THE BIG OWL TIKI BAR
410-827-6523
https://www.thebigowl.com/event-list
Fridays – Sunset Party, 6pm
Aug 29 – Justin Ryan, 3pm
Aug 29 – Rebound Band,m 7pm
Aub 30 – Mixed Business, 3pm
Sept 3 – Joe Bryan, 6pm
Sept 5 – Diamond Alley, 7pm
Sept 6 – Country Fry’D Gentlemen, 3pm
Sept 7 – Dave McKenny-Labor Day Weekend Show, 4pm
Sept 10 – Joe Esham, 6pm
Sept 12 – Michael Ferro & Friends, 3pm
Sept 12 – Fast Eddie & The Slowpokes, 7pm
Sept 13 – Nate & Jim Duo, 3pm
Sept 17 – John Haywood, 6pm
Sept 19 – Bryan Hanifee, 3pm
Sept 19 – Flower Ave, 7pm
Sept 20 – Mixed Business, 3pm
Sept 26 – Justin Ryan, 3pm
Sept 26 – Red Betty & The Ruchus, 7pm
BRIDGES ON KENT NARROWS RESTAURANT & BAR
410-827-0282
Aug 29 – Elena Barrett, 6pm
CARP DIEM ARTS
240-203-8908
Carpediemarts.org/brooklets-place
Sept 8 – Seth Kibel Trio, 12:15pm
Oct 13 – Amor y Luz, 12:15pm
Nov 10 – Dom Flemons, 12:15pm
Dec 8 – Bay Country Chorus, 12:15pm
CHESAPEAKE MANOR VINEYARD
443-249-3335
www.chesapeakemanorvineyard.com
Check website for entertainment.
CHESAPEAKE MUSIC
Location: The Ebenezer Theater, Easton
Sept 26 – ArcoStrum-violinist Strauss Shi & guitarist Ty Zhang, 7:30pm
Oct 18 – Circle of Friends w/violinist Randall Goosby & pianist Zhu Want, 3pm
Nov 21 – Synchrony Quartet, 7:30pm
2027 Performances
Feb 6 – Catherine Cho & Friends, 7:30pm
Mar 13 – Catherine Cho & Friends, 7:30pm
Apr 17 – Catherine cho & Friends, 7”30pm
June 11-20 – 42nd Annual Chesapeake Chamber Music Festival
CULT CLASSIC BREWERY
410-980-8097
3rd Sunday – Flea Market, 11am
Last Sunday – Beers & Gear, 10am
2nd Tues – Books & Beer, 6pm
4th Tues – Writers Cult, 6pm
Tuesdays – Car Meet, 5pm
2nd Wed & 4th Tues – Open Mic, 7:30pm
Wednesdays, WINGO, 6pm
1st Thurs – Karaoke, 6:30pm
Thursdays – KI Farmers Market, 3:30pm
Thursdays – Trivia Night, 6:30pm
Aug 29 – Raggae on the Bay-Bumpin Uglies, Ballyhoo!, Jah Works, The Candy Rocks, 4:30pm
Sept 5 – BURNSIE EP Release w/David Augustus & The Bitter Buffalo & Veronique, 7pm
Sept 10 – Medium Debbie Wojciechowski, 7pm
Sept 11 – Girls Just Wanna Have Fun tribute night, 7pm
Sept 13 – Kids Markets, 11am
Sept 18 – Unofficial Baygrass Pre-party w/The Wharf Rats, 7:30pm
Sept 19 – Eastern Shore Street Machines 1st Annual Car Show, 11am
Sept 19 – Pirate Party w/The Bards & their Sea Shanties, 7pm
Sept 24 – Random Thursdays Line Dancing, 6:30pm
Sept 25 – Banquet Hall Grand Opening w/Pressing Strings, Kentavius Jones, Daphne Eckman & Heartside, 6pm
Sept 26 – Balloon Burlesque “Animal Kingdom,” 7:30pm
Oct 2 – Swamp Donkey Newgrass, 7pm
Oct 15 – Scary Stories, 7pm
