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What's happening in town this weekend
Inside: The best apple pie in Westchester, new musicals, and fresh oysters
Welcome to Issue #26 of the Westchester Weekly!
October is here and the evenings are cool, but summer has one last gasp this weekend. It’s going to be (in our humble opinions) PERFECT weather from Friday to Sunday!!!
And lucky for all of us, Westchester is going to be pulsing with music, theater, fall flavors & foliage, and pre-Thanksgiving activities.
In this issue:
🎤 Belly laughs, Broadway hits, and a little musical magic to spice up your weekend
🎶 Legendary rock and tribute acts, big band swing, and jazz that moves your soul
🎨 Art exhibits and creative inspiration for all ages
🎃 Fall flavors, spooky adventures, and seasonal traditions to savor
🐾 Family-friendly mysteries, lantern-lit walks, and playful weekend fun for kids
🏡 Real Estate Deal of the Week 🏡
New this week in Pelham!
This home combines timeless character with modern upgrades, tucked under mature trees on one of Pelham’s most picturesque blocks. Inside, you’ll find sun-filled rooms with gleaming hardwood floors, coffered ceilings, and custom built-ins, all flowing beautifully from one space to the next. With elegant architectural details throughout and plenty of room for both everyday living and entertaining, this home offers the perfect balance of charm and comfort.
5 Beds
4 Full Baths
2,627 sq ft
Built in 1920
Lot of approximately 7,381 sq ft
Asking Price: $1,725,000
Open House: Saturday, October 4th, 12:00 PM - 2:00 PM
View the full listing here.
🧺 Family-Friendly Fun
Twilight Village at Sleepy Hollow transforms Philipsburg Manor into a Halloween destination with live storytellers, fire performers, a pop-up market, and even a Headless Horseman appearance!
🏚️ Myths & Mysteries of The Octagon House
Armour-Stiner Octagon House | Irvington | Starts October 2 | More
Step inside Irvington’s famous Octagon House for a guided tour of its strange history, spooky legends, and architectural wonders. A family-friendly mystery adventure!
🎃 The Headless Horseman Files
Philipsburg Manor | Sleepy Hollow | Starts October 3 | More
Peek into the “files” of Sleepy Hollow’s most famous ghost with interactive storytelling and exhibits that bring the legend to life.
📖 Irving’s Legend
Washington Irving's Sunnyside | Irvington | Starts October 3 | More
Washington Irving’s classic tale returns riverside with live performance, dramatic lighting, and an atmosphere that’s perfect for fall evenings.
👻 The Spirits of Sleepy Hollow Country
Philipsburg Manor | Sleepy Hollow | Starts October 3 | More
Historic storytelling meets ghostly lore in this candlelit evening of Hudson Valley haunts. An unforgettable way to experience local legends.
🌙 Twilight Village at Sleepy Hollow
Philipsburg Manor | Sleepy Hollow | Starts October 3 | More
A nighttime walk through lantern-lit grounds, filled with sights, sounds, and seasonal magic. Family-friendly, but with just enough spook to thrill.
🚶 Walk for Wishes
Kingsland Point Park | Sleepy Hollow | October 5 | More
Join the community walk supporting Make-A-Wish Hudson Valley. A heartwarming family outing that makes a real difference.
🌼 Family Fun Day
Untermyer Gardens | Yonkers | October 5 | More
Games, crafts, music, and nature exploration all set in the gorgeous backdrop of Untermyer Gardens. A picture-perfect Sunday for the whole family!
Together with Wonderland Holiday Lights!
Westchester Homeowners Can Save $150 on Holiday Lights
✨ Picture this: you pull into your driveway this December and your home is glowing with a perfect holiday display — without every touching a ladder.
Wonderland Holiday Lights makes it effortless. From custom design mockups to professional, white-glove installation, take-down, and climate-controlled off-season storage, Wonderland handles every detail so your holidays stay stress-free.
Plus, you’ll enjoy our Stay-Lit Guarantee (outages fixed in 48 hours or your money back), a complimentary timer, and professional dusk photos of your finished lights.
Spots are limited, and the best dates go fast.
Book your design consult today and let your home shine all season long while you cross one more thing off your to-do list.
🍻 Activities for Adults
Join acclaimed jazz vocalist Hilary Kole as she takes the Emelin stage with the legendary Birdland Big Band as they pay homage to Ella Fitzgerald and other jazz greats!
🎹 Thursday Organ Groove featuring Chris Vitarello
Jazz at the Lodge | Ossining | October 2 | More
Kick off October with some serious groove. Guitarist Chris Vitarello joins the Thursday Organ series for a night of soul, swing, and funk-filled jams.
🥧 Apple Pie Contest 2025
Pleasantville Farmers Market | Pleasantville | October 4 | More
It’s pie time! Bakers from across Westchester compete for the crown in this delicious annual tradition. Come for the judging, stay for the tastings.
🎸 Bostynx: The Ultimate Tribute To Boston & Styx
Emelin Theatre | Mamaroneck | October 3 | More
Classic rock fans, rejoice! This high-energy tribute show brings the soaring anthems of Boston and Styx to life for one unforgettable night.
🎭 Jagged Little Pill The Musical
White Plains Performing Arts Center | White Plains | Starts October 3 | More
The Tony Award-winning Broadway hit lands in White Plains. Set to Alanis Morissette’s iconic album, this musical delivers raw emotion, powerhouse vocals, and a story that hits hard.
🐶 The Manor Club presents Sylvia
The Manor Club | Pelham | Starts October 3 | More
A witty comedy about marriage, midlife crises, and the dog who shakes everything up. Smart, funny, and perfect for a local night out.
🎤 Hilary Kole and Birdland Big Band
Emelin Theatre | Mamaroneck | October 4 | More
Jazz vocalist Hilary Kole joins forces with the legendary Birdland Big Band for a night of swing, standards, and sensational energy.
🎶 Mandy Patinkin in Concert: JUKEBOX
Paramount Hudson Valley | Peekskill | October 4 | More
Stage and screen legend Mandy Patinkin brings his one-of-a-kind voice and storytelling to Peekskill with a concert full of songs and surprises.
🦪 First Annual Sleepy Hollow Oyster Count-Up
Horan's Landing Park | Sleepy Hollow | October 5 | More
Get your hands wet for a good cause! Help track oysters in the Hudson while learning about local ecology and enjoying a true community event.
🖼️ Katonah Museum of Art Exhibits
Katonah Museum of Art | Katonah | Until October 5 | More
Last chance to catch the current exhibits at KMA. Thought-provoking, family-friendly, and always worth the trip!
🚴 Bicycle Sundays
Bronx River Parkway | October 5 | More
A Westchester classic! The Bronx River Parkway closes to traffic and opens for bikes, joggers, walkers, and families. Roll into fall with this community favorite.
😂 105-TEN Sunday Night Comedy
105-TEN Bar & Grill | Briarcliff Manor | October 5 | More
End your weekend with a laugh. 105-TEN brings in a lineup of comics to keep the Sunday scaries at bay.
🌡️ Weather Report
☀️ Weekend Weather at a Glance
Friday (Oct 3): 🌤️ Mostly clear – High 72°F / Low 51°F – Bright start and comfortable; sweaters in the morning but perfect by afternoon!
Saturday (Oct 4): ☀️ Sunny – High 79°F / Low 55°F – Warm and lovely; great day to be outside – maybe for some yard work or a fall hike.
Sunday (Oct 5): ☀️ Sunny – High 81°F / Low 58°F – Gloriously sunny and warm; prime weather for relaxing outdoors or enjoying the early October vibes.
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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