway’s longest-running one-man comedy, performs at the Paramount Hudson Valley on October 26.
- At Tarrytown Music Hall on October 9, mandolin virtuoso Sierra Hull and singer-songwriter John Craigie share the stage.
- Film lovers can catch the 40th anniversary screenings of Day of the Dead at Jacob Burns Film Center (Oct. 24 & 31), or settle in for a spooky night with Candyman at Bedford Playhouse (Oct. 9).
Family-Friendly Festivals
Weekends in October are made for festivals, and Westchester has plenty to choose from:
- Pound Ridge Harvest Festival (Oct. 4) fills Town Park with Oktoberfest-style food, beverage gardens, award-winning music, and activities for kids.
- Stone Barns Harvest Fest offers hayrides, live music, animal encounters, farm demonstrations, and seasonal fare from local purveyors.
- ARToberFest (Bethany Arts Community) celebrates its sixth year with visual art, live music, food, and interactive projects...a magical experience for all ages.
The Call of the Outdoors
Peak foliage hits in mid-October, and there’s no better way to take it in than on Westchester’s trails:
- North County Trailway offers fiery views of the Croton Reservoir.
- DePew Park in Peekskill has peaceful strolls around Lake Mitchell or longer hikes into Blue Mountain Reservation.
- Teatown Lake Reservation features the Twin Lakes loop for woodland escapes.
- Ward Pound Ridge’s Rocks Trail challenges hikers with nearly five miles of rugged terrain and scenic rock formations.
- If hiking isn’t your style, wander through Tarrytown or Sleepy Hollow, where decorated homes, historic cemeteries, and cozy eateries set the mood. For a day trip, head across the river to Storm King Art Center, where monumental sculpture meets breathtaking autumn landscapes—best capped with dinner in Nyack.
Savor the Season
Autumn also means feasting, and Westchester’s farms and cider mills deliver.
- Pick-your-own adventures await at Harvest Moon and Outhouse Orchards in North Salem, Stuart’s Fruit Farm in Granite Springs, and Wilkens Fruit & Fir Farm in Yorktown.
- Sip fresh cider at Thompson’s Cider Mill in Croton-on-Hudson, or explore the Westchester Craft Beverage Trail, featuring breweries, cideries, and distilleries.
- Foodies should mark their calendars for Hudson Valley Restaurant Week, returning Oct. 27–Nov. 9. More than 140 restaurants will offer prix-fixe menus ranging from $24.95 to $44.95, including standouts like Crabtree’s Kittle House, Goosefeather, and Benjamin Steakhouse.
Whether you’re paddling with witches on the Hudson, hiking through foliage-lined trails, or indulging in a Restaurant Week feast, October in Westchester offers a perfect balance of thrills, flavors, and unforgettable moments. It’s a season that invites you to slow down, savor the magic, and celebrate fall in full color.