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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

3rd Thursdays starting in May
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! 🌅

Dates 

May 21

June 18

Jukly 16

August 20

September 17



Wednesday May 27
Wednesday May 27
Country Line dancing series

Grab your boots and join us this May for Country Line Dancing!
Whether you're a beginner or a seasoned dancer, everyone is welcome—bring your friends and family for a fun night on the dance floor. All ages are invited!
Please remember: closed-toed shoes are required for safety.
Come ready to learn, laugh, and dance the night away—we can’t wait to see you there!

Dates

May 27

June 24

July 29

Aug 26

Sept 30



July 28
July 28
Barrels & Bites Bourbon Dinner

An Evening of Bourbon Tastings & Curated Pairings
Join us in the Stone Bar for an unforgettable evening celebrating exceptional bourbon, handcrafted cocktails, and a thoughtfully curated diningexperience.

Our culinary team has created a three-course menu featuring farm-fresh ingredients, many sourced from local farms and producers, paired perfectlywith premium bourbon-inspired cocktails. From the first bite to the final sip, each course has been designed to showcase the rich flavors andcraftsmanship of both the food and spirits.

Your Evening Includes
Cocktail Hour & Stationary Appetizers

Artisan Cheese & Charcuterie Board
Spicy Peach Bourbon Glazed Wings
Braised Short Rib Poutine Potato Skins
Pastrami Smoked Salmon
First Course
Spinach Salad with candied bacon, goat cheese-stuffed dates, hot honey, candied pecans, and apricot vinaigrette

Second Course
Ancho-Coffee Rubbed Dry-Aged Ribeye with whiskey-smoked shrimp, smoked gouda potato purée, charred broccolini, herb butter, and sour cherrydemi-glace

Dessert Course
Salted Caramel Pecan Pie with vanilla ice cream, dark chocolate-covered pretzel stick, macerated blackberries, and maple syrup

Bourbon or Wine — Your Choice
Not a bourbon enthusiast? We’ve got you covered. Guests may choose expertly selected wine pairings in place of the bourbon cocktails, ensuring anequally memorable dining experience.

Space is limited. Reserve your seat today and join us for a truly distinctive culinary experience.



Purchase Tickets

Sunday October 18th 12pm
Sunday October 18th 12pm
Fall Round-Up with Circle R Arena

🤠🍂 Fall Round-Up Ride with Circle R Arena 🍂🐎
Grab your boots, saddle up, and join us for one of our favorite fall traditions! We're once again partnering with our amazing sponsor, The Woodstock Inn, for a day filled with scenic trails, great friends, and delicious food.

🍁 Sunday, October 18
📍 Meet at Smith Stables
3009 Hernwood Road
Woodstock, MD 21163

Please email Smith Stables with any questions

sstrailrides@gmail.com

🐴 Trail Ride Departs Promptly at 11:00 AM
Enjoy a beautiful guided ride through Patapsco Valley as we make our way to The Woodstock Inn for an afternoon of great food and even better company.

🍽️ Fall Buffet
12:00 PM – 3:00 PM
💲 $50 per person

🐎 Riding from somewhere else?
No problem! You're welcome to meet the group at The Woodstock Inn for the buffet, or ride in from wherever is most convenient for you.

❤️ Don't have a horse?
You're still invited! Come join us at The Woodstock Inn for the buffet, mingle with fellow horse lovers, and enjoy the afternoon. A buffet ticket is all you need!

We can't wait to celebrate another beautiful fall day with our incredible equestrian community. See you on the trail! 🍂🤠

Buffet Menu
Hummus Platter
Roasted Beet & Goat Cheese Salad
Tuscan Chicken & Gnocchi
Blackened Salmon
Sliced Pork Loin
White Rice
Brussel Sprouts
Assorted Mini Deserts



Purchase Tickets Today!

ENTERTAINMENT SCHEDULE

Thu, Jul 23rd
David Phenicie & Paula Richardson Dou

7-10pm

Fri, 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.


