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EVENTS AND ENTERTAINMENT

The Woodstock Inn is proud to offer a variety of festive events and live entertainment all year round. From live music and deejays to holiday-themed parties and pig roasts, there is always something exciting happening at our Inn. Join us for an evening or day of entertainment and fun, where you can make lasting memories. Keep an eye on this page for additions to our lineup, and we'll see you soon!


EVENTS

May 28th
May 28th
Country Line Dancing

Join us for a Boot-Scootin good time!
Make sure to wear your closed-toe shoes for an evening full of fun and dancing!
Don't miss out on the thrill—only $15 per person, which includes a drink coupon to get you started! Let’s have a blast together!



ENTERTAINMENT SCHEDULE

Thu, Jun 12th
Enslow
Enslow

7-10pm

Get ready to be blown away by the incredible talent of up-and-coming singer/songwriter ENSLOW. With a captivating blend of pop, country & soul, this rising star is sure to steal your heart and leave you wanting more. Don't miss out on her electrifying performances that promise to be nothing short of amazing.


Fri, Jun 13th
Enslow
Enslow

7-10pm

Get ready to be blown away by the incredible talent of up-and-coming singer/songwriter ENSLOW. With a captivating blend of pop, country & soul, this rising star is sure to steal your heart and leave you wanting more. Don't miss out on her electrifying performances that promise to be nothing short of amazing.


Sat, Jun 14th
Live entertainment in Woodstock Maryland
100 Proof

7-10pm

Music majors that met in college, bridging the gap between blues and bluegrass and anything in between! Its always a great time when 100 proof is in the house!


Sun, Jun 15th
Anton

2- 5pm

Led by requests, each shows one of a kind "If I can hear it. I'll play it!" - Mr. Jukebox
May Passion serve your purpose


Thu, Jun 19th
Woodstock In Performance
Mallow Hill Duo

Funk, blues, and soul music from Baltimore, MD with the amazing Mallow Hill!


Fri, Jun 20th
Live Entertainment
Two Suspects

7-10pm

Paul McGill & Keith Goodwin, originally from local band Suspect. An acoustic Duo covering a wide range of music from classic, modern and hard rock with some modern country tunes. Two guitars with strong vocal harmonies


Sat, Jun 21st
Woodstock Inn Show
Mama's Black Sheep

7-10pm

Sun, Jun 22nd
Red Sky Dawn
Red Sky Dawn

2- 5pm

Red Sky Dawn is a local cover duo hailing from Ellicott City with collective live performance experience of over 40 year. Covering all genres & eras including country, rock, classic rock, and a few pop jams from the 1960's through today.


Wed, Jun 25th
Country Line Dancing

6-9pm

Join us for a Boot-Scootin good time!
Make sure to wear your closed-toe shoes for an evening full of fun and dancing!
Don't miss out on the thrill—only $15 per person, which includes a drink coupon to get you started! Let’s have a blast together!


Thu, Jun 26th
Enslow
Enslow

7-10pm

Get ready to be blown away by the incredible talent of up-and-coming singer/songwriter ENSLOW. With a captivating blend of pop, country & soul, this rising star is sure to steal your heart and leave you wanting more. Don't miss out on her electrifying performances that promise to be nothing short of amazing.


Fri, Jun 27th
Live Music
Ruben Montoya

7-10pm

Funky Blues Roots Rock!


Sat, Jun 28th
Shake Rattle and and Roll Dueling Pianos

7-10pm

Dueling Pianos is an all-request, rock-and-roll party where YOU pick the playlist! Two top piano entertainers, mixing music, comedy and audience interaction in a singalong, laugh-along, dance-along show! It’s everything from Billy Joel to Bon Jovi, Britney Spears to Bruno Mars!
Nothing is off-limits from pop, rock, country, hip-hop, hairbands, disco, punk rock, standards, showtunes – if you can hum it, we can do it!

Feel free to bring lawn chairs as seating is limited 


Sun, Jun 29th
Woodstock In Performance
Mallow Hill Duo

2- 5pm

Funk, blues, and soul music from Baltimore, MD with the amazing Mallow Hill!


Thu, Jul 3rd
Woodstock In Performance
Mallow Hill Duo

7-10pm

Funk, blues, and soul music from Baltimore, MD with the amazing Mallow Hill!


