Maryland Wineries' Calendar of Promotional Events & Activities

Maryland's wineries offer hundreds of fun-filled events throughout the year. Whether you bring the whole family, a group of friends, or that special someone, events at Maryland's wineries can be both entertaining and educational.

Here you'll find the wineries' major events for the year.



Month:        Event Type:        Wine Trail:        Winery:  



October

October 15 - October 29

Wine Down Wednesday

Great Shoals Winery

performers to be announced*

Join us on Wednesdays throughout October for music & wine under the pavilion at our tasting room! Highlights include free pie samples from the farm bakery, exclusive tastes of our new fresh hard apple cider with ginger, $6 glasses of our warmed Spice Apple mulled wine, and staying warm around the outdoor fireplace! Upcoming dates: Oct 15, 22, 29

Great Shoals Winery

Cost:

When:
7-9pm

Where:
Great Shoals Winery
Get Directions


October 22

Trivia Night!

Perigeaux Vineyards and Winery

Trivia Night!

Test your knowledge on a variety of topics from movies and music to sports and current events. Win wine, prizes and points toward the series grand prize!

Perigeaux Vineyards and Winery

Cost:
0

When:
6:30 - 8:30 pm

Where:
Perigeaux Vineyards and Winery
Get Directions


October 23

Wine 101

Serpent Ridge Vineyard

Want to know just a little more about wine than you do now?

Feel Intimated going to wineries? Want to know about swirling and sniffing and why that doesnt make you a wine snob? Want to know just a little more about wine than you do now? Then come to Serpent Ridge Vineyard and take our new Wine 101 course. In less than two hours you will learn a bit of history, culture, myths and facts about wine, winemaking and viticulture, while tasting our wonderful wines. This is a course designed for beginners. We aim to “democratize” wine tasting. You may enjoy your wine more if you know more about wine, but you don’t need to take the fun out of drinking wine. Your “tuition” includes a talk about wine, wine glass, wine tasting, and educational book about wine. Sign up at: https://www.eventbrite.com/e/wine-101-at-serpent-ridge-vineyard-tickets-12994975321

Serpent Ridge Vineyard

Cost:
30.00

When:
6:30 - 8:30 pm

Where:
Serpent Ridge Vineyard
Get Directions


October 24

Karaoke Friday with DJ Dave

Running Hare Vineyard

Join us for a fun night of Karaoke with DJ Dave. Karaoke starts at 7PM. Special guest Spider Hall Farm will have delicious artisan cheeses, spreads and ice cream available for purchase. Pack a picnic and bring your family, friends and co-workers. A $5 cover fee includes a wine tasting. The Tasting Room will be open noon - 10PM.

Running Hare Vineyard

Cost:
5

When:
7:00 PM - 10:00 PM

Where:
Running Hare Vineyard
Get Directions


October 24

Saving Sgt. Pepper - The Beatles Tribute Band

DeJon Vineyard

Saving Sgt. Pepper is one of regions premier Beatles tribute band. They focus less on wardrobe changes and appearing to be someone they're not, and more on fine tuning their sound, to be near perfection of the full catalog, from this legendary band, The Beatles. Doors open @ 6:30pm. $10.00 admission per adult. Food Vendor on Site. Reservations preferred. By law, no outside alcohol permitted. No pets allowed.

DeJon Vineyard

Cost:
10.00

When:
7-10PM

Where:
DeJon Vineyard
Get Directions


October 24

Wine Down Friday with Rhyne McCormick

Knob Hall Winery

Wine Down Fridays are family-friendly. Admission is $5 for anyone over 21 and your first glass of non-premium wine is only $3. Food can be purchased through a caterer.

Knob Hall Winery

Cost:
5

When:
7:30 pm

Where:
Knob Hall Winery
Get Directions


October 25

Music on The Patio

Bordeleau Vineyards and Winery

enjoy music by Randy Lee Ashcraft and Jimmy Rowbottom. Bring your picnic baskets. We will be hosting a "apple bobbing contest" Are you feeling lucky??

