Almost Summer: Sunshine, Sounds & Weekend Energy ☀️🎶

Live Music, Outdoor Movies, Festivals & Family Fun Across Westchester

Welcome to the Westchester Weekly!

The final stretch of May is here, and you can feel it – longer days, warmer nights, and that unmistakable buzz that summer is just around the corner. This is the weekend where everything starts to spill outside: concerts fill the air, markets pop up, races hit the streets, and communities come together to celebrate the season ahead.

From big-name performances and local festivals to outdoor movie nights and colorful runs, this lineup is all about getting out, staying out, and soaking it all in. Whether you're planning a full weekend agenda or just looking for a few standout stops, there’s no shortage of ways to lean into the moment.

Consider this your warm-up for summer. Now let’s get into it!

☀️ In this issue:
🎶 Live concerts, tribute shows & can’t-miss performances
🎭 Comedy, readings & creative showcases
🎪 Festivals, markets & community events
🏃 Races, runs & outdoor activities
🎬 Family-friendly events, movies & hands-on fun

🏡 Real Estate Deal of the Week 🏡 

Just listed in New Rochelle!

Located on a quiet, tree-lined street in one of New Rochelle’s most desirable neighborhoods, this beautifully maintained home offers a perfect mix of charm, space, and modern comfort. Sun-drenched interiors showcase a welcoming layout with generous living areas, a stylish kitchen, and an easy flow for both everyday living and entertaining. With a private yard and close proximity to parks, schools, shopping, and transportation, this home checks all the right boxes for suburban living with convenience.

  • 5 Beds

  • 3 Baths

  • 2,500 sq ft

  • Lot size: ~0.25 acres

  • Built in 1950

  • Attached garage + private yard

Asking Price: $1,695,000

View the full listing here.

🧺 Family-Friendly Fun

Step right up for Circus Vazquez, a high-energy big top spectacular packed with jaw-dropping acrobatics, live music, and laugh-out-loud family fun under the tent!

🎪 Circus Vazquez
West Nyack | May 29 - June 6 | More
A full-scale traveling circus experience featuring acrobats, aerialists, clowns, and high-energy performances under the big top. It’s colorful, fast-paced, and packed with wow moments that keep kids (and adults) completely entertained.

♟️ Chess Tournament with NSCF
White Plains | May 30 | More
A fun and engaging tournament for young strategists of all skill levels. Whether competing or learning, it’s a great way for kids to sharpen their thinking while enjoying a bit of friendly competition.

🎬 Outdoor Movie Night – Inside Out
White Plains | May 30 | More
A family-favorite film shown under the stars for a cozy, community movie night. Bring blankets, snacks, and settle in for a heartwarming evening with this beloved animated classic.

🏃 PRT Running Festival (15K, 10K, 5K & Kids Run)
Valley Cottage | May 31 | More
A high-energy race day with options for all ages – including a fun, approachable kids run. It’s a great way to get active as a family while soaking in the lively event atmosphere.

🌈 Pound Ridge Color Run
Pound Ridge | May 31 | More
A playful, non-competitive run where participants are showered in vibrant रंग powders along the course. Expect lots of laughs, color, and a joyful, festival-like vibe.

👽 Cinema Studies: Close Encounters of the Third Kind
Pleasantville | May 31 | More
A special screening paired with educational insight, introducing kids (and families) to a sci-fi classic. A fun mix of entertainment and learning for curious young movie lovers.

🍻 Activities for Adults

Two-time GRAMMY winner Jason Mraz brings his feel-good hits and soulful storytelling to The Capitol Theatre for an uplifting night of pop, folk, and acoustic magic!

🫖 Afternoon Tea
Katonah | May 28 | More
A timeless and elegant afternoon set against the beautiful grounds of Caramoor. Enjoy tea, light bites, and a relaxing atmosphere that feels like a mini escape – perfect for a slower-paced, refined outing.

🎤 Luke K
Port Chester | May 28 | More
An up-and-coming artist bringing fresh energy to the stage with a live performance that blends catchy hooks and a modern sound. A great pick for discovering something new.

Billy Joel GIF

🎹 River of Dreams: A Tribute to Billy Joel
Peekskill | May 28 | More
A high-energy tribute celebrating the iconic hits of Billy Joel. Expect all the classics, from sing-along anthems to piano-driven favorites that keep the crowd going all night.

🍸 Cocktails for a Cause Fundraiser | Pace Women’s Justice Center
Rye | May 28 | More
An evening of cocktails, connection, and community support benefiting an important cause. Sip, socialize, and give back in a lively, feel-good setting.

