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  • 🎤 He Sold Out Madison Square Garden. This Week, He's at Tarrytown Music Hall.

🎤 He Sold Out Madison Square Garden. This Week, He's at Tarrytown Music Hall.

Loving Westchester turns one, Mamaroneck's carnival returns, and Patton Oswalt comes to town

June 23, 2026

Welcome back, friends!
 

Summer is officially here! The days are at their longest, the weather is headed towards its warmest, the schools are unleashing their kids on local parks and beaches, and the weeks of snow and frozen ground are a distant February memory.
 
What the calendar loses in school and kids sporting events, it’s gaining in county pool openings, summer parties, outdoor movies, and - at least for this week - stars of the music and entertainment world gracing Westchester stages. It’s a trade we’ll definitely take.
 
This week also marks Loving Westchester’s one year birthday! We’ve been here with you every Tuesday and Friday morning since June of last year and, since then, over 23,000 of you have joined us across our newsletter and social media channels. One reader, in particular, has also been here every Tuesday and Friday, reading each one of our 108 newsletter editions… special shout out to Jon Rose for the dedication!
 
Throughout the past year of building the Loving Westchester community with you all, we’ve met so many great people working to make the county a more fun and exciting place for the people who call it home. We’re kicking off this edition, and our second year, with something new called “Around Our County" where we’ll share with you a deeper look at the great things your neighbors are cooking up. Have one to share with us? Let us know and we’ll check it out!
 
Let’s get into it…
 

 
📍 Around Our County

 
TriState Standup has been bringing touring comedians to Westchester through pop-up shows at restaurants and breweries. This weekend, they're opening a dedicated room, TriState Comedy Club, and it’s on track to be one of the largest comedy clubs in the New York metro area.
 
The new venue is set under Z Prime Italian Restaurant in White Plains with seating capacity for 100 guests. The move means the team can continue to deliver the touring acts they always have but to much larger audiences. Comics from Netflix & HBO specials, comedy festival circuit names… coming to White Plains.
 
We've been telling you about TriState's pop-up shows for a while now and watching them grow. This is the next step. They’re calling it "an upscale live entertainment experience featuring premier stand-up comedy, craft cocktails, and an intimate luxury atmosphere."
 
Opening weekend kicks off June 26-27 with headliner Ben Kirsch, an up-and-coming comic who’s hit the festival scene in Portland and Connecticut and is also a regular on the Chaz and AJ morning show. A strong choice for the first weekend to bring some buzz around the brand new space.
 
Want to check out the new club? TriState has offered Loving Westchester readers an exclusive 40% off opening weekend tickets with code LW40 at checkout. Good for either the Saturday or Sunday show.
 
We'll see you there!

 

 
In today’s edition:

And a message from our partners, WingWoman by QueenBHive, giving you, your business, or brand the visibility and support it needs, and QueenBPoker, hosting your epic game night.

 

Now let’s get to it!

💓 The Pulse

Loving Westchester’s Featured Events!

🎬 Dog Man with Special Guest Peter Hastings
Wed., Jun. 24 | Bedford Playhouse, Bedford | 1p | $20
 
The DreamWorks animated adaptation of Dav Pilkey's beloved books, followed by a live Q&A with the film's director and voice actor Peter Hastings, a six-time Emmy and Peabody winner who has spent 35 years working on Animaniacs, Kung Fu Panda, and How to Train Your Dragon.
Your kid has read every Dog Man book and now they can meet the person who made the movie. That's a special afternoon →
 
🎤 Aziz Ansari: Hypothetical Tour
Wed., Jun. 24 | Tarrytown Music Hall, Tarrytown | 7p | $57+
 
The co-creator of Master of None and one of a handful of comedians to have sold out Madison Square Garden brings his newest tour to one of Westchester's most intimate venues.
He sold out Madison Square Garden. He's playing a 900-seat room in Tarrytown. Easy decision →
 
🎡 78th Annual Firemen's Carnival
Fri., Jun. 26 - Sun., Jul. 5 | Harbor Island Park, Mamaroneck | Rides 6p, Vendors 7p nightly | Free admission, $35 ride wristbands
 
Ten nights of carnival rides, food vendors, and games on the Mamaroneck waterfront, capped by a Firemen's Parade on July 1 and fireworks on July 4. One of Westchester's most reliably fun summer traditions.
78 years of carnival rides, food, and fireworks on the Mamaroneck waterfront →

Hey, everybody. This is Bec. Before Loving Westchester, I spent 20 years helping businesses, brands, and community organizations build visibility and find their audience. If you're a local business owner who knows you should be showing up more online but can't find the time between running the business and everything else, that's exactly what WingWoman is for. Business and communications strategy, social content, partnerships, launches. Just the right person in your corner connecting the dots and helping you get things done.
 
