Westchester's 250th Happenings and Getaway Giveaway
- Hudson Valley Happenings
- 2 days ago
- 9 min read
If there were ever a summer to explore Westchester, this is it.
As America celebrates its 250th anniversary, Westchester is coming alive with Revolutionary War reenactments, live readings of the Declaration of Independence, museum exhibitions, concerts, festivals, and unforgettable experiences stretching from White Plains to Katonah and beyond. To celebrate, we're partnering with some of Westchester's favorite destinations to give one lucky winner the ultimate America 250 getaway.
One lucky winner will receive the ultimate Westchester getaway, valued at more than $1,700, including a two-night stay at Sonesta White Plains Downtown, four tickets to Caramoor with a private Rosen House tour, four tickets to the Pleasantville Music Festival to see Ok Go, Old 97's, The Fixx, Yola, and more live, dinner for two at Freebird Kitchen & Bar, and dinner for two at Hudson Grille. Whether you're a history buff, music lover, foodie, or simply looking for an unforgettable summer escape, this giveaway is your chance to experience one of New York's most exciting anniversary celebrations.
Voices of We the People:
Reading of the Declaration of Independence
Two hundred and fifty years ago, one of the earliest public readings of the Declaration of Independence in New York took place from the steps of the courthouse in White Plains, where one of New York's earliest public readings of the Declaration took place during the birth of the new state, breaking from Britain as part of the new nation taking shape. In the weeks that followed, its words were carried across America and read publicly so citizens could hear the news of independence for themselves. On July 11, visitors can experience that history during Voices of We the People: Reading of the Declaration of Independence at White Plains & the Birth of New York State, commemorating one of the most significant moments in Westchester's Revolutionary story.
Hosted by the White Plains Historical Society, the event recreates the public reading that took place in White Plains during the summer of 1776, when New Yorkers first gathered to hear the Declaration and celebrate the colony's break from British rule. More than a reenactment, it's an opportunity to stand where history unfolded and reflect on the words that helped shape the nation.
The event is featured as part of Rooted in Westchester, a countywide initiative that connects Westchester County's Revolutionary history to the present day. Through Visit Westchester County, visitors can explore curated stories, Revolutionary landmarks, museums, exhibitions like Art in a Season of Revolution at ArtsWestchester, and an interactive calendar filled with America 250 events taking place throughout the year.
The celebration culminates with REV FEST 250 on October 24 and 25 at Ward Pound Ridge Reservation. The weekend will feature a large-scale Battle of White Plains reenactment, Revolutionary War encampments, demonstrations, music, food, and family-friendly activities, bringing one of the most important chapters of America's fight for independence back to life just miles from where it originally unfolded.
Westchester's history isn't just something you read about. It's something you celebrate. And this summer, there's plenty to celebrate.
At a Glance
July 12, 2026
11:30 AM Revolutionary Parade
Renaissance Plaza → American Legion Post 135
12:00 PM Reading of the Declaration of Independence
American Legion Post 135, 57 Mitchell Place
1:00 PM Wreath Laying at the DAR Monument
Armory Plaza (Site of the Original Courthouse)
1:30–5:00 PM Colonial Village Experience
Tibbets Park (between Main St. & Hamilton Ave.)
Admission: Free
Instagram: @rootedinwestchester - @westchestercountytourismny
Website: visitwestchesterny.com/250
The Pleasantville Music Festival
OK Go, Old 97's, The Fixx & Yola Take Over Pleasantville
On Saturday, July 11, the Pleasantville Music Festival returns to Parkway Field for its 20th anniversary, bringing together national touring acts, local talent, food, drinks, crafts, and thousands of music fans for one of Westchester's biggest summer traditions. And we're giving away four tickets to experience the festival firsthand.
This year's edition of New York's Backyard Jam spans decades, genres, and generations. OK Go headlines the Main Stage with the inventive energy and unforgettable songs that made them one of the most recognizable bands of the last two decades. Old 97's bring three decades of alt-country swagger, while The Fixx arrive with classics including "One Thing Leads to Another," "Saved by Zero," "Stand or Fall," and "Red Skies." Over in the Chill Tent, Yola's powerhouse vocals and genre-blending sound make her one of the festival's must-see performances.
The lineup runs deep. Brooklyn garage-rock favorites The Thing headline the Party Stage, while The Vindys bring their blend of rock, soul, and pop to the Main Stage. Local and regional acts including The Speakers, Similar Kind, Two-Man Giant Squid, Round Trip featuring Lara Cwass, Ari Hest, Dream Street, and Way Behind The Sun ensure there's always another set worth catching. With 14 acts across three stages, the day is filled with opportunities to discover your next favorite band.
