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  • 💗 From Taylor to Tarrytown: Loving Westchester’s Fall Favorites This Week

💗 From Taylor to Tarrytown: Loving Westchester’s Fall Favorites This Week

October brings glass pumpkins, grammy nominees, haunted tours, and harvest festivals

Author

Wes+Bec Willetts
September 30, 2025

Hi there!

 

How was your weekend? While one of us tackled shin guards and sports bottles, the other bounced around amidst a surprising number of Dads with equal amounts pints to cowboy hats, and kids with glitter and tulle as The Rock and Roll Playhouse took on the music of Chappell Roan at Garcia's. It was very sweet and fun. We also ventured out to the Children’s Book Festival in Chappaqua, returning home with signed books from many including Lauren Tarshis, a family fave who writes the ‘I Survived’ series.

 

While the sun is shedding its last summer-like rays and the leaves are revealing the true season, Halloween-mode is just about to click fully on. Westchester is so much fun this time of year and we intend to bring you all the very best of it.

 

Let us know what you’re into and up to as we ‘fall’ into October! (Sorry, not sorry)

 

Wes+Bec

 

 

In today’s edition:

Plus, a message from our partners, QueenBHive & Fallscapers.

 

Let’s go!

💓 The Pulse

Loving Westchester’s Featured Events!

Image from Make-A-Wish Hudson Valley

Thu., Oct 2 - Sat., Oct 5 | Kingsland Point Park, Sleepy Hollow | 10a-5p | FREE admission, pumpkins available for purchase

 

Make your way up to Sleepy Hollow, Westchester’s perfectly in-season town, collect a stunning glass pumpkin as a centerpiece for your Halloween decorations and support Make-A-Wish Hudson Valley in the process (20% of the process go to charity).

 

đŸ‘» With the start of October on Wednesday, we’re officially entering Halloween season and the Sleepy Hollow area is the place to be in Westchester. In addition to the glass pumpkin event above, here are a few others you can check out to get into the spirit of things


Partnered With QueenBHive

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Based in Westchester and proud to be part of this community.

 

🐝 Visit QueenBHive.com or email us here. Our flexible and friendly approach will help you figure out exactly what you need to grow with confidence.

📆 What’s Happening?

 

Kid-friendly Fun!

Image from Alamo Drafthouse

Thu., Oct 2 | Outhouse Orchards, North Salem | Festival entry slots from 9a-3.30p | Tickets $22.45 online, $27 at the gate

 

School Holiday Reminder! Outhouse Orchards’ Fall Festival runs every weekday and will have special early open hours on Thursday for families looking for some entertainment on the school holiday. Check the link for details and available times.

 

đŸ‘±â€â™€ïž A Swiftie Shindig at Alamo Drafthouse

Fri., Oct 3 - Sun., Oct 5 | Alamo Drafthouse, Yonkers | Times & tickets vary

 

Alamo hosts “The Official Release Party of a Showgirl” Fri. through Sun., an 89-minute celebration of Taylor Swift’s new Life of a Showgirl album. The screening includes a music video world premiere for “The Fate of Ophelia” and behind-the-scenes specials.

 

Fri., Oct 3 | Westmoreland Sanctuary, Mount Kisco | 10-11.30a | Tickets $10

 

Westmoreland Sanctuary welcomes Moms and their little ones every Friday for an animal introduction and petting session complete with self-directed play, color books and an animal cracker snack.

 

Sat., Oct 4 | Pound Ridge Town Park | 1-6p | VIP & parking tickets available, check link

 

The popular Pound Ridge Harvest Festival returns this Saturday with a food & craft beer garden, kids entertainment (bounce house, petting zoo & face painting), and a music line-up headlined by Grammy-nominated blues rockers, The Record Company.

 

Sat., Oct 4 | Toyota City, 619 Waverly Ave., Mamaroneck | 1p | GA Tickets $49.87, VIP $103.22

 

SteinyFest returns for its 6th year with a full, eight-act music lineup that includes a headline performance by Vulfpeck founding member, Theo Katzman. We caught a SteinyFest when it was held in a backyard in Larchmont - it’s a great indie vibe!

 

Grown Ups & Date Nights

Tue., Sep 30 | Irvington Theater | 7p | Tickets $12

 

Join novelist, poet, and essayist Paul Kingsnorth for a discussion of his new book “Against the Machine: On the Unmaking of Humanity,” which examines the dehumanization of the world in this technological age.

