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Autumn activities galore
Pumpkins, tea parties, fall cocktails, and more...
Welcome to Issue #23 of the Westchester Weekly!
I sure hope you’ve gotten outside this last week to enjoy this perfect fall preview weather. This week we have the first batch of autumnal events and can’t wait to see you at some of them (hint: it’s the one at Stone Barns).
But before we start, will you do us a favor?
Share the Westchester Weekly with a friend.
Forward it over email, call them up and read this issue over the phone, print it out and hang it on their front door. Doesn’t matter to us!
If you like what we’re doing for the community, we’d appreciate you helping us grow.
Now on to the good stuff.
In this issue:
🎃 Pumpkin Magic, Tea Parties & Treasure Hunts
🎷 Jazz Fest, Blues on the Hudson & Music Under the Stars
🎨 Fall Crafts, Local Art, and Creative Pop-Ups
😂 Comedy Nights, Cult Films & Artist Meet-Up’s
🏡 Real Estate Deal of the Week 🏡
A Sleepy Hollow beauty!
This beautifully updated craftsman-style Colonial, nestled on a quiet street, effortlessly combines historic Hudson Valley charm with modern upgrades.
Inside, sunlight fills the spacious living room framed by character-rich windows, while a large, renovated kitchen opens to a fully fenced backyard – ideal for both those relaxed family evenings and any sort of stylish entertainment!
3 Beds
1.5 Baths
1,900 sq ft
0.26-acre lot
Asking Price: $1,100,000
Click here to view the full listing.
🧺 Family-Friendly Fun
Get into the fall spirit with a trip to a Westchester institution, The Great Jack O’Lantern Blaze! Prepare you and your family for a night full of pumpkins and apple cider!
🎃 The Great Jack O’Lantern Blaze
Van Cortlandt Manor | Croton-on-Hudson | September 12-November 16 | More
Westchester’s most magical fall tradition is back! Walk through thousands of glowing pumpkins carved into dragons, dinosaurs, and towering displays – a must-do for families every autumn.
🍿 Pintwood 2025
Broken Bow Brewery | Tuckahoe | September 13 | More
Design and build your own racecar to duke it out against other friends and families at the Tuckahoe Pack 7's Adult Pintwood Derby Fundraiser!
🎉 SeptemberFest (Street Fair + Carnival)
Downtown | Mount Kisco | Fri–Sun | More
Carnival rides, street fair, food trucks & live music all weekend.
🪕 Revolutionary Harvest Festival
Philipse Manor Hall | Yonkers | September 13 | More
Travel back in time at this hands-on history fest. Kids can try colonial crafts, meet costumed interpreters, and celebrate harvest season the old-fashioned way.
☕ Belinda’s Bewitching Tea Party
Washington Irving's Sunnyside | Pocantico Hills | September 13 | More
A whimsical tea with Belinda the Good Witch – complete with storytelling, snacks, and a little magic sprinkled in. Perfect for younger kiddos who love fairy tales and costumes.
🍻 Activities for Adults
Enjoy the sounds of Ossining's trademark music festival, clad with some of the most talented and celebrated blue acts from all throughout the entire country!
🎞️ Out There Film Series: My Beautiful Laundrette
Jacob Burns Film Center | Pleasantville | September 11 | More
This cult classic from 1985 is equal parts punk, politics, and romance. Grab a glass of wine, sink into the plush JBFC seats, and let yourself be transported back to Thatcher-era London.
😂 Westchester Comedy Club @ Rye
Rye Grill & Bar | Rye | September 11 | More
Westchester’s own underground comedy scene is alive and well! Expect big laughs, a few surprises, and the kind of night that’ll leave your cheeks sore from smiling.
🎷 Jazz Fest White Plains
Downtown White Plains | September 11-14 | More
For four days, the heart of White Plains swings. From Grammy winners to rising stars, this is Westchester’s signature jazz party – pack your dancing shoes and join the block-wide celebration.
🎨 Fall Crafts at Lyndhurst
Lyndhurst Mansion | Tarrytown | September 12-14 | More
One of the prettiest shopping weekends of the year: hundreds of makers setting up shop on the rolling lawns of Lyndhurst. From jewelry to ceramics to treats you didn’t know you needed, this is artisan heaven.
🍹 Botanical Beverages 101
Stone Barns Center | Pocantico Hills | September 13 | More
Ever wanted to sip on a cocktail made with foraged flowers or roots? Stone Barns will show you how. Think of it as science class meets mixology – and yes, taste testing is encouraged.
🖼️ Art for Purchase 2025
Purchase Street | Rye | September 13 | More
Westchester talent on full display. Whether you’re a serious collector or just want something new for your living room, this is the spot to fall in love with local art (and maybe take a piece home).
🎶 UP THE RIVER Blues Festival
Louis Engel Waterfront Park | Ossining | September 13 | More
Hudson River views, smoky guitar riffs, and good food truck eats – Ossining knows how to throw a blues bash. A guaranteed good time for music lovers who like their nights a little gritty and a lot soulful.
🎡 Yonkers Riverfest
Downtown Yonkers | September 13 | More
One of Westchester’s biggest parties is back! Live music, food vendors, art, and the kind of crowd energy that makes downtown Yonkers feel electric.
🎼 Bedford Music Festival @ Caramoor
Caramoor Center for Music & the Arts | Katonah | September 13 | More
Destination 39.3 takes over Caramoor with an evening of incredible performances in one of the most magical music settings in the county. Trust me: bring a blanket, bring friends, and let the night unfold.
🖌️ Chad Crume: Through Light & Color Artist Reception
Croton River Artisans Gallery | Croton-on-Hudson | September 14 | More
Meet painter Chad Crume and experience his bold, light-drenched works in an intimate Croton gallery. It’s the perfect low-key Sunday outing with plenty of inspiration baked in.
🏃 Yonkers Marathon, Half Marathon & 5K
Yonkers | September 14 | More
Not for the faint of heart – the Yonkers Marathon is one of the oldest (and toughest!) in the country. Whether you’re running or just cheering with a coffee in hand, the city comes alive with race-day energy.
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🌡️ Weather Report
☀️ Weekend Weather at a Glance
Friday (Sep 12): ☀️ Mostly sunny and nice – High 76°F / Low 61°F
Saturday (Sep 13): ⛅ Pleasant with a blend of sunshine and clouds – High 74°F / Low 57°F
Sunday (Sep 14): ⛅ Pleasant with a mix of clouds and sun – High 79°F / Low 55°F
Thanks for reading!
If you know of anything interesting going on in Westchester, reply to this email and let us know.
— Ethan & The Westchester Weekly team
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