Beyond the music, Pleasantville has built its reputation on the full festival experience. Food vendors, beer, wine, cider, a Kids Fun Zone, community organizations, an inclusion initiative, and a zero-waste mission all help create an atmosphere that feels distinctly Westchester. Children 11 and under are admitted free with a ticketed adult, making it just as enjoyable for families as it is for lifelong music fans. Whether you're entering to win or buying your own tickets, it's one of the best summer days Westchester has to offer.
At a Glance:
Prize: Four tickets to the Festival
Saturday, July 11, 2026
Pleasantville Music Festival
Parkway Field, Pleasantville, NY
Gates Open: 11:30 AM
Music Begins: 12:30 PM
Headliners: OK Go • Old 97's • The Fixx • Yola • The Thing
Also Performing: The Vindys • The Speakers • Dream Street • Ari Hest • Round Trip featuring Lara Cwass • Similar Kind • Two-Man Giant Squid • Way Behind The Sun
Food vendors • Craft vendors • Beer, wine & cider • Kids Fun Zone
Good to Know:
Family-friendly event
Children 11 and under are free with a ticketed adult
Free parking and shuttle service available from Pace University
Instagram: @Pvillemusicfest
Website: www.pleasantvillemusicfestival.com
Caramoor
A Summer Tradition Celebrating Music, History, and America's 250th
As communities across the country celebrate America's 250th anniversary, Caramoor is joining the celebration with a week of special programming that blends music, history, and culture across its beautiful estate.. From June 28 through July 5, Caramoor Commemorates America at 250 features performances honoring the nation's rich musical traditions, making it the perfect time to visit the estate.
Set across 81 acres of gardens, woodlands, and historic architecture in Katonah, Caramoor has welcomed audiences since 1945 and remains one of the region's premier summer performance venues. The 2026 season features more than 30 performances spanning Broadway, classical, jazz, opera, roots, chamber music, and contemporary artists, including Kelli O'Hara, Isaac Mizrahi, Hélène Grimaud, the American Roots Music Festival, the Caramoor Jazz Festival, and more.
As part of this giveaway, one lucky winner will receive four tickets to the Caramoor performance of their choice* along with a private tour of the historic Rosen House, a Mediterranean-style villa listed on the National Register of Historic Places and filled with remarkable art, antiques, and treasures from around the world. Together, they offer a chance to experience both Caramoor's celebrated performances and the history at the heart of the estate.
Whether you're spreading out a picnic on the lawn, strolling the gardens, or enjoying dinner before the show, Caramoor makes it easy to spend an entire day on the property. Guests are welcome to bring their own picnic or pre-order gourmet picnic boxes and artisanal cheese boards, while the Bravo Bar and rotating lineup of local food vendors offer everything from wine and cocktails to barbecue, pizza, sandwiches, cheese boards, and ice cream. It's the perfect excuse to discover why Caramoor has become one of Westchester's most treasured summer destinations.
At a Glance:
Prize: Four tickets to the Caramoor performance of your choice* and a private Rosen House tour
June 28 – July 5, 2026
America at 250 Programming:
Caramoor
149 Girdle Ridge Road, Katonah, NY
2026 Highlights: 30+ performances • Kelli O'Hara • Isaac Mizrahi • Hélène Grimaud • American Roots Music Festival • Caramoor Jazz Festival • Broadway • Classical • Jazz • Opera • Chamber Music
Amenities:81-acre estate • Gardens • Historic Rosen House • Gourmet picnic pre-orders • Bravo Bar • Local food vendors
Instagram: @caramoor
Website: caramoor.org
*Performance selection is based on availability. Some restrictions apply.
Arts Westchester
Art in a Season of Revolution
As America marks 250 years since the signing of the Declaration of Independence, one of Westchester's most thought-provoking anniversary events isn't happening on a battlefield. It's happening inside a gallery.
Now through August 2, ArtsWestchester in White Plains presents Art in a Season of Revolution, a major exhibition inviting artists to explore what the American experience has meant over the past two and a half centuries and what it means today. Created in partnership with the Katonah Museum Artists' Association and the American Medallic Sculpture Association, the exhibition brings together paintings, sculpture, and mixed-media works that examine freedom, identity, democracy, culture, and the ongoing evolution of the nation.
Rather than looking at the Revolutionary War through a traditional historical lens, the exhibition asks artists to respond to the ideas that emerged from that era and how those ideas continue to shape life in America today. The result is a collection of work that connects the country's founding story with modern perspectives, creating conversations that feel just as relevant now as they did 250 years ago.
Located inside ArtsWestchester's historic gallery space in downtown White Plains, the exhibition offers visitors a chance to experience a different side of the America's 250 celebration. While many commemorative events focus on reenactments and historical sites, Art in a Season of Revolution explores the anniversary through creativity, interpretation, and contemporary voices.
