Rock Hall’s Annual Main Street FallFest - Live Music on Two Outdoor Stages10am - 5pmMain Street
2025-10-11 10:00 - 17:00 (America/New_York)
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Pub Night with Greg Ellingsworth - one of Delaware's top solo artists530-730pmFree admission! Free pizza!
2025-10-16 17:30 - 19:30

Piano Jazz Virtuoso Dick Durham and his Trio8pm$25
2025-10-18 20:00 - 22:00
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The sheer talent of our fiend and neighbor, local jazz piano virtuoso Dick Durham needs little introduction. He is one of the Mainstay’s most requested performers. Very few musicians start their professional career as an opening act for the legendary Count Basie Orchestra. Dick credits Errol Garner, Oscar Peterson, and Teddy Wilson as his major influences. He has had the privilege of sharing a bill with Stanley Turrentine, Grover Washington Jr., Billy Cobham, and many others.
Dick will be joined on stage by Max Murray on bass and Greg Burrows on drums.

Pub Night with Van Albert plays the Delta Blues530-730pmFree admission! Free pizza!
2025-10-23 17:30 - 19:30

Great Bluegrass with the Eastman String Band8pm$25
2025-10-24 17:30 - 19:30
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On Friday, October 24, the Mainstay in Rock Hall, Maryland, in partnership with the Hedgelawn Foundation, welcomes one of the Mid-Atlantic region’s most popular bluegrass groups – the Eastman String Band.
Silky vocals, soaring harmonies, hot picking, and heartfelt originals punctuate each performance of the Eastman String Band. Tim and Savannah Finch form the basis of the group. They began playing music together at the Friday Night jams once held at Tim’s music store, “Good Deale Bluegrass” in Deale, Maryland. Tim sings lead and harmony vocals and plays guitar, mandolin, banjo, and pedal steel. Savannah sings lead and harmony vocals and plays guitar. Tom is also a representative of Eastman Strings, renowned internationally for their stringed instruments, (hence the name of the band). The group also prominently features John Glik on fiddle. Glik had been a member of bluegrass giant Del McCoury’s Dixie Pals and has worked with David Grisman and Frank Wakefield. He has been a fixture on the Baltimore/Washington bluegrass scene since the 1970s. The band also includes Danny Stewart on bass, and special guest Jack Dunlap on lead guitar.
This concert is made possible with support provided by The Hedgelawn Foundation

Low Lily - Acoustic Trio8pm$25
2025-11-01 20:00 - 22:00

Stop the Bleed2-3PMRegistration requiredLimited seats available
2025-11-02 14:00 - 15:00
FREE personal STB Kit for all pre-registered attendees!
Minutes count! Someone who is severely bleeding from an injury such as a car crash, a gunshot or accidental wound can bleed to death in as little as 5 minutes. That’s why the R Adams Cowley Shock Trauma Center’s Center for Injury Prevention&Policy offers FREE life-saving bleeding control training through STOP THE BLEED®.
CLICK HERE TO REGISTER

Pub Night with Philip Dutton Trio530-730pmFree admission! Free pizza!
2025-11-06 17:30 - 19:30

Film Showing of "Death On The Chesapeake: A Hard Rain"7pm$10
2025-11-07 19:00 - 21:00

Pub Night with Jay Yerkes530-730pmFree admission! Free pizza!
2025-11-13 17:30 - 19:30

Pub Night SPECIAL GREG BURROWS ALBUM RELEASE530-730pmFree admission! Free pizza!
2025-11-20 17:30 - 19:30
Join Us for a Special Mainstay Pub Night!
Thursday, November 20 | 5:30–7:30 PM
The Mainstay takes great pride in sharing some exciting news with our community! At our weekly Mainstay Pub Night, we’ll be celebrating the worldwide release of Chestertown-based drummer Greg Burrows’ brand-new album, Let’s Not Wait: The Music of Ed Bonoff.
This will be a Record Release Celebration unlike any other, part listening party, part storytelling session, and all heart. Greg will take us behind the scenes of his latest project, sharing tracks from the album (officially released October 31), photos from the recording sessions, and personal reflections on the creative journey.
Following his recent performance with the blazing Dick Durham Trio, Greg returns to The Mainstay to bring this project to life for friends and fans,up close and personal. He’ll also take questions from the audience and share insights about the process of producing and releasing a new record, a fascinating, intricate effort that may give you a whole new appreciation for the music you love.
But that’s not all: this album carries a remarkable story. The music comes from Ed Bonoff, Greg’s longtime friend and fellow drummer from the New York City suburbs. Now in his mid-90s, Ed has been composing and arranging thrilling jazz for over half a century, music that, until now, has rarely been heard outside of his living room! Thanks to Greg’s dedication, this extraordinary body of work is finally being shared with the world.
Come enjoy a drink, complimentary pizza, some camaraderie, and a truly unique evening of music, conversation, and inspiration. Discover how friendship, passion, and creativity come together in Let’s Not Wait: The Music of Ed Bonoff.
Your generous support of The Mainstay and live music are greatly appreciated.

