Fall in Sleepy Hollow is not a single Halloween night. The season stretches for roughly seven weeks across ten miles of Hudson River towns, from Croton-on-Hudson in the north to Sleepy Hollow and Tarrytown in the south.
Three major events anchor the 2026 season, each offering a different way to experience the area. The Street Fair and Music Festival have concluded for the year; Blaze continues through November 8.
The big three at a glance
| Event | When | Cost | Format | Best for |
|---|---|---|---|---|
| The Great Jack O’Lantern Blaze | Sept. 18–Nov. 8 | From $24 | Evening walk-through | Families, first-timers, photographers |
| Sleepy Hollow Street Fair | Sept. 27, 2026 | Free | Daytime street fair | Families, locals, dog owners |
| Sleepy Hollow Music Festival | Oct. 3, noon–8 p.m. | $65 advance, $75 at gate | Full-day music festival | Adults, music fans, families with older kids |
1. The Great Jack O’Lantern Blaze
Van Cortlandt Manor, 525 South Riverside Avenue, Croton-on-Hudson
The Great Jack O’Lantern Blaze runs from September 18 through November 8, 2026. The event has 44 nights in total, with nightly dates throughout October and select evenings in September and November.
Tickets and dates
- Dates: September 18–November 8, 2026
- Tickets: From $24; advance purchase only
- Headless Horseman’s Hideaway: From $39
- Gourd & Goblet Tavern: From $64, ages 18+
- Free admission: Historic Hudson Valley members and children age 2 and under
Ticket prices vary by date and entry time. Nothing is sold at the gate, and October weekends can sell out weeks ahead. If a preferred date is sold out, FLEX and FLEX PLUS tickets allow entry on any open night without a reservation, subject to availability.
What you’ll see
More than 7,000 hand-carved, individually lit pumpkins fill the grounds of the 18th-century estate. For 2026, the trail is the longest in the event’s history.
- Creature Feature Forest, with classic movie monsters and a nod to the property’s drive-in history
- Literary Lane, where children’s stories are recreated in pumpkins
- A working carousel, life-sized dinosaurs, and a gourd planetarium
- A dance party on the manor house lawn
The walk takes roughly 45 minutes; allow more time for photos. Croton-Harmon on Metro-North’s Hudson Line is a short walk from the entrance.
2. Sleepy Hollow Street Fair
Beekman Avenue, Sleepy Hollow
The Street Fair is a daytime community event that turns Beekman Avenue into a pedestrian-friendly street of vendors, music, and visitors. The 2026 fair was rescheduled to Sunday, September 27, from 10 a.m. to 5 p.m.; guests planning ahead should watch for the 2027 announcement.
- Free admission and more than 145 vendors
- Live music and Headless Horseman appearances from 1 to 4 p.m.
- Dog-friendly atmosphere
Beekman Avenue closes to traffic during the event, and village parking can fill by mid-morning. For a future year, arrive early or come by rail and walk in from a nearby station.
3. Sleepy Hollow Music Festival
Kingsland Point Park, 299 Palmer Avenue, Sleepy Hollow
The third annual Sleepy Hollow Music Festival took place Saturday, October 3, 2026. Gates opened at 11 a.m., with music from noon to 8 p.m.
- Advance tickets: $65; day-of tickets: $75
- Re-entry permitted; up to two children age 12 and under free per ticketed adult
- VIP included expedited entry, a private bar, and shaded seating
- Two stages, eleven bands, and no overlapping sets
2026 lineup
The main stage included Everclear, The Smithereens featuring Marshall Crenshaw, Sophie B. Hawkins, Fastball, SoulShine, and Anthony Giaccio & the Assortments. The regional stage featured Rachel Ana Dobken, Imposters, The Altogether, a 90s DJ set, and School of Rock Briarcliff Manor.
Halloween programming
The day also included a kids costume parade, pumpkin-carving demonstrations by Blaze carvers, Witches Along the Hudson, Halloween Village, Headless Horseman appearances, food trucks, beer gardens, local brewery and distillery tastings, and more than 30 craft vendors.
Kingsland Point Park sits between Philipse Manor and Tarrytown stations on Metro-North. Bike parking is available. ADA parking is limited and must be reserved in advance. The re-entry policy made it easier to take a break during a nine-hour day.
Where to stay for a group
Stone Manor is in Briarcliff Manor, within driving distance of Croton-on-Hudson, Sleepy Hollow, and Tarrytown. The house has four bedrooms and sleeps up to 12 overnight guests, with room to regroup after a full day out. Check dates early for October weekends.