Dates & times
All times are local to the venue · America/New York
- From 10:45 AM
These are the previously published dates. Check the organizer for a new edition.
Check the organizer’s latest schedule ↗Sleepy Hollow Street Fair Day Trip: Two Ways to Join on Nov. 8
The timing changes what you can catch. Sleepy Hollow’s Street Fair runs from 10 a.m. to 5 p.m. on Sunday, Nov. 8, while a Meetup group leaving Midtown plans to arrive around 12:45 p.m. That puts its travelers in position for the afternoon appearances, but after the earliest music sets and the 11:30 a.m. performance by Witches Along The Hudson.
Choose where to join the trip
For the Manhattan departure, meet the group at McDonald’s, 18 E 42nd St., between 10:45 and 11 a.m. Hosted by Steven of Socially Awkward but I'm Trying, the outing plans a five-to-10-minute walk to Grand Central Terminal and an 11:25 a.m. Metro-North Hudson Line train, Train 8723. The organizer lists an approximate 12:21 p.m. arrival at Philipse Manor, then estimates reaching the fair around 12:45 p.m. Train timing and the walk are plans, not guaranteed arrival times.
Traveling separately? The group also plans to meet at Philipse Manor Metro-North Station, 78 Riverside Drive, Sleepy Hollow, at approximately 12:21 p.m. From there, the organizer estimates a 15-to-20-minute walk—about 0.9 to 1 mile—to the Pocantico Street end of Beekman Avenue. Check TrainTime for service changes if you are taking Metro-North.
Further reading: 🎃👻🍂 Sleepy Hollow Street Fair Day Trip! 🚆🎶🌭, Sun, Nov 8, 2026, 10:45 AM | MeetupBending Spoons ↗ · 🎃👻🍂 Sleepy Hollow Street Fair Day Trip! 🚆🎶🌭, Sun, Nov 8, 2026, 10:45 AM | MeetupBending Spoons ↗
The afternoon program has several distinct stops
The rescheduled Village fair is on Beekman Avenue from 10 a.m. to 5 p.m. Its listing advertises 145+ arts-and-crafts, food and beverage vendors, local eateries and shops, and Halloween-inspired merchandise. It also describes entertainment for families and says dogs are included.
For travelers arriving with the Meetup group, the Headless Horseman’s scheduled 1-to-4 p.m. appearance in front of Ganso Ramen, at Beekman Avenue and Route 9/Broadway, falls within the planned visit. Witches Along The Hudson performs at Beekman Avenue and Pocantico Street at 3 p.m., as well as at 11:30 a.m. The Beekman Lot also lists Luis Enrique’s Andean Flutes Band, with no start time provided.
Music at the Beekman Parking Lot Entrance begins at 11 a.m. with Jessica Star and continues through a 4-to-5 p.m. slot for Your Friends in Hell. The other listed acts are Brad & Nate – The Incumbents Acoustic, the BUMP and The Altogether. The Village also lists a Kids’ Zone at the Beekman Parking Lot without a published time. The timed schedule is useful if you want to plan around particular appearances; the two untimed listings do not offer a confirmed start.
Further reading: November 8 - Sleepy Hollow Street Fair | Sleepy Hollow, NYArrow LeftArrow RightSlideshow Left ArrowSlideshow Right Arrow ↗
Account for the street closure and station access
Beekman Avenue between Pocantico Street and Route 9 closes to vehicles from 6 a.m. to 6 p.m. The Village warns that parking is limited and traffic delays are expected, and encourages visitors from New York City and nearby rivertowns to use Metro-North’s Hudson Line. Tarrytown and Philipse Manor stations are both identified as within walking distance.
Philipse Manor needs an extra access check: the MTA says the station has ramps but no accessible path between its platforms. Tarrytown and Scarborough are the nearest fully accessible stations on the line. The Meetup listing does not identify which platform its train will use or give an accessible alternative for joining the group at Philipse Manor.
