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  • Seacrets
  • Greene Turtle
  • Bull on the Beach
  • BJ's on the Water
  • Hooters
  • Fresco's
  • Ruth's Chris
  • Jolly Roger Amusement Park
  • Splash Mountain Waterpark
  • Speedworld Go-Karts
  • Miniature Golf
  • Ripley's Museum
  • Lighthouse Sound Golf
  • GlenRiddle Golf
  • Dead Freddies
Goodie Bag
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open-air produce market with wooden crates full of food
September 25 `20
Trimper's Rides
Trimper's Greenmarket is the premiere destination for agricultural products sourced locally on the Eastern Shore. It is the best farmer's market in Ocean City, MD combining dozens of vendors including regional farmers, fishermen, and bakers, with local entertainment. Trimper's is committed to showcasing home-grown and homemade goods of all kinds from the Eastern Shore. Selling merchandise sought after by tourists, chefs, and boutiques of Ocean City, Maryland; locals and guests are in for a treat. Situated in downtown Ocean City, stop, chat, learn, and shop!
wine glasses with red white and rose
September 25 `20 - September 26 `20
Hugh T. Cropper Inlet Parking Lot
Wine on the Beach launched in 1994 to introduce the Maryland wine industry to the Delmarva region and extend the beach season into fall. Since then, this inlet wine festival and beach party has become an annual tradition among family and friends who like to learn about Maryland wines, taste and purchase new products, and stock up on old favorites. Wine on the Beach has also become a special place for class reunions and bachelorette parties, among others.
Wineries will be bringing more varieties and volume of their wine to the festival this year to keep up with increased demand. Unlike most wine festivals, Wine on the Beach has diversified and now features Maryland craft beers.  The festival will be larger this year as well, with more beach area and picnic tables to enjoy food and wine!
Wine on the Beach also features live music and popular regional bands! Check back for the entertainment schedule in 2021.