Sat, Jul 5th
Sidewalk Soul

7-10pm

Sidewalk Soul is a power trio from Washington, DC that plays in the style of guitar-driven classic rock and vocal-laden harmonies with a lot of jamming in between. Covering artists like Tom Petty, The Rolling Stones, Jimi Hendrix, Duran Duran, Simples Minds, Oasis and many others, they perform regularly in DC, Maryland and Virginia. Combining a wide range of styles and influences, Adam Forbes (guitar/vocals), Brad Ulreich (bass/vocals) and Mark Adams (drums) are sure to give you an unforgettable performance you won't want to miss!


Sun, Jul 6th
Enslow
Enslow

2- 5pm

Get ready to be blown away by the incredible talent of up-and-coming singer/songwriter ENSLOW. With a captivating blend of pop, country & soul, this rising star is sure to steal your heart and leave you wanting more. Don't miss out on her electrifying performances that promise to be nothing short of amazing.


Thu, Jul 10th
Keiron

7-10pm

Fri, Jul 11th
Woodstock In Performance
Mallow Hill Duo

7-10pm

Funk, blues, and soul music from Baltimore, MD with the amazing Mallow Hill!


Sat, Jul 12th
Enslow
Enslow

7-10pm

Get ready to be blown away by the incredible talent of up-and-coming singer/songwriter ENSLOW. With a captivating blend of pop, country & soul, this rising star is sure to steal your heart and leave you wanting more. Don't miss out on her electrifying performances that promise to be nothing short of amazing.


Sat, Jul 12th
Country Line Dancing

7-10pm

Join us for a Boot-Scootin good time!
Make sure to wear your closed-toe shoes for an evening full of fun and dancing!
Don't miss out on the thrill—only $15 per person, which includes a drink coupon to get you started! Let’s have a blast together!


Sun, Jul 13th
Doc Marten & the Flannels
Doc Marten & the Flannels

2-6pm

ROCK. GRUNGE. PARTY

Join us as we welcome Doc Marten and the Flannels back to our outdoor stage Sunday May 26th!! 🎶

Tickets are $10 and will be sold at the door the day of the event sorry no advance ticket sales.

Seating is limited you may bring a lawn chair.


Thu, Jul 17th
Justin Singleton
Justin Singleton

7-10pm

Justin Singleton is a up and coming singer/songwriter, and native of the eastern shore.
Highly influencing his sound by artists such as Tyler Childers, Chris Stapleton and Lynyrd Skynyrd. Just is know for his unique covers and an array of original songs such as "Scarecrow, No Doubt, California Cougar, Brewless and Roadkill Love"


Fri, Jul 18th
Live entertainment in Woodstock Maryland
100 Proof

7-10pm

Music majors that met in college, bridging the gap between blues and bluegrass and anything in between! Its always a great time when 100 proof is in the house!


Sat, Jul 19th
Homestead
Homestead

7-10pm

Sun, Jul 20th
Woodstock Inn Show
Mama's Black Sheep

2- 5pm

Wed, Jul 23rd
Country Line Dancing

6-9pm

Join us for a Boot-Scootin good time!
Make sure to wear your closed-toe shoes for an evening full of fun and dancing!
Don't miss out on the thrill—only $15 per person, which includes a drink coupon to get you started! Let’s have a blast together!


Thu, Jul 24th
Enslow
Enslow

7-10pm

Get ready to be blown away by the incredible talent of up-and-coming singer/songwriter ENSLOW. With a captivating blend of pop, country & soul, this rising star is sure to steal your heart and leave you wanting more. Don't miss out on her electrifying performances that promise to be nothing short of amazing.


Fri, Jul 25th
Red Sky Dawn
Red Sky Dawn

7-10pm

Red Sky Dawn is a local cover duo hailing from Ellicott City with collective live performance experience of over 40 year. Covering all genres & eras including country, rock, classic rock, and a few pop jams from the 1960's through today.


Sat, Jul 26th
Live Music
Ruben Montoya

7-10pm

Funky Blues Roots Rock!


Sun, Jul 27th
Live Entertainment
Two Suspects

2- 5pm

Paul McGill & Keith Goodwin, originally from local band Suspect. An acoustic Duo covering a wide range of music from classic, modern and hard rock with some modern country tunes. Two guitars with strong vocal harmonies


Thu, Jul 31st
Live acoustic singer
James Kelly

7-10pm

With roots in rock and bluegrass, Jim Kelly brings acoustic stylings of his own devise. His catchy original songs blend with covers that span genres and decades, combining emotion and talent on to bring you into his world of sounds.


Fri, Aug 1st
Woodstock In Performance
Mallow Hill Duo

7-10pm

Funk, blues, and soul music from Baltimore, MD with the amazing Mallow Hill!