Let's talk →

📆 What’s Happening?

Family Fun!

🎉 New Castle Summerfest
Wed., Jun. 24 | Recreation Field, 200 S. Greeley Ave., Chappaqua | 11a-1p | Free
 
A midday summer kickoff for kids in grades 5-8, with music, inflatable games, free pizza while supplies last, Bona Bona ice cream for purchase, and a mobile patch bar from Patch'd on site.
 
⚽ White Plains Soccer Fest
Wed., Jun. 24 | Mamaroneck Ave., White Plains | 5-8p | Free
 
White Plains Soccer Fest hosts a World Cup watch party this Wednesday, showing Haiti vs. Morocco alongside live music, games, giveaways, and light food options.
 
🎬 Movies on the Lawn: Back to the Future
Wed., Jun. 24 | Tarrytown House Estate, Tarrytown | At sunset | Free for hotel guests, $5 for the public
 
Marty McFly and the DeLorean on the historic estate lawn. Bring blankets and chairs. Tarrytown House Estate and Goosefeather will offer food and beverages available for purchase.
 
🎸 107.1 The Peak Summer Sessions: Eddie 9V and Michigander
Thu., Jun. 25 | The Barley Beach House, Rye | 7p | Free
 
Atlanta blues-rock guitarist Eddie 9V and indie rock act Michigander share the bill for a free outdoor show on the waterfront deck. Seating is first come, first served.
 
🎬 Movie Night at Ridge Hill: Lilo & Stitch
Thu., Jun. 25 | Ridge Hill Town Square, Yonkers | Pre-show 7p, film 8p | Free
 
The 2025 live action Lilo & Stitch on the jumbo LED screen in the open air. Pop-up experiences from Ridge Hill retailers and restaurants starting at 7p. Bring blankets and chairs.
 
🏊 Westchester County Pools Opening Day
Fri., Jun. 26 | Check the link above for locations, hours, and fees
 
County pools open for the season this Friday, running daily through Labor Day. Westchester County residency required (except Playland Pool); bring a valid NY State ID with a Westchester address or County Park Pass.
 
🌻 Summer Solstice Party at Hilltop Hanover Farm
Fri., Jun. 26 | Hilltop Hanover Farm, Yorktown Heights | 4-8p | Free
 
Live music, food trucks, and flower crown making at a working farm celebrating the longest days of the year. Bring a picnic or grab food on site.
 
☘️ Irish Heritage Day
Sat., Jun. 27 | Ridge Road Park, Hartsdale | 12-6p | $10 general / $5 seniors and children / Kids 13 and under free
 
Bagpipers, the Deirdre O'Mara School of Irish Dance, outdoor mass at 12:30p, Irish goods vendors, children's activities, and food all afternoon. Bring blankets or folding chairs.

 

 

Grown Ups & Date Nights

📚 Dolly All The Time with Annabel Monaghan
Tue., Jun. 23 | Bedford Playhouse, Bedford | 7p | $25
 
The New York Times bestselling author of It's a Love Story discusses her newest beach read at the Bedford Playhouse. Books available for purchase and signing.
 
😂 Patton Oswalt: Effervescent
Thu., Jun. 25 | Tarrytown Music Hall, Tarrytown | 8p | $57.50+
 
Six Grammy nominations, four Emmy nominations, and a voice role in Ratatouille. Patton Oswalt brings his newest hour to one of the best stages in the Hudson Valley.
 
🌿 Seasoned by Summer Dinner at Outhouse Orchards
Fri., Jun. 26 | Outhouse Orchards, Croton Falls | Cocktails 6:30p, Dinner 7p | $202.66 per pair
 
An open-flame, family-style dinner cooked by Chef Michael Lucente of Village Social, served under the barn overhang with orchard views. June menu: grilled lobster and NY strip, Maine shrimp rolls, steamed mussels, and a homemade brownie sundae.
 
