A Swingin’ Affair Announces 2026 Summer South Shore Outdoor Concert Series

Boston’s premier all-star Rat Pack tribute big band takes its signature swingin’ sound on the road this summer. A Swingin’ Affair presents a three-performance lineup of outdoor concerts spanning Boston’s South Shore. Led by bandleader and South Shore Conservatory Artistic Director Steve Bass, the celebrated 16-piece professional big band delivers the timeless music of Frank Sinatra, Dean Martin, Bobby Darin, Ella Fitzgerald and the Great American Songbook to audiences in Duxbury, Hingham and Plymouth during the summer of 2026.

Featuring acclaimed frontman vocalist Donnie Norton and special guest vocalist Sarah Bass, A Swingin’ Affair recreates the classic sound, style and excitement of the Rat Pack era with authentic big band arrangements performed by some of Boston’s top jazz and orchestral musicians. Audiences can expect beloved standards including “Fly Me to the Moon,” “New York, New York,” “I’ve Got the World on a String,” and more, paired with storytelling, swinging instrumentation, and the unmistakable charm of a bygone musical era.

“Experiencing a full-size professional big band live is increasingly rare.These concerts are designed to celebrate that tradition with our fans in vibrant, outdoor community settings,” shares Bass. “There’s something magical about hearing this music outdoors in the summertime — audiences connect immediately with the energy, nostalgia and joy this music genre always delivers.”

Saturday, June 27, 3 pm

South Shore Conservatory's Duxbury Music Festival, Duxbury Town Green, 71 Washington Street, Duxbury

Tickets are $40, available at: give.sscmusic.org/dmf-2026

Info: aswinginaffair.com/events/a-swingin-affair-at-duxbury-music-festival

Join SSC Artistic Director Steve Bass and acclaimed vocalist Donnie Norton for a relaxed and joyful afternoon celebrating the Great American Songbook on the Duxbury Town Green. This swingin’ outdoor concert features timeless favorites from the Rat Pack era—Frank Sinatra, Bobby Darin, Dean Martin—and welcomes special guest vocalist Sarah Bass performing beloved selections from the Ella Fitzgerald songbook. Set beneath a tent and backed by a 16-piece professional big band featuring some of Boston’s finest jazz musicians, this concert brings classic big band swing to life in a perfect summer setting.

Sinatra Under the Stars: A Swingin’ Affair in Concert

Saturday, July 25, 7 pm

South Shore Conservatory’s Premiere Concerts, Carr Amphitheater, One Conservatory Drive, Hingham

Tickets: Pavilion: $50; Lawn: $25; Children nine and under attend for free, available at give.sscmusic.org/eus-sinatra

Info: aswinginaffair.com/events/a-swingin-affair-at-sscs-evenings-under-the-stars

Artistic Director Steve Bass, alongside “Ol’ Blue Eyes” vocalist himself, Donnie Norton, presents an unforgettable night of music from the Great American Songbook. Featuring favorite crooners from the Rat Pack era, including Frank Sinatra, Bobby Darin, and Dean Martin, this swingin’ evening also welcomes special guest vocalist Sarah Bass, singing selections from the Ella Fitzgerald songbook. Backed by a 16-piece professional big band featuring some of Boston’s best jazz artists, this concert delivers big band swing at its finest.

A Swingin’ Affair at Project Arts’ Summer Concert Series

Wednesday, August 12, 6:30 pm

Project Arts’ Summer Concert Series, DCR Park, 79 Water Street, Plymouth

Admission is free

Info: aswinginaffair.com/events/klhwtns0lrygz7ws04w0avs52cfa4o

A Swingin’ Affair brings all the excitement and music of its indoor concerts to the outdoor stage to soak in that summer sun on the Plymouth Waterfront! Join us for an evening of beloved big band favorites with the best vocalists and instrumentalists in the business. Plymouth, here we come! Project Arts of Plymouth is celebrating 30 years of music, community, and seaside vibes with their FREE Summer Concert Series. Bring a picnic, blanket and/or folding chairs, as this is an open-air park venue with no event seating. Metered parking is available streetside or in adjacent street lots, learn more at ParkPlymouth.com.

A Swingin’ Affair’s public relations and creative media services are provided by Michelle McGrath PR | Media Relations, creating visibility for cultural institutions, nonprofits, and the small business sector, spanning the traditional, digital, and social media landscape since 2010. mcgrathpr.com

For more information, book A Swingin’ Affair for a performance, or to review A Swingin' Affair's Collaborative Music Education Enrichment Program (CEP) fundraisers for schools, email aswinginaffairband@gmail.com, visit A Swingin’ Affair at aswinginaffair.com, or follow on Facebook, Instagram or YouTube.