💗 Westchester's Orchards Star This Weekend

Plus, parties everywhere... retro in New Ro, pups in Port Chester & Rye's rocking!

Author

Wes+Bec Willetts
September 19, 2025

Happy Friday everyone!

 

This past week or so was special because with our various giveaways we got to have more contact with you and even meet some of you in person! It’s been great to hear how those we spoke with have been enjoying the newsletters. This is something we always did naturally and shared with friends, so to do it with more and more of you every week, has been incredible. Please do let us know if there’s anything we’re missing or you want to see more of, and don’t forget to share with a friend or two so we can grow this amazing community further. In the meantime, we’ll keep bringing you fun, joy, experiences, and excuses to make many more memories.

 

May your weekend sleeps be long, and your chores be short. Oh, and remember, Mystic Moon opens its gates tonight at Harvest Moon and tickets are still available. We’ve got a feeling that once people start to hear about it and see some pictures, tickets will be harder to come by. If you’re headed there tonight and see us, come say hello!

 

Otherwise, see you Tuesday!

 

Wes+Bec

 

 

In today’s edition:

  • Featured events
 go fly a kite and a legendary street fair.

  • Kid-friendly fun
 some great community events in Dobbs Ferry & Bedford and things are about to get Messi in Queens.

  • Grown ups & date nights
 a 90s glow in the dark bubble party and an Italian fest on the sound.

  • Live music beat
 14 gigs to groove to in the early part of your weekend.

  • Worth a drive
 a BBQ party at Barton and some grape-stomping action up north.

  • Eats-chester
 one of our pizza faves slinging more than just dough.

Plus, a message from our partners, QueenBHive & Fallscapers.

 

Let’s go!

💓 The Pulse

Loving Westchester’s Featured Events!

Sat., Sep 20 & Sun., Sep 21 | Outhouse Orchards, North Salem | Fall Festival runs 9a-5p | Tickets from $22.45 online, $27 at the gate, 3 & under FREE

 

Outhouse Orchards are adding a huge special event to this weekend’s Fall Festival with Westchester’s Great Kite Show! Massive kites will be launched (weather permitting) between 10a-4p for attendees to gaze at, all included with a normal ticket.

 

Sun., Sep 21 | Beekman Ave., Sleepy Hollow | 10a-4p | FREE admission

 

Westchester definitely has more of a fall vibe these days and it doesn’t get more “fall” than the Sleepy Hollow Street Fair. Catch live music, browse 200 vendor stalls, step in to local shops and come face to
 shoulders
 with the legendary Headless Horseman.

 

Sat., Sep 20 | Downtown Rye | 3-5.30p | Tickets $65

 

Take a stroll through downtown Rye and sample appetizers and drinks from seven of its culinary staples
 all for a good cause. 100% of ticket proceeds go to My Sisters’ Place, a nonprofit working to end domestic violence and human trafficking.

Partnered With QueenBHive

Want your brand to stand out?

We help brands cut through the noise.

With decades of experience running communications and partnerships for worldwide names, QueenBHive brings global experience to local businesses. Whether you’re stuck on what to post, how to grow, or how to sound like you online, QueenBHive makes it make sense.

 

With support and packages designed for businesses of all sizes, including help with visuals, content and PR, we take the stress out of building your brand.

 

Based in Westchester and proud to be part of this community.

 

🐝 Visit QueenBHive.com or email us here. Our flexible and friendly approach will help you figure out exactly what you need to grow with confidence.

📆 What’s Happening?

 

Kid-friendly Fun!

Sat., Sep 20 | Abendroth Dog Park, Port Chester | 11a-2p | FREE admission

 

SPCA Westchester hosts its Family Fun & Pet Extravaganza event. A doggy playground, a kitten cuddle station, agility courses and games will entertain the little ones. The mobile adoption truck will be on-site for those looking to add a friend to their family.

