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, and each offers a different way to experience the area:
- The Great Jack O’Lantern Blaze: A ticketed evening walk-through at Van Cortlandt Manor in Croton-on-Hudson.
- Sleepy Hollow Street Fair: A free daytime event on Beekman Avenue with vendors, live music, and Headless Horseman appearances.
- Sleepy Hollow Music Festival: A full-day outdoor event at Kingsland Point Park with live music, food, vendors, and Halloween programming.
If you’re planning a Hudson Valley fall trip, here’s what to know about the dates, ticket prices, what each event includes, transportation, and where to stay for a group visiting the area.
The Big Three Fall Events 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. 20, 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
- Purchase: 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 depending on the date and time. Nothing is sold at the gate, and October weekends can sell out weeks ahead.
If your preferred date is sold out, FLEX and FLEX PLUS tickets allow entry on any open night without a reservation, although availability is limited.
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.
New sections include:
- Creature Feature Forest, featuring classic movie monsters and referencing the property’s history as a mid-century drive-in
- Literary Lane, where children’s stories are recreated in pumpkins
- A working carousel
- Life-sized dinosaurs
- A gourd planetarium
- A dance party on the manor house lawn
The walk itself takes roughly 45 minutes, although you’ll want additional time if you plan to stop for photos.
Getting There
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 Sleepy Hollow Street Fair has a different atmosphere from the ticketed attractions. It is a daytime community event that turns Beekman Avenue into a pedestrian-friendly street filled with vendors, music, and visitors.
2026 Date and Details
The 2026 fair took place on Sunday, September 20, from 10 a.m. to 5 p.m. Since that date has passed, visitors planning ahead should watch for the 2027 announcement.
The fair typically takes place on a Sunday in mid to late September, with the date announced in late summer.
Highlights include:
- Free admission
- 145+ vendors
- Live bands
- Headless Horseman appearances from 1 to 4 p.m.
- Dog-friendly atmosphere
Parking
Beekman Avenue closes to traffic during the event, and village parking can fill by mid-morning.
If you’re planning for a future year, arriving early can make parking easier.
3. Sleepy Hollow Music Festival
Kingsland Point Park, 299 Palmer Avenue, Sleepy Hollow
The third annual Sleepy Hollow Music Festival takes place Saturday, October 3, 2026. Gates open at 11 a.m., with music running from noon to 8 p.m.
Tickets and Festival Details
- Date: Saturday, October 3, 2026
- Gates: 11 a.m.
- Music: Noon–8 p.m.
- Advance tickets: $65
- Day-of tickets: $75
- Re-entry: Permitted
- Children: Up to two children age 12 and under free per ticketed adult
- VIP: Available with expedited entry, private bar, and shaded seating
- Stages: Two
- Bands: Eleven
2026 Lineup
The main stage includes:
- Everclear
- The Smithereens featuring Marshall Crenshaw
- Sophie B. Hawkins
- Fastball
- SoulShine
- Anthony Giaccio & the Assortments
The regional stage features:
- Rachel Ana Dobken
- Imposters
- The Altogether
- A 90s DJ set
- School of Rock Briarcliff Manor
School of Rock Briarcliff Manor adds a local connection to the festival lineup.
There are no overlapping sets, making it easier to plan the day around the performers you want to see.
Halloween Programming
The festival also includes:
- 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 are also part of the festival.
Getting There
Kingsland Point Park sits between Philipse Manor and Tarrytown stations on Metro-North.
- Bike parking is available.
- ADA parking is limited.
- ADA parking must be reserved in advance.
Because the festival runs for nine hours, the re-entry policy can be useful for families or anyone who wants a break during the day.
Which Event Is Right for Your Trip?
| If you are… | Consider… |
|---|---|
| Visiting for the first time | The Blaze |
| Traveling with young kids | The Blaze with an early entry time |
| Looking for a free activity | Street Fair |
| Bringing the dog | Street Fair |
| Visiting for the music | Music Festival |
| Coming without a car | The Blaze or Music Festival |
| Looking for an adults-only add-on | Gourd & Goblet Tavern at the Blaze |
| Planning a full fall weekend | Multiple events, depending on dates |
When to Book
The Blaze
October weekends can sell out weeks ahead. If your preferred date is unavailable, check FLEX and FLEX PLUS ticket availability.
Music Festival
Advance tickets are $65 compared with $75 at the gate.
Street Fair
No ticket is required, but parking can become difficult as the morning progresses.
Accommodation
October is peak season throughout the corridor, and larger properties suitable for groups can fill quickly.
Where to Stay: Stone Manor
Sleepy Hollow gets busy during October. Rates can increase, minimum stays may appear, and parking becomes more difficult as visitors arrive for the season’s events.
Staying about fifteen minutes inland gives a group a quieter base while keeping the main attractions within a short drive.
Stone Manor at a Glance
Stone Manor in Briarcliff Manor, New York has:
- 4 bedrooms
- 4.5 bathrooms
- Sleeps 12
- Approximately 4,100 square feet
- Hudson River views
- Full kitchen
- Game room
- Gym
- Firepit
- Patio
- Free on-site parking
Rockefeller State Park Preserve and the Old Croton Aqueduct trail are nearby, and Scarborough station provides access to Metro-North.
How Far Is Stone Manor From the Events?
| Destination | Approx. Drive Time |
|---|---|
| The Blaze, Croton-on-Hudson | ~15 min |
| Kingsland Point Park | ~10 min |
| Beekman Avenue, Sleepy Hollow | ~10 min |
| Sleepy Hollow Cemetery | ~5 min |
| Kykuit | ~8 min |
For groups of eight to twelve, one house with a kitchen can also simplify the logistics of a fall weekend. Instead of coordinating several hotel rooms, everyone has one place to gather, prepare meals, and take a break between events.
Check fall availability at bookstonemanor.com.
FAQ
What are the biggest fall events in Sleepy Hollow?
The three major events covered in this guide are the Great Jack O’Lantern Blaze in Croton-on-Hudson, the Sleepy Hollow Street Fair on Beekman Avenue, and the Sleepy Hollow Music Festival at Kingsland Point Park.
Do I need tickets for the Jack O’Lantern Blaze in advance?
Yes. Nothing is sold at the gate, and October weekends can sell out weeks ahead. FLEX and FLEX PLUS tickets allow entry on any open night without a reservation, but they are limited.
How much are Jack O’Lantern Blaze tickets in 2026?
Tickets start at $24 and vary by date and time. The Headless Horseman’s Hideaway starts at $39, while the 18-and-over Gourd & Goblet Tavern starts at $64.
When is the Sleepy Hollow Music Festival 2026?
The festival takes place Saturday, October 3, 2026, at Kingsland Point Park. Gates open at 11 a.m., with music from noon to 8 p.m.
Is the Sleepy Hollow Street Fair free?
Yes. Admission is free. The 2026 fair took place on Sunday, September 20.
Can you visit these events without a car?
Yes. The Blaze is a short walk from Croton-Harmon station, while Kingsland Point Park is accessible from Philipse Manor and Tarrytown stations on Metro-North’s Hudson Line.
Where should a group stay for Sleepy Hollow fall events?
Staying outside the village can provide easier parking and access to larger accommodations. Stone Manor in Briarcliff Manor sleeps 12 and is approximately 15 minutes from the Blaze and about 10 minutes from the Sleepy Hollow events.
Are these events good for young children?
The Blaze is a walk-through experience suitable for all ages, and the Street Fair is family and dog friendly. The Music Festival runs for nine hours, although re-entry is permitted and up to two children age 12 and under can attend free per ticketed adult.