Upper Westchester, NY October 2025

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DESIGN + PROJECT MANAGEMENT

Savor the Season: Celebrating food, friends, and the flavors of fall

Dear Readers,

As the air turns crisp and the leaves begin to paint Westchester in shades of gold and red, there’s no better time to celebrate the joy of food, gathering, and the simple pleasures that make this season so special. Our October Foodie Issue brings together stories, flavors, and experiences that remind us why fall in our community is so magical.

This month, we’re thrilled to feature two inspiring stories of local women building powerful, purpose-driven brands. Diane Marie Pisera and Brittney Pellegrino of She Thrives Collective share how they’re reshaping the way women connect and grow together, while Hayley Apiscopa is empowering families with pediatric physical therapy.

We also sit down with Dana Cifone, the visionary and restaurateur behind Townhouse, who gives us her ultimate guide to where to eat, drink, and gather with friends this season. For those who love to cook at home, don’t miss our recipe for a maple pumpkin parfait, the perfect treat to welcome autumn flavors into your kitchen.

This issue also highlights the expansion of local business Root2Rise, bringing its nourishing mission to a new Westchester location, offering fresh ways to fuel body and soul. And finally, we join Christina Weiss on a scenic trip through October, where she shares her curated guide to the best activities, events, and hidden gems in and around our area.

As always, this issue is a reflection of the people, places, and passions that make Upper Westchester such a vibrant community. We hope it inspires you to savor the season, whether it’s through a night out at a local spot, cooking something new at home, or exploring the beauty of our towns this fall.

Happy reading, and happy gathering!

LAURA SABIA, PUBLISHER

Our publication serves the communities of Armonk, Bedford, Bedford Hills, Chappaqua, Katonah, Mount Kisco, Pound Ridge and Valhalla.

October 2025

PUBLISHER

Laura Sabia | laura.sabia@citylifestyle.com

PUBLICATION DIRECTOR

Emma Parente | emma.parente@citylifestyle.com,

ACCOUNT MANAGER

Adam Vohra | adam.vohra@citylifestyle.com

CONTRIBUTING WRITERS

Dana Cifone, Anna Barnes, Christina Weiss, Alyssa Lavy

CONTRIBUTING PHOTOGRAPHERS

Photography by Inga, Mary Jane Photography, Abby Cole Photography

Corporate Team

CEO Steven Schowengerdt

COO Matthew Perry

CRO Jamie Pentz

VP OF OPERATIONS Janeane Thompson

VP OF SALES Andrew Leaders

AD DESIGNER Rachel Kolich

LAYOUT DESIGNER Rhiannon Coffman

QUALITY CONTROL SPECIALIST Brandy Thomas

Learn how to start your own publication at citylifestyle.com/franchise.

RESIDENTIAL + COMMERCIAL

Restoration, Cleaning & Reconstruction

+ Mold Damage

As industry leaders in Restoration, Reconstruction and Cleaning– our vision is to continue providing strategic Consumer & Business Solutions while upholding our commitment to exemplary customer service and white glove workmanship. We work alongside our insurance partners as well as in the private sector to handle claims and home improvement projects. With our exclusive use of cutting-edge equipment and technology, our fully certified staff is capable of handling projects of any magnitude or complexity. (914) 787-9559 office@rainbowwestchester.com www.RBWWestchester.com

business monthly

Westchester Piano Celebrates Grand Opening and Expansion in Katonah

Westchester Piano, a musician-owned boutique piano showroom, announced its grand opening and expansion in the heart of Katonah. The showroom opened its doors at 152 Bedford Road in January and has since grown its business. It now occupies two levels of space at the same location. Founded by performer and educator Tyler Blanton, Westchester Piano offers concierge service and sourcing of fine pre-owned upright and grand acoustic pianos.

Green & Tonic Teams Up with Vita Coco

On the heels of its viral Blue Moves smoothie with fitness icon Anna Kaiser (trainer to Shakira, Sarah Jessica Parker, and Kelly Ripa), Green & Tonic has launched a new collaboration with Vita Coco. The limited-edition Vita Coco Strawberry Mango Matcha Cloud features Vita Coco Coconut Water with strawberry purée, mango, and creamy matcha cold foam. Designed to hydrate and energize, this drink reflects Green & Tonic's passion for wellness-focused innovation and feel-good, functional ingredients.

