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Paddleboarding Witches, Oktoberfest, and Fall Cycling
Plus to See: Grammy Award Winners, Historic Haunted Houses, and the Best Night of Comedy Yet
Welcome to Issue #27 of the Westchester Weekly! October is in full swing, and the county is in full Fall-fever – from laugh-out-loud comedy and Broadway favorites to Oktoberfest celebrations, inspiring talks, and family-friendly frights.
Whether you’re in the mood for a night of laughter at the Emelin, a pint with friends in White Plains, or a witchy paddle on the Hudson, this weekend’s lineup has something for everyone. So grab a sweater (or an umbrella if you can!), get out there, and let’s make the most of this golden season together.
And please do us a favor and share Westchester Weekly with your friends so that we can continue what we do.
In this issue:
🎭 Stage Lights, Stand-Up, and NPR Tiny Desk Star Power
🍺 Oktoberfest Weekends and Community Rides
🎵 Soulful Sounds and Jazz Under the Lights
🎃 Haunted Houses, Mask-Making & Witches on the Water
⚽ Soccer, Flea Markets & Fall Family Fun
🏡 Real Estate Deal of the Week 🏡
New to the market in Bedford!
Tucked away on nearly five private acres, this quaint ranch features vaulted beamed ceilings, stone fireplaces, and sunlit rooms that open to patios, gardens, and wooded views. Every corner feels warm and inviting – from the airy living spaces to the cozy nooks that overlook the property’s lush, landscaped grounds. It’s the epitome of charm, comfort, and quiet luxury!
3 Beds
2.5 Baths
2,880 sq ft
Lot size: 4.8 acres, with patios, decks, and mature landscaping
Asking Price: $1,199,000
Open Houses: October 9, 11, and 12
View the full listing here.
🧺 Family-Friendly Fun
Westchester County’s premier haunted house finally returns to Rye – be prepared to come face to face with zombies, clowns, skeletons, and more!
👻 Scared by the Sound at Rye Playland
Rye Playland | Rye | Starts October 10 | More
A Westchester Halloween classic returns! Brave the haunted house, creepy corridors, and ghostly surprises…if you dare!
🎭 Family Art Workshop: Masquerade Masks
Hudson River Museum | Yonkers | October 11-12 | More
Get creative and design your own festive fall mask! A hands-on weekend activity perfect for kids and parents alike.
🧹 SUP Witches of Sleepy Hollow Festival
Kingsland Point Park | Sleepy Hollow | October 12 | More
Paddle down the Hudson with a coven of costumed witches (and warlocks) for this beloved annual river spectacle. Family fun, photo ops, and serious Halloween spirit lies in the air!
⚽ FC Naples at Westchester SC
Memorial Field | Mount Vernon | October 12 | More
Catch some Sunday soccer action as Westchester SC hosts FC Naples – a must-watch match that’s great for fans of all ages!
🛍️ Hastings Flea Market
Metro North Commuter Lot | Hastings-on-Hudson | October 12 | More
Shop local at one of the county’s favorite markets, featuring handmade goods, vintage finds, live music, and small-town charm in spades.
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.
Locally-owned 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
Grammy Award-winning bassist and musical extraordinaire, Endea Owens, looks to share her soulful tunes and energy at the Purchase Performing Arts Center this Sunday!
🎭 A Bronx Tale: The One Man Show Starring Chazz Palminteri
Paramount Hudson Valley | Peekskill | October 10 | More
The Hollywood legend himself returns to Peekskill with the original one-man show that inspired the hit film – a powerful tale of family, loyalty, and the Bronx streets that shaped him.
🎤 The Linda Ronstadt Experience
Emelin Theatre | Mamaroneck | October 10 | More
An electrifying tribute to one of America’s greatest vocalists, this show channels Ronstadt’s hits with heart and authenticity.
😂 Ladies of Laughter
Emelin Theatre | Mamaroneck | October 11 | More
A powerhouse lineup of funny women takes over the Emelin for a night of sharp humor and fearless comedy.
🍺 Oktoberfest with Yonkers Brewing Co.
Cross County Center | Yonkers | October 11-12 | More
Raise your stein and celebrate the season with craft beer, live music, games, and Bavarian bites! A perfect weekend hangout to welcome the real days of fall.
🎡 White Plains OktoberFest 2025
Mamaroneck Ave | Downtown White Plains | October 12 | More
The city’s annual Oktoberfest returns with brews, bites, and beats – transforming downtown White Plains into a Bavarian-style bash!
🚴 Westchester Cycle Club Presents: The Golden Apple & The Dirty Apple
Lewisboro Town Park |South Salem | October 12 | More
Two epic rides through stunning fall scenery – one for the roadies, one for the gravel grinders. Whichever route you choose, the views (and vibes) are unbeatable!
🎬 One Revolution with Chris Waddell
Bedford Playhouse | Bedford | October 12 | More
A moving documentary screening and talkback with Paralympic champion Chris Waddell, exploring resilience, adventure, and redefining limits.
🎶 Endea Owens and The Cookout
The Performing Arts Center | Purchase | October 12 | More
Grammy-winning bassist Endea Owens brings her soulful jazz collective to Purchase for an evening of uplifting, high-energy music straight from the heart of Harlem.
🌡️ Weather Report
☀️ Weekend Weather at a Glance
Friday (Oct 10): ☀️ Sunny: High 63°F / Low 44°F – Crisp and clear; a cool day, so layer up and enjoy the fresh air.
Saturday (Oct 11): ⛅ Mostly cloudy: High 68°F / Low 50°F – Mild and calm; the clouds may dominate, but it’s still nice for getting outdoors.
Sunday (Oct 12): 🌧️ Rain likely: High 62°F / Low 56°F – Showers are expected, especially midday; a good day to plan indoor options or bring rain gear!
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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