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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

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

πŸ€ πŸ‚ Fall Round-Up Ride with Circle R Arena πŸ‚πŸŽ
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
πŸ“ 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
πŸ’² $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! πŸ‚πŸ€ 

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

October 27th
October 27th
Woodstock Supper Club Local Farm Dinner

Woodstock Supper Club: Local Farm Dinner 🌾🍽️
We’re excited to invite you to the very first Woodstock Supper Club β€” an intimate dinner experience celebrating local farms, seasonal ingredients, and the creativity of our kitchen.

Join us Tuesday, October 27th at 6:30 PM for our Local Farm Dinner, featuring a thoughtfully prepared multi-course menu showcasing ingredients from farms and producers throughout our area.

The evening begins with a selection of appetizers including Mushroom Coffee, Roasted & Tempura Vegetables, Lion’s Mane β€œMock” Crab Cakes, Eggplant Parmesan Bites, and Local Deviled Eggs.

Then settle in for three courses:

First Course: Local Pumpkin Curry Soup with coconut rice, Thai basil, Swiss chard, toasted pumpkin seeds, pumpkin seed oil, paneer cheese and curry chicken.

Second Course: Harissa Rubbed Lamb Chops with saffron couscous, North Acres Farm merguez sausage and roasted red pepper coulis.

Third Course: Bone-In Pork Chop with skin-on redskin mashed potatoes, green beans with bacon and sautΓ©ed onions, smoked pork fig & apple cider glaze and local apple chutney.

This isn't just dinner β€” it's what the Woodstock Supper Club is all about: smaller gatherings, special menus, incredible food, and experiences you won't find on our everyday menu.

πŸ“… Tuesday, October 27
⏰ 6:30 PM
πŸ“ The Woodstock Inn
🎟️ ONLY 25 SEATS AVAILABLE

Our inaugural Supper Club will be an intimate evening, and once these 25 seats are gone, they're gone.

Come hungry. Come curious. Welcome to the Woodstock Supper Club. 🌾πŸ₯‚

October 31st
October 31st
Annual Halloween Bash

πŸŽƒπŸ‘» WOODSTOCK INN'S ANNUAL HALLOWEEN BASH! πŸ‘»πŸŽƒ

Get ready for a spooktacular night at the Woodstock Inn! We're bringing the tricks, treats, music, and Halloween fun for our Annual Halloween Bash on Saturday, October 31st!

Grab your crew, put together your best costume, and join us for a wicked good time!

πŸ•ΈοΈ HERE'S WHAT'S HAUNTING THE INN:

🎧 DJ Starting at 10 PM
Dance the night away with your favorite party hits!

πŸ† HALLOWEEN COSTUME CONTEST – 11:30 PM
Think you've got the best costume in the house? Show it off for your chance to win a $100 Woodstock Inn Gift Card!

πŸ—³οΈ VOTE FOR THE BEST DRESSED BARTENDER!
Our bartenders are getting into the Halloween spirit, and YOU get to decide who wears it best!

🎁 WOODSTOCK INN MERCH GIVEAWAYS
We'll be giving away some Woodstock Inn goodies throughout the night!

🍹 HALLOWEEN COCKTAILS & SHOTS
Get into the spooky spirit with our Halloween-themed drinks!

πŸ“Έ HAUNTED PHOTO STATION
Capture your costumes and make some hauntingly good memories!

πŸ” LATE-NIGHT FOOD UNTIL 1 AM
Keep the party going! Our kitchen will be serving late-night food until 1 AM.

πŸŽƒ EVENT DETAILS
πŸ“… Saturday, October 31, 2026
🎧 DJ at 10 PM
πŸ† Costume Contest at 11:30 PM
πŸ“ The Woodstock Inn | Woodstock, Maryland

Whether you're coming dressed to scare, dressed to impress, or just ready for a fun night out, there's something for everyone!

πŸ‘» Come for the BOOS, stay for the BOOZE! 🍻

Tag your Halloween crew, share this event, and start planning those costumes!

#WoodstockInn #HalloweenBash #Halloween2026 #WoodstockMD #CostumeContest #HalloweenParty



Tuesday November 24th
Tuesday November 24th
Woodstock Supper Club Local Seafood Dinner

Woodstock Supper Club: Local Seafood Dinner
Join us for the next Woodstock Supper Club as we celebrate the flavors of our local waters!

