Things to Do in Westchester This September: The StacyKnows List
I say this every year: September might just be the best month to live in Westchester.
The humidity finally gives us a break. The orchards open. Everyone comes back from wherever they disappeared to in August. And suddenly there is something going on every single weekend.
Apple picking. Street fairs. Outdoor concerts. Art shows. Wine. Jazz. The Blaze.
Basically, if you’re bored this month, I can’t help you.
Here’s my StacyKnows list of what’s actually worth putting on the calendar between now and the first weekend of October.
First Things First: Apple Picking
Yes, apple season is officially here.
And my advice? Go now. Before apple picking turns into pumpkin picking turns into full-blown Halloween madness.
Outhouse Orchards — North Salem
Apple picking, a corn maze, cider donuts, hard cider, wood-fired pizza and plenty of fall activities.
But here’s what caught my eye: Fall Friday Nights.
They’re happening September 11, 18 and 25, plus October 2, 9, 16, 23 and 30 from 6–9 PM.
That sounds much more my speed.
Buy Outhouse Orchards tickets here.
Harvest Moon Farm & Orchard — North Salem
Another North Salem favorite—and one to know before you just jump in the car.
During Fall Festival weekends, admission is required to access the farm and outdoor areas, and they strongly recommend buying tickets in advance because peak dates can sell out.
Expect apple picking, a pumpkin patch, hayrides, live music, cider donuts, hard cider and plenty of food.
Fall Festival details and tickets.
Wilkens Fruit & Fir Farm — Yorktown Heights
Wilkens is celebrating its 110th harvest in 2026, which is pretty amazing.
There’s pick-your-own fruit, a bakery, farm market, cider donuts and even a winery.
If you’re the person who wakes up Saturday morning and announces, “Let’s go apple picking,” put this one on your list.
Check what’s available for picking before you go.
Stuart’s Fruit Farm — Granite Springs
Family-run since 1828, with weekend hayrides and plenty of old-school fall charm.
One important StacyKnows PSA: bring cash or a check.
Yes, checks still exist.
The Five I’d Actually Plan Around
If you only put five things on your calendar, start here.
The Great Jack O’Lantern Blaze — Croton-on-Hudson
Thousands of hand-carved jack o’lanterns take over Van Cortlandt Manor, and this is one Westchester tradition I never get tired of.
I’ve said it before and I’ll say it again: buy your tickets early.
The Blaze sells out, and every year someone waits until the end of October and starts looking for tickets.
Don’t be that person.
The Capitol Theatre Turns 100 — Port Chester
Saturday, September 19
The Capitol Theatre is celebrating its 100th birthday.
A theater only turns 100 once. Enough said.
Sleepy Hollow Street Fair
Sunday, September 20
Vendors, live music and, because this is Sleepy Hollow, the Headless Horseman.
This is basically the weekend Westchester collectively decides:
Fine. It’s Halloween now.
Armonk Outdoor Art Show
September 26 & 27, 10 AM–5 PM
One of my favorites—and practically in my backyard.
Now in its 64th year, the Armonk Outdoor Art Show brings approximately 160 juried artists from around the country to Armonk.
It’s a great wander-around-for-a-few-hours kind of day, and proceeds support the Friends of the North Castle Public Library.
Anyone 18 and under gets in free, and admission is good for the entire weekend.
Get Armonk Outdoor Art Show tickets here.
Sleepy Hollow Music Festival
Saturday, October 3 — Kingsland Point Park
This lineup had me at Everclear.
Add The Smithereens featuring Marshall Crenshaw, Fastball, SoulShine and more, spread across two stages with no overlapping sets.
General admission is $62.50. Gates open at 11 AM, music starts at noon and the festival wraps at 8 PM.
Get Sleepy Hollow Music Festival tickets.
September 11: Twenty-Five Years Later
The Westchester County 9/11 Memorial Ceremony takes place Friday, September 11 at 2 PM at The Rising and the 9/11 First Responders Memorial at Kensico Dam Plaza in Valhalla.
One hundred twenty-three names are memorialized there.
For the 25th anniversary, every name will be read aloud.
The ceremony is free and open to everyone.
Apparently Every Weekend Is a Festival
I’m not exaggerating.
Yorktown Grange Fair
September 11–13
Westchester’s only agriculturally based country fair is celebrating its 102nd year with the very excellent 2026 theme: “Goats, Games & Good Times.”
Rides, livestock, food, live entertainment, tractor parades and all the country-fair things.
Autumn Glow Festival at Glen Island Park
Starting September 11
More than 1,000 illuminated Chinese lanterns along the Sound.
This is new this year and looks extremely Instagrammable.
Music Across the Hudson
September 12
Free live music at waterfront locations throughout Westchester.
Mount Kisco SeptemberFest
September 18–20
Carnival, street fair, beer garden and food trucks.
In other words: something for everyone.
Fall Crafts at Lyndhurst
September 18–20
Shop original fashion, jewelry, home décor, fine art, ceramics, glass, woodwork and more on the gorgeous Lyndhurst grounds.
There are also craft demonstrations, family activities and plenty to eat.
Get Fall Crafts at Lyndhurst tickets here.
Yonkers Riverfest
September 19
Three stages, more than 140 vendors and one of Westchester’s biggest one-day festivals.
And it’s free.
Lewisboro Library Fair
September 19, 10 AM–4 PM
One of the biggest community days in Lewisboro, with a car show, live music, kids’ zone, food trucks, dunk tank, beer and wine garden, book sales, Attic Treasures and vendors.
Old-school Westchester in the best possible way.
Chappaqua Children’s Book Festival
September 26, 10 AM–4 PM
Meet authors and illustrators, catch storytimes and author talks and let the kids loose in the Family Fun Zone.
Admission is free.
If you have young readers in your house, this is one of the best days of the month.
Croton Oktoberfest
September 26
More than 65 vendors plus a free shuttle from Croton-Harmon.
Armonk Cider & Donut Festival
October 4 — Wampus Brook Park
Jamie’s 5K starts the morning, followed by the festival and carnival.
Cider. Donuts. Armonk in October.
You get the picture.