Sat, Jul 25th
Dan Heely

Playing a wide range of soulful, acoustic-driven covers across soul, folk, and acoustic rock—familiar songs delivered in a tasteful, stripped-down style that works for both background ambiance and upbeat moments Dan Heely is a must see!


Sun, Jul 26th
Live Music
Ruben Montoya

1-4PM

Funky Blues Roots Rock!


Fri, Jul 31st
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, 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
Bluegrass Jam hosted by The Fruit Jar Howlers

1-4PM

🪕 Pickin’ & Grinnin’ 🪕

Bluegrass Jam 7–9 PM 🎶

Musicians of all levels—grab your instrument and join the fun!

No pressure, just great music and great vibes.


Thu, Aug 6th
Bluegrass Jam hosted by The Fruit Jar Howlers

6-9pm

🪕 Pickin’ & Grinnin’ 🪕

Bluegrass Jam 7–9 PM 🎶

Musicians of all levels—grab your instrument and join the fun!

No pressure, just great music and great vibes.


Fri, Aug 7th
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, Aug 8th
The Ruben Montoya Band

7-10pm

Funky Blues Roots Rock


Sun, Aug 9th
Woodstock In Performance
Mallow Hill Duo

1-4PM

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


Thu, Aug 13th
David Phenicie & Paula Richardson Dou

7-10pm

Fri, Aug 14th
Dan Heely

7-10pm

Playing a wide range of soulful, acoustic-driven covers across soul, folk, and acoustic rock—familiar songs delivered in a tasteful, stripped-down style that works for both background ambiance and upbeat moments Dan Heely is a must see!


Sat, Aug 15th
garrett mabe
Garrett Mabe

7-10pm

Garrett Mabe is a Singer/Songwriter/Muli-Instrumentalist who has been playing weddings, festivals, corporate events, and venues all around the East Coast for years now. Starting at 14 playing in local bars, this 24 year old already has 10 years of musical experience under his belt. With a song list of 500+ songs


Sun, Aug 16th
Steven O'Boyle

1-4PM

Stephen Boyle hits the stage with a high-energy mix of country, 90’s rock ‘n’ roll, and everything in between. Expect familiar favorites, laid-back vibes, and fun that keeps the good times rolling.


Thu, Aug 20th
Bluegrass Jam hosted by The Fruit Jar Howlers

6-9pm

🪕 Pickin’ & Grinnin’ 🪕

Bluegrass Jam 7–9 PM 🎶

Musicians of all levels—grab your instrument and join the fun!

No pressure, just great music and great vibes.


Fri, Aug 21st
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, Aug 22nd
Homestead
Homestead

7-10pm

Sun, Aug 23rd
Acoustic Live Show
Sean Bera & DC

1-4PM

Thu, Aug 27th
David Phenicie & Paula Richardson Dou

7-10pm

Fri, Aug 28th
David Phenicie & Paula Richardson Dou

7-10pm

Sat, Aug 29th
Logan Chalk

8-11pm

Singer-songwriter Logan Chalk is taking the country music scene by storm—don’t miss your chance to see him live at the Woodstock Inn on Saturday, August 29, from 8 to 11 PM.


Sun, Aug 30th
Enslow
Enslow

1-4PM

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, Sep 3rd
Bluegrass Jam hosted by The Fruit Jar Howlers

6-9pm

🪕 Pickin’ & Grinnin’ 🪕

Bluegrass Jam 7–9 PM 🎶

Musicians of all levels—grab your instrument and join the fun!

No pressure, just great music and great vibes.


Fri, Sep 4th
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, 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

Thu, Sep 10th
David Phenicie & Paula Richardson Dou

7-10pm

Fri, Sep 11th
Dan Heely

7-10pm

Playing a wide range of soulful, acoustic-driven covers across soul, folk, and acoustic rock—familiar songs delivered in a tasteful, stripped-down style that works for both background ambiance and upbeat moments Dan Heely is a must see!


Sat, Sep 12th
Homestead
Homestead

7-10pm

Sun, Sep 13th
Woodstock In Performance
Mallow Hill Duo

1-4PM

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


Thu, Sep 17th
Bluegrass Jam hosted by The Fruit Jar Howlers

6-9pm

🪕 Pickin’ & Grinnin’ 🪕

Bluegrass Jam 7–9 PM 🎶

Musicians of all levels—grab your instrument and join the fun!

