🐲 Playland Opens Its Gates: The Countdown to Summer Is On

A castle hits the market in Irvington & The Who's Roger Daltrey comes to The Cap

May 15, 2026

Hello, Westchester!

 

Do we have any Traitors fans out there? It’s a huge hit with this family. Around here, the show is usually paired with Taco Tuesday and a bedtime that’s way, way too late. The over-the-top Alan Cumming wardrobes make the sluggish Wednesday mornings worth it, though. Anyway, you can swap the Scottish lochs and the deception for the rivertowns and the Hudson with a castle that’s hit the market in Irvington. What you do in the privacy of your own turret is up to you…

 

We’re somehow already in mid-May and signs of a Westchester summer are forcing their way through. Playland Park opens its gates this weekend for the pre-season, Suds on the Sound will have dozens of breweries descending on Rye Town Park, Westchester’s oldest craft brewery turns 20, and Bona Bona is throwing down the gauntlet with an ice cream eating contest that could earn you a free year of their delicacies.

 

It’s all kicking off. We’ll be here every Tuesday and Friday, as always, helping you cut through the noise and find those perfect outings for you and your family. Hope you enjoy reading as much as we enjoy writing. Now let’s get to it…

 

Bec+Wes

 

 

In today’s edition:

  • Featured events… hear those roars? Could be Playland’s Dragon Coaster or the crowd cheering on Bona Bona's ice cream eating contest.

  • Family fun… Picks & Pickleball is bringing goats, live music, a bubble show and Captain Lawrence beer to your Saturday.

  • Grown ups & date nights… Westchester’s oldest craft brewery is almost old enough to drink as Captain Lawrence turns 20 with a birthday bash.

  • Live music beat… don't get fooled again, The Who’s Roger Daltrey is coming to The Cap.

  • Worth a drive from Ardsley Car Wash… a special Stamford Saturday for Swifties under the stars.

  • Where the heart is… own your own castle in Irvington. Planning permission for a moat not guaranteed.

Plus, 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.

 

Let’s go!

💓 The Pulse

Loving Westchester’s Featured Events!

Sat.-Sun., May 16-17 | Playland Park, Rye | 12-7p | $20+, spectators and under 2 free

 

Playland welcomes guests back for the first time this season, with the iconic Gondola Wheel, Grand Carousel, and Kiddyland rides all returning alongside park food favorites and new offerings. The historic Westchester landmark begins its summer run this weekend.

 

Sat., May 16 | The Barley Beach House, Rye | 1-6p | $30+

 

The Barley Beach House's annual waterfront craft beer festival returns with 50-plus breweries, over 100 tastings, food trucks, live music, and 75 artisan vendors on the Sound. Bissell Brothers will be there, a big favorite of ours. Check ‘em out.

 

🍦 Bona Bona’s 6th Annual Ice Cream Eating Contest

Wed., May 20 | Bona Bona Ice Cream, Port Chester | 7p | Free to enter

 

Bona Bona is looking for contestants to compete in their 6th annual ice cream eating contest. First place will be enshrined as Champ, complete with a championship belt and free ice cream for a year. Second place wins an ice cream truck event for 20 people. New this year will be a youth competition (12 and under) with the winner taking down an epic Sprinkle Room ice cream party for 15 people and a Championship Chain. To enter, email [email protected] with the subject line “I EAT ICE CREAM!”

Are You a Business Owner, Author or Creative Leader Trying to Grow Your Visibility While Running Everything Else?

 

Many business owners and senior executives know they should be showing up more, sharing their story, getting media coverage, speaking, or building a stronger personal brand… but between running a business and life, it rarely happens.

 

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If you're building something meaningful but don’t have the time or structure to promote it properly, WingWoman provides thoughtful support without the weight or cost of a full PR and marketing agency. It’s for those busy building something who want someone experienced in their corner helping shape their narrative, identify opportunities, and represent them in the right conversations.

 

Do you feel like there are growth levels to your personal brand or business that you can’t dedicate the time to unlock?

 

Send us a message and let us show you how we can help.

📆 What’s Happening?

Family Fun!

🛠️ Maker Weekend at WCM

Sat.-Sun., May 16-17 | Westchester Children's Museum, Rye | 9:30a-5:30p | Regular admission

 

A weekend of hands-on making and creative projects at the museum, with a special highlight on Saturday at 3p: a student Fashion Show presented by Sew Fun 4 Kids, showcasing original designs from their Fashion and Design Sewing program.

 

Sat., May 16 | The Good Witch Coffee Bar, Hastings-on-Hudson | 10a-12p | Free

 

The Good Witch in Hastings and the Francie Malina Team are pairing up for a free pop-up petting zoo Saturday morning in Hastings. It’s the perfect pause button for what’s sure to be a busy weekend, so come get caffeinated while the kids get some cuddle time.

 

Sat., May 16 | FDR State Park, Yorktown Heights | 10a-1p | Check the link above for entry details

 

Walk the trails with your dog and browse the vendor village at Westchester's biggest animal event of the year, with an agility playground, food trucks, kids' activities, live music, and adoptable animals on site. Proceeds support SPCA Westchester.

 

Sat., May 16 | Memorial Plaza, Pleasantville | 10a-3p | Free

 

Pleasantville's annual community celebration fills Memorial Plaza with games, rides, activities, and local vendors for an afternoon of family-friendly fun in the heart of the village.

 

Sat., May 16 | Chilmark Park, Briarcliff Manor | 11a-4p | Free

 

This free spring festival combines pickleball play with live music from Dan Zlotnick, School of Rock Briarcliff Manor, and the Barn Vultures, plus food trucks, Captain Lawrence beer, and a full Kids' Zone with goats, crafts, a bubble show, and soft play.