Oct 16 – Monster Mash Murder Mystery Dinner, 6pm
Oct 24 – VW Air Raid-Pistons and Rings, 12N
Nov 7 – Holiday Book Festival, 12N
Nov 28 – Disciple of the Garden, 7pm
DOCK HOUSE
443-446-4477
www.dockhouserestaurant.com/entertainment
https://www.facebook.com/dockhouserestaurant
Aug 29 – Katelyn Christine, 5pm
FISHERMAN’S CRAB DECK
410-827-6666
www.facebook.com/FishermansCrabDeck/
Sept 3 – Mike Donato
Sept 4 – Byrd Daddy Band
Sept 11 – Matt Avery
Sept 18 – Justin Ryan
Sept 25 – Ashley Chapa
Oct 2 – Mike Donato
Oct 9 – Byrd Daddy Duo
Oct 16 – Uncultured Swine
Oct 23 – Rt 50 Trio
HARRIS CRAB HOUSE
410-827-9500
Live Music Thursday & Friday, 5-8pm
HUNTER’S SEAFOOD-Anchor Drop
410-827-8923
https://www.facebook.com/hunterscrabs
Check Facebook for entertainment
THE JETTY
410-827-4959
Mondays – Charm City Trivia, 7pm
Tuesdays – Bingo/Acoustic Duo, 6:30pm
Wednesdays – Karaoke Night, 7pm
Thursdays – Music Bingo & DJ w/DJ Juice, 7pm
Aug 29 – Rescue Party, 3pm
Aug 29 – Doc Marten and the Flannels, 8:30pm
Aug 30 – A Classic Case, 3pm
Aug 30 – The Cover Up, 7pm
Sept 4 – Tripwire, 8:30pm
Sept 5 – 1974, 3pm
Sept 5 – The Amish Outlaws, 10pm
Sept 6 – The Reagan Years, 8:30pm
Sept 7 – The Chucks, 3pm
Sept 11 – Vertigo Red, 8:30pm
Sept 12 – Johnny Seaton Band, 3pm
Sept 12 – Under the Covers, 8:30pm
Sept 18 – Shake the Room, 8:30pm
Sept 19 – Crushing Day, 8:30pm
Sept 19 – Here’s to the Night, 8:30pm
Sept 25 – My Chemical Bromance, 8:30pm
Sept 26 – Oracle, 8:30pm
Sept 27 – A Classic Case, 3pm
KENT ISLAND BAR & GRILL
443-249-3458
https://kibarandgrill.com/Home
Check Website for Entertainment
Live Music – Fri & Sat, 8-10pm
KENT ISLAND RESORT
410-643-5757
www.kentislandresort.com/events/list
Sept 11 – Taste of the Moview: Julie & Julia, 7pm
Sept 20 – An Island Harvest Fest, 12N
Sept 22 – Harvest and Hops… The Perfect Pairing, 6:30pm
Oct 16 – Soups & Sips, 6:30pm
KNOXIE’S TABLE – THE INN AT CHESAPEAKE BEACH CLUB
410-604-1933
www.baybeachclub.com/happenings
Aug 31 – Justin Taylor, 6pm
Sept 4 – Mike Newberry Duo, 6pm
Sept 7 – Wesley Spangler, 6pm
Sept 11 – Mack & Slim Duo, 6pm
Sept 14 – Chris Sacks, 6pm
Sept 18 – Tim Guilliams, 6pm
Sept 21 – Chesapeake Sons, 6pm
Sept 25 – Silent Tale Duo, 6pm
Sept 28 – Moe Stringz, 6pm
Oct 2 – Trish & Andy Duo, 6pm
Oct 5 – Tim Guilliams Duo, 6pm
Oct 9 – Mack & Slim Duo, 6pm
Oct 12 – Justin Taylor, 6pm
Oct 16 – Chris Sacks, 6pm
Oct 19 – Chesapeake Sons, 6pm
LIBBEY’S COASTAL KITCHEN
410-604-0999
www.facebook.com/LibbeysCoastalKitchen
Saturdays thru September – Waterfront Yoga. 10am.
