Events
Calendar of Events
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Sunday
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Monday
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Tuesday
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Wednesday
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Thursday
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Friday
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Saturday
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2 events,
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 |
1 event,
Every full moon, FREE Blue Moon swag for Blue Moon drinkers and a chance to win a Levitating Blue Moon (winner's name drawn May 31) & Blue Moon Leather Back… |
1 event,
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… |
1 event,
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.… |
2 events,
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LIP SYNC CONTEST WITH DJ ADAM Performances will be judged in the following categories: Lip sync abilities Appearance and stage presence Overall creativity Crowd appeal / audience response Each category… 
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! |
3 events,
Cornhole Tourney's at Bentley's are fun! The players are friendly and like to compete. Some of them enjoy adult beverages while competing! No partner, no worries, we'll hook you up! Each month you enter, $5 fee for a progressive jackpot given away at last tourney! Free swag from Lone Pine Brewery! Registration opens at 10… 
Playing all the hits from yesterday and today! If you like rock, dance, hip hop, classic rock and country, then you'll love The Inflatables! |
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1 event,
We are a Southern Maine band that plays a diverse set of cover songs around the New England area |
1 event,
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… |
1 event,
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.… |
1 event,
It's fun! Listening and watching talented people and not-so-talented people. |
1 event, |
3 events,
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Watch for more information about time the group meets at saloon to ride up to the Maine Veterans Home in Scarborough where registration takes place. There's a ceremony upon return… 
Deja Voodoo is predominantly a 90's and early 2000's Alternative Rock Band from New Hampshire! |
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1 event,
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! |
1 event,
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… |
1 event,
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.… |
1 event,
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A special evening going back to the days of the "Rat Pack" music with Ricky Lauria of the Flying Ivories to benefit Heartland Ranch, a safe haven for children trafficked or abused. Here, they rediscover their brightness. Bentley's Rolls Royce, originally owned by Dean Martin, will be on display for picture posing. It's an opportunity… |
1 event,
Classic rock, pop & blues band based in Southern Maine and the New Hampshire Seacoast. |
2 events,
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Every Wednesday Open Mic Night hosted by Ali & Nat Bailey and the OMN Band. PA / Stage Gear - Full Band Backup Provided. A Great Night of Music & Friends! This season is 20 years and special Saturday afternoon to celebrate! |
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2 events,
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At our first jeep show in 2025, we were happy to see 67 jeeps! We're excited to host this show again! There are no entry fees for jeep owners or spectators. Jeep owners eligible for door prizes, awards, a chance to win a $50 Bentley's Gift Card, a chance to win a FREE garage toolbox,… |
1 event,
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! |
1 event,
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… |
1 event,
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… |
1 event,
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! |
1 event,
Bringing back 90's Alternative Rock! Matty: Vocals. Mike: Lead Guitar. Mike: Bass. Aaron: Drum |
3 events,
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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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!! |
2 events,
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 |
1 event,
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! |
1 event,
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… |
2 events,
Every full moon, FREE Blue Moon swag for Blue Moon drinkers and a chance to win a Levitating Blue Moon (winner's name drawn May 31) & Blue Moon Leather Back Pack (winner's name drawn Sept 25)!!
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… |
1 event,
It's fun! Listening and watching talented people and not-so-talented people. It's also fun watching them play Stupid Bar Games. Free Swag from Orono! |
1 event,
New England’s rising rock cover band plays a great range of music & always gives an awesome time! |
4 events,
Cornhole Tourney's at Bentley's are fun! The players are friendly and like to compete. Some of them enjoy adult beverages while competing! No partner, no worries, we'll hook you up! Each month you enter, $5 fee for a progressive jackpot given away at last tourney! Free swag from Lone Pine Brewery! Registration opens at 10…
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Legend of Ozzy brings you an outstanding Ozzy show that recreates both the sound and visual appeal of Ozzy’s early very successful solo days, with a performance of many songs from Ozzy's first 2 albums of the Randy Rhoads era, plus other later Ozzy hits as well as some legendary early Black Sabbath favorites. With… |
