May Momentum: Arts, Festivals & Big Weekend Energy

Live Music, Street Fairs, Arts Weekend & Springtime Celebrations Across Westchester!

Welcome to the Westchester Weekly!

Mid-May is hitting its stride, and Westchester is fully leaning into it. The air is warm, the weekends are packed, and the county is buzzing with everything from arts festivals and outdoor markets to live concerts, comedy nights, and community celebrations that spill across every corner of the Hudson Valley.

This weekend brings a little bit of everything – high-energy music performances, thoughtful cultural events, lively street fairs, and plenty of family-friendly outings in the mix. Whether you’re catching a show in Port Chester, strolling through Nyack’s iconic street fair, or spending the afternoon at an arts weekend in Yonkers, there’s no shortage of ways to get outside and make the most of spring.

It’s one of those weekends where you don’t really need a plan – just pick a direction and you’ll find something worth stopping for.

Let’s get into it!

🌿 In this issue:
🎶 Live concerts, jazz nights & can’t-miss performances
🎨 Arts weekends, exhibitions & creative showcases
🛍️ Street fairs, markets & local shopping events
🎉 Community festivals, cultural celebrations & heritage events
⚽ Sports matchups, comedy nights & late-spring entertainment

🏡 Real Estate Deal of the Week 🏡 

Just listed in Croton-on-Hudson!

Set on over 3 acres along the scenic Quaker Ridge corridor, this striking mid-century modern home offers a rare blend of architectural design and natural beauty in one of Croton’s most coveted enclaves. Designed to seamlessly integrate with its surroundings, the residence showcases an open-concept layout with dramatic walls of glass, flooding the interiors with natural light and capturing seasonal Hudson River views and unforgettable sunsets.

The home is thoughtfully positioned on a private, landscaped property featuring expansive outdoor space and an in-ground pool – ideal for both quiet retreat and effortless entertaining. A newer roof and well-maintained systems enhance livability, while the serene setting offers complete privacy just minutes from the Croton-Harmon train, village shops, and parks!

  • 3 Beds

  • 4 Baths

  • 4,000 sq ft

  • Lot size: ~3.3 acres

  • Built in 1950

  • 2-car attached garage + walk-out lower level

Asking Price: $1,400,000

View the full listing here.

🧺 Family-Friendly Fun

Family Arts Bash Saturdays invites kids into ArtsWestchester’s galleries for hands-on creative workshops, playful art-making, and imaginative exploration led by professional artists!

Westchester SC vs. New York Cosmos
Memorial Field | Mount Vernon | May 15 | More
A high-energy matchup featuring fast-paced soccer action as Westchester SC takes on the legendary New York Cosmos. A perfect night out for families, with nonstop movement, loud crowd energy, and an easy way to get kids hooked on live sports.

🎨 Family Arts Bash Saturdays
ArtsWestchester | White Plains | May 16 | More
A hands-on creative playground where kids can explore painting, crafting, and interactive art stations. Each activity is designed to spark imagination and let families create side-by-side in a relaxed, welcoming space.

🌸 Spring Flower Stained Glass Suncatcher Workshop
KinoSaito | Verplanck | May 16 | More
A colorful, hands-on workshop where kids (and families) design beautiful floral suncatchers inspired by spring blooms. Expect plenty of color, creativity, and a take-home piece that lights up any window.

🛠️ Maker Weekend
Westchester Children’s Museum | Rye | May 16 | More
A creative, STEM-meets-art experience packed with building, experimenting, and hands-on discovery. Kids can tinker, design, and explore while learning how things are made in the most fun, interactive way possible.

🌱 White Plains Sustainability Fair
Plaza at the White Plains Public Library | White Plains | May 16 | More
An interactive community fair focused on eco-friendly living, featuring games, demonstrations, and kid-friendly sustainability activities. A great way to introduce environmental awareness in a fun, engaging setting.

