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- š” A Chappaqua Colonial Under $750K
š” A Chappaqua Colonial Under $750K
Dionne Warwick bids farewell in Peekskill, hear John Cusack 'say anything', and The Cap turns 100
Hello, Westchester!
Hopefully youāre all dried out without any damage after this weekendās rain! Some Sound Shore towns saw four inches of rainfall, resulting in the widely reported raft rescue of a few people stranded on top of their car under a Playland Parkway overpass.
Growing up (Iām dating myself here), we had a computer game called The Oregon Trail where you attempted to make the journey out west with your family in a covered wagon. When you got to a river, you had the option to āford the riverā and almost every time you lost your stuff, your oxen, your wagon, and maybe your family. The moral of that story is donāt drive through water if you donāt know how deep it is!
Once everything dried up on Sunday, our oldest visited the Reptile Expo in White Plains and weāre now the proud parents of a leopard gecko. Life comes at you quick.
You know what else came at us quickly? Autumn. It was just lying patiently in wait and now the local calendars are packed with fall and harvest festivals, plus we get the Great Jack OāLantern Blaze and Mystic Moon returning this week. Weāre spoiled for choice outside of the seasonal celebrations, too, as the legendary Dionne Warwick, John Cusack, and Chazz Palminteri all appear on county stages while The Cap celebrates its 100th anniversary with a Saturday night party.
Get those babysitters locked in! See you out there.
š Know Your County
Last Tuesday, we asked:
Of Playland Park, Westchester County Airport, and the Tappan Zee Bridge, which Westchester County landmark is the oldest?
The answer wasā¦ Playland Park!
Playland Park opened in 1928 and is recognized as the first master planned amusement park in the country, earning its National Historic Landmark designation in 1987. Over 1,000 workers began construction after Labor Day in 1927 and it was finished and open by the end of May the following yearā¦ imagine how long that would take now. Well done to the 72% of you who had that one lined up!
In August, we set out on an amazing road trip down south that had us touching ground in 10 different states over the course of 3.5 weeks. One of our main destinations was the Charleston area and one landmark, in particular, the incredible 400+ year old Angel Oak in Johns Island.
Westchester County has its own ancient oak landmark, which is managed and preserved by one of the countyās local historical societiesā¦
Where would you find it? |
Good luck!
In todayās edition:
Featured eventsā¦ Dionne Warwick, John Cusack, and The Cap celebrates 100!
Family funā¦ fall awakens with the Sleepy Hollow Street Fair and the return of Mystic Moon and the Great Jack OāLantern Blaze.
Grown ups & date nightsā¦ Chazz Palminteri brings A Bronx Tale to The Cap.
Worth a drive from Ardsley Car Washā¦ a musical porch party in Rhinebeck.
Where the heart isā¦ a move-in-ready home under $750K in Chappaqua.
And a message from our partners, QueenBHive, giving you, your business, or brand the visibility and support it needs, and QueenBPoker, hosting your epic game night.
Now letās get to it!
š The Pulse
Loving Westchesterās Featured Events!
š¤ Dionne Warwick: Over and Out Farewell Tour
Thu., Sep. 17 | Paramount Hudson Valley Theater, Peekskill | 8p | $84+
The six-time Grammy winner, with more than 75 charted hits and over 100 million records sold, brings her farewell tour to Peekskill for a night of "Walk On By," "I Say a Little Prayer," "Alfie," "Heartbreaker," and more. Discovered by Bacharach and David, she was a trailblazer and humanitarian across six decades. A rare chance to see a living legend take her final bow.
The voice behind a generation of standards, one last time ā
š¬ John Cusack and Say Anything
Fri., Sep. 18 | Paramount Hudson Valley Theater, Peekskill | 8p | $64+
A big-screen showing of the 1989 classic, boombox serenade and all, followed by a live audience Q&A with John Cusack himself. The star of High Fidelity, Being John Malkovich, and Grosse Pointe Blank shares stories from the film and a career spanning three decades. Limited VIP tickets include a post-show meet and greet.
Relive the boombox scene, then hear the man behind it ā
šø The Capitol Theatre 100th Anniversary Celebration
Sat., Sep. 19 | The Capitol Theatre, Port Chester | Doors 6p, Show 7:30p | $30+
The Cap turns 100, and it is marking the century with Pink Talking Fish performing as The Centennial Band, honoring the legendary artists who have played the room, joined by BERTHA: Grateful Drag, the world's first all-drag Grateful Dead tribute. A deep roster of special guests and surprise moments runs through a night spanning the 1970s psychedelic heyday to today's jam scene. 18+.
