Moments at SIP

From weekly favorites to special events and seasonal celebrations, SIP’s calendar is always moving. Take a look at what’s ahead and plan your next night out on Main Street.

View Entertainment Calendar

Featured Moments at SIP

Event Schedule
KJ & Brian Babbs
Mar 20
KJ & Brian Babbs

Acoustic guitars, tight harmonies, and classic covers that never go out of style. KJ & Brian Babbs bring an easygoing, feel-good sound perfect for sipping cocktails and settling in for the night.

Ben Tatam
Mar 21
Ben Tatam

Acoustic covers spanning decades. From The Beatles and Tom Petty to ’90s hits and today’s favorites, Ben Tatam delivers a familiar, feel-good set that’s easy to enjoy all night.

Pillow Talk
Mar 27
Pillow Talk
David Gerdt
Mar 28
David Gerdt

Original music with guitar and vocals. David Gerdt offers an intimate, songwriter-driven performance that’s perfect for guests who love live music with depth and authenticity.

Post Alone
Apr 3
Post Alone
KJ & Brian Babbs
Apr 4
KJ & Brian Babbs
Austin Beliles
Apr 10
Austin Beliles
The Wahkings
Apr 11
The Wahkings
Jaylen Martinez
Apr 17
Jaylen Martinez
8 bit audio
Apr 18
8 bit audio

Acoustic duo focusing on rock/pop/folk covers

Michael McCartney
Apr 24
Michael McCartney

A wide-ranging set from the ’60s through today. Michael McCartney brings timeless classics and modern hits together in a sound that feels both nostalgic and current.

Breanna Faith
Apr 25
Breanna Faith

National award-winning singer, songwriter, and musician from Indianapolis. Breanna Faith blends modern and classic country with a touch of pop and rock — mixing original songs with crowd-favorite covers for a dynamic, soulful live set.

Weekly Entertainment at SIP

Event Schedule
Trivia
Mar 18
Trivia

Put your knowledge to the test and your drinks to good use.

Open Mic
Mar 19
Open Mic

Whether it’s music, poetry, comedy, or something entirely unexpected, SIP offers a supportive stage and an attentive crowd.

KJ & Brian Babbs
Mar 20
KJ & Brian Babbs

Acoustic guitars, tight harmonies, and classic covers that never go out of style. KJ & Brian Babbs bring an easygoing, feel-good sound perfect for sipping cocktails and settling in for the night.

Boombox Bingo
Mar 21
Boombox Bingo

Think bingo… but with music. Instead of numbers, songs are played across different themes and eras.

Ben Tatam
Mar 21
Ben Tatam

Acoustic covers spanning decades. From The Beatles and Tom Petty to ’90s hits and today’s favorites, Ben Tatam delivers a familiar, feel-good set that’s easy to enjoy all night.

Trivia
Mar 25
Trivia

Put your knowledge to the test and your drinks to good use.

Open Mic
Mar 26
Open Mic

Whether it’s music, poetry, comedy, or something entirely unexpected, SIP offers a supportive stage and an attentive crowd.

Pillow Talk
Mar 27
Pillow Talk
Boombox Bingo
Mar 28
Boombox Bingo

Think bingo… but with music. Instead of numbers, songs are played across different themes and eras.

David Gerdt
Mar 28
David Gerdt

Original music with guitar and vocals. David Gerdt offers an intimate, songwriter-driven performance that’s perfect for guests who love live music with depth and authenticity.

Trivia
Apr 1
Trivia

Put your knowledge to the test and your drinks to good use.

Open Mic
Apr 2
Open Mic

Whether it’s music, poetry, comedy, or something entirely unexpected, SIP offers a supportive stage and an attentive crowd.

Post Alone
Apr 3
Post Alone
Boombox Bingo
Apr 4
Boombox Bingo

Think bingo… but with music. Instead of numbers, songs are played across different themes and eras.

KJ & Brian Babbs
Apr 4
KJ & Brian Babbs
Trivia
Apr 8
Trivia

Put your knowledge to the test and your drinks to good use.

Open Mic
Apr 9
Open Mic

Whether it’s music, poetry, comedy, or something entirely unexpected, SIP offers a supportive stage and an attentive crowd.

Austin Beliles
Apr 10
Austin Beliles
Boombox Bingo
Apr 11
Boombox Bingo

Think bingo… but with music. Instead of numbers, songs are played across different themes and eras.

The Wahkings
Apr 11
The Wahkings
Trivia
Apr 15
Trivia

Put your knowledge to the test and your drinks to good use.

Open Mic
Apr 16
Open Mic

Whether it’s music, poetry, comedy, or something entirely unexpected, SIP offers a supportive stage and an attentive crowd.

Jaylen Martinez
Apr 17
Jaylen Martinez
Boombox Bingo
Apr 18
Boombox Bingo

Think bingo… but with music. Instead of numbers, songs are played across different themes and eras.

8 bit audio
Apr 18
8 bit audio

Acoustic duo focusing on rock/pop/folk covers

Trivia
Apr 22
Trivia

Put your knowledge to the test and your drinks to good use.

Open Mic
Apr 23
Open Mic

Whether it’s music, poetry, comedy, or something entirely unexpected, SIP offers a supportive stage and an attentive crowd.

Michael McCartney
Apr 24
Michael McCartney

A wide-ranging set from the ’60s through today. Michael McCartney brings timeless classics and modern hits together in a sound that feels both nostalgic and current.

Boombox Bingo
Apr 25
Boombox Bingo

Think bingo… but with music. Instead of numbers, songs are played across different themes and eras.