Sat, Aug 2nd
Sidewalk Soul

7-10pm

Sidewalk Soul is a power trio from Washington, DC that plays in the style of guitar-driven classic rock and vocal-laden harmonies with a lot of jamming in between. Covering artists like Tom Petty, The Rolling Stones, Jimi Hendrix, Duran Duran, Simples Minds, Oasis and many others, they perform regularly in DC, Maryland and Virginia. Combining a wide range of styles and influences, Adam Forbes (guitar/vocals), Brad Ulreich (bass/vocals) and Mark Adams (drums) are sure to give you an unforgettable performance you won't want to miss!


Thu, Aug 7th
Acoustic Live Show
Sean Bera & DC

7-10pm

Fri, Aug 8th
Enslow
Enslow

7-10pm

Get ready to be blown away by the incredible talent of up-and-coming singer/songwriter ENSLOW. With a captivating blend of pop, country & soul, this rising star is sure to steal your heart and leave you wanting more. Don't miss out on her electrifying performances that promise to be nothing short of amazing.


Sat, Aug 9th
Live Music
Ruben Montoya

7-10pm

Funky Blues Roots Rock!


Thu, Aug 14th
Keiron

7-10pm

Fri, Aug 15th
Red Sky Dawn
Red Sky Dawn

7-10pm

Red Sky Dawn is a local cover duo hailing from Ellicott City with collective live performance experience of over 40 year. Covering all genres & eras including country, rock, classic rock, and a few pop jams from the 1960's through today.


Sat, Aug 16th
bilgewater bluegrass
Bilgewater Bluegrass

7-10pm

Sun, Aug 17th
Live acoustic singer
James Kelly

2- 5pm

With roots in rock and bluegrass, Jim Kelly brings acoustic stylings of his own devise. His catchy original songs blend with covers that span genres and decades, combining emotion and talent on to bring you into his world of sounds.


Thu, Aug 21st
Enslow
Enslow

7-10pm

Get ready to be blown away by the incredible talent of up-and-coming singer/songwriter ENSLOW. With a captivating blend of pop, country & soul, this rising star is sure to steal your heart and leave you wanting more. Don't miss out on her electrifying performances that promise to be nothing short of amazing.


Fri, Aug 22nd
Live Music
Ruben Montoya

7-10pm

Funky Blues Roots Rock!


Wed, Aug 27th
Country Line Dancing

6-9pm

Join us for a Boot-Scootin good time!
Make sure to wear your closed-toe shoes for an evening full of fun and dancing!
Don't miss out on the thrill—only $15 per person, which includes a drink coupon to get you started! Let’s have a blast together!


Thu, Aug 28th
Justin Singleton
Justin Singleton

7-10pm

Justin Singleton is a up and coming singer/songwriter, and native of the eastern shore.
Highly influencing his sound by artists such as Tyler Childers, Chris Stapleton and Lynyrd Skynyrd. Just is know for his unique covers and an array of original songs such as "Scarecrow, No Doubt, California Cougar, Brewless and Roadkill Love"


Fri, Aug 29th
The Viper Brothers

7-10pm

Specializing in covers of 90s and 2000s rock and alternative bands – one of the best eras of rock music. Our sets feature songs from bands like:

Jimmy Eat World
Foo Fighters
Third Eye Blind
Stone Temple Pilots
Matthew Sweet
Weezer
Tonic
The Gin Blossoms
The Hives
and many more!


Sat, Aug 30th
Woodstock Inn Show
Mama's Black Sheep

7-10pm

Sun, Aug 31st
Live Entertainment
Two Suspects

2- 5pm

Paul McGill & Keith Goodwin, originally from local band Suspect. An acoustic Duo covering a wide range of music from classic, modern and hard rock with some modern country tunes. Two guitars with strong vocal harmonies


Fri, Sep 5th
Homestead
Homestead

7-10pm

Sun, Sep 7th
Red Sky Dawn
Red Sky Dawn

2- 5pm

Red Sky Dawn is a local cover duo hailing from Ellicott City with collective live performance experience of over 40 year. Covering all genres & eras including country, rock, classic rock, and a few pop jams from the 1960's through today.


