Live music in Springfield, MA

Founding Fathers Car Club hosts a weekly cruise night at The Star Drive-In. The event features live music by Joe Mac and a 50/50 raffle benefiting Plymouth Veterans.

DSP Shows presents Ray LaMontagne’s Trouble 20th Anniversary Tour at Symphony Hall in Springfield with The Weather Station. Marking two decades since his first full length album, he will perform Trouble in full for the first time since its release, along with songs from across his broader catalog. His career spans nine studio albums, radio singles that topped the charts, a Grammy win and several additional nominations. In a personal reflection on the milestone, he highlights the importance of looking back and shares that Brian Lee and Bob Jackson at Waygate Mastering have completed the first vinyl-specific remaster of Trouble, revealing new detail in the vocals and instrumentation.

Sip wine and savor Italian cuisine while Jeffrey Thomas performs live at Villa Napoletana.

Forever Plaid delivers a lighthearted jukebox journey through the golden age of 1950s close-harmony guy groups. Four earnest friends... Sparky, Jinx, Smudge, and Francis... see their first big break cut short by a sudden accident, then find themselves in a limbo between life and afterlife. Granted one miraculous chance to return, the Plaids step into the spotlight to finally perform the show they never got to share. With charming banter, playful comedy, and boyish sincerity, the quartet revisits favorites like “Three Coins in the Fountain,” “Catch a Falling Star,” and “Love Is a Many-Splendored Thing.” As memories surface, their quirks and insecurities come to light, underscoring a deep camaraderie. Each number celebrates classic American pop while guiding the group toward long-awaited closure, creating a heartfelt tribute to friendship, nostalgia, and the power of harmony that concludes with a tender farewell.

Live music sets the scene at Brookside Cafe in Ludlow. Friendly staff and good food are highlighted, creating a warm setting to take in the performance.

A lively karaoke night with plenty of sing along fun.

The third annual motorcycle ride honoring Angela Santiago brings the community together at Moose Lodge 1849 in Chicopee, MA for a full day of bikes, music, food, and family fun. The day features registration and a group ride, plus live entertainment with DJ Seamus spinning favorites and a performance by The BoneYard. Food trucks and local vendors will be on site, and there are activities for kids along with a 50/50 and raffle prizes. Stop by the swag tent for official ASF gear. Admission is $20 per person for both riders and non-riders. All tickets are purchased at the door, and one price covers the entire day.

Celebrate the Tech Tigers community at an all years reunion hosted by Mike Borecki. Enjoy a relaxed cookout with barbecue served during the event, a cash bar, music from DJ Eddie, and raffles. Seating is open and parking is free. The gathering is open to everyone and will take place rain or shine. Tickets cost $25. When requesting tickets, include your name and the number of tickets you need. Payment is accepted in cash, by check mailed to Mike Borecki, or via Venmo @hoylola and Cash App $MikeBorecki. For more information, contact Mike Borecki through Messenger, by phone at 413-351-6572, or by email at mdborecki@gmail.com.

Enjoy Italian cuisine and wine accompanied by live music from Marco Turo.