One hundred years of the Cap, celebrated the only way it should be ā
Have an event you want to feature in Loving Westchester?
Got 99 ideas, but canāt execute 1?
Hey, everybody. This is Bec.
Iāve spent 20 years helping businesses, brands and community organizations grow through better strategy, communications and partnerships. If youāre a local business owner with 100 ideas but never enough time to move them forward, thatās exactly why I created QueenBHive. Think of me as the person in your corner. Helping you decide what matters most, connecting the right dots, creating momentum, and making sure the good ideas actually happen. Whether thatās your visibility, social content, a launch, a partnership or simply having someone strategic to think alongside.
Send me a message and let me be your WingWoman.
š Whatās Happening?
Family Fun!
ā½ Westchester Soccer Club vs. Richmond Kickers
Wed., Sep. 16 | The Stadium at Memorial Field, Mount Vernon | 7p | $12.45
Westchester SC returns home to host the Richmond Kickers in USL League One men's action. Doors at 5:30p, free parking, all ages.
š Yorktown Feast of San Gennaro
Wed.-Sun., Sep. 16-20 | 1826 Commerce Street, Yorktown Heights | Daily times vary
10th Anniversary of the Yorktown Feast of San Gennaro with five days of Italian food, live music entertainment, rides, and family fun.
š Mystic Moon at Harvest Moon
Opens Sep. 18, select evenings through Nov. 1 | Harvest Moon Farm and Orchard, North Salem | Evenings | $39+
A nighttime trail through the orchard woods, lit by dramatic uplighting under 80-year-old oaks, with enchanting scenes, mystical characters, and photo ops. Whimsical rather than scary, no jump scares. Kraken's Cove offers themed drinks and treats. Twilight Hour slots are softer-lit for young children.
š” SeptemberFest
Fri.-Sun., Sep. 18-20 | Downtown Mount Kisco | Free admission
Mount Kisco's three-day block party, with carnival rides, a food court and beer garden, a street fair of 75-plus vendors on Saturday, a Hometown Sound Showcase of local musicians, live bands, a $10,000 Rotary Club drawing, and Sunday big-screen football.
šØ Fall Craft Show by Artrider
Fri.-Sun., Sep. 18-20 | Lyndhurst, Tarrytown | Fri. 10a-5p, Sat. 10a-6p, Sun. 10a-5p | $6+
Makers selling fashion, jewelry, home dƩcor, furniture, photography, and ceramics, glass, metal, and wood work across Lyndhurst's grounds. Gourmet food, distillery and winery tastings, craft demos, and family activities including puppet theater and a scavenger craft hunt.
š The Great Jack O'Lantern Blaze
Select evenings, Sep. 18 - Nov. 8 | Van Cortlandt Manor, Croton-on-Hudson | Evenings | Ticket prices vary
More than 7,000 illuminated hand-carved jack o'lanterns across an 18th-century landscape, with themed displays, special effects, and an original soundtrack. New for 2026: an expanded Creature Feature Forest and a fairy-tale Little Literary Lane, plus the Gourd and Goblet Tavern and Headless Horseman's Hideaway.
šļø Revolutionary Harvest Festival
Sat., Sep. 19 | Philipse Manor Hall, Yonkers | 12p-5p | Free
Step back to the American Revolution with costumed reenactors, including George Washington on his horse Nelson and his enslaved servant William Lee. Live 18th-century music, country dancing, a cider press, printmaking, a code-breaking espionage activity, and colonial children's games.
š¶ Yonkers Riverfest
Sat., Sep. 19 | 1 Larkin Plaza, Yonkers | 12p-7p | Free
Westchester's largest one-day festival, presented by the Yonkers Downtown BID, with three stages of live music spanning jazz, soul, salsa, R&B, and rock, plus 140-plus food, arts, and craft vendors, a Kid Zone, rides, a Latin Corner, and an Art Stop.
š Sleepy Hollow Street Fair
Sun., Sep. 20 | Beekman Avenue, Sleepy Hollow | 10a-5p | Free
More than 145 arts, crafts, and food vendors along Beekman Avenue, heavy on Halloween-inspired items. The Headless Horseman appears from 1p to 4p, with Witches Along The Hudson, storyteller Jonathan Kruk, five live bands, and a Kids' Zone. Dogs welcome.
Grown Ups & Date Nights
šø Molly Tuttle
Tue., Sep. 15 | Tarrytown Music Hall, Tarrytown | 8p | $47.50+
The Grammy-winning guitarist and songwriter plays behind her 2025 album So Long Little Miss Sunshine, blending bluegrass, Americana, pop, and rock. The first woman named IBMA Guitar Player of the Year.
