49 West - Coffeehouse, Winebar & Gallery / Annapolis, Maryland

Dave Chappell & Friends- AKA HippieHappy Hour
2025-12-03 17:00 - 19:00, 2025-12-17 17:00 - 19:00 UTC | 49 West – The Back Room, 49 West St., Annapolis, MD, 21401, United States
Dave Chappell, Jimmy Jacobs, Rurik Reshetiloff & more!

Jeff Antoniuk & Helluvaband
2025-12-04 19:30 - 22:00 (America/Halifax)
Jeff Antoniuk – tenor sax
John Lee – guitar
Blake Meister – bass
Frank Russo – drums
See you at one of the hippest little listening rooms in the DMV!

1st Friday with Tom Mitchell & Friends
2025-12-05 20:00 - 22:00 (America/New_York)
The Blue Rhythm Boys Live
Tom Mitchell Guitar and Vocals
Jim Stephanson Guitar and Vocals
Jazz, Western Swing, Blues and lots of fun
$15 cover

John Jensen
2025-12-06 16:00 - 18:00, 2025-12-13 16:00 - 18:00, 2025-12-20 16:00 - 18:00 (America/Halifax)

Spa Creek Jazztet
2025-12-06 19:30 - 22:00 (America/New_York)
Please call for your reservations at 410-626-9796
The Spa Creek Jazztet is a modern jazz sextet playing jazz classics as well as original jazz compositions and arrangements. At 49 West, the sextet will play music by Charles Mingus, Wayne Shorter, Christian McBride, Dexter Gordon, and Herbie Hancock among others. A local mainstay, the Spa Creek band has been performing in the area since 1989. The band features Alan Caldwell on alto and tenor sax, Jim Tavener on trumpet and flugelhorn, Brian Priebe on trombone, Paul Morawski on piano, David Vermette on bass, and Mike Morris on drums.

Chocolate Bing Festival
2025-12-07 11:00 - 16:00 (America/New_York)
Chocolate Binge Tickets
Tickets on Sale NOW! A sweet day is ahead for you at the Annapolis Chocolate Binge Festival. Tickets sales are limited for everyone’s safety. This event is expected to sell out, so order your tickets online today. Chocolate Lovers come together to enjoy a day to celebrate the art of Chocolate. There is something for everyone including over 50+ Chocolate vendors, shopping from dozens of local artists, drinks, food, and live music, and did we mention Chocolate. This day includes a visit with Santa, a Gingerbread decorating contest and a few more surprises.
Plus live music and entertainment throughout the day.
This is a fun event that the whole family will enjoy in Historic Annapolis, Maryland. This wonderful event hosted by the Inner West Street Association fills West Street with holiday cheer.
This is a magical time to Visit Annapolis, Maryland and you can make it part of a weekend getaway by staying on West Street in the Annapolis Arts District at the Graduate Hotel, Hilton Garden Inn Annapolis Downtown, The Westin Annapolis, or Reynolds Tavern.
Your attendance ticket supports fun events and projects on West Street.
Please leave pets at home as chocolate is not safe for pets.
Get Annapolis Parking details – Closest garages are Gott’s and Whitmore.
https://www.annapolisparking.com/parking-locations/garages-and-lots/
Only accepting chocolate vendors at this time: https://www.iwsannapolis.com/vendor-application
Great Annapolis Gingerbread Houses
November 22 – December 19
Enter now for the Great Annapolis Gingerbread House decorating contest! Houses will be on display from November 22nd thru December 20th at the Annapolis Visitors Center on West Street. Winners will be announced on Dec 7th at the Annapolis Chocolate Binge Festival. Sponsored by Visit Annapolis and Anne Arundel County
Register Now: https://forms.gle/9Gsth6tinKGzZxTW9