Whether you're an art lover, a history enthusiast, or simply looking for a unique way to experience Westchester's Revolutionary War anniversary programming, this exhibition offers a fascinating look at how artists are interpreting one of the most significant milestones in American history.
At a Glance:
May 16 – August 2, 2026
ArtsWestchester
31 Mamaroneck Avenue White Plains, NY
Gallery Hours: Wed - Fri: 12 PM – 5 PM, Saturday: 12 PM – 6 PM, Sunday: 12 PM – 5 PM
Admission: Free
Instagram: @artswestchester
Website: artswestchester.org
Freebird Kitchen & Bar
The Rooftop, the Bourbon, the Fried Chicken
Fried chicken, bourbon, rooftop cocktails, and a table full of Southern comfort food. Freebird Kitchen & Bar has become one of downtown White Plains' favorite places to settle in for a great meal. As part of this giveaway, one lucky winner will enjoy lunch or dinner for two at this lively local favorite.
The kitchen turns out everything from crispy fried chicken and smoked wings to shrimp and grits, fresh seafood, burgers, steaks, and seasonal specials, while the bar backs it all up with an impressive bourbon collection, handcrafted cocktails, local beer, and wine. Whether you're stopping in for brunch, happy hour, or dinner, there's always something happening.
When the weather cooperates, the rooftop becomes one of the best places in White Plains to settle in for the evening. Good food, strong drinks, live energy, and a downtown location that's easy to make a night out of. It's exactly the kind of restaurant you hope to stumble across on a weekend getaway, except now you already know where to go.
At a Glance:
Prize: Dinner for Two
Freebird Kitchen & Bar
161 Mamaroneck Avenue White Plains, NY 10601
Instagram: @freebirdkitchenandbar
Website: freebirdkitchenandbar.com
Hudson Grille
An Elevated Night Out in Downtown White Plains
For more than 15 years, Hudson Grille has been one of downtown White Plains' go-to restaurants for everything from casual lunches to celebration dinners. As part of this giveaway, one lucky winner will enjoy dinner for two at Hudson Grille, one of downtown White Plains' longtime favorites for contemporary American cuisine, handcrafted cocktails, and an atmosphere that's just as suited for a casual night out as it is for a special occasion.
Since opening in 2010, Hudson Grille has become a staple of the city's dining scene. The menu covers everything from fresh seafood, steaks, and house-made pastas to brick oven pizzas, burgers, salads, and chef-driven seasonal specials, making it easy for everyone at the table to find something they'll love. Pair it with a signature cocktail, a glass of wine, or something from the extensive beer selection, and you've got all the ingredients for a memorable evening.
The beautifully designed dining room, year-round outdoor patio, and lively bar give the restaurant a polished but welcoming feel, whether you're settling in for a leisurely dinner or celebrating the perfect end to a day exploring Westchester.
At a Glance:
Prize: Dinner for Two
Hudson Grille
165 Mamaroneck Avenue White Plains, NY
Instagram: @hudsongrilleny
Website: hudsongrilleny.com
Sonesta White Plains Downtown
Your Home Base for the Ultimate Westchester Getaway
Every great getaway needs a great place to stay. As part of this giveaway, one lucky winner will enjoy a two-night stay at Sonesta White Plains Downtown, putting them right in the heart of Westchester's America 250 celebration.
Fresh from a complete renovation, Sonesta White Plains Downtown combines modern guest rooms with thoughtful amenities, including an indoor heated pool, a 24-hour fitness center, and on-site dining at Whisk Restaurant and Mix Bar & Kitchen. Its downtown location also means restaurants, shopping, entertainment, and many of the destinations featured in this giveaway are just minutes away.
Whether you're spending the day exploring Revolutionary history, taking in a concert at Caramoor, or enjoying dinner in downtown White Plains, Sonesta offers the perfect place to recharge before doing it all again the next day. It's the ideal home base for experiencing everything Westchester has to offer.
At a Glance
Prize: Two-Night Stay
Sonesta White Plains Downtown
66 Hale AvenueWhite Plains, NY 10601
Amenities:
Indoor heated pool • 24-hour fitness center • On-site dining • Walkable downtown location
Instagram: @sonestahotels
Website: sonesta.com
Two-night stay is based on availability. Holidays and holiday weekends are excluded. Prize must be redeemed within one year.
Spend the weekend where history was made, discover incredible music, enjoy unforgettable meals, wander world-class gardens and galleries, then unwind in the heart of downtown White Plains. America's 250th anniversary only happens once, and there has never been a better time to experience everything Westchester has to offer.
Enter below for your chance to win this unforgettable Westchester getaway.