 

⚜ Local Pro Soccer This Weekend & GOAT Watching in Queens

  • Sat., Sep 20 | New York City FC host Charlotte FC (Kid’s Night) | Yankee Stadium, Bronx | 12p | Tickets from $11.70

  • Sun., Sep 21 | Westchester SC host Texoma FC (Hispanic Heritage Night) | The Stadium at Memorial Field, Mount Vernon | 7p | Tickets from $16

  • GOAT Alert! | Wed., Sep 24 | New York City FC host Leo Messi’s Inter Miami | Citi Field, Queens | 7.30p | Tickets from $111

 

💧 Aquefest

Sat., Sep 20 | The Keeper’s House, Old Croton Aqueduct, Dobbs Ferry | 11a-4p | FREE admission

 

Head to Dobbs Ferry for a celebration of the Old Croton Aqueduct with a day full of live music, animal petting farms & parades, a “goat on a boat puppet theater”, and plenty of arts and crafts for the kids!

 

Sat., Sep 20 | Bedford Village Memorial Park | 3.30-8p | FREE admission

 

It’s a three-hamlet celebration when Bedford Hills, Bedford Village and Katonah come together to host Tri-Festa. Entertainment includes live music, inflatables, lawn games, mini golf and a bubble bus for the kids. Food & adult beverage trucks will be on-site.

 

Sun., Sep 21 | Yonkers Brewing Co., Yonkers | 2-5p | RSVP at the link above

 

The Netflix phenomenon, K-Pop Demon Hunters, hits Yonkers Brewing on Sunday. While the kids scream their little heads off to the movie and get their faces painted, parents get to sit back, relax and drink their own little soda pop at the bar.

 

Bonus Fun!

  • Magic Show & The Tiny Mess Club | Sat., Sep 20 | Chappaqua Farmers Market | 9a | FREE

  • Scarecrow Making Contest | Sat., Sep 20 & Sun., Sep 21 | Muscoot Farm, Katonah | 11a-3p | Registration $10 / family

  • Fairy Walk | Sat., Sep 20 | Muscoot Farm, Katonah | 12-3p | FREE

  • Penny Lick 10th Anniversary Party | Sat., Sep 20 | 580 Warburton Ave., Hastings on Hudson | 12-5p

  • Sleepy Hollow Arts Collective Fall Season Kickoff & Hootenanny | Sat., Sep 20 | Kingsland Point Park, Sleepy Hollow | 1-4p (Bring your instruments!)

  • Bicycle Sundays | Sun., Sep 21 | Bronx River Parkway | 10a-2p | FREE

 

Grown Ups & Date Nights

Sat., Sep 20 | Hudson Park, New Rochelle | 6.30-9p | FREE admission

 

New Rochelle Parks & Rec host a 90s themed glow in the dark bubble party this Saturday night. Dust off the kicks and head down to Hudson Park for DJ music, dancing and food trucks to keep the energy high. Event is 21+.

 

Sat., Sep 20 | Barley Beach House, Rye | 4-8p | Tickets $55

 

If fall is a state of mind, maybe you’re already picking pumpkins. If you’re one that points to the calendar, you know you’ve got a few days of summer left. Plenty of time to hit Barley’s Sip, Sound, Savor event with live music & food right on Rye Beach.

 

Sat., Sep 20 | ArtsWestchester’s Gallery, White Plains | 4-8p | Tickets $12.51

 

Celebrate the full-harvest moon at the Mooncake Night Market and enjoy a night of dancing, music, karaoke and food. Try your hand at Chinese cultural workshops like calligraphy, lantern-making, sugar painting & origami.

 

Sat., Sep 20 & Sun., Sep 21 | Tiki Beach, Rye | 1-9p

 

Head down Rye’s Playland Pier this weekend to Tiki Beach’s 3rd annual Italian Festival for some authentic Italian food, live music & DJ entertainment, face painting & balloons for the kids and a Vespa raffle. Doesn’t get more Italian than that!

 

đŸ» Prost!

Sat., Sep 20 - Sun., Sep 21 | Captain Lawrence Brewing Company, Elmsford | 1-10p | FREE admission

 

Oktoberfest season begins at Captain Lawrence Brewing Company in Elmsford on Saturday. Expect keg throwing, stein hoisting, barrel racing and a live Oompah band!

 

Mon., Sep 22 | The Capitol Theatre, Port Chester | Happy Hour & Doors: 6.30p, Show 8p | Tickets from $79.05

 

You now have a reason to look forward to Monday when The Revivalists take The Capitol Theatre stage with a special pizza guest appearance from Greenwich’s killer Grigg Street Pizza. We’ve experienced and loved all three - but never at once!

