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- 💗 Loving Westchester's Weekday Rundown: Swifties, Seussicals & Scares
💗 Loving Westchester's Weekday Rundown: Swifties, Seussicals & Scares
Plus, some great events in Peekskill and Westchester's top Halloween attractions all in one place
Wes+Bec Willetts
October 07, 2025
Hello, Westchester!
How are we all keeping? Summer refuses to call it a year and if you thought this past weekend was going to be one for flannels and boots, your apple picking trip was probably an uncomfortable one! No doubt we’ll all be missing this heat a month from now but it is meant to break a bit mid-week so we can all get back to our normal fall programming.
Travel sports took us to the upper ends of the county and, while in the neighborhood, we had to grab a few Trio slices to go… it would have been rude not to. We’re Sound Shore based but any time we head up north, especially with the weather we had, it always has us wondering what life is like with all the rolling hills and space. If you call that part of the county home, we’d love to hear from you and love even more to get some recommendations so we don’t miss anything next time!
We’ve got a really cool and diverse set of events as you read further that’ll hopefully break up the week heading into three-day weekend. If there’s anything you think we missed, let us know and we can share on Instagram ahead of our Friday edition.
Until then, have a great week!
Wes+Bec
In today’s edition:
Featured events… big week in Peekskill with Emmy-nominated improv and an iconic one-man show.
Kid-friendly fun… a play for Seuss and a party for Swift.
Grown ups & date nights… pop culture favorites Ghostbusters and Jeopardy make an appearance.
Live music beat… at least three gigs every weekday night to choose from.
Seasonal must sees… a look at Westchester’s major Halloween season attractions, can’t wait to get back to Twilight Village!
Where the heart is… a 5-bedroom Colonial smack in the middle of Scarsdale.
Plus, a message from our partners, QueenBHive & Fallscapers.
Let’s go!
💓 The Pulse
Loving Westchester’s Featured Events!
Wed., Oct 8 | Paramount Hudson Valley Theater, Peekskill | 7.30p | Tickets from $79
Catch current Whose Line Is It Anyway? cast members Greg Proops, Jeff B. Davis, Ryan Stiles and Joel Murray this Wednesday as part of their nationally touring improv comedy show WHOSE LIVE ANYWAY? Only a few tickets remaining!
Thu., Oct 9 | Wainwright House, Rye | 6-8.30p | Ticket options vary, check link for details
Join Wainwright House this Thursday as the sun sets over Milton Harbor for an evening of live music, seasonal eats by Bartleby & Sage and a celebration of those helping to shape the local community for the better.
Fri., Oct 10 | Paramount Hudson Valley Theater, Peekskill | 8p | Tickets from $72
Chazz Palminteri brings his legendary one-man autobiographical show (later turned feature film and musical) to the stage in Peekskill for one night only. Limited ticket availability as of writing!
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📆 What’s Happening?
Kid-friendly Fun!
Wed., Oct 8 | Pound Ridge Library | 4-5p | FREE with registration
Pound Ridge Library hosts its Children’s Chess Program every Wednesday for the little strategists out there with professional coaching from Norwalk’s RedBandit Chess. The program sessions are free, registration required at the link above.
Thu., Oct 9 & Fri., Oct 10 | Westchester Children’s Museum, Rye | 10a-5p | FREE with admission
Join Westchester Children’s Museum for World Space Week this Thursday & Friday, where the little ones can enjoy space-themed storytime and hands-on space-related activities.
Fri., Oct 10 | The Capitol Theatre, Port Chester | 7.30p | Tickets from $49
It’s a party at The Capitol Theatre this Friday with a Taylor Swift album release party and live tribute show from Let’s Sing Taylor. Party proceeds will help to benefit Backline Care, a mental health resource for musicians and their families.
Fri., Oct 10 | Yorktown Stage, Yorktown | 7.30p | Tickets from $24
You’re off to great places! Like Seussical Kids on Friday! Your ticket in Yorktown is waiting! So… get on your way!