Thu, Sep 18th
Justin Singleton
Justin Singleton

7-10pm

Justin Singleton is a up and coming singer/songwriter, and native of the eastern shore.
Highly influencing his sound by artists such as Tyler Childers, Chris Stapleton and Lynyrd Skynyrd. Just is know for his unique covers and an array of original songs such as "Scarecrow, No Doubt, California Cougar, Brewless and Roadkill Love"


Fri, Sep 26th
Red Sky Dawn
Red Sky Dawn

7-10pm

Red Sky Dawn is a local cover duo hailing from Ellicott City with collective live performance experience of over 40 year. Covering all genres & eras including country, rock, classic rock, and a few pop jams from the 1960's through today.


Sat, Sep 27th
Live Music
Ruben Montoya

7-10pm

Funky Blues Roots Rock!


Sun, Sep 28th
Live Music
Strings Attached

2- 5pm

A female Bluegrass Trio


  • Thu, Jun 12th
    Enslow | 7-10pm
  • Fri, Jun 13th
    Enslow | 7-10pm
  • Sat, Jun 14th
    100 Proof | 7-10pm
  • Sun, Jun 15th
    Anton | 2- 5pm
  • Thu, Jun 19th
    Mallow Hill Duo |
  • Fri, Jun 20th
    Two Suspects | 7-10pm
  • Sat, Jun 21st
    Mama's Black Sheep | 7-10pm
  • Sun, Jun 22nd
    Red Sky Dawn | 2- 5pm
  • Wed, Jun 25th
    Country Line Dancing | 6-9pm
  • Thu, Jun 26th
    Enslow | 7-10pm
  • Fri, Jun 27th
    Ruben Montoya | 7-10pm
  • Sat, Jun 28th
    Shake Rattle and and Roll Dueling Pianos | 7-10pm
  • Sun, Jun 29th
    Mallow Hill Duo | 2- 5pm
  • Thu, Jul 3rd
    Mallow Hill Duo | 7-10pm
  • Sat, Jul 5th
    Sidewalk Soul | 7-10pm
  • Sun, Jul 6th
    Enslow | 2- 5pm
  • Thu, Jul 10th
    Keiron | 7-10pm
  • Fri, Jul 11th
    Mallow Hill Duo | 7-10pm
  • Sat, Jul 12th
    Enslow | 7-10pm
  • Sat, Jul 12th
    Country Line Dancing | 7-10pm
  • Sun, Jul 13th
    Doc Marten & the Flannels | 2-6pm
  • Thu, Jul 17th
    Justin Singleton | 7-10pm
  • Fri, Jul 18th
    100 Proof | 7-10pm
  • Sat, Jul 19th
    Homestead | 7-10pm
  • Sun, Jul 20th
    Mama's Black Sheep | 2- 5pm
  • Wed, Jul 23rd
    Country Line Dancing | 6-9pm
  • Thu, Jul 24th
    Enslow | 7-10pm
  • Fri, Jul 25th
    Red Sky Dawn | 7-10pm
  • Sat, Jul 26th
    Ruben Montoya | 7-10pm
  • Sun, Jul 27th
    Two Suspects | 2- 5pm
  • Thu, Jul 31st
    James Kelly | 7-10pm
  • Fri, Aug 1st
    Mallow Hill Duo | 7-10pm
  • Sat, Aug 2nd
    Sidewalk Soul | 7-10pm
  • Thu, Aug 7th
    Sean Bera & DC | 7-10pm
  • Fri, Aug 8th
    Enslow | 7-10pm
  • Sat, Aug 9th
    Ruben Montoya | 7-10pm
  • Thu, Aug 14th
    Keiron | 7-10pm
  • Fri, Aug 15th
    Red Sky Dawn | 7-10pm
  • Sat, Aug 16th
    Bilgewater Bluegrass | 7-10pm
  • Sun, Aug 17th
    James Kelly | 2- 5pm
  • Thu, Aug 21st
    Enslow | 7-10pm
  • Fri, Aug 22nd
    Ruben Montoya | 7-10pm
  • Wed, Aug 27th
    Country Line Dancing | 6-9pm
  • Thu, Aug 28th
    Justin Singleton | 7-10pm
  • Fri, Aug 29th
    The Viper Brothers | 7-10pm
  • Sat, Aug 30th
    Mama's Black Sheep | 7-10pm
  • Sun, Aug 31st
    Two Suspects | 2- 5pm
  • Fri, Sep 5th
    Homestead | 7-10pm
  • Sun, Sep 7th
    Red Sky Dawn | 2- 5pm
  • Thu, Sep 18th
    Justin Singleton | 7-10pm
  • Fri, Sep 26th
    Red Sky Dawn | 7-10pm
  • Sat, Sep 27th
    Ruben Montoya | 7-10pm
  • Sun, Sep 28th
    Strings Attached | 2- 5pm