EVENTS AND ENTERTAINMENT

🎶🐴 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

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

🔥🦪 PIT BEEF, OYSTERS & LIVE MUSIC AT THE WOODSTOCK INN! 🎶🔥

Get ready for a Saturday night packed with smoky BBQ, fresh oysters, cold drinks, and live music!

📅 Saturday, September 19
⏰ 5–9 PM
🎸 Live music with the Ruben Montoya Band starting at 6 PM
🎟️ $65 per person

🌧️☀️ RAIN OR SHINE — THE PARTY IS ON!
Your $65 ticket guarantees you a seat under the tent, so no matter what the weather brings, you can sit back, relax, and enjoy the evening!

And come hungry because we’re serving up a feast:

🔥 Woodfire Smoked Pit Beef Sandwiches on potato rolls with assorted condiments
🦪 Fresh-Shucked Oysters from our Oyster Shucker
🦪 Fried Oysters
🔥 Grilled Oysters with garlic & herb butter and Parmesan cheese
🌽 Grilled Corn on the Cob
🥔 Potato Salad
🥬 Coleslaw
🫘 Pit Beans

Grab your friends and join us at The Woodstock Inn for an evening of great food, live music, and a whole lot of fun!

🎶 Come for the oysters. Stay for the music. Leave happy (and full)!

Saturday, September 19 | 5–9 PM
$65 per person — guaranteed seating under the tent!

🔥 This event is RAIN OR SHINE! 🌧️☀️

Space is limited, so grab your spot and get ready for one delicious Saturday night! 🦪🎸🔥

Woodstock Inn presents: A Taste of Maryland - Boordy Vineyards Wine Dinner

Join us on Tuesday, September 29th for an intimate evening celebrating Maryland wine, local ingredients, and a specially prepared menu from the Woodstock Inn kitchen.

For this one-night-only dinner, each course will be paired with a wine from Boordy Vineyards, one of Maryland’s best-known local wineries. From the opening reception through dessert, the wines have been selected to complement Chef’s menu and showcase the range of Boordy’s portfolio.

The evening begins with a selection of stationary and passed appetizers, including a fruit and cheese display, local mushroom bruschetta, local clams casino, mini beef Wellingtons, and Brie and raspberry phyllo bites. These will be accompanied by Boordy Rockfish and Boordy South Mountain Red.

The first seated course features a Poached Pear Salad with baby frisée and red mizuna lettuce, candied almonds, shaved fennel, fried goat cheese, and spiced pear vinaigrette, paired with Boordy Riesling.

For the entrée, Chef will serve Pan-Seared Local Golden Tilefish with lobster-Parmesan risotto, fresh tarragon, haricot verts, and lemon-caper beurre blanc, paired with Boordy Landmark Chardonnay.

The evening concludes with a Lemon Meringue Tart, filled with lemon curd and topped with toasted meringue and fresh raspberries, paired with Boordy Vidal Blanc.

This will be an intimate dinner with only 25 tickets available.

Tuesday, September 29, 2026
$125 per person - gratuity included
Limited to 25 guests

Advance reservations are required. Once all 25 seats have been reserved, the event will be sold out.

We invite you to join us for a special evening of thoughtfully prepared food, Maryland wine, and the hospitality of the Woodstock Inn.

Wine Pairings

Boordy Rockfish
Boordy South Mountain Red
Boordy Riesling
Boordy Landmark Chardonnay
Boordy Vidal Blanc

Oktoberfest 2026
🍺🥨 FARM, FOOD, PROST! — OKTOBERFEST AT THE WOODSTOCK INN 🥨🍺 Break out the lederhosen, grab your stein, and get ready for an afternoon of German food, cold beer, live music, contests & Oktoberfest fun! 📅 Sunday, October 4th ⏰ 1–4PM 📍 The Woodstock Inn 🎶 LIVE MUSIC The Bratwurst Boys take the stage from 1–4PM! 🍺 STEIN HOISTING CONTEST — 2PM Think you can hold your stein longer than everyone else? Put those arms to the test! 🏆 BEST DRESSED CONTEST — 3PM Lederhosen, dirndls and Oktoberfest attire encouraged — come dressed to win! 🍻 THE OKTOBERFEST BEER GARDEN — $75 PER PERSON This is the ticket you want! Your $75 Beer Garden Ticket includes: ✅ Guaranteed seating for the day ✅ Oktoberfest Buffet Ticket ✅ BOTTOMLESS DRAFT BEER featuring: • Miller Lite • Michelob Ultra • Yuengling • Sam Adams Oktoberfest Come hungry because Chef is putting together one serious Oktoberfest spread! 🥨 OKTOBERFEST BUFFET Charcuterie & Appetizers • Cheese & Charcuterie Board • Pretzel Bites with Beer Cheese & Assorted Mustards • Potato Latkes • Candied Almonds Entrées & Sides • Bratwurst with Sauerkraut & Pretzel Buns • Mini Pork Shanks with Dijon-Brandy Green Peppercorn Sauce • Beer-Brined Chicken Breasts with Creamy Mushroom Sauce • Smoked Pork Loin with Dark Beer Pork Gravy • German Potato Salad • Braised Red Cabbage with Apples Desserts • Apple Strudel • Black Forest Cheesecake 🍺 Come for the food. Stay for the beer. Compete for Oktoberfest glory. Beer Garden seating is limited, so advance tickets are strongly encouraged! Your Beer Garden ticket guarantees your seat, buffet access AND bottomless draft beer throughout the event. Gather your crew and get ready to raise a stein at the Woodstock Inn! PROST! 🍻

🤠🍂 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