Fri., Oct 10 - Sun., Oct 12 | Lake Isle Country Club, Eastchester | FREE admission, times vary
Columbus Day festivities kick off Friday evening in Eastchester with live music entertainment and carnival attractions. The party continues through the weekend with meatball and homemade wine competitions, a parade and fireworks show.
Grown Ups & Date Nights
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Tue., Oct 7 | Mamaroneck Cinemas | 7.30p | Tickets $18
A-Sides with Jon Chattman & LMC Media Center returns with a Video Vault screening of Ghostbusters this Tuesday at Mamaroneck Cinemas. Catch the pre-movie Bill Murray look-a-like contest!
Wed., Oct 8 | Alamo Drafthouse, Yonkers | 7p | Tickets $15
Answer: This Yonkers cinema hosts an interactive Jeopardy! event that puts attendees up against one another in real time on Wednesday night. Question: What is Alamo Drafthouse?
Wed., Oct 8 | Tarrytown Music Hall | 8p | Tickets from $44
The Wailers continue their 2025 tour at Tarrytown Music Hall, commemorating the 30th anniversary of Natural Mystic: The Legend Lives On, a continuation to the 1984 Bob Marley album Legend.
Thu., Oct 9 | Westmoreland Sanctuary, Mount Kisco | 7-9p | Tickets $65
Westmoreland Sanctuary hosts its October floral design workshop this Thursday focusing on late summer / early fall wildflower arrangements. This is an adults only event.
Fri., Oct 10 - Sun., Oct 12 | Makers Central, Tarrytown | 7p | Tickets $50
Anywhere Theatre Company in Tarrytown perform Sherlock Holmes and the Legend of Sleepy Hollow, a comedic thriller in which Holmes & Watson come to our side of the pond to investigate a possible return of the Horseman. Show run begins this Friday.
Fri., Oct 10 | ???, Peekskill | 7.30p Doors | Tickets $27
Don’t Tell Comedy returns to Westchester this Friday with one of its secret standup shows. What we know: the show is in Peekskill, indoors, BYOB and is 21+. Everything else is a mystery until day of show!
The Beat
Westchester’s Live Music Scene
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.
🎃 Seasonal Must Sees
Don’t miss these fall attractions across the county…
Twilight Village image from Historic Hudson Valley
This classic Croton attraction is now open every night through the month of October. Kid-friendly, super popular and highly photogenic, you don’t want to miss out on this one.
We caught this new North Salem attraction on opening night this year and loved it. Mystic Moon bills itself as more “enchanting” than “spooky” and definitely delivers. Very kid-friendly and highly recommended.
Running Fridays through Sundays (& Mon., Oct 13), Twilight Village is an immersive walk through Philipsburg Manor that we were lucky enough to catch last year and can’t wait to get back to. Kid-friendly with plenty of varied entertainment along the way.
This haunted house attraction has risen from the dead and takes up residence at Playland Park on Fridays through Sundays starting Oct 10. With a mortuary, asylum and clown hallway listed as attractions, it definitely seems like one for the older crowd!
This outdoor haunted walk-through at New Rochelle’s Hudson Park Children’s Greenhouse looks seriously spooky and is recommended for ages 10 and up. Open most Fridays through Sundays in October.
🏡 Where the Heart Is…
Incredible homes are listed in Westchester every week. Here’s one that caught our eye…
Listed by Houlihan Lawrence Inc.
26 Circle Road is a 5 bedroom / 4 bathroom 2,127 square foot Center Hall Colonial in the Fox Meadow neighborhood in Scarsdale. Easy on the eyes and move in ready, the home features wood beam ceilings, a wood-burning fireplace, a 3rd floor flex space, detached garage and full basement.
26 Circle Road is steps from downtown Scarsdale with its 32-minute express train into Grand Central and just a short drive to top-rated schools. If you’re looking to break into one of the more exclusive towns in the county, this one’s worth checking out!
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,
