Challapalooza

Challapalooza
is back!

11am-8pm
06.21.2026

Boston's Jew-ish Music Festival

Buy Tickets!
Early Bird ends June 1
Challapalooza Collage by Emily Marbach

Kendall Square, Cambridge, MA

Volunteer! Sell Art! Teach!

What's Happening?

Music all Day

A mix of Boston’s most joyful and genre-bending Jew-ish music, including Klezmer Conservatory Band, Alma Vatya (freako folk), The Ruth & Ben String Band (old-time), Dor Herskovits Trio (jazz), Phil and the Flying Leap (theatrical folk), Rebecca Mac Klezmer String Band, Somerville Symphony Orkestar (Balkan/global), and Levyosn Duo (Yiddish song). Read more about our amazing bands below.

Food

Kosher food trucks (including The Hummus Shop), ice cream, and locally made Wild Child Chocolate. There will also be a challah making competition—bring your best (vegetarian) challah, fun flavors encouraged. Best challah wins a prize!

Learning

Drop-in beit midrash tent with short, welcoming classes—no background needed. Highlights include Jewish weaving practices, Yiddish baking prayers, yoga, early halachic responsa on synagogue sheet music, and Talmud for teens (and the teen-curious).

Artists & Community

Jewish artists and makers (ceramics, stained glass, herbal teas, local chocolate, and more), along with local Jewish organizations and synagogues.

About Challapalooza

  • What is it?
  • Food
  • Venue
  • Organizers
  • Security
  • FAQ

Challapalooza, Greater Boston’s Jew-ish Music Festival, is back for a second amazing year. Last year we had over 400 people join us for a full day of joyful music from fifteen different musical groups in twelve different genres. Our second year will be an even bigger and better celebration — a full day of live music by fantastic local Jewish musicians, with delicious food from Jewish & kosher food trucks and fun in the park for all ages.

Enough nosh for all your Jewish-mother needs!

Stay tuned for an amazing selection of kosher food trucks,

Our Beautiful Outdoor Space in Cambridge

We have secured an incredible outdoor festival venue near Kendall Square (address sent to ticket holders). It is T, bike and car accessible, with lots of space to dance, throw a frisbee or just lie on the grass.

Volunteer Led

Challapalooza is a volunteer run effort, spearheaded by Akiva Jackson of Moishe House Somerville. Our amazing festival coordinator, Akiva Jacobs, is helping to make all the magic happen. Please join us, we always need more people, both for planning and day-of volunteering.

Security

We understand that many people are concerned about security, and we take this very seriously. Our team is implementing a comprehensive security plan in close consultation with local police and security experts. There will be a police presence at the event, and we are coordinating with the CJP security team to ensure best practices are followed. Your safety is our top priority, and we are committed to creating a secure and welcoming environment for everyone.

FAQ

Code of Conduct

Challapalooza is a community celebration of Jewish and Jew-ish culture. We’re committed to creating a welcoming, respectful, and family-friendly environment for all. By attending, you agree to:

  • Treat everyone with respect, regardless of background or beliefs.
  • Avoid political advocacy, debate, or signage—including around the Middle East. This is a space for people of all kinds and all politics to come together in joy and care, so we ask you to be gentle and open to differences.
  • Avoid social media posts or online behavior that target, shame, or escalate conflict between attendees or communities connected to the festival.
  • Refrain from harassment, discrimination, or disruptive behavior.
  • Help maintain a safe and joyful space for all ages.
  • Have fun!

Failure to follow these guidelines may result in removal from the event.

General Info

  • Do I need a ticket?
    Yes please!
  • What's the rain plan?
    We are currently securing a rain location in case of inclement weather. If there are only light sprinklings of rain, we'll dance in the rain!
  • What other activities will there be?
    Music, art, food, community — plus probably at least one child attempting interpretive dance.

Safety & Security

  • How are you handling security?
    We understand that many people are concerned about security, and we take this very seriously. Our team is implementing a comprehensive security plan in close consultation with local police and security experts. There will be robust police presence at the event, and we are coordinating with the CJP security team to ensure best practices are followed. Your safety is our top priority, and we are committed to creating a secure and welcoming environment for everyone.
  • What’s the cancellation policy?
    Tickets are typically non-refundable because we need to pay our amazing musicians. If you really need your money back, let us know and we can make it happen.
  • Will there be medical support?
    We will have a first aid table, and emergency medical services are nearby and ready to come at a moment’s notice.