Entertainment Schedule

To be announced
To be announced
silhouette of people facing a stage blue fog lights
September 25 `20
Skye Bar & Grille
Forming as a result to various jam sessions and guest appearances at Aaron's solo shows, The Aaron Howell Band has become one of the Ocean City area's top local draws.  Playing a more rock-heavy set, Bob and Adam lay down the rhythm while Aaron turns your head with his bluesy guitar leads, dynamic vocal work, and incredible stage presence.
Make sure you come for Happy Hour at Skye Bar from 3-6pm! Raw bar Happy Hour specials include $1 oysters and 1 1/4lb. lobster for $20. Drink specials include $5.00 Orange Crushes, $3.75 Rails, $1 off Drafts, and $5 House Wines.
Closeup of acoustic guitar being played
September 25 `20
Ropewalk Restaurant
Join Ropewalk for an evening of live music featuring Andrew Robear. This Maryland-based artist will put on a show you won't forget.  Enjoy drinks and dinner with your choice of indoor or outdoor dining available.
acoustic guitar being played on stage by male musician
September 25 `20
Dave Hawkins, an accomplished musician, has been playing music for what seems to be his entire life. Music is his passion and he is passionate about how it's perceived throughout his audience. He plays many guitars, harmonica, and fiddle and when you hear him you will think there is a whole band, not just one person. This is accomplished by what is known as looping.  There is never a "backing track" to play along with, which is used by some other players out there. His vocals and music will reach the deepest part of you while it sets your senses alive. He plays sounds from the current popular, to classic rock, to Dave Matthews, to his own original compositions as he touches on just about any genre you may desire.
closeup of a man playing guitar
September 25 `20
Coconuts Beach Bar & Grill
Catch Monkee Paw at Coconuts Bar & Grille in Ocean City. Monkee Paw's musical style ranges from duo to quartet, and they have spent almost a decade performing in Ocean City. Spanning a wide variety of genres, with a strong focus on vocal harmony. Band members include: Mike Givens, Rick Smith, Joseph Wirt, Ray Perrone, Dean Haemel and Adam Ask.  
back and white piano keys
September 25 `20 - September 26 `20
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 famous crab cakes and great selection from the bar.  
Lauren Glick with band members
September 25 `20
Downy Oshun Seafood Shack
Come to Downy OShun Seafood Shack Friday night to hear Lauren Glick.  Lauren Glick a native of Salisbury MD., and now back living on the Eastern Shore entertains crowds in and around the Ocean City, MD area. 
Don't forget to ask about food and drink specials.
group of band members on a stage with green lighting
September 25 `20 - September 26 `20
Horizons Oceanfront Restaurant
"On The Edge" was formed in 1984 and quickly became Maryland Eastern Shore's favorite dance band. The band is popular for their high energy presentation while entertaining their audiences with a wide variety of Pop hits from 60's Motown to modern pop tunes and everything in between! 
dj turntables surrounded by multi color stage lights
September 25 `20
Fager's Island
Returning to the area after several successful stints doing in-house DJ residencies at some of the hottest dance clubs in the D.C, and Baltimore area. Rob's unique DJ mixing skills prove why he remains one of the best in the business. Spinning everything from new-school hits to old-school jams and the hottest in international dance trax.
group on stage with blue lights in the background
September 25 `20
Pickles Pub
Come to Pickles Pub in Ocean City for a performance by the talented Joey Harkum. Enjoy this live show at the locals' favorite Downtown Ocean City watering hole. Live performances are always a great time at Pickle's Pub! 
closeup of a mans hands playing a guitar
September 25 `20
Are you ready to rock?  Tranzfusion Band is at playing live music just for you at Harpoon Hanna's Restaurant! Tranzfusion is a local rock/classic rock band that plays throughout Delmarva. Band members consist of Bobby Malaby, Tom Malaby. Hank Koening and Bob Davis.
man at a turntable spinning records
September 25 `20 - September 27 `20
Purple Moose Saloon
DJ Rut does not miss a beat... party with him at the Purple Moose Saloon on the Boardwalk in your favorite beach town!   DJ Rut throws down hot blends and cuts up like no one else.  For this DJ, no genre is off limits so don't be shy with your requests! 
live music text in bright neon lights
September 25 `20 - September 26 `20
Purple Moose Saloon
Bad with Names is excited to announce they are heading to Ocean City, Maryland. Where at? Of course, the famous Purple Moose located on the boardwalk in Ocean City, Maryland. Get ready for awesome tunes, drinks, and more!
Crowd at concert with pink lights behind
September 25 `20 - September 26 `20
Fager's Island
Firekite will be performing on the stage at Fager's Island! Don't miss this high energy modern alt-rock band when they stop by Ocean City. Hear covers from your favorite contemporary artists like Muse, Walk the Moon, and Neon Trees, and throwbacks from No Doubt, Alanis Morisette, and Led Zeppelin. You'll be entertained all night long! 
electric guitar
September 26 `20
Coconuts Beach Bar & Grill
Kevin Poole & Joe Mama are performing live at the one-and-only Coconuts Bar and Grille in Ocean City, Maryland. Coconuts Bar & Grille is known for amazing food-selections, entertainment, and more! Head over to this iconic location and see Kevin Poole & Joe Mama put on a performance like no other! 
person playing guitar up close
September 26 `20
Alley Oops Midtown
Join Pat O'Brennan for the best tunes to accompany your late lunch or dinner at Alley Oops Midtown location.  Also stop by Alley Oops Midtown for  Happy Hour Monday-Friday from 3-6pm and enjoy $5.50 crushes, $2 off all drafts, 1/2 price Liberty oysters, and even more!
live music band sign
September 26 `20
Skye Bar & Grille
This father/son duo plays a diverse range of covers.  
Rick La Ricci was born and raised in Baltimore, Maryland. While owning and operating a roofing business, Rick also played music on the side at various clubs. His biggest influence was singer/songwriter John Lennon and of course The Beatles. Rick has played various shows and clubs in Baltimore and Ocean City. While residing in Ocean City Rick's son Lennon La Ricci was born.