Further reading: Sleepy Hollow Street Fair - Traffic and Parking | Sleepy Hollow, NYArrow LeftArrow RightSlideshow Left ArrowSlideshow Right Arrow ↗ · Philipse Manor ↗ · 🎃👻🍂 Sleepy Hollow Street Fair Day Trip! 🚆🎶🌭, Sun, Nov 8, 2026, 10:45 AM | MeetupBending Spoons ↗
The fair is the outing’s fixed point
The Meetup page’s headline gives a 10:45 a.m.–12:45 p.m. event window, but its itinerary describes arriving at the fair around 12:45 and continuing afterward. It says there is no required time to stay, but supplies neither a group end time nor a return train. Further exploring, a food stop, a waterfront walk or a visit to the cemetery area are possibilities for the group to decide on, not confirmed parts of the trip.
The outing description also mentions the Rivertown Pumpkin Trail, but dates the displays through Nov. 1. They should not be counted on as a Nov. 8 attraction.
Further reading: 🎃👻🍂 Sleepy Hollow Street Fair Day Trip! 🚆🎶🌭, Sun, Nov 8, 2026, 10:45 AM | MeetupBending Spoons ↗ · 🎃👻🍂 Sleepy Hollow Street Fair Day Trip! 🚆🎶🌭, Sun, Nov 8, 2026, 10:45 AM | MeetupBending Spoons ↗
Timed appearances and music along Beekman Avenue
The afternoon arrival in the Meetup itinerary makes the 1-to-4 p.m. Headless Horseman appearance and the 3 p.m. Witches Along The Hudson performance particularly relevant. Music starts at 11 a.m. and runs through 5 p.m.; the Village gives no start time for Luis Enrique’s Andean Flutes Band or the Kids’ Zone.
Sunday, November 8, 2026 · Beekman Avenue & Pocantico Street
- Witches Along The Hudson
Sunday, November 8, 2026 · In front of Ganso Ramen, Beekman Avenue & Route 9/Broadway
- Headless Horseman
Sunday, November 8, 2026 · Beekman Lot at the top of Beekman and Route 9
- Luis Enrique’s Andean Flutes Band
Sunday, November 8, 2026 · Beekman Parking Lot
- Village of Sleepy Hollow Kids’ Zone
Sunday, November 8, 2026 · Beekman Parking Lot Entrance
- Jessica Star
- Brad & Nate – The Incumbents Acoustic
- the BUMP
- The Altogether
- Your Friends in Hell
Plan the day
Sunday, Nov. 8, 2026
The Village lists the rescheduled Sleepy Hollow Street Fair for 10 a.m.–5 p.m. on Beekman Avenue. The Meetup group gathers in Manhattan from 10:45 to 11 a.m. and plans to reach the fair around 12:45 p.m.
November 8 - Sleepy Hollow Street Fair | Sleepy Hollow, NYArrow LeftArrow RightSlideshow Left ArrowSlideshow Right Arrow ↗ · 🎃👻🍂 Sleepy Hollow Street Fair Day Trip! 🚆🎶🌭, Sun, Nov 8, 2026, 10:45 AM | MeetupBending Spoons ↗
Start in Midtown or at Philipse Manor
Manhattan meeting point: McDonald’s, 18 E 42nd St., New York, NY 10017. Arrive between 10:45 and 11 a.m. The group plans to walk about five to 10 minutes to Grand Central Terminal and take Metro-North Hudson Line Train 8723 at 11:25 a.m. The organizer lists arrival at Philipse Manor at approximately 12:21 p.m.
Alternate meeting point: Philipse Manor Metro-North Station, 78 Riverside Drive, Sleepy Hollow, NY 10591, at approximately 12:21 p.m. The organizer estimates 15 to 20 minutes on foot, or about 0.9 to 1 mile, from the station to the Pocantico Street end of Beekman Avenue. Check TrainTime for service updates.
Although the Meetup listing’s headline shows a 10:45 a.m.–12:45 p.m. window, the itinerary describes a fair arrival around 12:45 and possible plans afterward. It gives no group end time or return-train time.
🎃👻🍂 Sleepy Hollow Street Fair Day Trip! 🚆🎶🌭, Sun, Nov 8, 2026, 10:45 AM | MeetupBending Spoons ↗ · 🎃👻🍂 Sleepy Hollow Street Fair Day Trip! 🚆🎶🌭, Sun, Nov 8, 2026, 10:45 AM | MeetupBending Spoons ↗
The fair is free; buy your own train ticket
The Village lists free admission to the Street Fair. Anyone traveling with the Meetup group by Metro-North is responsible for their own train ticket. The Meetup listing does not state whether the group outing has a separate fee.