🌿 Super Seedlings
Van Cortlandt Park | Bronx | May 16 | More
A nature-based program where kids get hands-on with planting, gardening, and learning how seeds grow into full plants. Expect outdoor exploration, dirt-under-the-fingernails fun, and a strong connection to the natural world.

🍻 Activities for Adults

Yonkers Arts Weekend transforms the city into a vibrant, walkable gallery of art, music, and creativity, with live performances, pop-up exhibitions, and hands-on experiences taking over venues across town.

🎨 The 50th Anniversary Ground Glass Photography Exhibition
Rye Arts Center | Rye | May 14-16 | More
Celebrate five decades of photographic artistry with this special anniversary exhibition showcasing a diverse range of styles, subjects, and creative voices. From striking landscapes to intimate portraits, it’s a visual journey that highlights both tradition and innovation behind the lens.

💃 Spring Season Westchester
MorDance | Dobbs Ferry | May 14-16 | More
An inspiring evening of contemporary dance featuring powerful choreography, expressive storytelling, and world-class talent. Expect a dynamic mix of movement and emotion that brings fresh energy to the local arts scene.

🎱 Club BINGO Fundraiser
Friends Waterfront Bar & Grill | Mahopac | May 15 | More
A classic game night with a lively, social twist – think upbeat vibes, exciting prizes, and plenty of laughs. It’s a fun, low-key way to gather with friends while supporting a meaningful cause.

🎸 Oteil & Friends
Capitol Theatre | Port Chester | May 15 | More
A must-see for live music fans, this jam-band supergroup delivers an electrifying blend of rock, funk, and improvisation. Expect extended grooves, top-tier musicianship, and a crowd that’s fully along for the ride.

🎭 The 39 Steps
Elmwood Playhouse | Nyack | May 15 | More
A wildly entertaining stage adaptation packed with quick costume changes, clever staging, and nonstop humor. This fast-paced thriller-meets-comedy keeps you guessing — and laughing — from start to finish.

🎟️ Yorktown Stage Presents: Beetlejuice Jr.
Yorktown Stage | Yorktown | May 15-16 | More
A spirited, spooky-fun musical brought to life by talented young performers. With catchy songs, quirky characters, and lots of personality, it’s a high-energy show that’s as impressive as it is entertaining.

🎨 Yonkers Arts Weekend
Yonkers | May 15-17 | More
A citywide celebration of creativity featuring open artist studios, pop-up exhibits, live performances, and interactive installations. It’s the perfect chance to explore Yonkers’ vibrant arts scene and discover something new around every corner.

🐶 SPCA Dog Walk & Pet Fair
FDR Park | Yorktown Heights | May 16 | More
Bring your pup (or just your love for animals) for a feel-good day filled with a scenic group walk, pet-friendly vendors, and adoptable animals. A heartwarming community event that’s equal parts fun and meaningful.

Dog Chilling GIF

🐾 Let’s Pawty – Dog Party
Battle Hill Park | White Plains | May 16 | More
A playful gathering designed for dogs and their humans to mingle, socialize, and have a blast. Expect treats, activities, and plenty of tail-wagging moments in a relaxed, upbeat setting.

🌸 Future In Bloom Scholarship Luncheon
Cortlandt Colonial Restaurant & Ballroom | Cortlandt Manor | May 16 | More
An elegant and uplifting afternoon celebrating education, achievement, and community impact. Enjoy a thoughtfully curated luncheon while supporting scholarships that help empower future leaders.

🏀 Basketball: On the Court and Canvas (Talk)
Hudson River Museum | Yonkers | May 16 | More
A unique cultural conversation exploring the intersection of basketball, art, and identity. This engaging talk dives into how the sport has influenced visual culture and storytelling across generations.

🎷 Pete Rodriguez Jazz
BeanRunner Cafe | Peekskill | May 16 | More
A high-energy night of Latin jazz led by a dynamic performer known for infectious rhythms and vibrant sound. Perfect for music lovers looking to move, groove, and soak in a lively atmosphere.

