💗 A Spooky, Sparkling, Spectacular Weekend in Westchester

Starry nights and pumpkin lights flood a jam-packed weekend spent loving Westchester

Author

Wes+Bec Willetts
October 03, 2025

Hold tight folks,

 

This is a big one! While there’s always plenty to do in and around Westchester, this weekend is an absolute feast. Whether you’re flying solo, with your other half, or with munchkins in tow, there really is something for everyone, and tons of choice too.

 

The weather is set to be beautiful. You may even want to get some beach time in! But when you take a look at what we have for you, it’s probably more likely we’ll find you chilling with something pumpkin or apple infused, somewhere outdoors where a good band is playing, the sun is shining, and everyone’s smiling, except for the ghouls (talking decorations, not the other people there, of course!)

 

Have a wonderful time whatever you do! You deserve it!

 

Wes+Bec

 

 

In today’s edition:

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

 

On that note, if you’d like to chat about advertising with us, shoot us a mail at [email protected]. We love supporting local businesses and events.

 

Ok, let’s go!

💓 The Pulse

Loving Westchester’s Featured Events!

October has entered the room, and with it comes a few awesome events for great causes. Perfect opportunities to be entertained and give back at the same time!

 

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

 

Head north to Dutchess County to celebrate the amazing 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.

 

Sun., Oct 5 | Kingsland Point Park, Sleepy Hollow | 9a-2p | FREE admission

 

Head to Westchester County’s Halloweentown, Sleepy Hollow, on Sunday for the final day of the glass pumpkin patch, wish granting by Make-A-Wish Hudson Valley and a fundraising walk with the Headless Horseman. Festivities run until 2p.

 

Fri., Oct 24 | The Capitol Theatre, Port Chester | 8p | Tickets from $79.05

 

October is Domestic Violence Awareness Month, a time to recognize the reality that for too many, home is not the safest place to be. For survivors, often the first step toward safety is legal help. That’s why we’re calling out a very special concert coming up, where a great night out will help ensure someone who really needs it gets life-changing support.

 

Each year, Pace Women’s Justice Center provides free legal services to more than 3,500 survivors of domestic violence, sexual assault, and elder abuse in Westchester and Putnam, and their biggest fundraiser of the year, Raising the Bar, helps make this work possible.

 

So, mark October 24 in your calendars to enjoy a night of music and solidarity at The Capitol Theatre featuring Grammy Award–winning artists Colbie Caillat and Shawn Colvin live on stage! Join us in ‘Raising the Bar’ — for justice, for safety, and for those suffering right here at home.

Partnered With QueenBHive

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We help brands cut through the noise.

With decades of experience running communications and partnerships for worldwide names, QueenBHive brings global experience to local businesses. Whether you’re stuck on what to post, how to grow, or how to sound like you online, QueenBHive makes it make sense.

 

With support and packages designed for businesses of all sizes, including help with visuals, content and PR, we take the stress out of building your brand.

 

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!

Opens Fri., Oct 3 | Philipsburg Manor, Sleepy Hollow | Timed admission from 6.30-9p | Adult tickets $30, Children $25

 

Philipsburg Manor comes alive on Friday with the season opening of Twilight Village. Stroll through the grounds, listen to its roving musicians, experience its fire performers, hear your future and cross paths with a headless legend.

 

Sat., Oct 4 | Downtown Dobbs Ferry | 1-8p | FREE admission

 

This Saturday is party time in Dobbs Ferry at this year’s Festa and high-energy live music guest, Summer Fling, will help make sure of it! Make sure to catch their set along with other festivities, food, crafts, entertainment and more.

 

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

 

Catch Grammy-nominated blues rockers, The Record Company, headlining this year’s Pound Ridge Harvest Festival on Saturday. The whole family will be entertained by a food & craft beer garden and kids’ area (bounce house, petting zoo & face painting).

 

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

 

Indie hero SteinyFest returns for its 6th year on Saturday in Mamaroneck. Don’t miss its full, eight-act music lineup that wraps with a headline performance by Vulfpeck founding member, Theo Katzman.

 

Sat., Oct 4 | Ridge Hill (Park Plaza, Market St. & Town Square), Yonkers | 2-6p | FREE admission

 

The fall season starts with a bang at Ridge Hill’s Ridgetoberfest with live music from The Naked Soul Band, apple cider donuts from Grey’s Donuts, a Bronx Beer Hall trolley and a ton of family-friendly crafts, games and competitions.