Bordeleau Vineyards and Winery

Cost:
0

When:
1-4pm

Where:
Bordeleau Vineyards and Winery
Get Directions


October 25

Fall Melodies

Port of Leonardtown Winery

Join us for some amazing music from the Swing Away Jazz Duo.

Port of Leonardtown Winery

Cost:
0

When:
4:00-7:00pm

Where:
Port of Leonardtown Winery
Get Directions


October 25

Pet Halloween Costume Contest!

Perigeaux Vineyards and Winery

Pet Halloween Costume Contest

Bring your pet(s) dressed in their funiest, scariest, or most original Halloween costume and enter them in our contest to win a prize for yourself and for your pet(s)! Each bottle of wine sold results in a donation to the Calvert County Humane Society. Each pet receives a special Halloween treat!

Perigeaux Vineyards and Winery

Cost:
0

When:
2:00 - 4:00 pm

Where:
Perigeaux Vineyards and Winery
Get Directions


October 25

Live Music featuring Pfeiffer and Skow

Perigeaux Vineyards and Winery

Live Music with Pfeiffer and Skow

This talented local team has proven to be one of our most popular performances and returns by popular demand. If you like popular and folk music from the 60s and 70s, this one's for you!

Perigeaux Vineyards and Winery

Cost:
0

When:
1:00 - 5:00 pm

Where:
Perigeaux Vineyards and Winery
Get Directions


October 25

Live Music Saturday

Running Hare Vineyard

featuring Mark Scott

Join us for wine tasting and live music by Mark Scott. Pack a picnic and bring your family and friends. A $5 cover includes wine tasting. The Tasting Room is open noon - 6:00 PM.

Running Hare Vineyard

Cost:
5

When:
Noon - 4:00 PM

Where:
Running Hare Vineyard
Get Directions


Harvest at Swan Harbor Farm
October 25

Harvest at Swan Harbor Farm

Join MD wineries, growers and agricultural producers as we celebrate Maryland's harvest at the site of one of Maryland's earliest recorded vineyards.  Live music, local restaurants and children's activities on hand.

Read More

Cost:
$20 Advance, $25 At Gate

When:
11- 5



October 25

WIne and Canvas Paint Night

Serpent Ridge Vineyard

Paint, Sip and have fun!

Come for our regularly scheduled monthly painting event! No experience needed and you will create a work of art to bring home that evening! Talented instructors will guide you step-by-step and the wine tasting makes it even better! Sign up for this date at: https://www.wineandcanvas.com/wine-and-canvas-calendar-baltimore-md.html

Serpent Ridge Vineyard

Cost:
35.00

When:
6:30 - 9:30 pm

Where:
Serpent Ridge Vineyard
Get Directions


October 25 - October 26

Fall Festival

Big Cork Vineyards

Big Cork Vineyards 1st annual Fall festival!

Get a sneak peak at our new tasting room while enjoying our wine, local food vendors, a large kids activity area, pumpkin picking, live music, harvest hayrides and much more.

Download Flyer
Big Cork Vineyards

Cost:
Free Entry

When:
12-6pm

Where:
Big Cork Vineyards
Get Directions


October 26

Art Wine & Canvas

Charis Winery

Enjoy an evening learning to paint. All paint, canvas, brushes and a glass of the wine of your choice are included for the fee. $25 to $35 Reservations required

Charis Winery

Cost:
$25 to $35

When:
5 till 8pm

Where:
Charis Winery
Get Directions


October 26

Live Music Sundays

Catoctin Breeze Vineyard

Wine Tasting and Live Jazz

Join us for wine tasting and live music by local jazz group, The Monocacy Jazz Quartet. Bring your family and friends to enjoy a picnic outdoors underneath our new pergola! Free educational walk through the vineyard with our winemaker or vineyard staff at 2pm! No reservations required. Tastings are $6 for a featured sampling of 5 wines. Locally made cheeses are also available for tasting and purchase.

