Earlier this year, I published a comprehensive guide to vintage festivals and 1920s-themed events in 2025, a calendar filled with glittering celebrations that transport us to the golden age of jazz, swing dance, and Art Deco glamour. Among the highlights, I featured three standout events that have earned international acclaim for their elegant and immersive throwbacks to the Roaring Twenties: the Art Deco Festival in Napier, New Zealand, the Jazz Age Lawn Party on Governors Island in New York, and the Roaring Twenties Lawn Party at the Crane Estate in Ipswich, Massachusetts.
In previous blog entries, I took you deep into the heart of the Napier Art Deco Festival, an awesome celebration set against the backdrop of one of the world’s most intact Art Deco cities. I also explored the magic of Governors Island’s Jazz Age Lawn Party, where thousands gather in the shadow of Manhattan to swing and sip cocktails like it’s the 1920s. These events, each in their own way, offer a extraordinary lens into the timeless charm and cultural rebirth of the Roaring Twenties.
Now, it’s time to turn our attention to Castle Hill on the Crane Estate, a breathtaking coastal mansion where the Roaring Twenties come alive in the most spectacular fashion. Many of our La Vie Delight customers have shared photos and enthusiastic stories of the Roaring Twenties Lawn Party when they participated in their Roaring Twenties fashion outfits in earlier versions of this event. So, I felt compelled to write a blog about this one-of-a-kind event too.
This blog will take you inside one of the most beloved vintage gatherings in the United States, a weekend where flappers, jazz musicians, and vintage enthusiasts from all walks of life gather on the grand lawns for dancing, fashion, music, and history. Whether you're a seasoned vintage enthusiast or newly curious about the Jazz Age revival, the Roaring Twenties Lawn Party at the Crane Estate promises an unforgettable step back in time. Let’s explore the story behind this stunning event.
Stepping on the Grand Allée up to Castle Hill
This year’s Roaring Twenties Lawn Party will take place on August 2-3. Again, thousands of Roaring Twenties enthusiasts will arrive at the Crane Estate in fringed flapper costumes, sports dapper suits, cloche hats, and pearls, stepping into a living, breathing homage to the sparkling heyday of the Jazz Age. Hosted by Boston Swing Central in partnership with The Trustees of Reservations, this two-days festivity will transport guests across a century, making them feel like stepping into a Jazz Age film.
The roots of the Lawn party date back to 2013. Inspired by the Jazz Age Lawn Party on Governor’s Island, the founder of Boston Swing Central – Mike Hibarger – envisioned the idea of creating an own version at Castle Hill. The thought was to honor Lindy Hop and swing dance cultures in a setting reminiscent of the Jazz Age. The Crane Estate, under Trustees care since 1949, provided the perfect setting – landscaped terraces and a stylish Casino building echoing early 20th-centure atmosphere. The setting, historical connections, and swing dance community amalgamated to give birth to a one-day happening of live music, dancing, and vintage style.
Since its inception, the event has evolved from a modest one-day swing dance get-together into a two-day extravaganza. Guest counts have reached over 3,000, justifying an expanded format and extensive themed programming. The event now includes Italian Garden afternoon teas, expanded food and beverage offerings, poetry brothels, vintage fairs, and the exclusive Crane VIP experience with private tents and mansion roof tours.
Reimagine the Jazz Age for a Better Future
Over the years, the Roaring Twenties Lawn Party has grown into far more than just a festive vintage celebration. It’s a dynamic, evolving event that continues to reinvent itself while remaining firmly rooted in the spirit of the Jazz Age. Behind the scenes, the organizers have put a great deal of passion and dedication into shaping an experience that has real cultural weight – not just a glamorous fancy dress party, but a meaningful moment of reflection and celebration. They've worked hard to give the event a sense of gravitas, and in the last couple of years, that mission has taken on a new level of relevance.
With the arrival of a new 1920s, the team behind the Lawn Party recognized the opportunity—and the responsibility—to redefine what the “Roaring Twenties” means today. Their "Reimagine the Jazz Age" campaign marks a thoughtful pivot. It acknowledges the joy and elegance of the original era while confronting the social inequalities and cultural exclusions that also defined it. Through this lens, the event embraces inclusivity and diversity, using the glamour of the past as a canvas for more conscious storytelling.
As the United States – and indeed much of the world – navigates a new decade filled with its own social divisions and cultural reckonings, the Roaring Twenties Lawn Party invites attendees to take a step back and draw parallels between the 1920s and the 2020s. What are the echoes we hear today? What aspects of the past still charm us, and what must we reimagine for a better future?
