Get ready for an unforgettable evening of jazz with the sensational Diana Tuffin alongside the O.Henry Jazz Trio in the Social Lobby at the O.Henry Hotel! ✨

From sultry swing to timeless standards, Diana’s unique vocal style — both soulful and sophisticated — blends perfectly with the Trio’s classic jazz grooves. Whether you’re winding down after work or planning a special night out, it’s the perfect setting for great music, vintage craft cocktails, and delectable Mediterranean-inspired small plates.

Enjoy jazz every Monday evening with the talented Diana Tuffin and Karon Click. Three additional musicians will join the duo and feature different guest performers at each show.

Enjoy jazz every Monday evening with the talented Diana Tuffin and Karon Click. Three additional musicians will join the duo and feature different guest performers at each show.

Enjoy jazz every Monday evening with the talented Diana Tuffin and Karon Click. Three additional musicians will join the duo and feature different guest performers at each show.

Enjoy jazz every Monday evening with the talented Diana Tuffin and Karon Click. Three additional musicians will join the duo and feature different guest performers at each show.

Step back into the Roaring ’20s for a night of vintage glamour, lively rhythms, and timeless style. Flappers & Jazz: A Roaring ’20s Evening features the Matthew Kendrick Trio with songstress Diana Tuffin, performing classic jazz with piano, vocals, and bass guitar. Enjoy fine wines, soak in the spirit of the Jazz Age, and experience an atmosphere inspired by speakeasies and golden‑era elegance.

Guests are encouraged to dress in their best flapper or vintage attire for an unforgettable evening of music, sophistication, and celebration.

Enjoy jazz every Monday evening with the talented Diana Tuffin and Karon Click. Three additional musicians will join the duo and feature different guest performers at each show.

Enjoy jazz every Monday evening with the talented Diana Tuffin and Karon Click. Three additional musicians will join the duo and feature different guest performers at each show.

Enjoy jazz every Monday evening with the talented Diana Tuffin and Karon Click. Three additional musicians will join the duo and feature different guest performers at each show.

Enjoy jazz every Monday evening with the talented Diana Tuffin and Karon Click. Three additional musicians will join the duo and feature different guest performers at each show.

Enjoy jazz every Monday evening with the talented Diana Tuffin and Karon Click. Three additional musicians will join the duo and feature different guest performers at each show.

O.Henry has become a popular venue for live jazz. Enjoy vintage craft cocktails and delightful seasonal Mediterranean tapas while listening to The O.Henry Jazz Trio and the impressive Diana Tuffin perform various styles of jazz in the O.Henry Social Lobby.

Enjoy jazz every Monday evening with the talented Diana Tuffin and Karon Click. Three additional musicians will join the duo and feature different guest performers at each show.

My performance at the O. Henry Hotel has been cancelled. They experienced a major leak, and the lobby is unavailable. Be on the lookout for a new performance there soon.

Enjoy jazz every Monday evening with the talented Diana Tuffin and Karon Click. Three additional musicians will join the duo and feature different guest performers at each show.

The O. Henry Hotel uniquely blends live jazz and Mediterranean flavors. On New Year's Eve, the hotel’s social lobby transforms into a vibrant jazz venue, featuring guest vocalist Diana Tuffin and the Matt Reid Trio. Vintage craft cocktails and seasonal Mediterranean tapas further enhance the experience, creating a sophisticated yet relaxed atmosphere.

Join us for our third annual Christmas concert! The Matt Kendrick Quartet featuring Diana Tuffin will be returning to provide you with your jazzy Christmas favorites while you craft away in holiday bliss.

Make ornaments, “gingerboard” houses, mini-trees or cards, all while listening to live heartwarming holiday hits.

Each ticket includes your choice of activity. Pick from our daily menu or holiday specials (which include access to the Craft Buffet full of glitter, ribbon, paint, botanicals, beads, hot glue, and anything else you can imagine).

This powerful performance weaves together the legacy of tobacco labor activism in Winston-Salem with the music that gave voice to the movement. Walk a Mile In My Shoes blends historical insight with stirring live renditions of songs that fueled the 1947 R.J. Reynolds tobacco factory strikes, where artists like Paul Robeson and Woody Guthrie stood in solidarity with workers demanding racial and economic justice.

Featuring:

Diana Tuffin as a union leader, channeling the spirit of resistance through jazz

Jason McKinney as Paul Robeson

Joseph Terrell (Mipso) as Woody Guthrie

Historical narration by Phil Archer, Camel City Co-curator

This event bridges art and activism, honoring the music that moved a movement.

Note: Saturday’s performance is SOLD OUT!

O.Henry has become a popular venue for live jazz. Enjoy vintage craft cocktails and delightful seasonal Mediterranean tapas while listening to The O.Henry Trio and the impressive Diana Tuffin perform various styles of jazz in the O.Henry Social Lobby.

The Palmetto Spiritual Voices Ensemble was formed in 2006 and is a professional choir that strives to support the legacy of the Concert Spiritual while sharing the vision that this unique American art form is available to all. The ensemble features alumni singers from throughout the Southeast. They have performed at the South Carolina Music Educators Conference, Carnegie Hall, the Southern Division American Choral Directors Association, the National ACDA Convention in Dallas, TX, and the Music Educators National Conference.