Breanna Faith
Apr 25
Breanna Faith

National award-winning singer, songwriter, and musician from Indianapolis. Breanna Faith blends modern and classic country with a touch of pop and rock — mixing original songs with crowd-favorite covers for a dynamic, soulful live set.

Past Moments at SIP

Event Schedule
Lilly Rose
Mar 14
Lilly Rose
Boombox Bingo
Mar 14
Boombox Bingo

Think bingo… but with music. Instead of numbers, songs are played across different themes and eras.

St. Patrick's Day at SIP
Mar 14
St. Patrick's Day at SIP

We’re celebrating a little early — the SIP way.

Join us Saturday, March 14 for a night of elevated cocktails and festive energy. Featuring our March specials: Emerald After Dark, Clover Crush, and our limited-time St. Patrick’s shot.

Come early, stay late, and celebrate differently.

8 bit audio
Mar 13
8 bit audio

Acoustic duo focusing on rock/pop/folk covers

Stand-Up Comedy Night at SIP
Mar 12
Stand-Up Comedy Night at SIP

Laugh your way through the night at SIP Cocktails on Main with live stand-up comedy featuring headliner Ryan Hole, with Jeremy Seward and host Zach Sterling. Expect sharp wit, bold humor, and handcrafted cocktails in an intimate lounge setting.

 🎟 $10 cover at the door
🍸 2-drink minimum per person
Seating is first come, first served.

Perfect midweek plans: great drinks, big laughs, and a fun crowd.

Trivia
Mar 11
Trivia

Put your knowledge to the test and your drinks to good use.

Breanna Faith
Mar 7
Breanna Faith

National award-winning singer, songwriter, and musician from Indianapolis. Breanna Faith blends modern and classic country with a touch of pop and rock — mixing original songs with crowd-favorite covers for a dynamic, soulful live set.

Boombox Bingo
Mar 7
Boombox Bingo

Think bingo… but with music. Instead of numbers, songs are played across different themes and eras.

Brett Denney
Mar 6
Brett Denney

A versatile mix of pop, rock, and country. Brett Denney delivers crowd-pleasing covers and contemporary favorites with a polished, engaging style that keeps the room energized.

Open Mic
Mar 5
Open Mic

Whether it’s music, poetry, comedy, or something entirely unexpected, SIP offers a supportive stage and an attentive crowd.

Trivia
Mar 4
Trivia

Put your knowledge to the test and your drinks to good use.

David Gerdt
Feb 28
David Gerdt

Original music with guitar and vocals. David Gerdt offers an intimate, songwriter-driven performance that’s perfect for guests who love live music with depth and authenticity.

Michael McCartney
Feb 27
Michael McCartney

A wide-ranging set from the ’60s through today. Michael McCartney brings timeless classics and modern hits together in a sound that feels both nostalgic and current.

Open Mic
Feb 26
Open Mic

Whether it’s music, poetry, comedy, or something entirely unexpected, SIP offers a supportive stage and an attentive crowd.

Boombox Bingo
Feb 25
Boombox Bingo

Think bingo… but with music. Instead of numbers, songs are played across different themes and eras.

Trivia
Feb 25
Trivia

Put your knowledge to the test and your drinks to good use.

DJ Melko
Feb 21
DJ Melko

A high-energy DJ set designed to keep the night moving. DJ Melko blends crowd favorites and danceable tracks for a fun, social atmosphere at SIP.

Karaoke
Feb 20
Karaoke

Open Mic
Feb 19
Open Mic

Whether it’s music, poetry, comedy, or something entirely unexpected, SIP offers a supportive stage and an attentive crowd.

Boombox Bingo
Feb 18
Boombox Bingo

Think bingo… but with music. Instead of numbers, songs are played across different themes and eras.

Trivia
Feb 18
Trivia

Put your knowledge to the test and your drinks to good use.

DJ Lodien
Feb 14
DJ Lodien

An open-format DJ set with a blend of current hits and familiar favorites. Expect a fun, easygoing soundtrack that lets the night unfold naturally.

Valentine’s Day at SIP
Feb 14
Valentine’s Day at SIP

Valentine’s Day at SIP is all about great cocktails, warm lighting, and an atmosphere that feels intimate without feeling overdone. Whether you’re celebrating love, a long-standing partnership, or just the joy of a really good night out, SIP is the perfect place to unwind together.

Brett Denney
Feb 13
Brett Denney

A versatile mix of pop, rock, and country. Brett Denney delivers crowd-pleasing covers and contemporary favorites with a polished, engaging style that keeps the room energized.

Galentine’s Night at SIP
Feb 13
Galentine’s Night at SIP

Galentine’s Night at SIP is a celebration of friendship, fun, and fabulous cocktails. Gather your group, dress up (or don’t), and settle into a night filled with laughter, conversation, and drinks made to match the mood.

Open Mic
Feb 12
Open Mic

Whether it’s music, poetry, comedy, or something entirely unexpected, SIP offers a supportive stage and an attentive crowd.

Boombox Bingo
Feb 11
Boombox Bingo

Think bingo… but with music. Instead of numbers, songs are played across different themes and eras.

Trivia
Feb 11
Trivia

Put your knowledge to the test and your drinks to good use.

Austin Beliles
Feb 7
Austin Beliles

Country soul with heart. Austin Beliles blends smooth vocals and soulful influences into a sound that’s both relaxed and expressive — ideal for sipping, listening, and lingering.

Lonestar Lenny
Feb 6
Lonestar Lenny

Classic country. Lonestar Lenny brings familiar favorites, storytelling lyrics, and an easygoing sound that pairs perfectly with a laid-back night at SIP.