Rain or Shine: Your Memorial Day Weekend Starts Here

Live Music, Festivals, Workshops & Memorial Day Events Across Westchester

Welcome to the Westchester Weekly!

Memorial Day weekend is here – and while a little rain may be in the forecast, it’s not slowing anything down. Across Westchester and the Hudson Valley, the calendar is packed with live music, theater, hands-on workshops, cultural festivals, and meaningful community gatherings that bring the long weekend to life.

This is the kind of weekend where you pivot, not pause – duck into a cozy concert, catch a show, explore a local festival between showers, or lean into the holiday with a parade or remembrance ceremony. From high-energy nights out to laid-back daytime plans, there’s plenty to mix, match, and make your own.

Rain or shine, there’s no shortage of ways to make the most of it.

Let’s get into it!

🌧️ In this issue:
🎶 Live music, concerts & nightlife picks
🎭 Theater, comedy & creative performances
🎨 Workshops, art events & hands-on experiences
🎉 Festivals, markets & cultural celebrations
🇺🇸 Memorial Day parades, races & commemorations

🏡 Real Estate Deal of the Week 🏡 

Just listed in Katonah!

Tucked away on a quiet, scenic road in Katonah, this beautifully maintained home offers the perfect blend of privacy, space, and everyday comfort. Bright, sun-filled interiors highlight a warm and inviting layout, featuring generous living spaces, a well-designed kitchen, and seamless flow for both relaxing and entertaining. Set on a peaceful property surrounded by nature, yet just minutes from Katonah Village, Metro-North, and local favorites, this home delivers the best of Westchester living.

  • 4 Beds

  • 3 Baths

  • 2,700 sq ft

  • Lot size: ~2 acres

  • Built in 1978

  • Attached garage + expansive yard

Asking Price: $1,700,000

View the full listing here.

🧺 Family-Friendly Fun

Get hands-on at a Plant Dissection workshop, where you’ll explore the inner workings of plants and uncover the science behind how they grow and function!

🌱 Plant Dissection
Yorktown | May 23 | More
A hands-on science experience where kids can explore the inner workings of plants up close. Expect interactive learning, discovery, and a fun introduction to biology that feels more like play than school.

🐢 World Turtle Day Celebration – Animal Meet & Greet
Redding | May 23 | More
Celebrate these fascinating creatures with an up-close meet & greet featuring real turtles and tortoises. Kids can learn fun facts, see different species, and even create a themed craft to take home.

🎢 Playland Grand Opening
Rye | May 23 | More
The iconic amusement park reopens for the season with rides, games, and classic boardwalk fun. It’s the unofficial kickoff to summer – perfect for families looking for thrills, treats, and a full day of excitement.

🎨 Mini Sun Print Workshop
Verplanck | May 24 | More
A creative drop-in workshop where kids can experiment with cyanotype (sun print) techniques to make their own artwork. All materials are provided, and the process is simple, hands-on, and perfect for all ages and skill levels.

🍻 Activities for Adults

Get hands-on at Slip Studio’s charcuterie board workshop, where you’ll craft your own custom ceramic serving piece in a fun, social setting perfect for creatives of all skill levels!

🧘 Westchester Breathes (Breath & Movement Practices)
Yonkers | May 21 | More
A calming, reset-style experience focused on guided breathwork and gentle movement. Perfect for unwinding after a long week and reconnecting with your body in a peaceful, supportive setting.

🎺 Miles Davis @ 100!
Purchase | May 21 | More
A special centennial tribute celebrating the legendary jazz icon with an evening of live music inspired by his groundbreaking sound. Expect rich improvisation, iconic melodies, and a deep appreciation for one of music’s greatest innovators.

🎭 The 39 Steps
Nyack | May 22 | More
Back by popular demand, this fast-paced theatrical comedy blends mystery, suspense, and clever staging. With rapid character changes and nonstop humor, it’s a wildly entertaining night at the theater.

🎸 Peter Calo
Peekskill | May 22 | More
An intimate live performance from a seasoned guitarist known for his smooth style and genre-spanning sound. Ideal for a relaxed night out with great music in a cozy venue.