 

 

The Beat

Westchester’s Live Music Scene

Image from Paramount Hudson Valley Theater

Thanks to our partner, Fallscapers!

 

Let Fallscapers transform your doorstep into an autumn wonderland!

We’ve hit September, and soon the best fall displays will sell out! Fallscapers is offering limited availability for this season with prime installation dates booking quickly.

 

Reserve with ease – no commitment necessary – we have limited availability, so grab one of the last spots now.

 

 

🚗 Worth a Drive

There are a ton of great things going on outside Westchester county lines this coming weekend


Sat., Sep 20 & Sun., Sep 21 | Barton Orchards, Poughquag (Dutchess) | 11a-6p | Tickets: 13 & older $37, ages 4-12 $25

 

Tons to do this weekend at Barton Orchards with magic shows, pig races, a corn maze, a fun park and a carousel for the kids and BBQ, beer & cider on tap for the grown ups. Throw in apple and pumpkin picking and it’s a full day. Trust us
 it’s hard to leave!

 

đŸ§˜â€â™€ïž Rockland Yoga Fest

Sat., Sep 20 | Memorial Park, Nyack | 9a–5p | FREE

 

Spend a mindful day in Nyack as Yoga Fest parks up along the river to offer music, food trucks, wellness vendors, sound baths, and yoga for absolutely everyone from a sleuth of top yoga venues and talented instructors. Give the kids more Zen they can handle and chill out with some stretching and stretchy-pants style grazing.

 

🍇 Stomp + Sip Season Is Here 

Sat., Sep 20 & Sun., Sep 21 | Two ways to crush the weekend at Hudson Valley wineries | Drinking and non-drinking tickets available

Benmarl Winery (Marlboro) 11a-8p: Live music, wine, hay rides and grape stomping to epic Hudson Valley views

Robibero Winery (New Paltz) 11a–5.30p: Stomp, wine taste, sip caramel apple sangria, & play lawn games. Stop at Apizza in downtown New Paltz before heading home!

🍕 Eats-chester

 

I think you know by now we’re a pizza-lovin’ family, and this edition’s highlight has been mentioned previously as one of our favorites, but what we also love about this place is that its talents are not just limited to dough, and they are forever getting our attention with their ongoing thirst trap specials. We know some of you already know this but if you haven’t checked out Pizzeria La Rosa in New Rochelle, then you’re simply missing out.

 

Our first La Rosa experience came in the form of takeout, and despite Neapolitans being known for losing quality with every mile you drive to get it home, we didn’t have that problem at all
 because it was long gone when we pulled in our driveway. Their Bolognese pizza is insane, and if you can handle weighing this juicy slice down slightly more, pop their Pepperoni cups on top. Yes, just do it. If you’re a margarita person like our son, then that’s great too
 as are their seasonal pies, largely because they are not afraid to be bold with ingredients (caramelized pineapple, what?!). Our recommendation would be to go on a Tuesday and make sure you get their 75c wings (has to be Gold Rush sauce) and $6 draft beers. However, we’ve yet to go on a Thursday for their smash burgers, which we’ve heard are excellent.

 

There’s something very old school about La Rosa but with Michelin style, mad scientist style vibes. I think it’s because you can tell they truly care about what they’re doing, and that likely can be traced back to owner Matt DiGesu who has honed his art across New York and California for many years. In founding Pizzeria La Rosa, he didn’t just open his own place, he restored a historic pizzeria and painstakingly took eight months to rebuild a 100-year-old baking oven into a woodfire brick oven, the heart of the restaurant. It can be often difficult to put your finger on what separates a really great place from a great one, and I think it’s that
 Commitment, passion
. love. Once you witness and experience it, it’s hard to accept anything less.

 

Thanks for reading Loving Westchester!

 

We’re really enjoying putting this together twice a week and hope you enjoy reading it. We’ll say it again
 we love to hear from you! You can reach us at [email protected].

 

Check us out on Instagram for additional highlights outside of our normal Tuesday & Friday e-mails and, as always, please send this along to a friend who’s always asking, “What’s going on this weekend?”

 

Until next time,