Catoctin Breeze Vineyard

Cost:
Free Admission

When:
12pm-5pm

Where:
Catoctin Breeze Vineyard
Get Directions


October 26

Kid's Halloween Party

Layton's Chance Vineyard and Winery

Games, crafts, storybook hay rides featuring The True Story of the Three Little Pigs, trick or treating and a costume contest at 3:30pm that will be judged by local elementary school principals. All proceeds go to East New Market Fire Hall. Food available for purchase.

Layton's Chance Vineyard and Winery

Cost:
5/family

When:
1pm - 4pm

Where:
Layton's Chance Vineyard and Winery
Get Directions


October 26

Live Music Sunday

Running Hare Vineyard

featuring A Beautiful Noise

Join us for wine tasting and live music by A Beautiful Noise. Pack a picnic and bring your family and friends. A $5 cover includes wine tasting. The Tasting Room is open noon - 6:00 PM.

Running Hare Vineyard

Cost:
5

When:
1:00 PM - 5:00 PM

Where:
Running Hare Vineyard
Get Directions


October 26

Paint & Wet your Palette "Birch Tree Pathway"

Dove Valley Winery

Paint & Wet Your Palette at Dove Valley Winery Enjoy Painting and Sipping on Dove Valley Wine. NO EXPERIENCE NECESSARY….All supplies included, Professional Artist providing Step by Step directions.. Call 410-658-8388 for Reservations.. Booking Tickets Now!!! Limited Seating

Dove Valley Winery

Cost:
30.00 Includes a glass of wine

When:
3-5pm

Where:
Dove Valley Winery
Get Directions


October 29

Trivia Night!

Perigeaux Vineyards and Winery

Trivia Night!

Test your knowledge on a variety of topics from movies and music to sports and current events. Win wine, prizes and points toward the series grand prize!

Perigeaux Vineyards and Winery

Cost:
0

When:
6:30 - 8:30 pm

Where:
Perigeaux Vineyards and Winery
Get Directions


October 31

Halloween Costume Party, Trivia and Movie Night

Perigeaux Vineyards and Winery

Halloween Costume Party, Team Trivia, and Outdoor Movie Night

Celebrate All Hallow's Eve with a wine and cheese Halloween Costume Party. Prizes awarded for best individual and group costumes. Enjoy a sampling of our estate wines paired with local artisan cheeses while testing your trivia knowledge of all things Halloween! Then enjoy a glass of wine, a bag of treats and settle in for an outdoor Halloween themed movie! Reservations required. Call 410-586-2710 or email us at john@perigeaux.com.

Perigeaux Vineyards and Winery

Cost:
$15 per person

When:
6:00 - 10:00 pm

Where:
Perigeaux Vineyards and Winery
Get Directions


October 31

Halloween Party at Knob Hall!

Knob Hall Winery

Admission is $5 for anyone over 21 and your first glass of non-premium wine is only $3. Food can be purchased through a caterer.

Prizes for the best male and female costumes. Is the barn haunted or was that you that closed that door and turned off the lights? Ah, where are you…..

Knob Hall Winery

Cost:
5

When:
7:30 pm

Where:
Knob Hall Winery
Get Directions


October 31

Halloween Happy Hour & Best Carved Pumpkin Contest

Serpent Ridge Vineyard

The ghoolies are out! Come for happy hour at the spooky vineyard!

Just a little Halloween fun and wine discounts this scary evening. Feel free to dress up! Contest and prize for best carved pumpkin!

Serpent Ridge Vineyard

Cost:
0

When:
5pm - 9pm

Where:
Serpent Ridge Vineyard
Get Directions


November 01

Live Music featuring "Landing Mary"

Perigeaux Vineyards and Winery

Live Music with "Landing Mary".

Back by popular demand, this young local duo plays all the music you know and love from the radio and going back to the 90s! You don't want to miss it!

Perigeaux Vineyards and Winery

Cost:
0

When:
1:00 - 4:00 pm

Where:
Perigeaux Vineyards and Winery
Get Directions


November 01

Fall Melodies

Port of Leonardtown Winery

Tell your friends to join you at the winery for fall tunes with Gerrie Swarbrick on the patio.