Now Open in Thornwood: nest & nook

nest & nook is a modern indoor co-working and play space for remote workers, parents, caregivers, and young children. Founded by Westchester native and mom of two Nicole Batiste, it offers flexible access options from memberships to drop-in visits and a mission rooted in community care. Featuring warm, minimalist design, sage accents, and natural textures, the ADA-accessible space offers comfort for adults and safety for kids—supporting families to work, connect, and thrive together.

Photography by Gina Palumbo, Keep It Captured Photography

the CITY LIST

We have such amazing, innovative business leaders in our community who are proud to serve you, our residents, with class and quality. We’ve compiled some of our top company picks for the services that might be on your mind this month in an effort to make your lives a little easier.

Grocery Store

DeCicco & Sons deciccoandsons.com | 914.499.1100

Chappaqua Village Market chappaquavillagemarket.com/home/ | 914.238.4948

Sgaglio's Marketplace sgagliosmarketplaceny.com | 914.232.9444

Bedford Gourmet bedfordgourmet.com | 914.234.9409

A & S Marketplace asmtkisco.com | 914.241.6919

Fine Dining

Moderne Barn Restaurant modernebarn.com | 914.730.0001

La Crémaillère lacremny.com | 914.234.9647

Want to suggest a monthly pick?

Lenny's North Seafood & Steakhouse lennysnorth.net | 914.273.8686

Bedford Post Tavern bedfordpostinn.com/bedford-post-tavern/ | 914.292.9516

Blue Hill At Stone Barns bluehillfarm.com | 914.366.9600

Coffee Shop

G.E. Brown Fine Food & Provisions gebrown.com/menus | 914.234.3185

Susan Lawrence Gourmet Foods susanlawrence.com | 914.238.8833

Katonah Reading Room katonahreadingroom.com | 914.334.8019

The Twisted Branch thetwistedbranch.com | 914.437.8000

Lukumadness lukumadnessusa.com | 914.358.4552

Sushi Restaurants

Osaka osakatarrytown.com | 914.631.8888

Oishii Bistro oishiiasianfusion.com | 914.666.2348

KOKU kokujapanese.com | 914.730.0077

Dai Sushi daisushirestaurant.com | 914.769.0638

Waka Asian Bistro wakafusion.com | 914.861.2727

Newly Opened

La Bastide labastidebyac.com | 914.485.1518

Antique Garage Rye antiquegarage.com | 914.249.9399

Vida vidarestaurantny.com | 914.825.8020

Wogies Bar & Grill, Katonah wogies.com | 914.200.6176

Talia talia-restaurant.com | 914.201.3566

ARTICLE AND PHOTOGRAPHY BY ALYSSA LAVY, MS, RD, CDN

Maple PUMPKIN

Parfait

A FALL-INSPIRED MAPLE PUMPKIN GRANOLA WITH PUMPKIN YOGURT

(yields approximately 4.5 cups or 18 – ¼ C servings):

INGREDIENTS

• 2 ½ C rolled oats

• 1 C pumpkin seeds, hulled

• ½ C unsalted walnuts, chopped

• 2 Tbsp canned pumpkin puree (Note: the only ingredient should be pumpkin – this is different than pumpkin pie filling)

• 1 Tbsp water

• 2 Tbsp avocado oil or vegetable oil

• ½ C pure maple syrup, divided into 2- ¼ C servings

• 2 tsp pure vanilla extract

• 1 tsp ground cinnamon

• 1 tsp pumpkin pie spice

• ¼ tsp salt

• Nonstick cooking oil spray

MAPLE Pumpkin GRANOLA PUMPKIN Yogurt

(yields approximately 1 C yogurt):

INGREDIENTS

• ¾ C plain Greek yogurt of choice

• ¼ C canned pumpkin puree

• ¼ cinnamon

• ¼ tsp pure vanilla extract

• 1 ½ tsp honey

Alyssa Lavy, MS, RD, CDN, CPT is a registered dietitian, personal trainer and mom of 2. She earned her Bachelor of Science in Exercise Science from The George Washington University and her Master of Science in Nutrition and Exercise Physiology from Teachers College Columbia University, where she also completed her dietetic internship. She has been an ACSM certified personal trainer for over a decade.