After moving back to Baltimore and seeing his father play music his whole life Lennon had taken an interest in music himself. One day while strumming on a guitar, Rick asked Lennon what instrument he wanted to play. Lennon chose the piano/keyboard as his first instrument.  Rick's dream was to play on the same stage as his son so he decided to take him to his old friend Jim Jones who runs and operates a music school called The Music Work Shop. Jim Jones took a special interest in Lennon and started giving him personal lessons. Ricks dreams would come true quicker than expected because 6 months later he and Lennon played together for the first time at The Horse You Came In On in Fells Point, Md. They started doing monthly gigs at The Horse You Came In On Saloon in Baltimore Maryland where they would hone their skills. As Lennon's music skills progressed he started learning more sets and doing longer shows. Rick and Lennon have played at Oregon Ridge Blues Festival, Hampden Festival, Hot August Blues, Bill Bateman’s, The Horse, The Hon Fest and all over Ocean City Maryland.

Lennon's life long dream is to become a professional songwriter and musician.  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.

Make sure you come for Happy Hour at Skye Bar from 3-6pm! Raw bar Happy Hour specials include $1 oysters and 1 1/4lb. lobster for $20. Drink specials include $5.00 Smirnoff Crushes, $3.75 Rails, $1 OFF Drafts, and $5 House Wines.
Rick and Lennon Laricci
September 26 `20
Skye Bar & Grille
Come to Skye Bar and Grille to hear Rick and Lennon Laricci at Skye Bar on Saturday. Rick was born and raised in Baltimore, where he owned his own roofing company. On the side, he played music at various clubs throughout Baltimore. His dream was always to play on the same stage as his son, and after taking him to a music workshop called The music School, Lennon and Rick played at a bar in Fells Point six months later.
Acoustic guitar and strings being played
September 26 `20
Ropewalk Restaurant
This duo/trio of musicians performs a wide variety of genres all around the Delmarva area!  They do a variety of covers, as well as a few originals. Paws Up; it's time to Paw-ty at Ropewalk in Ocean City!
man playing drums on stage with purple lights
September 26 `20
Dave Sherman writes and performs original material but his specialty is Baby Boomer music. Primarily influenced by The Beatles, his musical tastes range from 60's R&B to Jazz Rock. He covers many Classic Rock pieces from the '60s, '70s, '80s with a little modern country thrown in and of course some Jimmy Buffett.
human connection band members
September 26 `20
OC 360 Eats & Drinks
Good music continues, - we are happy to have Human Connection perform their  set with us. Please join us for a evening of great music, dinner and drinks with a view.
kayak in water while the sun sets
September 26 `20
Full Moon Paddle with Bonfire and Refreshments
Register Today; Limited Participants
Ayers Creek Adventures
Explore and experience the surreal beauty of Maryland's coastal waterways at this unique paddle in full moon light! whole new light. Depart at sunset to enjoy a peaceful paddle to a bald eagle nesting area as we watch the sunset and the full moon rise over the water. Drift quietly over the calm water for a front row seat as dozens of native birds jostle for their nightly roost. Join us for a BYOB post paddle bonfire while the moon rises majestically over the creek. Appropriate for all levels of paddlers.  Adults only tour
With our enhanced Covid-19 safety procedures the 2020 Full Moon Paddles will be limited to 8 guests and we will not be serving food and beverages. We encourage you to bring your own food and beverage and join us for the bonfire. We have adjusted our price accordingly.

electric guitar
September 26 `20
Stealing Savanah, party cover band hailing from Southern New Jersey and spreading infectious noise up and down the East coast. Come see the talented band members live at Seacrets Jamaica USA in Ocean City, Maryland! 
live music
September 26 `20
Come and relax at Teaser's Bar at Sunset Grille!  While you are here;  check - out the talented band members of Late Last Night! Sunset Grille is known for its iconic location in Ocean City, Maryland, food-specials, live entertainment, bar-specials and more! See you on the dance floor!
Best Western Plus Ocean City
From $279.00 per night
Crystal Beach Oceanfront Hotel
From $319.00 per night
Fenwick Inn
From $499.00 per night
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