🏛️ Rosen House Focus Tour: Inside Lucie’s Wardrobe
Katonah | May 29 | More
Step inside Caramoor’s historic Rosen House for a unique, behind-the-scenes look at fashion, history, and personal storytelling. A fascinating deep dive for design and history lovers alike.

😂 Heroes Off Duty Comedy Tour
Tarrytown | May 29 | More
A night of stand-up featuring veteran comedians sharing hilarious, real-life stories with a sharp, relatable edge. Expect big laughs and a high-energy crowd.

🎶 The Righteous Brothers: Bill Medley & Bucky Heard Farewell Tour
Peekskill | May 29 | More
A legendary farewell tour celebrating decades of timeless hits. Experience iconic songs and powerful vocals in a nostalgic, can’t-miss live performance.

📝 The People’s Mic
Sleepy Hollow | May 29 | More
An open mic-style evening centered around storytelling, poetry, and spoken word. Whether performing or listening, it’s an inspiring and intimate creative space.

🎶 Jason Mraz with Gregory Page
Port Chester | May 29 | More
A laid-back, feel-good concert featuring the chart-topping singer-songwriter alongside special guest Gregory Page. Expect smooth vocals, uplifting energy, and crowd favorites.

🛍️ Spring Tag Sale
Pelham | May 29-30 | More
A community-wide tag sale filled with hidden gems, vintage finds, and bargain treasures. Perfect for a casual stroll and a little weekend treasure hunting.

🚶 Rye Parkinson’s Walk
Rye | May 30 | More
A meaningful community walk supporting Parkinson’s research and awareness. Join others in a positive, uplifting environment focused on connection and impact.

Darren Criss Singing GIF by The Voice

🎤 An Evening with Darren Criss
Peekskill | May 30 | More
An intimate evening of music and storytelling with the award-winning performer. Expect a mix of songs, personal insights, and engaging stage presence.

🍻 German Fest Time
Putnam Valley | May 30–31 | More
A lively cultural festival featuring traditional German food, beer, music, and dancing – all under a festive tent atmosphere. A fun, high-energy weekend celebration.

🛍️ Wickers Creek Market
Dobbs Ferry | May 31 | More
A curated outdoor market showcasing local vendors, handmade goods, and artisan products. A great spot to shop small and enjoy a relaxed Sunday outing.

🚗 27th Annual Vehicle Fair at the Rye Library
Rye | May 31 | More
A unique and interactive event where visitors can explore a variety of vehicles up close—from trucks to emergency vehicles. Fun, hands-on, and surprisingly engaging for all ages.

🌱 Seed: Germinal Roots and First Respiration
Yorktown Heights | May 31 | More
A creative, immersive experience exploring growth, nature, and transformation through art and performance. Thought-provoking and visually engaging.

😂 Brad Williams
Port Chester | May 31 | More
A nationally known comedian delivering sharp, unapologetic humor with a fast-paced, high-energy style. Expect a packed room and plenty of laughs.

📚 A Reading with the Meridian Series of Contemporary Chinese Poets
Sleepy Hollow | May 31 | More
An enriching literary event featuring contemporary voices in poetry. A unique opportunity to hear powerful work and engage with global perspectives.

🏺 Made in Earnest: Ceramic Work by Jon Townley
Port Chester | Through May 31 | More
A striking exhibition showcasing thoughtful, handcrafted ceramic pieces that highlight form, texture, and artistic intention.

🏺 Finding The Center: The Clay Art Center Historic Collection
Port Chester | Through May 31 | More
A deep dive into the Clay Art Center’s rich history through a curated selection of works. A must-see for art lovers and anyone curious about the evolution of ceramic art.

🌡️ Weather Report

May Day GIF by Chibird

☀️ Weekend Weather at a Glance

Friday (May 29): 🌥️ Mostly cloudy, mild – High ~65–72°F / Low ~55–61°F – A pretty neutral start; lots of clouds, maybe a stray shower, but overall calm and workable.

Saturday (May 30): 🌧️ Showers & possible thunderstorms – High ~56–83°F / Low ~49–59°F – The wildcard day. Expect periods of rain (and possibly a rumble of thunder), with temps bouncing around depending on timing—either way, not the most reliable for outdoor plans.

Sunday (May 31): ☀️ Sunny and much nicer – High ~71–81°F / Low ~48–60°F – A strong rebound. Sunshine returns, temps warm up, and it finally feels like we’re closing out May on a high note!

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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