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Ocean City Events Calendar

Ocean City Maryland
Ocean City Maryland > Ocean City MD Events Calendar
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live music signage
October 21 `25
Live Music at Harpoon Hannas
Bar Bingo with DJ Rupe
Harpoon Hanna's
Join us tonight for live music featuring great bands at Harpoon Hanna's in Fenwick Island, Delaware. Get ready for a great time filled with tunes, and bar-specials!
 
 
Don't miss our Trivia Nights, Bar Bingo, Karaoke and more.
red bingo chips and bingo card
October 21 `25
Bar Bingo with DJ Rupe
Harpoon Hanna's
Join us every Tuesday night for Bar Bingo with DJ Rupe. Games from 6:00 pm - 8:00 pm with a winner every game.   A great time where you can get food and drink specials just for players, with Mystery Balls for even deeper discounted drink prices.
 
Free to play! 
live music signage
October 22 `25
Live Music at Harpoon Hannas
Featuring Shortcut Sunny
Harpoon Hanna's
Join us tonight for live music featuring great bands at Harpoon Hanna's in Fenwick Island, Delaware. Get ready for a great time filled with tunes, and bar-specials!
 
 
Don't miss our Trivia Nights, Bar Bingo, Karaoke and more.
silhouettes of people facing a stage blue fog lights
October 23 `25
Steve O'Boyle Country
Skye Bar & Grille
Steve O'Boyle Country is playing live tonight at The Skye Bar and Grille.  Stop by for Happy Hour from 3 to6pm with great specials such as $1 Oysters, 1 1/4 lb lobsters, $7 Smirnoff Crushes, $5.50 Rail Drinks, $6 House Wines and $1 off Drafts. 

live music signage
October 23 `25
Live Music at Harpoon Hannas
Featuring Cecilia Grace
Harpoon Hanna's
Join us tonight for live music featuring great bands at Harpoon Hanna's in Fenwick Island, Delaware. Get ready for a great time filled with tunes, and bar-specials!
 
 
Don't miss our Trivia Nights, Bar Bingo, Karaoke and more.
band equipment set up on stage with stage lighting
October 24 `25
Lauren Glick
Skye Bar & Grille
Lauren Glick can deliver just about any style of music, but she is known as the "Janis Joplin" of the beach. Lauren sings from the heart and soul, giving it all she's got. On the other side of the spectrum, her original music is influenced by Tori Amos, Kate Bush, Sara McLaughlin, and Amy Mann.
 
Happy hour is from 3-6pm and features specials such as $1 Oysters, 1 1/4 pound lobsters for $26.  Happy hour drink specials include $6.75 Smirnoff Crushes, $5.00 Rails, $1 Off Drafts and $5.50 House wines. 
 
live music signage
October 24 `25
Live Music at Harpoon Hannas
Featuring Union Road Duo, 5pm; Turning Point, 9 pm
Harpoon Hanna's
Join us tonight for live music featuring great bands at Harpoon Hanna's in Fenwick Island, Delaware. Get ready for a great time filled with tunes, and bar-specials!
 
 
Don't miss our Trivia Nights, Bar Bingo, Karaoke and more.
back and white piano keys
October 24 `25 - October 25 `25
Phil Perdue - "The Piano Man"
Captain's Table Restaurant and Bar
Enjoy Phil Perdue "The Piano Man" on the grand piano at the Captain's Table in Ocean City, Maryland.  Enjoy fine dining at its best with South African lobster tails, delicious crab cakes, certified angus beef steaks and great selection from the bar. Phil's smooth sounds on the grand piano are a local's favorite on Friday and Saturday nights.  
people cheers with red wine in wine glasses
October 24 `25
Live Music & Wine at Windmill Creek Winery
Annual Bonfire & Live Music Featuring AMP
Windmill Creek Winery & Farm Kitchen
Live music, great food, and of course the best wine on the lawn at Windmill Creek today! Bring your lawn chair to Windmill Creek Vineyard and Winery for the time of your life!  Or reserve your Igloo for a unique dining experience.
live music signage
October 25 `25
Live Music at Harpoon Hannas
Shortcut Sunny, 12 pm; Union Road Duo, 4 pm; The Rogue Citizens, 9 pm
Harpoon Hanna's
Join us tonight for live music featuring great bands at Harpoon Hanna's in Fenwick Island, Delaware. Get ready for a great time filled with tunes, and bar-specials!
 
 
Don't miss our Trivia Nights, Bar Bingo, Karaoke and more.
Silver Microphone on a stage with colorful lights
October 25 `25
Jess Arms Live
Featuring Jess Arms
Skye Bar & Grille
Check out Jess Arms with your family and friends at the Skye Bar and Grill in Ocean City, MD! Enjoy live entertainment while taking advantage of the awesome Happy Hour drink specials that are offered daily from 4:00 pm to 8:00pm and have a delicious meal together.  Good time guaranteed!
people cheers with red wine in wine glasses
October 25 `25
Live Music & Wine at Windmill Creek Winery
Featuring Shore Blues Band
Windmill Creek Winery & Farm Kitchen
Live music, great food, and of course the best wine on the lawn at Windmill Creek today! Bring your lawn chair to Windmill Creek Vineyard and Winery for the time of your life!  Or reserve your Igloo for a unique dining experience.
yellow electric guitar
October 25 `25
Lowercase Blues Band
High Stakes Bar & Grill

Lowercase Blues plays blues-based rock with a funkified rhythm – lyrical melodies above percussive bass lines woven around a jazzy drumbeat. Come see the band live at High Stakes Bar and Grill in Fenwick Island which always features some of the best local talent!


close up of a football on a field
October 26 `25 - October 27 `25
Watch the NFL Football Game
NFL Sunday Ticket
Skye Bar & Grille
Get here early and grab a seat to watch the NFL football games with us at the Skye Raw Bar and Grill.  The Skye Bar has the NFL ticket so you won't miss a single play!  The Tailgate menu is on point and the kitchen crew will make sure you have a happy belly!
 