🎶 MJ Territo Quartet
Jazz On Main | Mount Kisco | May 16 | More
An intimate jazz performance featuring smooth melodies, rich improvisation, and a relaxed, welcoming vibe. Ideal for a laid-back evening with great music and great company.

🕵️ Interactive Murder Mystery Comedy
Friends Waterfront Bar & Grill | Mahopac | May 16 | More
Step into the story as you help solve a hilarious whodunit filled with twists, turns, and audience participation. Part theater, part game night – and all-around unforgettable.

Washington Dc James GIF by D.C. Pickleball Team

🎾 Glow-In-The-Dark Pickleball Event
Sportime Pickleball | Yorktown | May 16 | More
Pickleball gets a neon makeover with glowing courts, upbeat music, and a party-like atmosphere. Whether you’re competitive or just playing for fun, it’s a unique way to experience the sport.

🎸 Westchester Collaborative Theater Presents: The Oren Neiman Quartet
Westchester Collaborative Theater | Ossining | May 16 | More
A captivating blend of jazz and global influences performed in an intimate creative space. Expect rich compositions, skilled musicianship, and a performance that feels both personal and immersive.

😂 Westchester Comedy Club @ WP: Fabrizio Copano, Jessica Brodkin & Friends
Tre Angelina | White Plains | May 16 | More
A standout comedy lineup featuring sharp, witty performers delivering big laughs all night long. The perfect pick for a fun, easygoing Saturday night out.

🎉 Pinkster Jubilee 2026 & Yonkers Arts Weekend
Philipse Manor Hall | Yonkers | May 16 | More
A vibrant cultural festival celebrating history, heritage, and community through music, storytelling, and live performances. A meaningful and lively experience rooted in tradition.

🚴 Gran Fondo NY World Championship Bike Race
Route 9W | Palisades | May 17 | More
A premier international cycling event drawing elite riders and passionate competitors alike. Even as a spectator, it’s an exciting way to take in the scenic Hudson Valley and high-level racing.

🛍️ Nyack Famous Street Fair
Main, Broadway and Cedar Streets | Nyack | May 17 | More
One of the region’s most beloved street fairs, packed with food vendors, unique shopping, and live entertainment. Expect a lively, festive atmosphere that’s perfect for strolling and exploring.

🎻 An Intimate Portrait: Classical Guitar & Voice
Old Stone Meeting House | Nyack | May 17 | More
A beautifully stripped-down performance highlighting the elegance and emotion of classical music. A refined, relaxing experience for those who appreciate artistry and nuance.

🎷 Westchester Jazz Alliance Quartet
KinoSaito | Verplanck | May 17 | More
A polished jazz performance set in a unique, art-forward venue. Expect sophisticated sounds, strong improvisation, and an atmosphere that blends music with visual creativity.

🎬 American Dream
Jacob Burns Film Center | Pleasantville | May 17 | More
A thought-provoking film screening that explores ambition, culture, and modern identity. Stick around after for reflection or discussion — it’s the kind of film that stays with you.

🌡️ Weather Report

Sun Sunrise GIF

☀️ Weekend Weather at a Glance

Friday (May 15): 🌤️ Mostly sunny with a slight shower chance – High ~68°F / Low ~57°F – A really pleasant start overall; mostly bright with just a small chance of a passing shower, nothing disruptive!

Saturday (May 16): 🌤️ Mild and mostly sunny – High ~69°F / Low ~56°F – Arguably the best day of the weekend – comfortable temps, light winds, and just a minimal chance of rain.

Sunday (May 17): ⛅ Partly cloudy with a slight chance of showers – High ~68°F / Low ~54°F – A touch more cloud cover rolls in with a small shower risk, but still plenty workable for outdoor plans!

Thanks for reading!

If you know of anything interesting going on in Westchester, reply to this email and let us know.

— Ethan & The Westchester Weekly team

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