Alyssa is the owner of Alyssa Lavy Nutrition & Wellness, a wellness brand offering nutrition communications, program development and consulting services for individuals and corporations.

Website: alyssalavy.com

Instagram: @alyssalavyrd

GRANOLA

DIRECTIONS

1. Preheat oven to 250 degrees Fahrenheit.

2. Combine canned pumpkin, water, oil, vanilla extract and ¼ C maple syrup) and mix until well combined.

3. Add rolled oats and salt to wet ingredients and mix until oats are evenly coated.

4. Line a large baking sheet (9 x 13 inches works well) with parchment paper and spray with nonstick cooking oil spray. Transfer oats to baking sheet and spread in a thin, even layer.

5. Bake in oven for 1 hour, mixing at 30 minutes and 45 minutes.

6. Remove oats from oven briefly. Add pumpkin seeds, chopped walnuts, cinnamon, pumpkin pie spice and remaining ¼ C pure maple syrup. Mix with a spatula and return to oven to bake for another 30 minutes, mixing halfway through. Remove from oven and allow to cool for 5 minutes before using a spatula to transfer to container. Do not wait too long to transfer granola as it can stick to the parchment paper as it cools.

YOGURT

DIRECTIONS

1. Combine all yogurt ingredients in a medium sized bowl. Top with a handful of the maple pumpkin granola, serve immediately and enjoy!

Note: This granola can be stored in an airtight container and stored in a cool, dry place for up to 1 week. While this granola is made with gluten free ingredients, I recommend using certified gluten free ingredients if needed . Yogurt can be made with a suitable dairy-free alternative if you need this recipe to be dairy-free and the honey can be swapped for pure maple syrup to make the dairy-free yogurt recipe suitable for a vegan diet. The granola and the yogurt can each be enjoyed on their own, but they complement each other so nicely!

This Maple Pumpkin Granola Parfait is a perfect way to celebrate autumn’s most famous flavors in a nutritious way! Pumpkin, maple syrup and warm spices, such as cinnamon and pumpkin pie spice, give cozy vibes that are traditionally found in baked goods this time of year. However, while pumpkin bread, muffins, cookies and other fall flavored baked goods are certainly delicious and should be enjoyed, this Maple Pumpkin Granola Parfait provides the satisfaction of those fall flavors in a lighter way, while providing ample protein and fiber. It is the perfect, slightly sweet and balanced way to start the day – or to enjoy anytime!

Lighting Is Everything

• Installing indoor and outdoor lighting for over 55 years.

• Mark Mosello is a leading design expert in the field.

• Professionally light your art, home and landscaping with customized service.

• Smart & eco-friendly options.

• Certified generator dealer + installation.

• Our style illuminates dark spaces, creating a more enjoyable and luxurious atmosphere.

YO U R WEEKENDSTARTSHERE

THE ULTIMATE GUIDE TO WHERE TO EAT, DRINK, AND GATHER WITH FRIENDS

ALL WEEKEND—FROM FRIDAY NIGHT ENERGY TO SUNDAY CALM.

Townhouse Dana Cifone

Townhouse in Greenwich, Connecticut, was always intended to be more than just a restaurant—it’s a destination. My vision was to reimagine this historic two-story building into a space where every detail matters: layered textures, warm lighting, and a thoughtful flow between rooms. The result is a setting that feels both stylish and inviting, designed to bring people together for moments that are elevated yet effortless.

Townhouse offers experiences for every mood and time of day. Sunlit lunches on the patio, cocktails at the buzzing bar, chic Saturday brunches with friends, and vibrant dinners in one of our interior rooms; all capture a downtown energy. Whether you’re celebrating, gathering, or simply treating yourself, Townhouse provides the perfect backdrop for connection.