 
 

 

 
 
live music signage
October 27 `25
Live Music at Harpoon Hannas
Trivia Night: Sign-In at 5:30 pm
Harpoon Hanna's
Join us tonight for live music featuring great bands at Harpoon Hanna's in Fenwick Island, Delaware. Get ready for a great time filled with tunes, and bar-specials!
 
 
Don't miss our Trivia Nights, Bar Bingo, Karaoke and more.
live music signage
October 28 `25
Live Music at Harpoon Hannas
Bar Bingo with DJ Rupe
Harpoon Hanna's
Join us tonight for live music featuring great bands at Harpoon Hanna's in Fenwick Island, Delaware. Get ready for a great time filled with tunes, and bar-specials!
 
 
Don't miss our Trivia Nights, Bar Bingo, Karaoke and more.
red bingo chips and bingo card
October 28 `25
Bar Bingo with DJ Rupe
Harpoon Hanna's
Join us every Tuesday night for Bar Bingo with DJ Rupe. Games from 6:00 pm - 8:00 pm with a winner every game.   A great time where you can get food and drink specials just for players, with Mystery Balls for even deeper discounted drink prices.
 
Free to play! 
neon live music sign
October 29 `25
Carley Twigg
Skye Bar & Grille
Talented, local singer and guitarist, Carley Twigg plays all of your favorite Pop, Country, Rock and Blues live tonight at Sunset Bar and Grille.  Stop in for a great show, dinner with your friends and of course your favorite Skye Bar & Grille cocktails and amazing views! 
back and white piano keys
October 31 `25
Phil Perdue - "The Piano Man"
Captain's Table Restaurant and Bar
Enjoy Phil Perdue "The Piano Man" on the grand piano at the Captain's Table in Ocean City, Maryland.  Enjoy fine dining at its best with South African lobster tails, delicious crab cakes, certified angus beef steaks and great selection from the bar. Phil's smooth sounds on the grand piano are a local's favorite on Friday and Saturday nights.  
back and white piano keys
November 1 `25
Phil Perdue - "The Piano Man"
Captain's Table Restaurant and Bar
Enjoy Phil Perdue "The Piano Man" on the grand piano at the Captain's Table in Ocean City, Maryland.  Enjoy fine dining at its best with South African lobster tails, delicious crab cakes, certified angus beef steaks and great selection from the bar. Phil's smooth sounds on the grand piano are a local's favorite on Friday and Saturday nights.  
electric guitar being played at an angle in B&W
November 1 `25
Dust N' Bones
High Stakes Bar & Grill
Come to High Stakes Bar and Grill in Fenwick Island, DE to hear live entertainment. Listen to musicians playing with the talented artists - Dust N' Bones. This should be a great night of entertainment! 
live music signage
November 3 `25
Live Music at Harpoon Hannas
Trivia Night: Sign-In at 5:30 pm
Harpoon Hanna's
Join us tonight for live music featuring great bands at Harpoon Hanna's in Fenwick Island, Delaware. Get ready for a great time filled with tunes, and bar-specials!
 
 
Don't miss our Trivia Nights, Bar Bingo, Karaoke and more.
red bingo chips and bingo card
November 4 `25
Bar Bingo with DJ Rupe
Harpoon Hanna's
Join us every Tuesday night for Bar Bingo with DJ Rupe. Games from 6:00 pm - 8:00 pm with a winner every game.   A great time where you can get food and drink specials just for players, with Mystery Balls for even deeper discounted drink prices.
 
Free to play! 
back and white piano keys
November 7 `25 - November 8 `25
Phil Perdue - "The Piano Man"
Captain's Table Restaurant and Bar
Enjoy Phil Perdue "The Piano Man" on the grand piano at the Captain's Table in Ocean City, Maryland.  Enjoy fine dining at its best with South African lobster tails, delicious crab cakes, certified angus beef steaks and great selection from the bar. Phil's smooth sounds on the grand piano are a local's favorite on Friday and Saturday nights.  
man plays a brown acoustic guitar at a 45 degree angle
November 8 `25
Rick & Lennon La Ricci
High Stakes Bar & Grill
It is rare to find a father-son musician duo performing in the Ocean City and Delaware Beaches area. Ricky and Lennon LaRicci are one very popular duo.
 
Rick and Lennon play at venues all over the Ocean City area as well as “back home” in Baltimore. Here’s a unique quote from Lennon’s website: “Along the way bandmates have come and gone, but what still remains is Rick and his son Lennon doing what they love everyday…playing music.”
Best Western OC Hotel & Suites
From $69.49 per night
Howard Johnson® By Wyndham Oceanfront Plaza Hotel
From $159.00 per night
Fenwick Inn
From $69.00 per night
Sea Bay Hotel
From $69.49 per night
Carousel Oceanfront Hotel & Condominiums
From $79.00 per night
Best Western Plus Ocean City
From $89.49 per night
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