Tuesday, November 24
6:30 PM
The Woodstock Inn
$75 per person

Chef Rob and our culinary team have created a special Local Seafood Dinner, beginning with an assortment of seafood appetizers followed by three individually prepared courses.

APPETIZERS
β€’ Beer-Battered Snakehead Bites
β€’ Oyster Bar
β€’ Clams Casino
β€’ CalamariΒ 

FIRST COURSE
Maryland Crab-Stuffed Squash Blossom
Sweet corn purΓ©e, avocado & tomato salad, pea shoots and fried green tomato.Β 

SECOND COURSE
Pan-Seared Black Bass & Bay Scallops
SautΓ©ed spinach, white wine-lemon butter sauce and fresh dill.Β 

THIRD COURSE
Local Blue Catfish Γ‰touffΓ©e
Blackened cornmeal-dusted catfish over Cajun jambalaya rice with smoked shrimp and crawfish Γ©touffΓ©e.Β 

Tickets are $75 per person
Our Supper Club dinners are designed to be intimate, special evenings with limited seating available.

Advance ticket purchase is required, and once the seats are gone, they’re gone!

Gather your favorite seafood lover and join us for an evening celebrating Maryland and local seafood in true Woodstock Inn style.

Local waters. Local flavors. One incredible night.

Tuesday, November 24 β€’ 6:30 PM β€’ $75 per person

Grab your tickets and join us at the table!

Thanksgiving Day
Thanksgiving Day
We are OPEN

πŸ¦ƒπŸ‚ THANKSGIVING DAY AT THE WOODSTOCK INN! πŸ‚πŸ¦ƒ

Let us do the cooking this Thanksgiving!

Gather your family, bring your friends, and join us at The Woodstock Inn for a delicious Thanksgiving celebration filled with great food, good company, and holiday cheer!

Whether you're looking for a traditional Thanksgiving feast or just want to escape the kitchen for the day, we've got a seat waiting for you!

🍁 THURSDAY, NOVEMBER 26, 2026

πŸ•š Doors Open: 11 AM – 2 AM

🍽️ Kitchen Hours: 11 AM – 8 PM

πŸ“ The Woodstock Inn | Woodstock, Maryland

πŸ¦ƒ OUR THANKSGIVING MENU

Chef Rob and our kitchen team have put together a special holiday menu featuring traditional favorites and a few Woodstock twists!

πŸ— Holiday EntrΓ©es

Traditional Turkey Platter with all the fixings – $24
Holiday Ham Platter – $24
Roast Beef Platter – $26
12 oz. Smoked Bone-In Pork Chop – $26
πŸ₯— Seasonal Starters & Sides

Enjoy holiday-inspired favorites including Smoked Turkey Cornbread Fritters, Fried Brussels Sprouts, Creamy Butternut Squash Soup, Baked Brie, and fresh seasonal salads.

πŸ₯§ Save Room for Dessert!

Finish your Thanksgiving meal with Pumpkin Cheesecake, Apple Strudel Γ  la Mode, Bourbon Pecan Pie, or a Brownie Sundae!

🍻 THE CELEBRATION DOESN'T END AFTER DINNER!

Our kitchen will be serving until 8 PM, but the Woodstock Inn will remain open until 2 AM! Stop by for a holiday drink, catch up with old friends, and enjoy Thanksgiving evening with us.

❀️ We're thankful for our incredible Woodstock community!

Whether you're celebrating with a big group, enjoying a quiet holiday meal, or just stopping in for a drink, we'd love to spend part of Thanksgiving with you.

πŸ‚ Skip the prep, the cooking, and the dishes. Make The Woodstock Inn part of your Thanksgiving tradition!

πŸ“² Invite your family and friends, share this event, and make your Thanksgiving plans with us!

Happy Thanksgiving from all of us at The Woodstock Inn! πŸ¦ƒβ€οΈ



ENTERTAINMENT SCHEDULE

We will be updating our Entertainment Schedule ASAP. Please check back, follow us on social media, or give us a call.

The Woodstock Inn: 410.750.3673

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