While my heart is here, I also love stepping into the dining rooms of fellow restaurateurs—taking in their creativity, soaking up the energy, and appreciating the hospitality that defines our industry. Visiting other restaurants is not only inspiring, it’s a way to celebrate our shared passion that brings us all to the table.

Follow along as I share a few local spots for your weekend at home, from Friday night cocktails to Saturday indulgences to a welcomed Sunday reset. townhousegreenwich.com | @townhousegreenwich

CONTINUED >

Pour

Friday Night Buzz

Pour in Mount Kisco creates a perfect blend of sophistication and ease for Friday night drinks, pairing craft cocktails with a vibrant neighborhood energy. Located at 241 East Main Street in Mount Kisco, this boutique bar and eatery is set inside a charming early 19th-century Victorian home, offering a warm and intimate ambiance. Soft candlelight fills the cozy rooms, encouraging relaxed conversations and a welcoming space to unwind.

The bar features an impressive collection of rare whiskies, including sought-after bottles like Pappy Van Winkle’s Family Reserve and A.H. Hirsch Reserve, providing a unique tasting experience for aficionados. Complementing the drink selection is a thoughtfully curated menu of small plates, flatbreads, charcuterie, and cheeses, crafted to perfectly accompany the beverages.

Whether you’re looking to decompress after a long week or start your weekend with friends, Pour offers a lively yet comfortable atmosphere. Its intimate setting and exceptional offerings make it a standout destination for an unforgettable Friday night.  pourmtkisco.com | @pour_mtkisco

Bedford Post

Saturday Night Indulgence

Bedford Post Inn offers an elevated dining experience perfect for a Saturday night indulgence. Set in a beautifully restored historic inn, the restaurant combines rustic charm with refined elegance to create an inviting atmosphere for a special evening. Guests can enjoy thoughtfully crafted dishes that highlight fresh, locally sourced ingredients and seasonal flavors, expertly prepared to delight the palate.

The menu features a sophisticated mix of contemporary American cuisine with creative twists, from savory appetizers to indulgent entrées. Whether savoring rich steaks, fresh seafood, or vegetarian options, diners are treated to carefully balanced flavors and artful presentation.

Complement your meal with a curated selection of wines, craft cocktails, and local brews from the well-appointed bar. With attentive service and a cozy yet upscale setting, Bedford Post Inn provides the perfect backdrop for celebrating a memorable Saturday night. It’s an ideal destination for guests seeking a luxurious, relaxed dining experience that feels both special and welcoming.  bedfordpostinn.com @bedfordpostinn

La Crémaillère

Sunday Reset

La Crémaillère brings a touch of effortless elegance to Sunday afternoons, offering a refined yet relaxed brunch experience in the heart of Bedford. Set in a beautifully restored 1750 farmhouse, the restaurant marries classic European sophistication with intimate charm—creating a setting that feels equal parts chic and comforting.

Every Sunday, guests can enjoy a curated prixfixe menu that highlights the season’s finest ingredients. The offerings shift regularly but often include elegant starters like fresh oysters, hand-cut steak tartare, or house-made pâté de campagne. Entrées might range from luxurious Jonah crab eggs Benedict and brioche French toast to perfectly grilled Faroe Island salmon or the signature Niman Ranch burger dressed with truffle aioli.

The atmosphere is sunlit and inviting, elevated by gracious service and a pace that encourages lingering over each course. With its relaxed sophistication and thoughtful cuisine, La Crémaillère makes Sunday brunch feel like a quiet indulgence—one best enjoyed slowly, with good company and even better food. lacremny.com | @lacremailliere1947

Friends Building a Future Together

Diane Marie Pisera knows what it means to carve her own path. An Italian immigrant and the first in her family to build a legacy in business, Diane launched DianeMarieB.com to help women step into their power. Her story began in college, where personal development books lit the spark that inspired her to pivot away from teaching and into coaching, content creation, and entrepreneurship. Today, her work focuses on helping women reclaim their identity, embrace their confidence, and build lives they’re proud of.