 

Sun., May 17 | Joseph F. Fosina Field, New Rochelle | 4p | $13+

 

New York Gridlock, Westchester’s professional women’s ultimate frisbee team, hosts the Philly Surge in their final home game of the season. With championship weekend implications on the line, Gridlock controls its own destiny heading into this matchup. Come down early for a youth clinic (ages 9–18) starting at 2p, with Gridlock players joining throughout the afternoon and halftime field access for participants. Other local pro teams, including Westchester SC and the NY Empire, will also be part of the day. Loving Westchester readers can grab discounted tickets at the link above.

 

 

Grown Ups & Date Nights

Fri., May 15 | Rory Dolan's Restaurant & Bar, Yonkers | 7-9:30p | $35.98+

 

Hard Headed Comedy hosts a stand-up night at Rory Dolan's benefiting Sunflower of Westchester, a nonprofit supporting foster children and young adults aging out of the foster care system. The lineup features Dara Jemmot, Feraz Shere, Calvin Cato, and Luz Michelle.

 

Sat., May 16 | Captain Lawrence Brewing Company, Elmsford | 1-6p | Free entry, $20 beer pass

 

Captain Lawrence marks two decades of brewing with a free entry outdoor celebration featuring food, live music, vendors, and kids' activities. An optional beer pass includes unlimited pours, commemorative pint glass, and entry into a golden ticket giveaway for free beer for a year.

 

Sat., May 16 | Harvest Moon Farm & Orchard, New Salem | 5-9p | $15

 

A live 90s cover band brings the nostalgia to the orchard, with crepe and hot dog trucks, permanent jewelry, and a photo booth rounding out the retro atmosphere. Ticket includes one token redeemable for a pint of beer or cider, or a kids' train ride.

 

Sat., May 16 | Tre Angelina, White Plains | 8p | $28.52

 

Netflix and Late Late Show comic Fabrizio Copano headlines alongside Jessica Brodkin (AMC, TruTV), Ryan Heilman, Tom Kelly (ABC), and Ben Rosenfeld (SiriusXM) in Tre Angelina's private room in White Plains.

 

Sun., May 17 | Hemato Institute, Katonah | 11a-12p | $44.52

 

Explore brewed green tea, matcha, and whole leaf preparations in this hands-on workshop, with a small dessert pairing, a matcha whisking demo, and a black matcha latte tasting. A gentle and delicious morning at the Hemato Institute.

 

Sun., May 17 | Hudson Valley Writers Center, Sleepy Hollow | 6:30p | $10 suggested

 

Sleepy Hollow Arts Collective presents an evening of songs, poetry, dance, and performance exploring motherhood across all its phases, featuring Jessica Carmen Courtney, Stephanie Granade, Katie Klaus, Nina Pajak, Giverny Petitmermet, Allie Scherich, and Rebecca Thomas.

 

 

The Beat… Westchester’s Live Music Scene

 

Featured Gig

 

Tue., Sep. 22 | The Capitol Theatre, Port Chester | 8p | $95+

 

The Who's legendary frontman brings an intimate solo show to The Cap, blending classics, rarities, and solo favorites backed by a semi-acoustic rock band, with storytelling from one of rock's icons woven throughout. Tickets are available from May 15.

Thanks to our partner, QueenBPoker!

 

Go All In and Host Your Own Game Night

 

Whether it’s a casual poker home game, a corporate celebration, a beginners' poker evening or a night that gives back, QueenBPoker comes to you and delivers unforgettable poker and gaming experiences right in your home, venue or business.

No experience or equipment needed; we’ll teach, host, and handle every detail.

 

 

Sat., May 16 | Stamford Museum & Nature Center Planetarium, Stamford, CT | 9p | $12+

 

Taylor Swift’s hits fill the planetarium dome in a fully immersive laser and light show, transforming the space into a visual concert experience. A fun Saturday night out for Swifties of all ages (6+).

 

Sun., Dec. 6 | Palace Stamford, Stamford, CT | 2p | $39+

 

Mark your calendars. Blippi and Meekah are joined by live musicians to explore sounds, rhythms, and instruments through all the favorite Blippi hits in this brand-new interactive show. Tickets are available from May 15.

🏡 Where the Heart Is

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

 

Behold, 16 Lewis Road. Known as Villa Keen, this 5-bedroom, 6-bathroom, 3,502 square foot Mediterranean-style estate was built in 1929 on 2.43 acres in Irvington, and its guest list over the decades is an old-school Hollywood who’s who. Lloyd Stratton, former president of the Associated Press, once called it home. So did Robert Wright, producer of the Carol Burnett Show. And most notably, Academy Award-winning actress Shirley Jones, Tony Award-winning actor Jack Cassidy, and their son Shaun Cassidy all lived here during the property's heyday. The bones of that history are still present… the original Chesney fireplace mantle, a Schonbek Austrian crystal chandelier, Mackenzie-Childs fixtures, and a stately oak library are all intact. The grand dining room, formal living room with fireplace, and a private courtyard entered through 15-foot stained glass gates give the home a scale that's genuinely hard to find. There's also a pool, a pool house, and hardwood floors throughout. The property sits on a quiet dead-end street with updated systems, and there's room to put your own stamp on it while preserving everything that makes it one-of-a-kind.

 

Thanks for reading Loving Westchester!

 

We love to hear from you! Give us a shout at [email protected] or reach us on Instagram @lovingwestchester. And don’t forget to forward this on to a friend who’s always asking “what’s going on this week?”

 

Until next time,