🎤 WCT Presents: Verses & Vignettes
Ossining | May 22 | More
An engaging evening of short-form theater, poetry, and storytelling. Each piece brings a fresh perspective, making for a creative and thought-provoking showcase.

🎶 The Ledbetters
Port Chester | May 22 | More
A high-energy tribute band delivering all the grit and nostalgia of classic rock favorites. Expect a lively crowd, sing-along moments, and a Friday night full of throwback hits.

📖 Rip Van Winkle’s Journey
Sleepy Hollow | May 23 | More
Step into a live storytelling experience rooted in Hudson Valley folklore. This immersive performance blends history, theater, and local legend in a uniquely atmospheric setting.

🎉 The Pinkster Festival
Sleepy Hollow | May 23 | More
A vibrant cultural celebration honoring early African American traditions through music, dance, food, and storytelling. A meaningful and lively event that brings history to life.

🏛️ Open Hours at the Thomas Paine Historical Association
New Rochelle | May 23 | More
Explore the legacy of one of America’s most influential thinkers with open access to exhibits and historical insights. A low-key but enriching stop for history lovers.

🧀 Craft Your Own Charcuterie Board Workshop
White Plains | May 23 | More
A hands-on culinary workshop where you’ll design and style your own charcuterie board. Learn presentation tips, flavor pairings, and leave with a creation that’s almost too pretty to eat.

🔥 The M '80s Rock Experience – Saturday BBQ
Mahopac | May 23 | More
Big hair, big sound, and big energy – this outdoor BBQ pairs classic ‘80s rock hits with great food and a lively, nostalgic atmosphere.

🎶 Tallman Beach & Pool Club Concert Series
Sparkill | May 23 | More
Live music meets waterfront views in this relaxed outdoor concert setting. Bring a chair, soak in the scenery, and enjoy an easygoing evening by the river.

🥂 Sunday Brunch with Alejandro Meola
Mount Kisco | May 24 | More
A smooth blend of live jazz and brunch favorites creates the perfect Sunday vibe. Great food, great music, and a laid-back way to ease into the day.

🏃 47th Annual South Salem Memorial Day Races
South Salem | May 25 | More
A long-standing community tradition featuring scenic race routes and strong local spirit. Whether you’re running or cheering, it’s an energizing way to kick off Memorial Day.

Memorial Day Veterans GIF by enCOMPASS

🇺🇸 Valhalla Memorial Day Parade, Ceremony & Open House
Valhalla | May 25 | More
A heartfelt tribute honoring those who served, featuring a classic hometown parade and remembrance ceremony. A meaningful way to connect with community and country.

🇺🇸 Memorial Day at Wave Hill
Wave Hill | Bronx | May 25 | More
Spend the holiday surrounded by blooming gardens and sweeping Hudson River views. A peaceful, scenic option for reflecting and enjoying the day outdoors.

🇺🇸 Memorial Day Parade & Ceremony
White Plains | May 25 | More
A classic community gathering featuring a parade, ceremony, and moments of remembrance. Expect patriotic spirit and a strong sense of local pride.

🇺🇸 Memorial Day Commemoration
Mount Vernon | May 25 | More
A reflective and respectful ceremony honoring the meaning of Memorial Day. A chance to pause, remember, and pay tribute in a historic setting.

🌡️ Weather Report

Celebrate American GIF by Hello All

☀️ Weekend Weather at a Glance

Friday (May 22): ⛅ Cooler with partial sun – High ~65°F / Low ~48°F – A quieter, cooler reset after the midweek heat; not bad, just noticeably less summery.

Saturday (May 23): 🌧️ Rainy, breezy, and chilly – High ~52–58°F / Low ~50°F – The roughest day of the stretch—steady rain, gusty winds, and temps that feel way more April than late May.

Sunday (May 24): 🌧️ Damp with lingering showers – High ~58–60°F / Low ~50°F – Not a total washout, but gray, drizzly, and cool; not exactly ideal for outdoor plans.

Memorial Day (Monday, May 25): ☁️ Mostly cloudy with spotty showers – High ~59–68°F / Low ~51°F – Slight improvement, but still more “meh” than “summer kickoff”—clouds stick around with a few passing showers.

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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