Port of Leonardtown Winery

Cost:
0

When:
4:00-7:00pm

Where:
Port of Leonardtown Winery
Get Directions


November 02

Art Wine & Canvas

Charis Winery

Enjoy an evening learning to paint. All paint, canvas, brushes and a glass of the wine of your choice are included for the fee. $25 to $35 Reservations required

Charis Winery

Cost:
$25 to $35

When:
5 to 8pm

Where:
Charis Winery
Get Directions


November 02

Food is Art-Food Photography Workshop with Edwin Remsberg

Crow Vineyard and Winery

Come spend the day with professional cookbook photographer Edwin Remsberg and feast on a wonderful gourmet lunch as he teaches you how to compose and light masterly crafted food. The workshop will include a tour of Crow winery, wine tasting, and an amazingly wonderful 3-course lunch prepared by Chef Matt Whitehair, from Molly's Inn, Kennedyville, MD. Any level of food photography enthusiast is welcome! You don't need experience or expensive cameras, just come with a love of good food and desire to learn. Edwin will be concentrating on lighting and composition of the dishes, and using light to give shape, color, and texture to food. Learn how to show ideas like moistness, warmth, and crunch, use composition, backgrounds, and styling to visually convey taste and feel.

Crow Vineyard and Winery

Cost:
75.00 rsvp at crowvineyardwines@gmail.com

When:
1pm-4pm

Where:
Crow Vineyard and Winery
Get Directions


November 07

Leonardtown First Fridays

Port of Leonardtown Winery

Don’t miss the live music of Josh Airhart on First Friday out on the patio playing from 5:30 – 8:30 pm. Unwind from your busy week with our award winning wines & great music.

Port of Leonardtown Winery

Cost:
0

When:
5:30-9:00pm

Where:
Port of Leonardtown Winery
Get Directions


November 07

Karaoke Happy Hour

Layton's Chance Vineyard and Winery

Join us for singing, dancing, and all around good times! Bring your dinner or some snacks. Table reservations taken on the day of the event only.

Layton's Chance Vineyard and Winery

Cost:
0

When:
6-10pm

Where:
Layton's Chance Vineyard and Winery
Get Directions


November 08 - November 09

Schucker's Saturday

Galloping Goose Vineyards

The first person to eat an oyster must have been a wine lover!

Oysters and wine, what could be better? Try oysters on the half shell and oyster stew. Combine this with our oyster friendly wines and you have the perfect marriage of food and beverage. R.S.V.P.

Galloping Goose Vineyards

Cost:
$25

When:
12-5pm (Oyster schucking Saturday only)

Where:
Galloping Goose Vineyards
Get Directions


November 08

Music on the Patio

Bordeleau Vineyards and Winery

Music by Chris English

Bordeleau Vineyards and Winery

Cost:
0

When:
1-4pm

Where:
Bordeleau Vineyards and Winery
Get Directions


November 08

Ladies Night (w/ Lovestory)

DeJon Vineyard

Ladies Night is one of the most popular nights of the year, which features the live entertainment duo, Lovestory, and a bevy of boutique shopping and food vendors. 6-9PM, doors open @ 5:30PM. $10.00 Admission per Adult. More details and info coming soon.

DeJon Vineyard

Cost:
10.00

When:
6-9PM

Where:
DeJon Vineyard
Get Directions


November 08

Fall Melodies

Port of Leonardtown Winery

We honor our Veterans by offering 10% off all wine purchases all weekend. Bring your favorite veterans & friends to listen to live music from Joe Parsons on the patio later in the afternoon.