Gary Wright & Leah Weiss
2025-12-07 16:00 - 18:00 (America/Halifax) | 49 West – The Front Room, 49 West St., Annapolis, MD, 21401, United States
GARY WRIGHT & LEAH WEISS play roots-Americana music. Drawing from the traditions of Appalachian old-time and country music, their repertoire is a blend of originals, reinvented traditional songs and tunes, and innovative contemporary covers. Driving fiddle lines and tight harmony singing are trademarks of their sound.
No Cover Charge

Tom Lagana & Darden Purcell
2025-12-07 19:30 - 21:30 (America/New_York)
Tom Lagana and Darden Purcell perform a holiday concert! Tickets are $20 and will be added to your bill on-site so please call 410-626-9796 to make your reservations because space is limited!
We hope to see you there!

Sound of Presents- The December Jingle Pop Up Show
2025-12-08 19:30 - 22:00 (America/New_York)

Seth Mitchell Band & Friends
2025-12-09 19:30 - 22:00 (America/New_York)

Pam & Paula Classical Duo
2025-12-10 16:30 - 18:30 (America/Halifax)
Join us for classical night every 2nd Wednesday of the month.

Songbird Collective
2025-12-10 19:30 - 22:00 (America/New_York)

Annapolis Round Up
2025-12-11 19:30 - 22:00 (America/New_York)

Jeff Muller & Friends
2025-12-12 19:30 - 22:30 (America/New_York)
Join us for an evening celebrating the diverse roots of American folk music, from the hills of the British Isles to the shores of West Africa, and beyond. This month’s all-star band includes Amadou Kouyate (kora and djembe), Leah Weiss (fiddle and vocals), Gary Wright (guitar, banjo and vocals), and Jeff Muller (bass, banjo and vocals). $20 cover. Reservations are highly recommended as these shows typically sell out. Call 49 West at 410-626-9796 to reserve your seat today!

Cyphers Band
2025-12-13 19:30 - 22:30 (America/New_York)

Evan Sky
2025-12-14 17:30 - 19:30 (America/New_York)
EVAN SKY AND THE CLOUDS IS BACK
For our last full band show of the year 😤
@49west_winebar_gallery in Annapolis, MD 🦀
We’ll be playing all the best christmas hits 🎅
I’m gonna play piano this time 🎹
You do NOT wanna miss ❌