Getting to the fair and meeting the group
Manhattan departure
Meet at McDonald’s, 18 E 42nd St., New York, NY 10017, between 10:45 and 11 a.m. The organizer plans a five-to-10-minute walk to Grand Central Terminal for the 11:25 a.m. Hudson Line Train 8723 to Philipse Manor. Check TrainTime for service changes.
🎃👻🍂 Sleepy Hollow Street Fair Day Trip! 🚆🎶🌭, Sun, Nov 8, 2026, 10:45 AM | MeetupBending Spoons ↗ · 🎃👻🍂 Sleepy Hollow Street Fair Day Trip! 🚆🎶🌭, Sun, Nov 8, 2026, 10:45 AM | MeetupBending Spoons ↗
Joining at Philipse Manor
The group plans to meet separately traveling attendees at Philipse Manor Metro-North Station, 78 Riverside Drive, Sleepy Hollow, NY 10591, at approximately 12:21 p.m. The organizer estimates a 15-to-20-minute walk to the Pocantico Street end of Beekman Avenue.
The MTA says the station has ramps but no accessible path between platforms. The meetup listing does not identify the group’s platform or give an accessible alternative for joining there.
🎃👻🍂 Sleepy Hollow Street Fair Day Trip! 🚆🎶🌭, Sun, Nov 8, 2026, 10:45 AM | MeetupBending Spoons ↗ · Philipse Manor ↗
Fair location, roads and parking
The Street Fair is on Beekman Avenue between Pocantico Street and Route 9. That stretch closes to vehicles from 6 a.m. to 6 p.m. The Village reports limited parking and expected traffic delays, recommends Metro-North, and identifies Tarrytown and Philipse Manor as stations within walking distance.
For drivers from Rockland County or the south, the Village directs visitors to Tarrytown Train Station parking. From the north, its directions are Route 9 to Pocantico Street, right on Continental Avenue, then the East Parcel lot at 60 Continental Street. The Village also suggests Hudson Link, Bee-Line or ride services for travel from other destinations in Rockland or Westchester County.
Before you make a plan
What time does the Meetup group expect to reach the fair?
The itinerary estimates arrival around 12:45 p.m. after a planned 11:25 a.m. Metro-North departure from Grand Central; actual timing may vary.
🎃👻🍂 Sleepy Hollow Street Fair Day Trip! 🚆🎶🌭, Sun, Nov 8, 2026, 10:45 AM | MeetupBending Spoons ↗ · 🎃👻🍂 Sleepy Hollow Street Fair Day Trip! 🚆🎶🌭, Sun, Nov 8, 2026, 10:45 AM | MeetupBending Spoons ↗
Can I meet the group in Sleepy Hollow instead of Midtown?
Yes. The organizer plans to meet separately traveling attendees at Philipse Manor Station, 78 Riverside Drive, at approximately 12:21 p.m., then walk about 15 to 20 minutes to the fair.
🎃👻🍂 Sleepy Hollow Street Fair Day Trip! 🚆🎶🌭, Sun, Nov 8, 2026, 10:45 AM | MeetupBending Spoons ↗ · 🎃👻🍂 Sleepy Hollow Street Fair Day Trip! 🚆🎶🌭, Sun, Nov 8, 2026, 10:45 AM | MeetupBending Spoons ↗
Is admission free, and do I need to pay for the train?
The Village lists free admission to the fair. Meetup travelers must buy their own Metro-North tickets; a separate fee for the outing is not stated.
🎃👻🍂 Sleepy Hollow Street Fair Day Trip! 🚆🎶🌭, Sun, Nov 8, 2026, 10:45 AM | MeetupBending Spoons ↗
Location & Google Maps
Meetup gathering at McDonald's, followed by travel to the Sleepy Hollow Street Fair on Beekman Avenue; participants may instead meet the group at Philipse Manor Metro-North Station.
McDonald's, 18 E 42nd St, New York, NY 10017 (Manhattan meeting point). Fair: Beekman Avenue, Sleepy Hollow, NY. Alternate meeting point: Philipse Manor Metro-North Station, 78 Riverside Drive, Sleepy Hollow, NY 10591.
Map search by venue and address. Check the organiser’s entrance details before travelling.