HOW DIANE AND BRITTNEY ARE RESHAPING WOMEN’S GROWTH WITH SHE

THRIVES COLLECTIVE

“SHE THRIVES COLLECTIVE IS MORE THAN EVENTS, IT’S A MOVEMENT WHERE WOMEN RISE TOGETHER, SUPPORTED BY REAL CONNECTION, SHARED GROWTH, AND A COMMUNITY THAT FEELS LIKE HOME.”

Brittney Pellegrino’s journey grew out of her desire for authenticity and community. Having walked through seasons of uncertainty herself, she dreamed of a safe space where women could be real about both their struggles and their ambitions. For Brittney, connection and truth are the heart of growth, and her work centers on reminding women that they’re allowed to evolve, dream bigger, and take up space.

Together, Diane and Brittney have combined their strengths, stories, and passions to create She Thrives Collective, a community designed to normalize the “next level” for women. Their partnership proves that when two people come together with a shared mission, the result is greater than the sum of its parts.

She Thrives Collective hosts both in-person and online experiences that go beyond networking. It’s about belonging, encouragement, and lifting each other up. The women who attend leave with more than strategies; they leave with friendships, accountability, and a renewed sense of purpose. From transformative coaching and empowering events to the upcoming membership launch this fall, Diane and Brittney are building something women didn’t even know they needed until they walked into the room.

Both founders agree that their favorite moments are watching women realize they’re not alone, that they’re supported, seen, and capable of much more than they imagined. It’s the quiet breakthroughs, the new business launches, and the mothers rediscovering their own passions that remind Diane and Brittney why they started in the first place.

Their friendship, their vision, and their relentless commitment to helping others thrive are what make She Thrives Collective more than a brand. It’s a movement.

How Developmental Steps in Mount Kisco empowers families with pediatric physical therapy, early intervention, and compassionate care tailored to every child’s unique journey.

HELPING CHILDREN THRIVE, ONE STEP FORWARD

For more than two decades, Developmental Steps has been a trusted name in pediatric physical therapy across Westchester County. What began with one clinic in Port Chester has grown into two thriving locations, with the newest expansion in Mount Kisco offering a state-ofthe-art space dedicated to children’s growth and wellness. For co-founders and Katonah residents, Hayley Apiscopa, DPT and Joe Kiefer, PT opening and expanding in Mount Kisco was deeply personal. “We both dreamed of servicing the children in our own community,” they shared. The February 2025 move into a larger space marks not only growth but also a renewed commitment to supporting children and families with expert care in a welcoming environment.

SUPPORTING CHILDREN AT EVERY STAGE

At Developmental Steps, therapists tailor treatment to each developmental stage, from infancy through school age. For infants, early intervention focuses on foundational skills such as tummy time, rolling, sitting, and crawling, with hands-on coaching for parents. Toddlers work on balance, coordination, and walking through play-based activities designed to feel more like fun than therapy. Preschoolers build strength and confidence as they refine motor

skills, preparing for the demands of school. For older children, therapy addresses coordination, balance, sports-related injuries, and developmental conditions such as cerebral palsy or Down syndrome, with the goal of maximizing independence and participation in everyday life.

A PROVEN APPROACH

The practice’s three-fold approach—understanding development, assessing root causes, and empowering solutions—has changed countless lives. One memorable case involved a threemonth-old boy with torticollis and early head flattening. His nervous parents left the very first visit with tools they could confidently use at home. Over just six visits, their baby gained full range of motion, improved head alignment, and met critical milestones—all while his parents gained peace of mind and empowerment.

PROGRAMS THAT BUILD COMMUNITY

Beyond traditional therapy, Developmental Steps offers unique programs like free monthly tummy time classes and Mommy & Me sessions for infants aged 2–8 months. These programs not only support children but also foster parent confidence and community. Parents gain practical tools, make connections with other families, and discover that early development can be guided in joyful, engaging ways.

