September in Westchester: Events Worth Putting on Your Calendar
Fall festivals, live music, family activities & a few of our favorite things happening around Westchester County this month.
September might be one of the best months to live in Westchester. Summer isn't quite over, fall is starting to show up, and suddenly there is something happening every weekend.
From New Rochelle and White Plains to Armonk, Mamaroneck and beyond, here are a few events worth adding to your September calendar.
Bedford Music Festival
SEPTEMBER 6 · KATONAH
Live music takes over the beautiful grounds of Caramoor for an afternoon of outdoor performances, food, drinks and activities.
Why we like it: Good music, a beautiful setting and an easy way to spend one of the first September weekends.
Autumn Glow Festival
BEGINS SEPTEMBER 11 · NEW ROCHELLE
Glen Island Park gets a fall transformation with an illuminated outdoor experience along the waterfront. The evening event combines traditional Chinese lantern artistry with modern LED displays along the Long Island Sound.
And since it runs beyond September, there are plenty of chances to fit this one into your fall calendar.
Yorktown Grange Fair
SEPTEMBER 11–13 · YORKTOWN HEIGHTS
A true Westchester fall tradition. The 102nd annual fair returns with animals, rides, live music, food, local vendors, children's activities and the always-fun tractor parade.
A classic fall weekend in Westchester.
Bicycle Sundays
SEPTEMBER 13, 20 & 27 · BRONX RIVER PARKWAY
One of those uniquely Westchester activities we love — and especially convenient if you're in Scarsdale, Edgemont or White Plains.
Portions of the Bronx River Parkway close to cars, giving cyclists, walkers and families a chance to take over the road.
The Great Jack O'Lantern Blaze
BEGINS SEPTEMBER 18 · CROTON-ON-HUDSON
It wouldn't be fall in Westchester without the Blaze.
Thousands of illuminated pumpkins transform Van Cortlandt Manor into one of the area's most popular fall experiences.
Our tip: This is one to book ahead.
Fall Crafts at Lyndhurst
SEPTEMBER 18–20 · TARRYTOWN
Art, design, shopping and one of Westchester's most beautiful historic properties.
Spend the day browsing work from artists and makers on the grounds of Lyndhurst — and make a day of Tarrytown while you're there.
New Rochelle Street Fair
SEPTEMBER 19 · NEW ROCHELLE
A local one that's definitely on our list.
Head downtown for the annual New Rochelle Street Fair featuring local vendors, food, entertainment and plenty of community spirit.
JazzFest White Plains
SEPTEMBER 23–27 · WHITE PLAINS
Five days of live jazz throughout White Plains, with performances and events happening at venues around the city.
A great excuse for dinner + live music in White Plains.
Armonk Outdoor Art Show
SEPTEMBER 26–27 · ARMONK
One of our favorites on the list.
The annual Armonk Outdoor Art Show brings juried artists from around the country to Westchester for a weekend filled with art, food and activities.
If you love art, interiors or design, put this one on your calendar.
One More Reason We Love Westchester
One of our favorite things about living here is how much there is to do without going very far.
Whether home is Scarsdale, New Rochelle, Larchmont, Mamaroneck, Rye, Rye Brook, White Plains, Bronxville, Pelham, Harrison, Purchase, Armonk, Chappaqua or Edgemont, there's always another town, restaurant, event or local tradition to discover.
Save a few dates, get outside and enjoy September in Westchester.
We'll see you around town.
— The Keslow Hurwitz Team at Compass
Event dates and details are current as of September 2026. Please check directly with event organizers for the latest schedules, tickets and weather-related changes.