Accessibility & Families

  • Will there be seating?
    We’ll have some chairs, but it’s mostly sit-on-the-ground, bring-your-own-pillows and blankets.
  • Are there bathrooms available?
    Yep — port-a-potties. We apologize in advance, but it’s a festival tradition.
  • Is it family-friendly?
    Totally. Bring the kids! We just ask that parents don’t let their toddlers crowd-surf.

Getting There

  • How can I get there?
    We'll send you the address when you get your ticket; the festival space is near Kendall Square in Cambridge, MA. It is T accessible (10 minute walk from the T, 3 minutes from the nearest bus station) and bikeable. Metered parking is available nearby, and there are garages within a five-minute walk.
  • Is there parking or bike parking available?
    There’s some parking nearby, but biking or T-ing is easier.

Get Involved

  • How can I volunteer?
    Yes please! We’d love help. Fill out the form on our site, we need everything from social media help to EMTs.
  • How can I support or donate?
    Please donate here! All funding goes directly towards making the festival happen.
  • How can I perform or vend at future events?
    We love new talent. Reach out through our contact page, just be prepared to wow us.
  • Who are the organizers, and how can I contact them?
    We’re a scrappy group of local Jewish volunteers who love music and community. This event is put on by the amazing teams of all the Moishe Houses in Boston and many dedicated volunteers, led by Akiva Jackson of Moishe House Somerville and our incredible Festival Coordinator, Akiva Jacobs.
You can contact us anytime — but please don’t call at 3 a.m. with banjo requests.

Disclaimer

Challapalooza is a broad community festival featuring many independent artists, vendors, organizations, and participants representing a wide range of perspectives. Views expressed by performers, speakers, vendors, exhibitors, or attendees are their own and do not necessarily reflect the views of Challapalooza, its organizers, sponsors, partners, or volunteers.

The Music

Turkish, Jazz, Blues, Old Time, Scottish, Balkan, Hip Hop & More

Klezmer Conservatory Band
Klezmer Conservatory Band
Klezmer & Yiddish Songs

For over 45 years, the Klezmer Conservatory Band (KCB) has been a leading global voice in Jewish music. From "A Prairie Home Companion" to touring with Itzhak Perlman on the world's largest stages, KCB continues to thrill audiences with Yiddish standards and rousing dance medleys.

Somerville Symphony Orkestar
Somerville Symphony Orkestar
International Party Music

Blossoming from the Slavic heart of Greater Boston, the Somerville Symphony Orkestar plays all-original International Party Music. Blending elements of Balkan music with Jazz and Funk, the SSO is the ultimate party band for the crowd that wants to dance all night.

Dor Herskovits Trio
Dor Herskovits Trio
Jazz / Improvised Music

Rooted in the traditions of American improvised music, this trio combines eclectic genres with top notch musicianship and improvisational mastery.

The Ruth & Ben String Band
The Ruth & Ben String Band
Old Time

The Ruth & Ben String Band is a high energy, driving, and groovy old time string band featuring mother-son duo Ruth Rappaport (guitar/vocals) and Ben Wetherbee (fiddle/vocals) alongside Joel Wennerstrom (banjo) and Gian Criscitiello (bass).

Phil and the Flying Leap
Phil and the Flying Leap
Theatrical Folk

Phil and the Flying Leap twists and re-imagines music across multiple genres of classic American song spanning Vaudeville to Nashville to Somerville and everywhere in-between. Songwriter Phil Berman's melodies and lush string arrangements offer vibrant live performances full of heart, joy, and rich vocals.

Rebecca Mac Klezmer String Band
Rebecca Mac Klezmer String Band

Led by Boston-based Rebecca Mac (of the award-winning klezmer ensemble, Mamaliga), the Rebecca Mac String Band plays intricate and off-beat arrangements of original fiddle tunes, drawing inspiration from the traditional soundscapes of Klezmer and Eastern-European folk music. Rebecca released her debut record “Night Bird” in April 2026, featuring ten original Klezmer-inspired compositions. For this concert, Rebecca will be joined by accordionist Dmitri Gaskin and bassist Akiva Jacobs.

Alma Vatya
Alma Vatya
Freako Folk

ALMA VATYA is an Arizonan trans-planted guitarist, singer, and banjo player who performs American vernacular music inspired and informed by a lifelong exploration of pre-war country blues, ballads, and spirituals.

Levyosn Duo
Levyosn Duo
Yiddish Song

Join us for a special duo performance by Adah Hetko and Lysander Jaffe of Levyosn. The band takes its name from the Ashkenazi Hebrew word for the leviathan, a mythical sea creature traveling the world's oceans collecting songs, krill, and dreams.

Stay tuned for our full lineup!