 

Thu., Oct 2 | Tarrytown Music Hall | 8p | Tickets from $44.50

 

Grammy-nominated singer songwriter, Iris DeMent, celebrates the 30th anniversary of her debut album Infamous Angel, recently named one of the greatest country albums of all-time, with a show this Thursday night in Tarrytown. Very limited tickets remaining!

 

Looking to introduce the stress-reducing benefits of bonsai tree trimming and the mood-enhancing benefits of award-winning beer into your life? Do both at Captain Lawrence this week:

  • Thu., Oct 2 | Captain Lawrence Brewing Company, Elmsford | 6.30p | $85

  • Fri., Oct 3 | Captain Lawrence Barrel House, Mount Kisco | 6.30p | $85

 

Opens Fri., Oct 3 | White Plains Performing Arts Center | Times & tickets vary, check link

 

The White Plains Performing Arts Center’s production of the Tony and Grammy award-winning musical, Jagged Little Pill, opens this Friday, with 14 total performances through the month of October. Tickets available now.

 

đŸ€˜ Bostyx

Fri., Oct 3 | Emelin Theatre, Mamaroneck | 8p | Tickets from $44

 

Gonna hitch a ride to Emelin Theater on Friday for Bostyx, a group of pro musicians who’ve come together to pay tribute to 70s / 80s rock icons, Boston & Styx. The show’s been reviewed as
 “it’s as close as you can get to seeing the originals in their prime.”

 

Fri., Oct 3 | Paramount Theatre, Peekskill | Times & tickets vary, check link

 

The Paramount is celebrating 10 years of community and creativity with Strange Company, an evening of spine-tingling live radio drama, cocktails, and theatrical flair. Expect mad scientists, mysterious visitors, and live sound conjured by Peekskill’s own award-winning Foley artist, Leslie Bloome. Choose from tiered experiences including VIP cocktail receptions, on-stage afterparties with the cast, or just come for the show.

 

 

The Beat

Westchester’s Live Music Scene

Image from The Capitol Theatre

Thanks to our partner, Fallscapers!

 

Let Fallscapers transform your doorstep into an autumn wonderland!

That time of year has arrived, and availability is now extremely limited to give your front porch a fall glow up.

 

Grab one of the last spots remaining and Fallscapers will do the heavy lifting for you
 literally.

 

 

🚗 Worth a Drive

There are also great things going on outside Westchester county lines this coming week


Fri., Oct 3 | Upper Landing Park, Poughkeepsie (Dutchess County) | 6-10p | Tickets from $195

 

It’s an anniversary celebration of Walkway Over The Hudson in Poughkeepsie with live music, art, special guest performances and chef-crafted dishes paired with local wine, beer & spirits. Check the link for additional details and tickets.

 

Fri., Oct 3 | Ridgefield Playhouse, Ridgefield, CT | 8p | Tickets from $56

 

The iconic comedy troupe that launched the careers of Eugene Levy, Martin Short, John Candy, John Belushi and so many others celebrates its 65th anniversary with a touring performance of some of its most memorable characters, sketches and songs.

 

LEGOLAND New York, Goshen (Orange County) | Check above link for dates and ticket details

 

Halloween has come early at LEGOLAND with its Brick-or-Treat event where monsters have taken over for meet & greets, dance parties and daily shows. Guests can participate in Halloween-themed builds and trick-or-treating across the park.

🏡 Where the Heart Is


Incredible homes are listed in Westchester every week. Here’s one that caught our eye


 

Listed by Julia B Fee Sothebys Int. Rlty

24 Sleepy Hollow Road is one of those “oh wow, look at that one” homes you’d point out as you’re driving through backroads in the north of the county. With it’s sprawling white picket fence lining Sleepy Hollow Road, inviting front porch and overall Notebook-esque appearance, curb appeal on this one is sky high.

 

Inside, you’ll find 5 bedrooms, 4 bathrooms and 3,500 square feet of modern farmhouse living space complete with wide-plank flooring, high ceilings and multiple working fireplaces. The home is set on a blank canvas of 2 acres with a 3 car garage and just minutes from the nearest city-bound train station. Definitely one to check out
 or at least drive by!

Thanks for reading Loving Westchester!

 

We’re really enjoying putting this together twice a week and hope you enjoy reading it. We’ve said it before and we’ll say it again
 we love to hear from you! You can reach us at [email protected].

 

Check us out on Instagram for additional highlights outside of our normal Tuesday & Friday e-mails and, as always, please send this along to a friend who’s always asking, “What’s going on this weekend?”

 

Until next time,