Below Deck Music – Wednesdays & Fridays 5pm, Sundays 2pm
Aug 30 – Jordan Sokel, 2pm
LOVE POINT VINEYARDS AND WINERY
443-786-2765
Aug 30 – Vineyard Vibes w/Chesapeake Sons duo, 1pm
Sept 6 – Vineyard Vibes w/Tranzfusion and Nick Pizza DC
Sept 19 – Glassblowing Day, 11:30am
MARYLAND HALL, 801 CHASE ST, ANNAPOLIS
443-714-8109 or 443-223-5789
Maryland Hall, Annapolis
Aug 29 – Maryland Hall presents BloomHaven: “Road to Baygrass”: The Annapolis Fiddler’s Pick-nic & Bday Bash, 3pm
Sept 2 – Rams Head Presents: Patti Smith Quartet, 8pm
Sept 13 – Rams Head Presents: Valerie June w/Judy Blank, 8pm
Sept 18 – Official Annapolis Baygrass Kick-off Party w/Jammy Buffet, 6:30pm
Sept 25 – Park Books Presents: Jeneva Rose Sometimes I Scare Myself Author Event, 7pm
Oct 11 – Ailey II, 7pm
Nov 16 – Rams Head Presents: Lalah Hathaway, 7pm
MID ATLANTIC SYMPHONY ORCHESTRA
888-846-8600 (call or visit web site for locations)
Sept 24 – From London to America; Florence price, Dvorak, Haydn, 7:30pm, Easton Church of God
Oct 11 – Horn Trio & Piano Trio, 4pm, Academy Art Museum
Nov 3 – Mary howe Rediscovered, 7:30pm, Easton Church of God
Dec 3 – Holiday Joy, 7:30pm, Todd Performing Arts Center, Wye Mills
Dec 20 – Holiday Brass, 4pm, Christ Church, Easton
Dec 31 – A Toast to the New Year, 7pm, Christ Church, Easton
Feb 7 , 2027 – Woodwinds & Strings-Beethoven’s Legacy, 4pm, Academy Art Museum
Mar 14, 2027 – Elizabeth Loker International Concerto Competition, 3pm, Todd Performing Arts Center, Wye Mills
Apr 8, 2027 – Canyons, Constellations & Classics, 7:30pm, Todd Performing Arts Center, Wye Mills
Apr 29, 2027 – Discoveries, Reflections & Healing, 7:30pm, Easton Church of God
May 16, 2027 – String Quartet-Italian Masters, 4pm, Academy Art Museum
OXFORD COMMUNITY CENTER
410-226-5904
Dec 4 – Jazz on the Stage, Dominick Farinacci & Friends, 7:30pm
POUR HOUSE PUB
443-249-3242
Live acoustic entertainment – Thurs 7:30-10:30pm & Fri and Sat nights 8:30-11:30pm.
QUEEN ANNE’S COUNTY CENTRE FOR THE ARTS
410-758-2520
queenannescountyarts.com/summer-free-concert-series.html
Thursdays in the Park
Sept 17 – The Chris Sacks Band, Cascia Winery, 6pm
RAMS HEAD ON STAGE, 33 West St, Annapolis
410-268-4545
https://www.ramsheadonstage.com/events
Aug 29 – The Verve Pipe, 8pm
Aug 30 – Mike Phillips, 8pm
Sept 4 – Garrison Keillor w/special guests Robing & Linda Williams, 8pm
Sept 5 – Garrison Keillor w/special guests Robing & Linda Williams, 2pm
Sept 6,7 – Tuba Skinny, 8pm
Sept 9 – Drivin N Cryin, 8pm
Sept 11 – Songwriters in the Round, 7pm
Sept 12 – Songwriters in the Round, 11am
Sept 12 – Maggie Rose Band W. Twinnie, 8pm
Sept 13 – Josiah and the Bonnevilles, 8pm
Sept 14 – AMFM Presents: In the Vane of Billy Joel, 7pm
Sept 16 – The Robert Cray Band: All Amped Up Tour, 8pm
Sept 17 – here come the Mummies, 8pm
Sept 18 – Davy Knowles, 8pm
Sept 19 – Sam Grisman Project, 8pm
Sept 20 – Cyril Neville Plays the Dead, 8pm
Sept 23 – Sean Hayes w/Etienne De Rocher, 8pm
Sept 24 – Brett Dennen: Art Is Life
Sept 26 – Southern Culture on the Skids w/Poi Rogers, 8pm
Sept 28 – Michael Franti Trio: Heartstrings & Dynamite w/Wheeland Brothers, 8pm
Sept 29 – Los Lonely boys w/Lisa Morales, 8pm
RAMS HEAD SHORE HOUSE
410-643-2466
Wednesdays – Music Bingo-all ages, 6pm
Thursdays – Think N’ Drink Trivia, 7:30pm
Aug 29 – Livengood Project, 7pm
RED EYE’S DOCK BAR
