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  • Jolly Roger Amusement Park
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  • Dead Freddies
Goodie Bag
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wine glasses with red white and rose
September 27 `19 - September 28 `19
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. In 2019, Anheuser-Busch products will be featured, including OC favorite Land Shark Lager. 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 out the entertainment schedule below.

Entertainment Schedule

Friday
12:30pm - 3:30pm: Kevin O'Brennan and Shoreline
4:00pm - 7:00pm: Pat O'Brennan Music
 
Saturday
12:30pm - 3:30pm: 3 Penny Opera
4:00pm - 7:00pm: Bird Dog and The Road Kings
Acoustic guitar and strings being played
September 27 `19
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!!
siloeutte of man wearing a hat with red background
September 27 `19
Hooters of Ocean City
Stop by Hooters of West Ocean City, 97.1 The Wave' afternoon personality;  DJ BK  will help you get your weekend started by playing your favorite dance tunes  from 7-9pm!    
man with guitar on his back walking a concrete path
September 27 `19
Bethany Boathouse
Kevin has been playing music professionally in Ocean City, MD since 1993.  Kevin recorded his first album, Going Home, in 1996, a mix of tempos and styles. Kevin's second album Troubador was released in 2001. Troubador is a very layered and meticulously recorded CD created with a large band and encompassing many musical styles. In 2006 Kevin's third album, Scenic Route was released. Scenic Route is a fun lighthearted CD with an eclectic mix of originals and covers, including covers of the Beatles, Elvis Costello, The Church and more. Originals such as A.D.D., Stairway to Kevin, King Midas, and the crowd favorite, Redneck Nascar Honey, which has received a lot of airplay in the Maryland/Delaware area. 
silouette of person with hat at dj turntable
September 27 `19
Cottage Cafe
It's finally Friday! Come have dinner, drinks and hang out with us at Cottage Cafe for our TGIF Party!  Every Friday night with DJ Bump to keep the party going!  
blue acoustic guitar in front of white background close
September 27 `19
Pizza Tugos
Head to Pizza Tugo's and listen to live music at the West OC location at the Tiki Bar! Enjoy your favorite jams from local artists while watching the palm trees sway in the evening breeze. Snack on your preferred slice of pizza and don't forget to order your favorite brew. It's craft beer heaven - with over 40 beers on draft and more to love in bottles!
 
Friday, September 27th: Darren McDowell
 
Friday, October 4th: Frankie Moran
 
Friday, October 11th: Sean Loomis
 
Friday, October 18th: Anna Burgess
 
Friday, October 25th: Sean Loomis
closeup of a guitar being played at an angle
September 27 `19
Nick's Original House of Ribs
Enjoy a solo session in the pub at Nick's Original House of Ribs. Great music, good eats and drinks, and a whole lotta fun!
 
Schedule:
 
Sept 13: "King Neptune" Chris Miller
 
Sept 20: Darren McDowell Francis
 
Sept 27: Adam Bilenki
 
Oct 4: Darin Engh
 
Oct 11: Anna Burgess
 
Oct 18: Frankie Moran
 
Oct 25: Adam Bilenki
band
September 27 `19
Ocean Pines Yacht Club
This group of talented musicians has been together for years.  They primarily play rock music.  In 2009, Tranzfusion won the Coconut Times' Entertainer of the Year Award.  In 2008 the band won the Daily Times' #1 All-time Favorite Band Award.
September 27 `19
Brew River
Established in 2000, Glass Onion Band is one of Delaware's premier party bands.   You are in for a treat at Brew River tonight as their music genre can be described as rock and roll along with R & B style tunes! 
close up of brown electric guitar being played
September 27 `19
Randy Lee Ashcraft has been entertaining people all over the country for over 20 years and has returned home to the Eastern Shore to perform for his favorite fans! His music is often referred to as "beach country". A former Green Beret in the United States Army, Randy has released five albums, which combined have sold over 20,000 copies to places as far reaching as Europe. In 1999, he received a citation from Governor Parris Glendening of Maryland honoring his "dedicated efforts to share the beauty of the Eastern Shore of Maryland region through his music and the song 'Shore Thing'".  Randy is also the '02, '03, '04, and '05 winner for Best Entertainer/Singer of the Eastern Shore, the '03, '04, and '05 winner for Best Singer/Songwriter on Delmarva, and the '08 Entertainer of the Year as presented by the Coconut Times.
 
September 27 `19 - September 28 `19
Dublin 5
Celtic Music At It's Best
Shenanigan's Irish Pub
Dublin 5 has taken the Celtic music scene by storm thanks to an eclectic mix of traditional roots and blazing instrumentals with an amped up rock twist. Their musicianship and show is nothing short of high octane. 
 