Port of Leonardtown Winery

Cost:
0

When:
4:00-7:00pm

Where:
Port of Leonardtown Winery
Get Directions


November 08

Wine Club Pickup/Shipment

Rocklands Farm

Our last wine club pickup for the year. Join us! For more info on the club see here: http://www.rocklandsfarmmd.com/wine-club.html

Rocklands Farm

Cost:
55

When:
10am to 5pm

Where:
Rocklands Farm
Get Directions


November 08

Live Music Saturdays

Catoctin Breeze Vineyard

Wine Tasting and Live Jazz

Join us for wine tasting and live music by local jazz group, The Monocacy Jazz Quartet. Bring your family and friends to enjoy a picnic outdoors underneath our new pergola! Free educational walk through the vineyard with our winemaker or vineyard staff at 2pm! No reservations required. Tastings are $6 for a featured sampling of 5 wines. Locally made cheeses are also available for tasting and purchase.

Catoctin Breeze Vineyard

Cost:
Free Admission

When:
12pm-5pm

Where:
Catoctin Breeze Vineyard
Get Directions


November 09

Art Wine & Canvas

Charis Winery

Enjoy an evening learning to paint. All paint, canvas, brushes and a glass of the wine of your choice are included for the fee. $25 to $35 Reservations required

Charis Winery

Cost:
$25 to $35

When:
5 to 8pm

Where:
Charis Winery
Get Directions


November 15

Fall Melodies

Port of Leonardtown Winery

We welcome our first Bluegrass band to the winery. Stop in to listen to 15 Strings play the best of Bluegrass on the patio.

Port of Leonardtown Winery

Cost:
0

When:
4:00-7:00pm

Where:
Port of Leonardtown Winery
Get Directions


November 15

The Golden Girls Murder Mystery (Dinner & Show)

Dove Valley Winery

Without A Cue Productions,LLC presents…. The Golden Girls Murder Mystery at Dove Valley Winery... Dinner & Show $35.00 Includes a Glass of Wine RSVP Needed..(Limited Seating) Tickets available at www.missiontix.com or 410-658-8388 On the Menu: Chicken Cordon Bleu Roasted Potatoes Green Beans Caesar Salad Dinner rolls & Butter Followed by Carrot Cake Catered by the Buck's Restaurant

Dove Valley Winery

Cost:
$35.00 (Includes Glass of Wine, Show & Dinner)

When:
6-10pm

Where:
Dove Valley Winery
Get Directions


November 16

Art Wine & Canvas

Charis Winery

Enjoy an evening learning to paint. All paint, canvas, brushes and a glass of the wine of your choice are included for the fee. $25 to $35 Reservations required

Charis Winery

Cost:
$25 to $35

When:
5 to 8pm

Where:
Charis Winery
Get Directions


November 22

3rd Annual Turkey Trail Trot Run/Walk

Crow Vineyard and Winery

Benefiting Character Counts Kent County. 5k route offers runners and walkers the opportunity for a true Kent County experience with a unique course that passes through vineyard rows, travels alongside pastures of grazing cows, and winds among fields of eastern shore crops. Register online. Register now, http://www.active.com/event_detail.cfm?event_id=2132841

Crow Vineyard and Winery

Cost:
30

When:
Register at 8am- Starts at 10am

Where:
Crow Vineyard and Winery
Get Directions


November 22

Fall Melodies

Port of Leonardtown Winery

We will be rocking at the winery with the Southern rock sounds of John Luskey out on the patio. This will be the last music on the patio until warm weather returns in 2015 so you don’t want to miss this one!

Port of Leonardtown Winery

Cost:
0

When:
4:00-7:00pm

Where:
Port of Leonardtown Winery
Get Directions


November 27

Thanksgiving

Sugarloaf Mountain Vineyard

We will be closed for the holiday.

Sugarloaf Mountain Vineyard

November 28

Black Friday Sale

Sugarloaf Mountain Vineyard

Our biggest sale of the year. Come on out and take advantage of the best prices we ever offer on our wine.

Sugarloaf Mountain Vineyard

Cost:
0

When:
12-6

Where:
Sugarloaf Mountain Vineyard
Get Directions


November 28

Post-Gobble Day

DeJon Vineyard

The day after Thanksgiving can be quite stressful in an effort to get the best deals and discounts. We, at DeJon, don't believe that should be so. Come out, bring your leftovers (we'll provide dessert), and relax with some of the very best wines around, while enjoying live music entertainment. There will be a few boutique shopping vendors and there's a 10% discount on all DeJon wine. More details and info coming soon.

