🎆 This Weekend in Westchester: Our Biggest Events Calendar Yet

American Roots Music Festival

Sat. Jun 28 | Katonah | Caramoor | Details

Caramoor’s annual American Roots Music Festival features six acts rotating on four stages spread throughout its beautiful grounds. Concerts kick off with Grammy-winning Westchester local Rebecca Haviland at 12.30p and end with The Rumble ft. Chief Joseph Boudreaux Jr. at 6p who Caramoor describes as “a blend of traditional Mardi Gras Indian music with the irresistible groove of a funky brass band” with many more in between! Tickets are $63 for adults, $19 for children and can be purchased directly from Caramoor.

Mamaroneck Firemen’s Carnival

Thu. Jun 26-Sat. Jul 5 | Mamaroneck | Harbor Island Park

Check out the Firemen’s Parade Friday night at 7p and then get back down to the park for your fill of rides, games and carnival fare. Wristbands for unlimited rides are $35 and are available every night except July 4th.

Fireworks Night

Sat. Jun 28 | Pound Ridge | Pound Ridge Town Park | Details

Pound Ridge hosts its annual fireworks celebration on Saturday with celebrations starting at 4.30p. Food trucks will be on site with live music keeping you entertained until the fireworks start. The event is free, but heavy attendance is expected, and parking permits are required.

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🚲 Bicycle Sundays

Sun. Jun 29 | Bronx River Parkway | Westchester County Parks | 8a-12p

After last weekend’s rainout, Bicycle Sundays on the Bronx River Parkway is scheduled for Sunday, Jun 29th. Some rain is expected in the very early hours of Sunday but looks like it’ll clear well before the 8a opening time for non-motorized bicyclists, scooters, in-line skaters, walkers and joggers. Admission is free.

🎇 Firefly Festival

Fri. Jun 27 | Cross River | Ward Pound Ridge Reservation | 6.30-9.30p | Details

We recommended this one for your family in our Tuesday edition, but here’s your reminder to grab tickets to this magical, little evening featuring kids shenanigans, firefly specialists, Captain Lawrence, Stonefire Pizza, and American Swirl Soft Serve! Tickets $15 per person, kids 2 and under free.

🍄 Movies on the Trail: The Super Mario Bros. Movie

Fri. Jun 27 | Dobbs Ferry | Old Croton Aqueduct | 8.30p | Details

This evening, grab a blanket and head to the east lawn of the Keeper’s House in Dobbs Ferry for some peaches, peaches… peaches, peaches, peaches (that’s one for the kiddos…). But seriously, visit for what has quickly become a family favorite under the stars, The Super Mario Bros. Movie.

Bring your own snacks, drinks, and cozy setup. It’s a free, all-ages event that’s perfect for kicking off a summer weekend. And why not make it a movie double header? Head to Valhalla the following night for Despicable Me 4. (Full listing below.)

⭐ Screenings Under the Stars: Despicable Me 4

Sat. Jun 28 | Valhalla | Kensico Dam Plaza | Entertainment from 5p, Movie at sundown | Details

Westchester County Parks and Sharc Creative present this year’s Screenings Under the Stars series, kicking off with the brand-new Despicable Me 4 (PG). Enjoy a summer night with pre-movie entertainment, food vendors, and Gru’s latest misadventures under the open sky. Bring a blanket, a folding chair, and your best villain laugh.

Admission and parking are free (Westchester residents only). Event will take place rain or shine (except in severe weather).

🍎 Outhouse Orchards Summer Nights: Bubble Bus

Sat. Jun 28 | North Salem | Outhouse Orchards | 6-9p | Details

Think Ibiza foam party but with less techno and more toddler, and instead of the east coast of Spain, you’re in a Westchester orchard.

The Bubble Bus rolls into Outhouse Orchards to unleash thousands of floating bubbles for a memorable evening of pure kid joy. Add a balloon artist (6–8p), bounce houses, hayrides, a full taproom, food, and ice cream, and you’ve got a night ‘kids’ of all ages won’t forget.

Gates open at 5p. North Salem will be poppin’... (I had to!).

Tickets $11.29, kids 2 and under free.

🍕 New slice on the block: Frankie's Pizza & Pasta

Sat. Jun 28 | Briarcliff Manor | 10.30a Ribbon Cutting, 11a-2p

Frankie's is opening in Briarcliff and making it a proper party.

Expect fun and treats for the whole fam with free Italian Ice with any purchase, fire truck tours with the Briarcliff and Ossining Fire Departments, raffles, giveaways, desserts from Fleetwood Bakery, and a special visit from Captain America himself.

🎨 Arts Westchester Arts Mobile visits Westchester Children's Museum

Sun. Jun 29 | Rye | Westchester Children’s Museum | 3.30-5.30p

Craft and create outside the museum with Arts Westchester Arts Mobile.

In case of rain, activities will be moved inside.

📺 Eat My Shorts, White Plains: The Simpsons Installation

Now on display | White Plains | YWCA | Catch it while you can

Springfield has landed in Westchester! Bigger-than-life Simpsons characters are posted up outside the YWCA in White Plains, and they're drawing plenty of double takes. If you’re a fan of Bart, Marge, Homer, and the gang or just want to snap a fun summer photo, swing by before they vanish like a Squishee on a hot day.