THE IMPORTANCE OF EARLY INTERVENTION

One of the practice’s strongest messages is the power of early intervention. Addressing concerns as soon as they appear often prevents challenges from becoming more significant. “We take pride in teaching children their first crawl, first steps, or even first jump,” CONTINUED >

the founders note. The progress is deeply rewarding for both families and therapists, with smiles and milestones serving as the ultimate motivation.

EMPOWERING FAMILIES AT HOME

Progress doesn’t stop when a session ends. Developmental Steps prioritizes teaching parents simple, practical exercises to reinforce

skills at home. Everyday activities become opportunities for growth, and families feel more confident in supporting their child’s unique needs. By working as a team—child, therapist, and family—the practice ensures faster progress and long-lasting results.

REACHING FAMILIES ACROSS WESTCHESTER

MATTERS—

“AT DEVELOPMENTAL STEPS, EVERY MILESTONE

FROM A BABY’S FIRST TUMMY TIME TO A SCHOOL-AGED CHILD GAINING INDEPENDENCE. OUR MISSION IS SIMPLE: EMPOWER FAMILIES, NURTURE CHILDREN, AND CELEBRATE EVERY DEVELOPMENTAL STEP FORWARD.”

With clinics in Port Chester and Mount Kisco, plus partnerships with 11 school districts, Developmental Steps serves families across a wide swath of Westchester, Greenwich, and New Canaan. Whether in the clinic, at school, or through community outreach, the goal remains the same: helping children thrive with expert, compassionate care.

A FOCUS ON FAMILIES

Navigating insurance can be daunting, but Developmental Steps helps simplify the process with complimentary benefits checks. As an out-of-network provider specializing exclusively in pediatrics, they ensure families know their costs upfront and receive care designed specifically for children.

At the heart of it all is a clear mission: to help every child reach their fullest potential. By combining clinical expertise, play-based methods, and an unwavering dedication to families, Developmental Steps continues to transform lives, one milestone at a time.

rlacoste@houlihanlawrence.com

Roots of Wellness

PLANT-BASED CAFÉ ROOT2RISE BRINGS HEALING, FLAVOR, AND COMMUNITY TO WESTCHESTER

For more than three decades, Jyoti and Raj Tewani have called Pleasantville home. Long before they opened the doors to their first café, the couple shared a deep belief in the healing power of food. “Food is the most powerful tool we have to take control of our health,” Jyoti says. “We bring the nourishment of plant-powered Mother Earth—completely hormone- and cruelty-free—to improve your health and feed your soul.” That philosophy has since become the heartbeat of Root2Rise NY, a full-service

plant-based café, bakery, and cold-pressed juice bar now with two thriving locations in Westchester. They first opened in Pleasantville in 2021 and, in 2024, expanded to Larchmont in response to constant requests from their growing community.

In the crowded world of health-focused dining, Root2Rise NY distinguishes itself by refusing to compromise. Every dish is 100% plant-based, vegan, gluten-free, organic, and locally sourced. No processed ingredients. No preservatives. No refined sugars. No cheap oils. Ever. The menu draws inspiration from global comfort foods, with rich flavors woven throughout.

This summer, Larchmont Root2Rise NY raised a glass to innovation with the debut of its vegan biodynamic wine selection. The new pairing menu highlights wines chosen to complement the café’s globally inspired vegan dishes. Just as flavorful as traditional vintages, biodynamic wines are usually more sustainable and easier on those with sensitivities. Now diners can pair their plant-based meals with organic wines- proving indulgence and wellness can coexist beautifully.

Jyoti’s path to restaurateur did not begin in a commercial kitchen, but at home, cooking for her family. With a degree in math and physics, she stayed home to raise three children while nurturing her lifelong love of cooking. Over the years, she deepened her knowledge with nutrition and culinary studies, focusing on the direct connection between what we eat and how we feel. “I always dreamed of building something of my own,” she says. “Raj helped make that dream a reality.” The name Root2Rise NY reflects Jyoti’s yoga practice, borrowing from one of yoga’s foundational principles: finding your roots in order to rise. “It’s about grounding yourself before you can grow,” she explains—a fitting metaphor for a business built from the ground up.