Hit the beach with Dublin 5 at Shenanigan's Ocean City, MD
members of the band element K
September 27 `19
Seacrets Jamaica USA
Element K moves seamlessly between multiple genres and performs some of your favorite classics, in addition  to the hottest new songs--not to mention some cool surprises along the way!  
band dublin 5
September 27 `19 - September 28 `19
Shenanigan's Irish Pub & Grille

Shenanigan's Irish Pub and Grille Ocean City, MD has voted Best Irish Bar at the Beach! Enjoy Irish favorites and head the one-and-only, Dublin 5! Dublin 5 has taken the Celtic music scene by storm thanks to an eclectic mix of traditional roots and blazing instrumentals with an amped up rock twist.


DJ at turntable with red light in background
September 27 `19 - September 28 `19
Seacrets Jamaica USA
Come dance the night away to beats from DJ Tuff at Seacrets in Ocean City, MD. Enjoy a cold drink with a few friends while jamming along to your favorite club tunes.
first class band members
September 27 `19 - September 28 `19
Ocean Club Night Club
First Class is the choice for the best live top 40 and variety entertainment on the market.  From sax powered ballads to classics to today’s current hits. First Class sits at the top.  First Class is a strong four piece band with strong vocals, tight rhythm section, and serious sax playing. 
September 27 `19
Seacrets Jamaica USA
Stellar Mojo is an exciting five piece band from the Jersey Shore. Assembled from the most seasoned, yet freshest musicians in South Jersey, Stellar Mojo will move and entertain any crowd. They regularly play venues such as the Field House in Philadelphia and Mad River in Manayunk as well as many Jersey Shore clubs and more. They specialize in every genre of fun, upbeat party music and will play everything from Lady Gaga and Kanye West to Dave Matthews Band and Michael Jackson. Don’t just book another band…book a whole party! Book Stellar Mojo! 
September 28 `19
Fager's Island
One of the most well known names in live music in and around the Baltimore area. Crushing Day was formed in 1993 and has played all over the east coast from Killington, VT to Key West, FL. 
surfer with surfboard coming out of water
September 28 `19
35th St. Beach
Check out the Delmarva ESA Surf Competition! This is the largest amateur surfing association in the world featuring family oriented programs to promote a healthy and active lifestyle. The Delmarva ESA encourages participation by surfers of all ages and all skill levels.
Farmers Market items veggies
September 28 `19
Ocean Pines Farmers Market
Buy Local: Eat Fresh
Ocean Pines Community Center
Located at White Horse Park, the Ocean Pines Farmer's Market is every Saturday beginning in mid March. Shop for seasonal produce, farm fresh eggs, organics, seafood, herbs, flowers, honey, apples, natural pet treats, artisan breads potatoes, greens, tomatoes, pumpkins, kettle korn, crafts & more!
 
 
Silhouettes of people doing yoga on the beach at sunset
September 28 `19 - September 29 `19
Dunes Manor Hotel, Court & Suites
Start your morning off right with yoga on the beach. YogaRise is a class for all to experience the foundations of yoga while experiencing Ocean City's beach. Unite your mind, body and soul towards a relaxing state. All levels are welcome!
Silhouettes of people doing yoga on the beach at sunset
September 28 `19
Aloft Ocean City
Start your morning off right with yoga at Aloft Hotel. YogaRise is a class for all to experience the foundations of yoga while experiencing Ocean City's beach. Unite your mind, body and soul towards a relaxing state. All levels are welcome!
September 28 `19
Side Project is an acoustic band that performs around Ocean City, MD. In the mood for rock, rap and country? 80's and Top 40? A little Eminem, Baby Got Back and Wagon Wheel? We've got you covered.
September 28 `19
Hooters of Ocean City
Classic Vibe is back at Hooters of West Ocean City! Their music is sure to satisfy and electrify the soul with their acoustic blend of classic rock, country and blues hits. Come on down during the Hooters Happy Hour, from 3-6 pm! You're bound to have a hootin'-tootin' time!  
Closeup of acoustic guitar being played
September 28 `19
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. Come for Happy Hour at the bar from 2-6pm Monday-Friday for $2 off all drafts, $4 house wines, slushies, and rails, $5.50 crushes, $2.50 Bud/Bud Light 16oz aluminums, and 1/2 price bada bing/wings/Liberty oysters!
graphic words identity crisis
September 28 `19
VFW Ocean View
Identity Crisis, formed in 2000, progressed from a three piece accoustic trio, into a five piece electric/acoustic, multi-genre dance band aimed toward crowd entertainment with the emphasis on fun! 

Come see the band live at the VFW in Ocean View DE. 

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