The event has started weaving these questions into its programming, offering panel discussions, classes, and thoughtful conversations for those keen to engage more deeply. For guests looking to go beyond the Lindy Hop and champagne, there’s an opportunity here to reflect on history with fresh eyes – and perhaps carry a bit of its wisdom into the present.
Dazzling Jazz, Dances and Performances: Bring the Party to Life
At the heart of the Roaring Twenties Lawn Party is the energetic pulse of Jazz music – a sound that defined the 1920s era and continues to delight a century later. The Lawn Party channels this energetic pulse, creating a living, breathing homage to the music that made the 1920s roar.
One of the most delightful aspects of the Lawn Party is how organically the music pops up into every corner of the event. Bands rotate across the Crane Estate property throughout the day, creating a musical voyage as you explore the event. One moment you may find yourself enjoying a polished orchestra like the Baby Soda Jazz Band at the main stage, and the next you’re picnicking with other guests while a three-piece ensemble delivers a pleasant afternoon set nearby. The ever-changing rhythm keeps the atmosphere lively and joyfully unpredictable, just like jazz itself.
Ultimately, the music at the Roaring Twenties Lawn Party is far more than background entertainment – it’s the soul of the event. Whether you're a seasoned jazz devotee or simply swept up in the mood of the day, the music ensures that every guest, at least for a moment, can feel what it is to truly live in the Roaring Twenties.
This year 2025, the Roaring Twenties Lawn Party brings again an unforgettable music experience to the scenic grounds surrounding the Crane Estate, with a dynamic lineup that will turn every corner of the property into a performance space. The event will offer live music not just on the Main Stage and the Casino Stage, but also in more intimate corners like the Italian Garden and throughout the Vintage Fair, ensuring that wherever you stroll, you are never far from the captivating rhythms of the Jazz Age.
At the heart of the weekend’s musical magic are the Baby Soda Jazz Band, the enchanting Tamar Korn, and the soulful Gordon Webster. The Baby Soda Jazz Band is a beloved fixture at the Lawn Party since its inception. Their cheerful, vintage-rooted sound will once again take center stage. Tama Korn has become a cherished part of the event’s identity as well. Her vocal stylings – equal parts nostalgic and fresh – will again transport listeners straight back to the prohibition era. Gordon Webster, who is renowned for leading one of the most popular swing bands and celebrated internationally as a top name in the swing dance world, will set the tone for an event built on joy, rhythm, and connection.
The KS Swinglet will bring the vibes you won't want to miss. Led by Kevin Sihlanick, this band is comprised of local Boston musicians who love playing jazz music for swing dancers, music lovers and lovers of the vintage era. You ears are in for a treat. The Castle Hill Hot 6, another Boston's swing band and consisting of local musicians and dancers, will delight the audience with upbeat hot Dixie jazz and dance music of the 1920s. And with even more musicians and surprise guest performers rounding out the schedule, the Roaring Twenties Lawn Party will once again prove that the jazz revival is not just alive, but thriving.
In addition to the incredible lineup of musicians and bands, the Roaring Twenties Lawn Party will feature live performances and dance showcases throughout the estate – not only on the central stages but also in scenic spots like the Italian Garden and along the 2nd Allee. These performances bring the vintage atmosphere to life with dynamic renditions of Lindy Hop, Charleston, and vernacular jazz dance, offering lively energy and period-accurate flair across the grounds. Dancers will entertain and inspire with routines that honor the movement and rhythm of the 1920s, making every corner of the Crane Estate feel like a stage from a bygone era.
Activities, Experiences and Immersive Fun
The Roaring Twenties Lawn Party is more than a vintage-themed gathering – it’s a full-on immersive experience, packed with activities that completely transport the guests to the heart of the 1920s. While the dazzling music and vintage attire set the stage, it’s the interactive elements what truly revive the spirit of the Jazz Age in every detail. From dancing and parading to lawn games and playful contests, there’s truly something for every lover of the Gatsby-era.
A highlight of the event – and a favorite for first-timers and seasoned dancers alike – are the swing dance lessons held on custom-built wood dance floors laid out across the main lawn. These open-air classes provide an inviting way to learn the fundamentals of Lindy Hop and Charleston, giving participants the confidence and steps to fully enjoy dancing to the live jazz and swing bands playing throughout the day.
