Why Westchester's Event Scene is Your Golden Ticket

I get this question all the time from new clients: "Jess, I'm moving to Westchester, but I'm worried about finding my people. How do I build community here?"
My answer is always the same: You have to show up.

Here's the beautiful thing about Westchester – this county practically rolls out the red carpet for connection. Every weekend, there's something happening. Farmers markets in Tarrytown. Art walks in White Plains. Summer concerts in Rye. Fall festivals in every town from Yonkers to Yorktown.

But here's what I've learned after years of helping families plant roots here: the community doesn't come to you. You have to go to it.

Westchester Makes It Easy (If You Let It)

 The truth is, Westchester is practically begging you to get involved. Consider this just a small sampling of what's happening regularly:
  • Farmers markets in nearly every town
  • Library story times and adult programs
  • Park district classes and activities
  • Religious services and community groups

Seasonal Celebrations:

  • Summer concert series in village greens
  • Fall harvest festivals and Halloween parades
  • Holiday tree lightings and winter markets
  • Spring garden tours and Earth Day cleanups

Year-Round Opportunities:
  • Youth sports leagues (hello, soccer parent friendships!)
  • Adult recreation leagues
  • Volunteer organizations
  • Historical societies and museums events

The Real Estate Connection You Didn't Expect

Here's something most people don't realize: the neighborhoods with the strongest property values are often the ones with the most active community involvement. When people show up for their town, they're invested. When they're invested, they take care of their properties, support local businesses, and create the kind of place where everyone wants to live.


It's not just about home values, though. It's about life values. The families who thrive here – and I mean really thrive – are the ones who understand that community isn't something that happens to you. It's something you create by consistently showing up.


Start Where You Are, With What You Have


You don't need to volunteer for the PTA on day one (though they'd probably love you if you did). Start small:


Walk your dog to the same local coffee shop each morning

Take your kids to the same playground regularly

Attend one town board meeting (I promise it's more interesting than you think)

Join a single seasonal activity – a CSA, a walking group, a book club


The key is consistency. Community isn't built in grand gestures; it's built in repeated small moments of connection.


Your Westchester Story Starts Now


If you're thinking about moving to Westchester, know this: we're not just selling you a house. We're inviting you into a community that's ready to welcome you – if you're ready to show up.



And if you're already here but feeling disconnected, your story isn't over. It's never too late to start showing up. The community you're craving is happening right now, probably within a few miles of your front door.


The question isn't whether Westchester has community. The question is: are you ready to be part of it?


Ready to find your place in Westchester? I'm Jess Watts, and I help families not just find houses, but find home. Let's talk about which Westchester community might be perfect for your family's story.

By Jessica Watts September 3, 2025
To the small businesses who showed up with beauty, knowledge and talent- Thank you! It was the best morning. ❤️ @shopshapero @audracedrone @verylovelysoles @myfavoriteyogastrap @ajgsieger 📸: @hudvalleyphoto
By Jessica Watts August 26, 2025
When you think of New York, your mind immediately goes to towering skyscrapers, bustling streets, and the relentless energy of the city that never sleeps. But I want to challenge that narrow perception entirely. Instead of concrete and steel, picture rolling farmland.
By Jessica Watts August 21, 2025
Photos by Hudson Valley Photo
More Posts