CONTINUED >

At its core, Root2Rise NY is about more than what’s on the menu, it’s about challenging how we think about food. Jyoti emphasizes that in a nation as wealthy as ours, we should be eating more mindfully, recognizing food as both nourishment and a powerful tool for healing. She is especially passionate about teaching families and children to cook in ways that prioritize nourishment and long-term well-being. The café takes food intolerances seriously, with transparent ingredient lists and staff training to ensure allergens are handled with care. “Some allergens can be life-threatening,” Jyoti stresses. “We don’t take chances.”

Education is central to Root2Rise NY’s mission. The cafés host cooking classes on preventing chronic inflammation and making food choices that support long-term health. Customers linger not only for the food, but for the conversation, sharing experiences with health, wellness, and the personal journeys that brought them there. “We’re building a community of people with a common interest,” Jyoti says. “Through this mission, I’ve had the opportunity to make a difference in how people understand healthy eating.”

At 58, Jyoti isn’t slowing down. “My only competition is me,” she says. Her vision is clear: to bring the café’s mission—and its menu—to as many communities as possible, challenging the way people think about food, one nourishing meal at a time. In a world where convenience often outweighs nutrition, Root2Rise NY stands as a reminder that eating well isn’t just about living longer—it’s about living better.

root2riseny.com

FALL IN FULL

C O L O R

UPPER WESTCHESTER’S OCTOBER GUIDE

Crisp mornings, golden afternoons, and the crunch of leaves underfoot! October in Westchester is pure magic. Whether you’re after apple orchards, spooky legends, artful evenings, or trails lined with fiery foliage, this season has something for everyone. Here’s your curated guide to the best of fall 2025 in Upper Westchester and beyond.

THE HEART OF HALLOWEEN

No county embraces Halloween like Westchester, birthplace of Washington Irving’s The Legend of Sleepy Hollow.

• The Great Jack O’Lantern Blaze once again transforms Van Cortlandt Manor with more than 7,000 glowing pumpkins arranged in whimsical, larger-than-life displays.

• SUP Witches of Sleepy Hollow Festival returns to Kingsland Point Park, where costumed paddlers take to the Hudson for a witchy paddle parade, while spectators enjoy live music, food, brews, vendors, and spooky views.

• Peek-a-Boo, River’s Edge Theatre Company’s provocative immersive haunt, is back at Bethany Arts Community after a sold-out 2024 run. Expect intimate encounters, voyeuristic thrills, and stories inspired by Hudson Valley’s hidden histories.

• The Sleepy Hollow Haunted Hayride delivers goosebumps as wagons rumble past the Old Dutch Church and into the dark woods where hoofbeats and shrieks echo through the night. A lively block party on Beekman Avenue, with live music and vendors, keeps spirits high.

• For those who prefer history with a hint of haunt, Lyndhurst After Dark invites visitors on candlelit tours exploring the mansion’s shadowy past, while the Gothic Harvest Market adds seasonal flair. Meanwhile, the Armour-Stiner Octagon House in Irvington offers eerie tours like Myths and Mysteries and the ghostly performance The Lady in White.

ARTS, CULTURE & BIG-NAME ACTS October isn’t only about scares—it’s also packed with world-class performances and screenings.

• On October 24, Colbie Caillat and Shawn Colvin headline The Capitol Theatre in Port Chester for Pace Women’s Justice Center’s Raising the Bar Benefit Concert.

• Humorist David Sedaris brings his wit to The Performing Arts Center on October 4, while Steve Solomon, author and star of Broadway’s longest-running one-man comedy, performs at the Paramount Hudson Valley on October 26.

• At Tarrytown Music Hall on October 9, mandolin virtuoso Sierra Hull and singer-songwriter John Craigie share the stage.

• Film lovers can catch the 40th anniversary screenings of Day of the Dead at Jacob Burns Film Center (Oct. 24 & 31), or settle in for a spooky night with Candyman at Bedford Playhouse (Oct. 9).

