Rock The Summer At Toot’s Bar With Live Music, Karaoke And Southern Maryland’s Biggest Party Weekends

HOLLYWOOD, Md. — If your summer plans include live music, cold drinks and unforgettable nights with friends, Toot’s Bar has you covered all month long. From weekly karaoke and trivia to live concerts, themed events and a massive Independence Day celebration, there’s something happening every day at one of Southern Maryland’s most iconic live music venues.

Following new ownership and a complete renovation, Toot’s Bar is entering an exciting new era while honoring its nearly 80-year history. The refreshed Hollywood landmark offers an expanded lineup of live entertainment, weekly events and community gatherings, creating even more ways for longtime regulars and first-time visitors to make Toot’s their new favorite hangout.

Celebrate Independence Day At Toot’s With An All Day Rock And Karaoke Party

The Fourth of July at Toot’s Bar isn’t just another concert—it’s an all-day celebration packed with live music, karaoke, cash prizes and one of Southern Maryland’s best holiday parties.

The fun kicks off at 3 p.m. with the Rockstar Karaoke Contest, where aspiring performers can compete for $500 in cash prizes across multiple categories, including Best Male Voice, Best Female Voice, Most Unique Voice, Wildest Performance, Crowd Favorite and even Best Shower Singer. Best of all, there’s no cover charge to join the fun.

As the sun goes down, the party transforms into the July 4th Invasion at Toot’s, bringing a full lineup of live rock to the stage from 7 to 11 p.m. Guests can enjoy performances from DJ Kitty Scratches Karaoke, Red Skies Dawning, Others May Fall and Shallow Deep, making it the perfect place to celebrate Independence Day with friends.

Whether you’re ready to grab the microphone, cheer on contestants or rock out to live music all evening, Toot’s has your Fourth of July plans covered.

The event is 21 and older, runs into the evening and has no cover charge, making it one of Southern Maryland’s best places to celebrate Independence Day.

Don’t Miss Toot’s Biggest Rock Weekend

The excitement continues the following weekend with Toot’s first-ever Triple Header Weekend, bringing together three nights of live music. Get the weekend pass for $25! 

Friday, July 10
Rock out with Doc Marten and The Flannels, with support from South Creek.

Saturday, July 11
Don’t miss No Green JellyBeenz, making their first appearance at Toot’s.

Sunday, July 12
The weekend wraps up with Joey Tippett and the Highway Ramblers.

Tickets are $15 per show, but music fans can save money with a $25 weekend pass that includes admission to all three concerts. Advance ticket purchases are recommended before the shows sell out. Get tickets here.

July is packed with live bands, DJs, karaoke, trivia, line dancing, beer pong and bingo, making it easy to find a fun night out. 

Catch other live performances throughout the month by DJ Buddy Tippett & Blue Grass, South Creek, In2Deep, Never 2 Late, Southbound 4 and the Joe Cox Band. 

The month wraps up with two can’t-miss shows featuring Jasmine Cain on July 26 and Toot’s first national touring act, Awake at Last, on July 31 with support from Red Skies Dawning. Tickets for Awake at Last are just $10 and are available now.

There’s Always Something Happening

Even between concerts, Toot’s keeps the fun going every week. Relax on the covered outdoor deck, challenge your friends to a free game of pool outside, grab a cold drink and enjoy a full lineup of recurring events and live entertainment. 

• Mondays: Dance Hall Ghost, 1–4 p.m.
• Tuesdays: Barstool Bingo at 6 p.m., benefiting a different local nonprofit each week. July’s featured organizations include Clement’s Cuties, Hollywood Volunteer Fire Department, Hollywood Volunteer Rescue Squad and the Leonardtown Lions Club.
• Wednesdays: Tiff’s Tunes Karaoke & Trivia at 8:30 p.m.
• Thursdays: Beer Pong Night, sign-ups at 7 p.m., games begin at 8 p.m.
• Fridays, Saturdays and select Sundays: Live bands, DJs and special events.

Whether you’re planning a night out with friends, celebrating the holiday weekend or catching your favorite local band, Toot’s Bar offers something new every week all summer long.

Toot’s Bar is located at 23971 Mervell Dean Road, Hollywood, MD 20636.

Follow Toot’s Bar on Facebook for the latest event updates, and purchase concert tickets early for the month’s biggest shows before they’re gone.

See the full event calendar here.

---