No pressure, just great music and great vibes.


Fri, Sep 18th
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, Sep 19th
The Ruben Montoya Band

7-10pm

Funky Blues Roots Rock


Sun, Sep 20th
Steven O'Boyle

1-4PM

Stephen Boyle hits the stage with a high-energy mix of country, 90’s rock ‘n’ roll, and everything in between. Expect familiar favorites, laid-back vibes, and fun that keeps the good times rolling.


Thu, Sep 24th
David Phenicie & Paula Richardson Dou

7-10pm

Fri, Sep 25th
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 26th
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


Sun, Sep 27th
Enslow Duo

1-4PM

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 23rd
    David Phenicie & Paula Richardson Dou | 7-10pm
  • Fri, Jul 24th
    Enslow | 7-10pm
  • Sat, Jul 25th
    Dan Heely |
  • Sun, Jul 26th
    Ruben Montoya | 1-4PM
  • Fri, Jul 31st
    Sidewalk Soul | 7-10pm
  • Sat, Aug 1st
    The Viper Brothers | 7-10pm
  • Sun, Aug 2nd
    Bluegrass Jam hosted by The Fruit Jar Howlers | 1-4PM
  • Thu, Aug 6th
    Bluegrass Jam hosted by The Fruit Jar Howlers | 6-9pm
  • Fri, Aug 7th
    100 Proof | 7-10pm
  • Sat, Aug 8th
    The Ruben Montoya Band | 7-10pm
  • Sun, Aug 9th
    Mallow Hill Duo | 1-4PM
  • Thu, Aug 13th
    David Phenicie & Paula Richardson Dou | 7-10pm
  • Fri, Aug 14th
    Dan Heely | 7-10pm
  • Sat, Aug 15th
    Garrett Mabe | 7-10pm
  • Sun, Aug 16th
    Steven O'Boyle | 1-4PM
  • Thu, Aug 20th
    Bluegrass Jam hosted by The Fruit Jar Howlers | 6-9pm
  • Fri, Aug 21st
    Two Suspects | 7-10pm
  • Sat, Aug 22nd
    Homestead | 7-10pm
  • Sun, Aug 23rd
    Sean Bera & DC | 1-4PM
  • Thu, Aug 27th
    David Phenicie & Paula Richardson Dou | 7-10pm
  • Fri, Aug 28th
    David Phenicie & Paula Richardson Dou | 7-10pm
  • Sat, Aug 29th
    Logan Chalk | 8-11pm
  • Sun, Aug 30th
    Enslow | 1-4PM
  • Thu, Sep 3rd
    Bluegrass Jam hosted by The Fruit Jar Howlers | 6-9pm
  • Fri, Sep 4th
    100 Proof | 7-10pm
  • Sat, Sep 5th
    The Viper Brothers | 7-10pm
  • Sun, Sep 6th
    Keiron | 1-4PM
  • Thu, Sep 10th
    David Phenicie & Paula Richardson Dou | 7-10pm
  • Fri, Sep 11th
    Dan Heely | 7-10pm
  • Sat, Sep 12th
    Homestead | 7-10pm
  • Sun, Sep 13th
    Mallow Hill Duo | 1-4PM
  • Thu, Sep 17th
    Bluegrass Jam hosted by The Fruit Jar Howlers | 6-9pm
  • Fri, Sep 18th
    Sidewalk Soul | 7-10pm
  • Sat, Sep 19th
    The Ruben Montoya Band | 7-10pm
  • Sun, Sep 20th
    Steven O'Boyle | 1-4PM
  • Thu, Sep 24th
    David Phenicie & Paula Richardson Dou | 7-10pm
  • Fri, Sep 25th
    Red Sky Dawn | 7-10pm
  • Sat, Sep 26th
    Two Suspects | 7-10pm
  • Sun, Sep 27th
    Enslow Duo | 1-4PM
Rafael's Steak and Oyster

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