FAMILY-FRIENDLY FESTIVALS

Weekends in October are made for festivals, and Westchester has plenty to choose from:

• Pound Ridge Harvest Festival (Oct. 4) fills Town Park with Oktoberfest-style food, beverage gardens, award-winning music, and activities for kids.

• Stone Barns Harvest Fest offers hayrides, live music, animal encounters, farm demonstrations, and seasonal fare from local purveyors.

• ARToberFest (Bethany Arts Community) celebrates its sixth year with visual art, live music, food, and interactive projects...a magical experience for all ages.

THE CALL OF THE OUTDOORS

Peak foliage hits in mid-October, and there’s no better way to take it in than on Westchester’s trails:

• North County Trailway offers fiery views of the Croton Reservoir.

• DePew Park in Peekskill has peaceful strolls around Lake Mitchell or longer hikes into Blue Mountain Reservation.

• Teatown Lake Reservation features the Twin Lakes loop for woodland escapes.

• Ward Pound Ridge’s Rocks Trail challenges hikers with nearly five miles of rugged terrain and scenic rock formations.

• If hiking isn’t your style, wander through Tarrytown or Sleepy Hollow, where decorated homes, historic cemeteries, and cozy eateries set the mood. For a day trip, head across the river to Storm King Art Center, where monumental sculpture meets breathtaking autumn landscapes—best capped with dinner in Nyack.

SAVOR THE SEASON

Autumn also means feasting, and Westchester’s farms and cider mills deliver.

• Pick-your-own adventures await at Harvest Moon and Outhouse Orchards in North Salem, Stuart’s Fruit Farm in Granite Springs, and Wilkens Fruit & Fir Farm in Yorktown.

• Sip fresh cider at Thompson’s Cider Mill in Croton-on-Hudson, or explore the Westchester Craft Beverage Trail, featuring breweries, cideries, and distilleries.

• Foodies should mark their calendars for Hudson Valley Restaurant Week, returning Oct. 27–Nov. 9. More than 140 restaurants will offer prix-fixe menus ranging from $24.95 to $44.95, including standouts like Crabtree’s Kittle House, Goosefeather, and Benjamin Steakhouse.

Whether you’re paddling with witches on the Hudson, hiking through foliage-lined trails, or indulging in a Restaurant Week feast, October in Westchester offers a perfect balance of thrills, flavors, and unforgettable moments. It’s a season that invites you to slow down, savor the magic, and celebrate fall in full color.

events

NOW - NOVEMBER 16TH

The

Great Jack O'Lantern Blaze

525 S Riverside Ave, Croton-On-Hudson NY

Meander through an 18th-century landscape and discover a breathtaking display of more than 7,000 illuminated jack o’ lanterns—all designed and hand-carved on site. Complete with synchronized lighting and an original soundtrack, this one-of-a-kind event is not to be missed!

FIRST 2 WEEKENDS IN OCTOBER (SATURDAY & SUNDAY)

The Barley Beach House: Fall Family Festival

The Barley Beach House, Rye NY | 11:00 AM

Get ready for the ultimate fall celebration! The Barley Beach House is bringing the orchard to you with two weekends of nonstop family fun. Pick from over 2,000 pumpkins, enjoy cider donuts, live music, hayrides, axe throwing, face painting, food, shopping vendors and more. Free parking and no long drive make it the perfect fall day.

OCTOBER 4TH

Stayin' Alive 5k and Fun Run

Armonk, NY | 8:00 AM

Get ready for an exciting day of fun and fitness! This vibrant event invites participants of all ages to lace up their sneakers and join in the spirit of community while supporting a great cause. All proceeds from this event go to Stayin' Alive, Inc., dedicated to supporting the brave First Responders of Northern Westchester.

OCTOBER 11TH

Chappaqua Farmers Market

108 Allen Place, Chappaqua NY | 8:30 AM

Shop the Chappaqua Farmers Market in Westchester County, NY for locally-sourced fruits and vegetables, prepared foods, baked goods, fish and meats, spirits and more. Their commitment to sustainability, freshness and taste means you can trust that the food you eat is good for you and for the environment. Visit and experience the local farm-to-your-kitchen difference.

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