The Eric Scott Trio Annual Holiday Concert-2 SHOWS!
2025-12-15 19:00 - 23:00 (America/New_York)
Eric Scott Trio Annual Holiday Concert
We are excited to announce that the very special guest is
Tony Denikos!
The 7 PM show is SOLD OUT!
We have added a new show at 9 PM
Presented by ITZALL Goode Music & SHC Music Tribe
Monday, December 15 @ 7:00 PM AND 9:00 pm
$25 Door
If you purchase a ticket, please do not call the venue to make a reservation. Your ticket is your reservation. You can also reserve and pay at the door by calling 410-626-9796.
It’s the annual ITZALL Goode Christmas event! Come out Monday night, 12/15, to see the incredible Eric Scott, Deren J Blessman, and Dan Leaonard. It will be a blast.
49 West Coffeehouse and Winebar
49 West Street – Annapolis, MD
shcmusictribe.com
49westcoffeehouse.com
Limited Seating.
ABOUT ERIC:
Website: ericscottmusic.com
Videos:
Live at Blue House Productions: https://www.youtube.com/watch?v=jMQnEGN8OJ4
Red: https://www.youtube.com/watch?v=2i8lSdXLo5Q
“…a great artist who has not succumbed to the dictates of artifice pop…masterfully recorded and mixed…proof that human hearts, souls,
and expressive artistry will move as much air as gargantuan samples, but are much more spiritually moving…a splendid EP.” — Jon Carroll, Multiple Grammy Award winner
Honesty, soul, and the celebration of life’s joy and pain. These are the things that consistently define Eric’s music and performance. As an artist, he’s powerful, sensual, and kind; with a keen insight into what makes us all “tick” that translates into his signature R&B/Rock/Pop flavored songs that reach the hearts of his audience.
ABOUT TONY:
Website: tonydenikos.com
Videos: Gravity Wins: https://www.youtube.com/watch?v=5x3BZGgq714
Under The Church: https://www.youtube.com/watch?v=w6F3XS_31qg
“Tony Denikos has garnered so much praise and reviews that I wasn’t left with hardly any adjectives for my own review. …There’s a warmth and natural soulfulness to this sound that is as much approachable as it is admirable…. Next time I sit beside Prine at Arnold’s Meat & Three, I am going to hip him to the fact that I know who is going to fill his shoes when he retires.”–Gary Allen (JJ Cale/The Charlie Daniels Band/Stonewall Jackson)
Some of Tony’s earliest memories are of riding along the country roads of central Maryland, singing songs like — “Jack O’ Diamonds” by Tex Ritter, “Born to Lose” by Ray Charles, “Caldonia” by Louis Jordan and “Pendulum Swings” by Roger Miller — along with his dad and sisters while his mom smiled at the landscape gliding by… a seed had been planted.
After years of playing pubs and bars in various configurations, Tony decided it was time to record a collection of songs he’d written and released his first CD, Naked & Smiling (1999). The Washington Post reviewed it, calling Tony a “Tunesmith in the best sense of the word”, and folks started coming out to listen to his originals. A tradition of recording songs about real life, mixed with humor, heartache, and wit, was born.
Tony’s latest record, released in 2020, “Gravity Wins”- A stripped-down, raw, and romantic take on all things life. Tony collaborates with Scott and Jen Smith, Geoffrey Himes, and David E. Moulton on three tunes and pens the rest of this collection of ten superbly produced and performed compositions.
From South Carolina to Texas to upstate New York, you can find Tony performing in any number of configurations. Be it an intimate acoustic solo show to a full-on, five-piece band, Tony’s is truly a must-hear, must-see experience for anyone who values first-rate songwriting and performances.

Unified Jazz Ensemble
2025-12-16 19:00 - 21:30 UTC | 49 West – The Back Room, 49 West St., Annapolis, MD, 21401, United States
Playing the 1st, 3rd (and sometimes) the 5th Tuesdays of the Month!
The Unified Jazz Ensemble is a dynamic group of masterful musicians from the USA. This ensemble has years of experience educating and entertaining diverse audiences. This is acoustic jazz, a classic American art form, done to perfection with audience interaction at its best.

Mr VCR & Friends
2025-12-17 19:45 - 22:00 (America/New_York)

Not Your Mothers Paint Night
2025-12-17 19:45 - 22:30 (America/New_York)

Redd Byrd Christmas with Sue Matthews
2025-12-19 20:00 - 22:00 (America/New_York)
Please call for your reservations at 410-626-9796

Dean Rosenthal’s 5 Piece Racket
2025-12-20 19:30 - 22:00 (America/New_York)

The Befuddlers
2025-12-21 16:00 - 19:00 (America/New_York)

Dream Punch & Friends
2025-12-21 19:30 - 22:00 (America/New_York)

Songwriters Night
2025-12-22 19:30 - 22:00 (America/New_York)
Charlie Young, Ryan Moran & Dan Heely
Please make your reservations at 410-626-9796

CLOSED FOR CHRISTMAS BREAK AT 4PM!!
2025-12-23 16:00 - 2025-12-24 00:00 UTC
MERRY CHRISTMAS TO YOU ALL!!!!!
49WEST HOLIDAY HOURS WILL BE:
CLOSED DEC 23RD AT 4pm
CLOSED DEC 24TH- CHRISTMAS EVE
CLOSED DEC 25TH- CHRISTMAS DAY
OPEN AT 10AM DEC 26TH

CLOSED FOR CHRISTMAS EVE!!!
2025-12-24 07:00 - 2025-12-25 00:00 (America/Halifax)
WE HOPE YOU HAVE A MERRY CHRISTMAS EVE!
