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

March 14th

Annual St Patricks Day Ride

Saddle Up for Our Annual St. Patrick’s Day Trail Ride!
Equestrian lovers of ALL kinds — this one’s for you!
Join us at The Woodstock Inn on Saturday, March 14 for our annual St. Patrick’s Day Ride and celebrate the luck of the Irish in true trail-riding style.
Ride starts at 11 AM
Starting point:
Smith Stables
3014 Hernwood Rd.
Festive vibes, beautiful trails, and an unforgettable ride
Don’t forget to enter our Best Dressed Contest!
Dress up your horse & yourself for a chance to win a Cowgirl Essentials Gift Basket courtesy of The Woodstock Inn. The more festive, the better!
Ever dreamed of riding your horse right up to The Woodstock Inn?
Here’s your chance. Contact Paige Reynolds at Circle R Arena today for horse rentals and parking passes 410-596-5112
Tag your riding crew, dust off the green gear, and we’ll see you in the saddle!

March 17th

St Patricks Day

SAVE THE DATE!
Get ready to shamrock and roll at The Woodstock Inn!
$2 Green Beers
$5 Green Teas
$5 Guinness
Doors open at 6:30am!
Great drinks, festive vibes, and a party you won’t want to miss.
Grab your crew and get ready to celebrate Irish-style!

March 21

White Lie Party

🤍 WHITE LIE PARTY at The Woodstock Inn 🤍

Everyone has a little white lie… wear yours proudly 😏

Join us for a White Lie Party on Friday, March 21 starting at 10 PM!
Rock a white shirt with your favorite harmless lie written on it and get ready for a night of music, drinks, and laughs.

🗓 Date: March 21
⏰ Time: Starting at 10 PM
📍 Location: The Woodstock Inn
🪪 21+ ID required at the door

Whether it’s “I’m on my way” or “I’ll only have one drink,” we won’t judge 😉
Grab your friends and come lie with us (just a little).

3rd Thursdays starting in May

Saddles & Sunsets

🎶🐴 Saddles & Sunsets – 3rd Thursdays at Woodstock Inn!

Starting in May, we’re bringing our equestrian community together for a night of music, connection, and sunset vibes.

Riders from all disciplines are invited to join us every 3rd Thursday evening to:

• Meet and network with fellow horse lovers

• Enjoy great live music

• Catch up with friends (and make new ones!)

• Celebrate our shared love of the equestrian lifestyle

Call up your barn friends and make it a night out — we’ll see you at Woodstock Inn! 🌅

ENTERTAINMENT SCHEDULE

Sun, May 3rd

Keiron

1-4PM

Sat, May 9th

The Ruben Montoya Band

7-10pm

Funky Blues Roots Rock

Sat, May 16th

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!

Sun, May 17th

Mallow Hill Duo

1-4PM

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

Fri, May 22nd

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!

Sat, May 23rd

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, May 30th

Homestead

7-10pm

Fri, Jun 5th

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 7th

Keiron

1-4PM

Sat, Jun 13th

The Ruben Montoya Band

7-10pm

Funky Blues Roots Rock

Fri, Jun 19th

Two Suspects

7-10pm

Sat, Jun 20th

Homestead

7-10pm

Sun, Jun 21st

Mama's Black Sheep

1-4PM

Sat, Jun 27th

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!

Sun, Jun 28th

Mallow Hill Duo

1-4PM

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

Fri, Jul 3rd

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, Jul 5th

Keiron

1-4PM

Sat, Jul 11th

Homestead

7-10pm

Sun, Jul 12th

Mama's Black Sheep

1-4PM

Fri, Jul 31st

Sidewalk Soul

7-10pm

Sat, Aug 1st

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!

Sun, Aug 2nd

Keiron

1-4PM

Fri, Aug 7th

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, Aug 8th

The Ruben Montoya Band

7-10pm

Funky Blues Roots Rock

Sun, Aug 9th

Mallow Hill Duo

1-4PM

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

Fri, Aug 21st

Two Suspects

7-10pm

Sat, Aug 22nd

Homestead

7-10pm

Fri, Sep 4th

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, Sep 5th

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!

Sun, Sep 6th

Keiron

1-4PM

Sat, Sep 12th

Homestead

7-10pm

Sun, Sep 13th

Mallow Hill Duo

1-4PM

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

Fri, Sep 18th

Sidewalk Soul

7-10pm

Sat, Sep 26th

Two Suspects

7-10pm

Sun, May 3rd
Keiron | 1-4PM
Sat, May 9th
The Ruben Montoya Band | 7-10pm
Sat, May 16th
The Viper Brothers | 7-10pm
Sun, May 17th
Mallow Hill Duo | 1-4PM
Fri, May 22nd
Sidewalk Soul | 7-10pm
Sat, May 23rd
Two Suspects | 7-10pm
Sat, May 30th
Homestead | 7-10pm
Fri, Jun 5th
100 Proof | 7-10pm
Sun, Jun 7th
Keiron | 1-4PM
Sat, Jun 13th
The Ruben Montoya Band | 7-10pm
Fri, Jun 19th
Two Suspects | 7-10pm
Sat, Jun 20th
Homestead | 7-10pm
Sun, Jun 21st
Mama's Black Sheep | 1-4PM
Sat, Jun 27th
The Viper Brothers | 7-10pm
Sun, Jun 28th
Mallow Hill Duo | 1-4PM
Fri, Jul 3rd
100 Proof | 7-10pm
Sun, Jul 5th
Keiron | 1-4PM
Sat, Jul 11th
Homestead | 7-10pm
Sun, Jul 12th
Mama's Black Sheep | 1-4PM
Fri, Jul 31st
Sidewalk Soul | 7-10pm
Sat, Aug 1st
The Viper Brothers | 7-10pm
Sun, Aug 2nd
Keiron | 1-4PM
Fri, Aug 7th
100 Proof | 7-10pm
Sat, Aug 8th
The Ruben Montoya Band | 7-10pm
Sun, Aug 9th
Mallow Hill Duo | 1-4PM
Fri, Aug 21st
Two Suspects | 7-10pm
Sat, Aug 22nd
Homestead | 7-10pm
Fri, Sep 4th
100 Proof | 7-10pm
Sat, Sep 5th
The Viper Brothers | 7-10pm
Sun, Sep 6th
Keiron | 1-4PM
Sat, Sep 12th
Homestead | 7-10pm
Sun, Sep 13th
Mallow Hill Duo | 1-4PM
Fri, Sep 18th
Sidewalk Soul | 7-10pm
Sat, Sep 26th
Two Suspects | 7-10pm