🍓 Saturday Farmers’ Markets

• Bronxville | 8.30a-1p | Stone Place at Paxton Avenue

• Chappaqua | 8.30a-1p | Chappaqua Train Station

• Hastings | 8.30a-1p | Parking lot opposite Metro North station

• Larchmont | 8.30a-1p | Metro North Upper Parking Lot

• Ossining | 8.30a-1p | Parking Lot at Spring & Main

• Peekskill | 9a-2p | 1 Bank Street

• Pleasantville | 8.30a-1p | Metro North Parking Lot

• Tarrytown & Sleepy Hollow | 8.30a-1.30p | Patriots Park

🍓 Sunday Farmers’ Markets

• Irvington | 9a-1.30p | 101 Main Street

• Mount Kisco | 11a-3p | S. Moger Avenue

• Rye | 8.30a-1p | Theodore Fremd Ave Parking Lot

• Scarsdale | 9a-2p | Spencer Place at Chase Road

🎬 Peekskill Film Festival

Fri. Jun 27-Sat. Jun 28 | Peekskill | Paramount Hudson Valley Theatre | Fri: 6p, Sat: 10a | Details

Celebrate a decade of independent cinema at the 10th Annual Peekskill Film Festival! Held at the historic Paramount Hudson Valley Theater, this milestone weekend features award-winning shorts, features, documentaries, and innovative animation.

Whether you're a filmmaker, a film buff, or just love a great story, this is your chance to experience bold storytelling and creativity. Tickets range from $15-25 with a 2-day ticket for $35 and can be purchased at the link above.

🍎 Outhouse Orchards Dinner Series

Fri. Jun 27 | North Salem | Outhouse Orchards | Cocktails 6.30p / Dinner 7-9p | Details

Dine under the stars at this open-flame feast nestled in the orchards of North Salem. Created in partnership with Village Social and Chef Michael Lucente, the evening features a seasonal four-course meal cooked over a fire pit… NY strip steak, porchetta, shrimp skewers, fresh summer salads, whipped feta, dessert, drinks, and more.

It’s local, family-style, and limited to just 50 platters, so don’t sleep on it. Views, vibes, and vanilla ice cream (with cinnamon streusel topping).

🎭 Comedy From Scratch

Sat. Jun 28 | Larchmont | The Idea Kitchen, 1940 Palmer Ave. | 8p

This twice-monthly series brings comics from SNL, Netflix, and HBO to Larchmont for longer, unfiltered sets you won’t hear anywhere else. June 28 features the brilliant Kendra Cunningham (Last Comic Standing, SNL) and Natan Badalov (Adult Swim, Chosen Comedy Fest), hosted by local legend Ben Asher.

BYOB and snacks, and enjoy a night of big laughs with no drink minimum and free parking.

👮‍♂️ Party With the Police: BBQ & Pool Party

Sat. Jun 28 | Purchase | Location Upon RSVP | 11a-4p | Details

“Party With the Police” is a fundraising event in its 4th year hosted by the Nick Loeb Foundation in an effort to cover college expenses for local law enforcement families. This year’s party will feature Mets & Yankees alums: Jim Leyritz, Dwight Gooden, Mookie Wilson, Howard Johnson, Ray Negron & Roy White with the BBQ overseen by celebrity chef David Burke. Individual tickets $250, VIP ticket (celeb baseball game participation) $450.

⚾ Bernie Williams in Concert

Sat. Jun 28 | Millbrook, NY (Dutchess County) | Millbrook Winery | 6p | Details

Before Chisholm Jr., the most notable “Jazz Yankee” was Bernie Williams. The 5x All-Star, 4x World Series champion and career .297 hitter has carved out an impressive post-baseball career in the jazz music scene, earning himself a Latin Grammy nomination. Bernie takes his musical talents to Millbrook Winery this Saturday for a concert at the vineyard. Tickets start at $70.

Plenty of chances to check out live music across Westchester this weekend. Check out our list below so you don’t miss a beat!

• Yonkers Waterfront Live: Las Guaracheras | Fri. Jun 27 | Waterfront Amphitheatre, Yonkers | 6.30-8p [FREE]

• Friday Night River Jam: 1 Wild Night | Fri. Jun 27 | Waterfront Park, Dobbs Ferry | 7p [FREE]

• Troy Ramey (The Voice) | Fri. Jun 27 | Irvington Theatre | 7.30p

• Daniil Trifonov | Fri. Jun 27 | Caramoor | 7.30p

• Legends of Country Rock ft. Pure Prairie League, Firefall & Richie Furay | Fri. Jun 27 | Tarrytown Music Hall | 8p

• Al Di Meola | Sat. Jun 28 | Tarrytown Music Hall | 8p

• Rumours ATL (Fleetwood Mac Tribute) | Sat. Jun 28 | The Capitol Theatre, Port Chester | 8p

• Westchester Songwriters’ Circle | Sat. Jun 28 | Bethany Arts Community, Ossining | 8-9.30p

• 107.1 The Peak Summer Sessions: Lamont Landers | Sun. Jun 29 | Barley Beach House, Rye | 6p [FREE]

***All live music events require tickets unless noted as [FREE]

⏰ Ticket Alert

The Capitol Theatre announced that 2x Grammy-winning rock group Cage The Elephant are coming to Port Chester on Tuesday, October 28th and Wednesday, October 29th. Tickets are on sale today, Friday, June 27th at 10am through Ticketmaster.

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