The Mainstay Community Players present A Night at the Opry8pm$20
2025-11-22 20:00 - 22:00

Opera On The ChesapeakeThe Main Line Opera Singers4pm$20
2025-11-23 16:00 - 18:00
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The Mainstay’s Classical Music Series continues with Opera on the Chesapeake, an unforgettable Sunday afternoon of beloved arias, duets, and ensembles presented by the Main Line Opera Singers of Philadelphia. Sponsored by retired Philadelphia Court of Common Pleas Judge, James M. Lynn, this concert will bring world-class voices to Rock Hall for one special performance on Sunday afternoon, November 23, 2025 at 4pm.
Philadelphia-based pianist and opera coach, Tim Crawford, will accompany an outstanding cast of vocalists including sopranos Teresa Anstatt, Christi Sutton and Andrea Broido, baritone Enrico Adriano, and baritone Judge James Lynn himself. Collectively, these artists have performed on some of the world’s most renowned stages, from Carnegie Hall and the Kennedy Center to international festivals across Europe.
The program will feature highlights from Verdi, Puccini, Mozart, Delibes, Rodgers & Hammerstein, and more. Audiences will be treated to arias such as “Caro nome” from Rigoletto, “Vissi d’arte” from Tosca, and “Quando m’en vo” from La Bohème, as well as duets including “Dôme épais” from Lakmé and “Sull’aria” from The Marriage of Figaro. The evening will open with a spirited ensemble of Rodgers & Hammerstein’s It’s a Grand Night for Singing, setting the tone for a night of beauty, drama, and celebration.
Opera on the Chesapeake is sure to be a highlight of The Mainstay’s fall season, blending the grandeur of opera with the intimacy of The Mainstay’s beloved venue.

Harp and Soul "Songs of the Season"4pm$25
2025-12-07 16:00 - 18:00

Buffalo Rose8pm$25
2025-12-13 20:00 - 22:00

NY Eve Community Potluck Dinner!6pmNo Charge - Bring a covered dish!
2025-12-31 18:00 - 2026-01-01 00:00
KICK OFF THE NEW YEAR AT THE MAINSTAY!
ANNUAL NEW YEARS EVE POT LUCK DINNER
WITH JOE HOLT – DECEMBER 31st
No Charge – Bring a covered dish!

Community Meet & Greet Forum6pmAn informal evening of conversation, connection and community
2026-02-04 18:00 - 20:00

Honoring Black History Month with Karen Somerville, Sombarkin and Guests730pm$25
2026-02-07 19:30 - 21:30

Make a Date With Deanna Bogart - Valentines Day730pm$30
2026-02-14 19:30 - 21:30

Celebrate Mardi Gras with Philip Dutton and The Alligators730pm$25
2026-02-17 19:30 - 21:30

Special Friday Series with Joe Holt - Clash of the Countertenors730pm$25
2026-02-20 19:30 - 21:30

THE BLACK EYED SUZIES - All Female Bluegrass Band730pm$25
2026-02-28 19:30 - 21:30

JAMES FERNANDO JAZZ TRIO - Philly 3 Album Release730pm$25
2026-03-07 19:30 - 21:30

Mike Agranoff - An Evening of Folk Music and Storytelling730pm$25
2026-03-14 19:30 - 21:30

Old Time Musical Magic with Ken and Brad Kolodner730pm$25
2026-03-21 19:30 - 21:30

Special Sunday Afternoon with Dick Durham4PM$25
2026-03-29 16:00 - 18:00

Tracy Grammer - Nationally Acclaimed Singer-Songwriter730pm$25
2026-04-04 19:30 - 21:30

An Evening of Love and Bossa Nova730 PM$25
2026-04-11 19:30 - 21:30

Special Friday Series with Joe Holt - Rhonda Apple and Kiara Vos - Welcome to My World730pm$25
2026-04-17 19:30 - 21:30

The Chesapeake Youth Symphony Orchestra - Classical Music Series4PM$15
2026-04-19 16:00 - 18:00
