PAID · NOT FREE · DATE NIGHT

Date Night / Paid Activities $

Things to do that cost money — not dinner. NYC first, then Lower New York (Long Island, Westchester & Rockland) and New Jersey near the city. Everything else on this site is free.

3 of 82 places · price levels $ (under ~$25/person) · $$ (~$25–60) · $$$ (over ~$60). Open/closed status is in New York time.

🎃 Haunted & Halloween$$

The Headless Horseman Files

📍 Sleepy Hollow, Westchester Lower New York ★ Halloween season · through 10/31

Closed · opens at 10 AM today (NY time)

A 45-minute live-action walking mystery around Philipsburg Manor: gather clues about what really happened to Ichabod Crane.

PAID Adult $35, senior/young adult $34, child $25; members save 15%

⏱ Est. time spent: 45 min

Hours & address

Philipsburg Manor, 381 N Broadway, Sleepy Hollow, NY 10591 · Map

Sun 10/25	10 AM–4:15 PM
Fri 10/30	10 AM–4:15 PM
Sat 10/31	10 AM–4:15 PM

Timed entries 10 AM–4:15 PM on Oct 25, 30 and 31; the experience lasts 45 minutes.

Booking: Timed admission. Availability not confirmed.

Hours and prices from the business's own site, checked Oct 24–25, 2026. Confirm before you go.

Visit website ↗

🎃 Haunted & Halloween$$

Twilight Village at Sleepy Hollow

📍 Sleepy Hollow, Westchester Lower New York ★ Halloween season · through 10/31

Closed · opens at 6 PM today (NY time)

An outdoor Halloween village you roam: storytellers, fire performers, a brass band, fortune tellers and a Headless Horseman sound-and-light moment on Philipsburg Manor's grounds.

PAID Adult $35, child $25, senior/young adult $34

⏱ Est. time spent: 1.5–2 hrs

Hours & address

Philipsburg Manor, 381 N Broadway, Sleepy Hollow, NY 10591 · Map

Sun 10/25	6 PM–9 PM
Fri 10/30	6 PM–9 PM
Sat 10/31	6 PM–9 PM

Run Oct 2–31, 2026; remaining dates Oct 25, 30 and 31.

Who can go: All ages recommended.

Booking: Advance tickets only; standard tickets are not sold on site. Some dates show limited or sold out.

Optional extras: Tarot readings, food and drinks.

Hours and prices from the business's own site, checked Oct 24–25, 2026. Confirm before you go.

Visit website ↗

🎃 Haunted & Halloween$$

Lyndhurst Halloween Roam on Your Own

📍 Tarrytown, Westchester Lower New York ★ Halloween only · through 10/31

Closed · opens Sat at 9 AM (NY time)

Explore Lyndhurst's decorated Gothic Revival mansion at your own pace on Halloween instead of a standard guided tour.

PAID $24–$30 plus service fees

⏱ Est. time spent: 1–1.5 hrs

Hours & address

Lyndhurst, 635 S Broadway, Tarrytown, NY 10591 · Map

Sat 10/31	9 AM–4 PM

Sat Oct 31, 9 AM–4 PM; last mansion entry 4 PM.

Who can go: Public; involves walking through a historic building.

Booking: Timed entry; buy ahead, since on-site tickets aren't guaranteed. Availability not confirmed.

Hours and prices from the business's own site, checked Oct 24–25, 2026. Confirm before you go.

Visit website ↗

Activities only: food is listed only when it's the activity (cooking classes, food tours, eat-and-play). We're not paid by these businesses. Know a great spot? Tell us.

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