🌀 Bashar: The University of Earth
Sat., Jun. 27 | Paramount Hudson Valley, Peekskill | 11a-7p | $284+
 
A full-day channeling event exploring consciousness, extraterrestrial civilizations, and the purpose of human experience. VIP tickets include premium seating and a Bashar journal. For fans of this world and possibly others.
 
🎬 Wuthering Heights (1939) with Q&A
Sat., Jun. 27 | Jacob Burns Film Center, Pleasantville | 2p | $15+
 
The seven-time Oscar-nominated William Wyler film with Laurence Olivier and Merle Oberon on the big screen, followed by a book talk with Penn State professor Deborah Lutz, author of a new Emily Bronte biography.

 

 

The Beat… Westchester’s Live Music Scene
 

🎸 An Acoustic Evening with Trey Anastasio
Tue., Jun. 23 & Wed., Jun. 24 | The Capitol Theatre, Port Chester | Doors 6p, Show 7:30p | Resale tickets available at the link above
 
The Phish frontman and one of Rolling Stone's 250 greatest guitarists of all time strips it down for a pair of acoustic nights at the Cap, joined by Jeff Tanski. These shows sold out fast, which tells you everything about the demand for a Trey night in an intimate room.
Check here for resale tickets →

 

Game nights are having a moment in Westchester, and if you've ever wanted to host a poker or casino night without the stress of figuring out the rules or rounding up chips, QueenBPoker is the answer. They come to your home, venue, office, and handle everything you may need from teaching the table to running the night. Casual, corporate, charity. No experience needed, just people who want a good time.
 
Plan your game night →

🏺 Hops on Hudson Makers Market
Sat., Jun. 27 & Sun., Jun. 28 | 1 Chestnut Street, Cold Spring | 11a-5p | Free admission
 
Kid sports season finally over and not sure what to do with all that extra time? Seventy local designers, creators, artisans, and artists set up this weekend in the Hudson Valley’s Cold Spring for a Hops on the Hudson Makers Market.
 
🎬 Movies Under the Walkway: Zootopia 2
Sat., Jun. 27 | Upper Landing Park, Poughkeepsie | Doors 7:30p, Film at sundown | Free
 
Zootopia 2 on a big screen at the base of the Walkway Over the Hudson, right on the riverfront. Bring blankets and chairs.
 
⚽ World Soccer Championship Food Festival Viewing Party
Sat., Jun. 27 | MJN Convention Center, Poughkeepsie | 4-11:30p | $16.17
 
World Cup matches on the big screens inside the arena alongside food vendors from around the world, a soccer village, games, and giveaways. Wear your team colors.

🏡 Where the Heart Is

Incredible homes are listed in Westchester every week. Here’s one that caught our eye

 

The Key Details: 3 bedrooms, 3 bathrooms, 2,010 square feet on 1.14 acres ($597 / square foot)
 
What We Love About It: Seven figures for a fixer-upper is a big ask, but the canvases don’t get much better than this. 100 Devoe Road is a 2,010 square foot Colonial sitting on a flat 1.14 acres just a few minutes away from Chappaqua’s highly rated schools and the Metro North Station. The listed square footage doesn’t include an unfinished basement (~400 sq. ft.) or a sunroom (150 sq. ft.) in the total, according to the listing. The next owner of 100 Devoe will be surrounded by Chappaqua convenience, their own land, and homes valued $500-800k more than the list price here. Definitely worth a look if you’re not scared away by a project!
 

"Thank you for your emails highlighting the wonderful events happening throughout Westchester. They are such a great resource and reminder of how much Westchester has to offer." — A Loving Westchester Reader
 
Loving Westchester is written by a real-life husband and wife team, completely free, and in your inbox every Tuesday and Friday. If it adds something to your week, even a small contribution helps us keep it going and growing.

 

We love to hear from you — give us a shout at [email protected] or find us on Instagram @lovingwestchester. And don't forget to forward this to a friend who's always asking "what's going on this week?"
 
See you Friday,