Looking for a good selfie spot, or three, in the Sleepy Hollow area? You’re in luck. We’ve rounded up a few local haunts that serve as the perfect backdrop for your Halloween season photos.
Read on to learn about each location. And if you take a selfie at any of the spots, post your photo to Instagram and tag us @lohud for a chance to be featured!
Horsefeathers, Tarrytown
Horsefeathers, named to USA TODAY’s Bars of the Year list for 2025, is Halloween central when it comes to seasonal tricks and treats. Known for having its Halloween decor up by August, make sure you hit up the nostalgic Tarrytown bar this spooky season.
If you go: 94 N Broadway, Tarrytown, horsefeathersny.com.
SUP Witches of Sleepy Hollow Festival
The SUP Witches of Sleepy Hollow Festival is headed back to town for its 6th year this October. Enjoy live music from The Fortunate Few, peruse the wares of more than 50 vendors, and witness the magic that is the SUP Witches Paddle. Can witches float? Test the theory for yourself by registering for the Witches on the Hudson paddle, remember to bring a costume!
If you go: Festival starts at noon on Oct. 12 (rain date Oct. 19), Tarrytown Light-Kingsland Point Path, Sleepy Hollow, admission is 8$. rivertownssupyoga.com/sup-witches-festival-2025.
DeCicco & Sons, Sleepy Hollow
Where else can you find a grocery store with multiple levels, vaulted ceilings a Headless Horseman-themed bar and costumes from the 1999 Tim Burton film “Sleepy Hollow”? Don’t miss DeCicco & Sons Sleepy Hollow store, the company’s largest in Westchester.
If you go: 1 Legend Dr, Sleepy Hollow, deciccoandsons.com/sleepy-hollow.
Washington Irving’s Sunnyside, Irvington
The legacy of New York author Washington Irving, of “The Legend of Sleepy Hollow” and “Rip Van Winkle” fame, lives on at his Sunnyside estate in Irvington. Take a tour of his home, which includes the study he worked in.
If you go: 3 W Sunnyside Lane, Irvington, hudsonvalley.org/historic-sites/washington-irvings-sunnyside.
The Headless Horseman Bridge
While the original, wooden, Headless Horseman Bridge from Washington Irving’s tale has rotted away, the agreed upon location is at 415 North Broadway in Sleepy Hollow. You can spot a historic landmark plaque at the site, perfect for selfies.
Even better, perhaps, is a replica of the original wooden bridge at Sleepy Hollow Cemetery. Be mindful if you do decide to check out the replica bridge, as the cemetery is still actively used for burials today.
If you go: Both bridge sites are in the village of Sleepy Hollow. Historic landmark bridge site – 415 N. Broadway; Old Style Horseman wooden bridge – Sleepy Hollow Cemetery, 540 N. Broadway. visitsleepyhollow.com/see/headless-horseman-bridge.
Horseman Bagels, Sleepy Hollow
This bagel shop in Sleepy Hollow has it’s own Headless Horseman statue out front, and festive Halloween bagels.
If you go: 276a N Broadway, Sleepy Hollow.
Twilight Village at Sleepy Hollow
The Philipsburg Manor, once a colonial-era mill and trading center, transforms into the Twilight Village at Sleepy Hollow just in time for Halloween. The outdoor experience, in its second year, features live performances, an artisan’s market and more. Tickets start at $25 for kids, $29 for seniors and young adults, $30 for adults. Members receive 15% off.
If you go: Philipsburg Manor, 381 North Broadway, Sleepy Hollow, hudsonvalley.org/events/twilight-village-at-sleepy-hollow.
Lyndhurst Mansion, Tarrytown
The sprawling grounds of the Lyndhurst Mansion are a must-see for anyone new in town, as is the historic manor itself. From gardens to trails, to the 19th century embellishments of the interior, Lyndhurst is a feast for the eyes, history buff or not.
Book a Fall Classic Mansion Tour to check out the first two floors of the manor, lavishly decorated for fall.
Admission starts at $10 plus fees for a Grounds Pass, and must be purchased online (members receive free admission). Tours add an extra cost.
If you go: 635 S. Broadway, Tarrytown. Go to lyndhurst.org/visit or call 914-631-4481 to learn more.
This article originally appeared on Rockland/Westchester Journal News: Check out this list of some of Sleepy Hollow and Tarrytown’s best Halloween selfie spots
Reporting by Staff Reports / Rockland/Westchester Journal News
USA TODAY Network via Reuters Connect