 

Sat., Oct 4 & Sun., Oct 5 | Harvest Moon Farm & Orchard, North Salem | Check available daily entry times & tickets at the above link

 

Dust off the cowboy boots and head north to the farm for Country Music Weekend at Harvest Moon. Two alternating stages will be rocking all afternoon with BBQ on the grill, hard cider & local beer on tap and the unmissable Cider Smash.

 

Sun., Oct 5 | Muscoot Farm, Katonah | 12-3p | FREE

 

Muscoot Farm is hosting its kid-friendly Boo Walk on Sunday, where costumed kiddos can roam the farm’s (non-scary) Halloween-themed wooded trails. Event is free, no registration required.

 

Bonus Fun:

  • Pumpking Fest (Tastings & Fun Festivities) | Fri., Oct 3 | Harvest Moon Farm & Orchard, North Salem | 5-9p

  • Apple Pie Contest | Sat., Oct 4 | Pleasantville Farmers Market | 8.15-11a | FREE admission

  • Rotary Club of Peekskill Fall Festival | Sat., Oct 4 | Riverfront Green, Peekskill | 11a-5p | FREE admission

  • Bedford Katonah Art Crawl | Sun., Oct 5 | Depot Plaza, Bedford Hills | 12-4p | FREE admission

 

Grown Ups & Date Nights

Fri., Oct 3 - Sun., Oct 5 | Westchester County Center, White Plains | Daily times & tickets vary, check link for details

 

The 9th annual Blood and Ink Tattoo & Horror Convention hits the Westchester County Center this weekend featuring hundreds of tattoo artists with guests appearances from Bam Margera and many more across the horror / thriller genre.

 

Sat., Oct 4 | Soul Brewing, Pleasantville | 1-10p

 

Did you know that Soul Brewing’s Oktoberfest Lager is a Great American Beer Festival Gold Medal winner 2x running? You can find out why this Saturday at their Oktoberfest celebration while you listen to the smooth sounds of the Smoky O Trio. Prost!

 

Sat., Oct 4 | Hudson Park, New Rochelle | 2-7p | FREE admission

 

New Rochelle Parks & Rec hosts this year’s Views & Brews fest this Saturday complete with live music from the M80s, a beer garden, lawn games, food and more.

 

Sat., Oct 4 | Irvington Theater | 7p | Tickets from $33

 

Join mentalist & magician, Eric Walton, for a show that Gothamist said “will leave you speechless and perhaps just a little freaked out.” Click the link above to be entered into a drawing for 2 free tickets (by noon Friday) or use code MAGIC25 for 25% off at checkout.

 

Sat., Oct 4 | Hudson Valley Writers Center, Sleepy Hollow | 7p | Tickets $10

 

The Sleepy Hollow Arts Collective steps back in time on Saturday night with a staged reading of the original 1938 War of the Worlds radio broadcast that sent shockwaves around the United States.

 

Sun., Oct 5 | Laughing Horse Coffee & Tea Co., Harrison | 3-6p

 

Our friends at Laughing Horse Coffee & Tea Co. have gotten into the spirit of the season with their first Oktoberfest Fall Festival with live music, kids crafts, light bites and hard cider tastings from 1911.

 

  • Fri., Oct 3 | Strange Company Presents An Evening of Radio Plays | 8p | Tickets from $40.00

  • Sat., Oct 4 | Mandy Patinkin in Concert: Jukebox | 8p | Tickets from $88.50

  • Sun., Oct 5 | Serial Killers w/ Dr. Scott Bonn | 7p | Tickets from $44.00

 

  • Fri., Oct 3 | Oteil & Friends | 8p | Tickets from $60.15

  • Sat., Oct 4 | Violent Femmes | 8p | Tickets from $99.50

  • Sun., Oct 5 | YES | 8p | Tickets from $65.15

 

Sat., Oct 4 & Sun., Oct 5 | Waterwheel Vineyard, Poughquag (Dutchess County) | 11a-6p | GA tickets $10, VIP $25, Kids 12 & Under FREE

 

If you’re leaf-ing Westchester this weekend to see the start of fall colors, head towards Poughquag for Waterwheel Vineyards Harvest Festival where apple cider donuts & slushies,

 

 

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.

 

 

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,