Among the most spirited traditions of the weekend is the Suffrage & Florence’s Parade, proudly hosted by the Massachusetts Women’s History Center. This joyful, historical march invites guests to dress in their finest flapper attires, pick up a vintage suffrage sign, and parade across the Crane Estate in a vintage dressed-up celebration of women’s rights and Jazz Age style.
For guests seeking a more relaxed old-fashioned experience, the estate presents a charming selection of vintage lawn games. Whether it's a classic round of croquet, a spirited match of badminton, or a challenge with giant chess, there’s plenty to enjoy at a gentler pace. Families and explorers alike will also be drawn to the Castle Hill I Spy Game – a charming hunt adventure designed to explore the Crane Estate in a playful and interactive way
Another standout experience is Vintage Girl Photography, where guests can step into the elegance of a bygone era. These studio-style sessions provide everything needed for a full vintage makeover – from period-authentic clothing and set design to expert make-up and hair styling. The outcome is a striking portrait that captures the allure of the 1920s. Whether channeling a flapper, a silent film star, or a Jazz Age debutante, each participant walks away as a timeless icon – for a moment (or a lifetime) on film.
Dancers eager to show off their best moves are invited to take part in the Castle Hill Charleston Challenge – a lively, high-energy contest where participants can demonstrate their stuff to an enthusiastic audience. With prizes up for grabs and bragging rights at stake, it’s one of the weekend’s most spirited and entertaining competitions.
For a deeper and more intimate dive into history, immersive tours of the Great House invite guests inside the mansion. Costumed as 1920s footmen and maids, the knowledgeable staff lead visitors through elaborately preserved rooms, sharing stories of the estate’s rich and vibrant past. The tour includes a rare opportunity to visit the iconic rooftop with its sweeping ocean views.
Bringing a playful edge to the program, crowd-pleasing contests such as pie-eating and watermelon seed-spitting add bursts of laughter and a healthy dose of silliness to the otherwise elegant setting. These lighthearted competitions invite guests of all ages to join in, keeping the cheerful spirit of summer alive throughout the day.
For lovers of literature and theatrical flair, the Poetry Brothel offers a an unforgettable cabaret-style escape. This one-of-a-kind experience blends poetry readings, vaudeville theatrics, and personal literary encounters, as costumed poets perform their verses with dramatic flair and emotional depth.
And for those seeking a little extra luxury, the Crane VIP Experience offers an upgraded take on the festivities. VIP guests are treated to exclusive lounge seating, access to a private bar, complimentary refreshments, and curated activities designed to elevate the day with extra ease and charm – all set amid the breathtaking scenery of Castle Hill’s rolling lawns and grand architecture.
With such a rich and diverse slate of experiences, the Roaring Twenties Lawn Party invites guests to not only look the part but to live, dance, laugh, and reflect as if they were part of the 1920s themselves – with all the nuance, energy, and style that made the Jazz Age unforgettable.
Why the Roaring Twenties Lawn Party Is a Must-Experience Event
The Roaring Twenties Lawn Party at the Crane Estate is more than just an event – it’s a living time capsule that transports guests from the present into a beautifully reimagined version of the past. What sets this gathering apart is its seamless fusion of authentic 1920s charm – think live jazz ensembles, Great Gatsby fashion, 1920s dance styles, and classic lawn games – with a modern sensibility. Through thoughtful programs like Reimagine the Jazz Age, the event invites reflection, inclusivity, and a fresh perspective on a bygone era.
Unlike a typical costume party or music festival, this experience delivers a vibrant blend of cultural depth, thoughtful programming, and sheer joy across every corner of Castle Hill’s storied landscape. Whether you’re learning the Lindy Hop, soaking in poetry beneath a cabaret tent, enjoying a pie-eating contest, or joining a suffrage-inspired parade, it feels like you’re part of something both enchanting and meaningful.
It’s a place where history comes alive, community thrives, and imagination runs free. Whether you’re a 1920s vintage lover, jazz fan, dancer, artist, curious family, or history lover, the Roaring Twenties Lawn Party offers an unforgettable celebration of beauty, expression, and pure delight. In the end, you don’t just go to this event—you step into it and become part of its story.
This blog is written based on information from the Roaring Twenties Lawn Party web site and other internet sources, as well as on enthusiastic stories from La Vie Delight customers. Most of the photos used in this blog are from submissions from our customers wearing La Vie Delight dresses at this event.