410-304-2072
https://www.facebook.com/redeyesdockbar/
Aug 29 – Boh Daddies, 3pm
Aug 29 – Swarm of Bees, 8pm
Aug 29 – DJ Dev James, 9pm
Aug 30 – Bikini Contest Semi-Finals w/DJ Manila, 2pm
ST. MICHAELS COMMUNITY CENTER-Muskrat Park
Sept 3 – Saved by Zero, 6pm
THE AVALON FOUNDATION – 2026 Summer Concert Series
https://avalonfoundation.org/events
Aug 29 – Julie Parsons Jazz Trio at Easton Farmers Market, 10am
Aug 29 – Motown & More, Outdoors, 7pm
Aug 29 – The Kennedys, Stoltz Listening Room 7:30pm
Sept 3 – Danah Denice, Stoltz Listening Room, 6:30pm
Sept 4 – Ampersand, Stoltz Listening Room, 6:30pm
Sept 5 – Wayne Wheeler at Easton Farmers Market, 10am
Sept 5 – Eric Byrd Trio, Stoltz Listening Room, 6:30pm
Sept 11 – Omari Banks, Stoltz Listening Room, 6:30pm
Sept 12 – Michael Kelly at Easton Farmers Market, 10am
Sept 12 – Coastal Plain, Stoltz Listening Room, 6:30pm
Sept 18 – Jennifer Knapp, Stoltz Listening Room, 6:30pm
Sept 19 – The KG Band Trio at Easton Farmers Market, 10am
Sept 19 – Anthony Devito, Stoltz Listening Room, 6:30pm
Sept 24 – The Wailers (dance floor open), Avalon Theatre, 6:30pm
Sept 25 – Brett Dennen-Art is Life, Avalon Theatre, 6:30pm
Sept 26 – Allegro Academy at Easton Farmers Market, 10am
Sept 26 – Julian Velard, Stoltz Listening Room, 6:30pm
Oct 2 – A Tribute to Carlos Santana & Jimi Hendrizx featuring David B. Cole, Avalon Theatre, 5:30pm
Oct 3 – Wayne Wheeler at Easton Farmers Market, 10am
Oct 3 – Cosi Fan Tutte by Wolfgang Amadeus Mozart, Avalon Theatre, 12:30pm
Oct 3 – Kat Parsons, Avalon Theatre, 6:30pm
Oct 8 – An Evening w/The Del McCoury Band, Avalon Theatre, 6:30pm
Oct 9 – Lee Fields, Avalon Theatre, 6:30pm
Oct 10 – Lisa Rowe at Easton Farmers Market, 10am
Oct 10 – The Jersey Tenors, Avalon Theatre, 6:30pm
Oct 15 – Antje Duvekot & Bobby Hecht, Avalon Theatre, 6:30pm
Oct 17 – Coffee for Two at Easton Farmers Market, 10am
Oct 17 – MacBeth by Giuseppe Verdi, Avalon Theatre, 12:30pm
Oct 23 – Cris Jacobs & Pressing Strings, Avalon Theatre, 6:30pm
Oct 24 – Gypsy Wind at Easton Farmers Market, 10am
Oct 24 – Amy Speace w/special guest Jesse Lynn Madera, Stoltz Listening Room, 6:30pm
Oct 25 – Neko Case w/Destroyer, Avalon Theatre, 6:30pm
Oct 29 – The Stillhouse Junkies, Stoltz Listening Room, 6:30pm
Oct 31 – Jeffrey Jones at Easton Farmers Market, 10am
Nov 5 – Jake Shimabukuro, Avalon Theatre, 6:30pm
Nov 7 – Wayne Wheeler at Easton Farmers Market, 10am
Nov 12 – Ali Webb & Friends, Stoltz Listening Room, 6:30pm
Nov 14 – Jeffrey Jones at Easton Farmers Market, 10am
Nov 20 – The Reagan Years, Avalon Theatre, 6:30pm
Nov 21 – Nicholas Sparacino at Easton Farmers Market, 10am
Dec 4 & 5 – Medium Debbie Wojciechowski, Stoltz Listening Room, 6:30pm
Dec 5 – Samson Et Dalila by Camille Sanit-Saens, Avalon theatre, 11:30am
Jan 23 – La Fanciulla Del West by Giacomo Puccini, Avalon Theatre, 12:30pm
Mar 20 – Silent Night by Kevin Puts & Mark Campbell, Avalon Theatre, 12:30pm
Mar 21 – Larry, Steve & Rudy: The Gatlin Brothers, Avalon Theatre, 6:30pm
Apr 3 – Manon by Jules Massenet, Avalon Theatre, 11:30am
Apr 24 – Otello by Giuseppe Verdi, Avalon Theatre, 12:30pm
June 5 – Parsifal by Richard Wagner, Avalon Theatre, 11:30am
TEN EYCK BREWING CO.
443-347-3637
First Wednesday of Month – Open Mic Night, 6-8pm
Fridays – Let’s Do Trivia, 6:30pm
Sept 2 – Open Mic Nite w/Kevin Brown, 6pm