DeJon Vineyard

Cost:
FREE

When:
12:30-5PM

Where:
DeJon Vineyard
Get Directions


November 30

Closed November 30th

Galloping Goose Vineyards

Galloping Goose Vineyards

December 05

Karaoke Happy Hour

Layton's Chance Vineyard and Winery

Join us for singing, dancing, and all around good times! Bring your dinner or some snacks. Table reservations taken on the day of the event only.

Layton's Chance Vineyard and Winery

Cost:
0

When:
6-10pm

Where:
Layton's Chance Vineyard and Winery
Get Directions


December 05

Leonardtown First Fridays

Port of Leonardtown Winery

Take a break from Holiday planning to relax to the live music of Groove Span. Sip some wine as you decide who goes on the Naughty or Nice list.

Port of Leonardtown Winery

Cost:
0

When:
5:30-9:00pm

Where:
Port of Leonardtown Winery
Get Directions


December 06

Pet Photos with Santa Paws

Sugarloaf Mountain Vineyard

Details to come...

Sugarloaf Mountain Vineyard

Cost:
TBA

When:
12-5:00

Where:
Sugarloaf Mountain Vineyard
Get Directions


December 07

Christmas in the Barn

Linganore Winecellars

Our stunning Abisso Hall will be transformed into a Holiday Bazaar, with gifts of all kinds from our favorite vendors. Enjoy an afternoon of holiday music, wine tasting, shopping and merriment with your friends. Just stop by or stay for the day. Food available for purchase.

Linganore Winecellars

Cost:
0

When:
12pm-4pm

Where:
Linganore Winecellars
Get Directions


December 12

Romancing in the Holidays

Galloping Goose Vineyards

Romantic Candlelight Evening

Small plate buffet. Menu to be published at a future date. R.S.V.P.

Galloping Goose Vineyards

Cost:
TBD

When:
5-9pm

Where:
Galloping Goose Vineyards
Get Directions


December 13 - December 14

Romancing in the Holidays

Galloping Goose Vineyards

Fireside Afternoon

Small plate buffet by the fireside. Wine and food pairings. R.S.V.P.

Galloping Goose Vineyards

Cost:
TBD

When:
12-5pm

Where:
Galloping Goose Vineyards
Get Directions


December 13

Christmas Bazaar & Family / Pet Photos with Santa

Dove Valley Winery

Selfie with Santa!!! Santa Claus is coming…… to Dove Valley Winery!! Come out and enjoy the day shopping local Arts & Crafts and get your FAMILY or PET(Dog)photo with Santa!!! Saturday, December 13th 12pm - 5pm Free Wine Tasting!! Children and Pets are free to attend and visit with Santa! So don’t forget your cameras ....

Dove Valley Winery

Cost:
Free ...Selfie with Santa!!

When:
12-5pm

Where:
Dove Valley Winery
Get Directions


December 15

Closed for the Season

Galloping Goose Vineyards

Enjoy the winter. Cheers

Galloping Goose Vineyards

Cost:
0

When:
Spring 2015 March

Where:
Galloping Goose Vineyards
Get Directions


December 19

Lovestory

DeJon Vineyard

Spend an unforgettable evening with the incomparable, high-energy duo, Lovestory. This husband-and-wife team will engage and entertain you the entire time with their amazing renditions of the very best of Mo-Town and more! Food Vendor on Site: TBD. 7-10PM, doors open @ 6:30PM. $10.00 Admission per adult. Reservations preferred. By law, no outside alcohol permitted. No pets allowed.

DeJon Vineyard

Cost:
10.00

When:
7-10PM

Where:
DeJon Vineyard
Get Directions


December 25

Christmas

Sugarloaf Mountain Vineyard

We will be closed for the holiday.

Sugarloaf Mountain Vineyard