š„ Beyond Agave: A Mezcal, Sotol and Artisan Cheese Experience
Thu., Sep. 17 | Westchester Wine Warehouse, White Plains | 6p-7:30p | Ticket prices vary
Explore two of Mexico's spirits through six artisan cheese pairings and a welcome cocktail, guided by Julia Gross of Mezcal Mal Bien and Steve Martin of Cardenxe Sotol. Ages 21+, free parking, doors at 5:45p.
š Beach Bash
Fri., Sep. 18 | The Barley Beach House, Rye | Doors 5p, Music 6p | $10
The Beach Deck's final concert of the season, with party band Shorty Long and The Jersey Horns playing rock, Motown, funk, and pop over the Long Island Sound. Concession stand and full bar open. Bring a chair or blanket.
š· Old World Rivals: Spain vs. France Blind Tasting Challenge
Fri., Sep. 18 | Westchester Wine Warehouse, White Plains | 6p-7p | Ticket prices vary
Sommelier Olivier Flosse leads a blind tasting of four wines from Bordeaux, the RhƓne Valley, Rioja, and Ribera del Duero. With the labels hidden, can you tell France from Spain?
šŗ '90s Freestyle and Hip Hop Glow in the Dark Party
Fri., Sep. 18 | Hudson Park Bandshell, New Rochelle | 7:30p-10p | Free
The City of New Rochelle turns back the clock with a glow-in-the-dark bubble party mixing '90s freestyle classics and golden-age hip hop. Ages 21 and over; food and drinks for purchase.
š A Bronx Tale: One Man Show starring Chazz Palminteri
Fri., Sep. 18 | The Capitol Theatre, Port Chester | 8p | $39.50+
The Academy Award-nominated actor performs the one-man show that started it all, the acclaimed play he wrote and first staged in 1989 that became the classic 1993 film. 18+; under 10 not permitted.
šæ Herb Fair and Market
Sat., Sep. 19 | Caramoor, Katonah | 10a-4p | Free
The Herb Society of America's annual fair, with a marketplace of fresh herbs and artisan goods, member-baked treats, signature lovage soup, hands-on workshops, free speaker presentations, and a children's plant scavenger hunt. Rain date Sun., Sep. 20.
Game nights are having a moment in Westchester, and if you've ever wanted to host a poker or casino night without the stress of figuring out the rules or rounding up chips, QueenBPoker is the answer. They come to your home, venue, office, and handle everything you may need from teaching the table to running the night. Casual, corporate, charity. No experience needed, just people who want a good time.
Plan your game night ā
š Godfrey
Fri.-Sun., Sep. 18-20 | Levity Live, West Nyack | Multiple showtimes | $37.17+
The stand-up and actor behind Showtime's Regular Black, with roles in Zoolander and Soul Plane, headlines five shows across the weekend.
šø Rhinebeck Porchfest
Sat., Sep. 19 | Village of Rhinebeck | Free
A free, volunteer-run community music festival where front porches, lawns, and outdoor spaces become neighborhood stages for a full day of music, from classic rock and indie folk to New Orleans jazz. Stroll from performance to performance through the village.
Loving Westchester is written by a real-life husband and wife team, completely free, and in your inbox every Tuesday and Friday. If it adds something to your week, contributions help us keep growing - including our first in-person Loving Westchester event we're working toward for the fall.
"Thank you for your emails highlighting the wonderful events happening throughout Westchester. They are such a great resource and reminder of how much Westchester has to offer." ā A Loving Westchester Reader
š” Where the Heart Is
Incredible homes are listed in Westchester every week. Hereās one that caught our eye
 |  |
The Key Details: 3 bedrooms, 2 bathrooms, 1,414 square feet on a 4,487 square foot lot ($530/square foot)
What We Love About It: A move-in-ready home under $750K in the Chappaqua School District is about as rare as it gets in Westchester. This 1858 Colonial keeps its historic charm, hardwood floors, original millwork, a fireplace-anchored living room, while quietly upgrading everything that matters: a 2020 furnace, 2023 hot water heater, 2023 electrical panel, and a 2022 septic system. The kitchen's been refreshed too, with stainless steel appliances and quartz counters. Best of all, it's a 0.3-mile sidewalk walk to Metro-North, making this one of the easiest commutes in the village.
We love to hear from you! Give us a shout at [email protected] or find us on Instagram @lovingwestchester. And don't forget to forward this to a friend who's always asking "what's going on this week?"
See you out there!
