A Sinatra Christmas w/ Rich DiMare & Ron Poster Trio

“A Sinatra Christmas” brings Rich DiMare and the Ron Poster Trio to City Winery Boston for an evening combining seasonal standards with beloved Frank Sinatra songs. The program includes holiday favorites such as “Jingle Bells” and “White Christmas,” alongside Sinatra classics including “My Way” and “New York, New York.”

DiMare is an American singer specializing in the Sinatra songbook. He has performed professionally for 20 years, including 15 years on Boston’s KISS 108 morning show, *Matty in the Morning*, and work as a host on Boston’s Fox25 TV. Pianist and keyboard artist Ron Poster is a Boston-based performer focused on popular and classic American music. He has served as the Boston Bruins’ organist at TD Garden since 2001 and previously toured with Missing Persons. Their shared familiarity with Sinatra’s music and onstage rapport shape the show’s Rat Pack-inspired atmosphere.

When: November 30, 2026

Showtime: 7:30 PM

Doors: 6:00 PM

Tickets: Start at $30.00

Venue: Main Stage, City Winery Boston

Address: 80 Beverly Street, Boston, MA 02114

Performers: Rich DiMare and the Ron Poster Trio

Music: Sinatra classics including “My Way” and “New York, New York,” along with holiday songs such as “Jingle Bells” and “White Christmas.”

Dining: Food and beverage service is available directly at concert tables. Guests seeking a broader menu and a more relaxed meal may arrive early to dine in the restaurant; reservations are encouraged through Resy beginning one month before the show.

Wine service: Guests can reserve a preferred bottle in advance and have it waiting at their table.

Venue note: City Winery does not require a two-item food or beverage minimum, but strongly encourages each guest to purchase two items to support the venue staff, service, artists, and production.

Run time: Not specified.