Events
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Jake Ash Band!
Northeast Country music, from the drinking buddies you haven't met yet!
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Taco Eating Contest
How many tacos can you eat in an hour? 50 cent tacos during contest time 5:58 to 6:58 pm. Winner gets $100 Bentley's gift card, free tacos and chance to win Modelo cooler and swag!! $6 margaritas every Monday!
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Cruisin’ Night Tuesday Car Shows
We have weekly Cruisin' Night Tuesday Car Shows that start May 19, 2026 through September 22, 2026, weather permitting, from 5 pm til dusk (no Tues show on June 16 during Biker Rally). All special interest cars are welcome, and it's one of our favorite nights of the week to get together to enjoy the…
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Open Mic Night every Wednesday 7 to 10 pm
It's 20 years this year since Open Mic Night started at Bentley's with Ali and Nat Bailey! Special reunion celebration of bands on July 18th from 2 to 6 pm. Every Wednesday Nat and Ali and their band provide PA -Stage Gear - Full Band Backup. It's also a band audition night! Every Wednesday Wing…
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Karaoke with DJ Adam 7 to 10 pm
It's fun! Listening and watching talented people and not-so-talented people. At DJ Adam's July 2 show, Lip Sync Contest too!! $500 for winner plus prizes for 2nd & 3rd place!
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Matty and the Penders!
Bringing back 90's Alternative Rock! Matty: Vocals. Mike: Lead Guitar. Mike: Bass. Aaron: Drum
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Bentley’s Balls Day – Win Cash – FREE TO ENTER
This will be the 12th year that we give away $1000 the last Saturday of every month for playing with Bentley's Balls!! All day free to enter, and 6 people are guaranteed to win $100 and one person is going to win $500. All you have to do is enter your name, and it's free…
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MooseJuice Band (Grateful dead inspired!)
6 piece Boston based jam band that specializes in the Grateful Dead with surprises thrown in (Pink Floyd, The Band, etc). Moosejuice was picked to play Jerry Day at Fenway Park this year!!
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Bad Habit
Rock, Alternative Rock, Metal, Classic Rock, Country, 5 piece Cover Band out of Southern Maine. At the August 29th show, we're having a Mullets & Daisy Dukes costume party! $100 gift cards from Bentley's for favorite Mullets and favorite Daisy Dukes!!
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Henry Lowery Music
Very talented country musician! Full Band: Local legends join Henry! may 10, aug 16, sept 13 Henry Solo- So much Talent! may 31, june 28, july 26, aug 30, sept 27, oct 18
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Chase Job Music
Young talented country musician!
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Country Line Dance Lessons 2nd Monday & Fun Dance Lessons 4th Monday of Month
Join Judy with country line dance lessons the 2nd Monday of every month. It's fun!! The fourth Monday of every month, Judy spices it up with other dance moves!