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 01

Wine Down Wednesday

Great Shoals Winery

free admission, wine and ciders available for purchase by the glass or bottle

Join us under the pavilion at Heyser Farms for another Wine Down Wednesday, featuring music by Sara Nuttle! We will be selling glasses and bottles of our wines, ciders, and cocktails in the tasting room.. and may even have a sneak peak of our NEW Fresh Hard Cider with Ginger for you to try!

Great Shoals Winery

Cost:

When:
7-9pm

Where:
Great Shoals Winery
Get Directions


October 02

Women Who Wine

Knob Hall Winery

Knob Hall Winery

Cost:
5

When:
7:00 pm

Where:
Knob Hall Winery
Get Directions


October 03

Wine Down Friday with The Flashbacks!

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 03

Leonardtown First Fridays

Port of Leonardtown Winery

Breeze by the winery to celebrate Breast Cancer Awareness Pink Friday in Leonardtown. Craig Gildner will be playing live on the patio so bring a picnic & your best girl friends to raise a glass in the fight against Breast Cancer. Be sure to wear pink!

Port of Leonardtown Winery

Cost:
0

When:
5:30-9:00pm

Where:
Port of Leonardtown Winery
Get Directions


October 03

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


October 03

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


October 03

Date Night in the Vineyard

Running Hare Vineyard

featuring Billy Breslin and Spider Hall Farm

Looking for a great way to end your work week? Come to the vineyard, the best place to start your weekend in Calvert County! Live music by Billy Breslin starts at 7PM. Special guest Spider Hall Farm will have delicious treats and ice cream available for purchase. Pack a picnic and bring your family, friends and co-workers. A $5 cover charge includes a wine tasting. The Tasting Room will be open noon - 11PM.

Running Hare Vineyard

Cost:
5

When:
7:00 PM - 11:00 PM

Where:
Running Hare Vineyard
Get Directions


October 03

Last Outside First Friday Event

Serpent Ridge Vineyard

Music and Art Show

Acoustic music from our repeat artist, Bill Hooper! Bring your friends, some snacks and enjoy music by the vineyard. ALSO - THE PAINTED LADIES OF CAPE COD are back in town! Coming back to the First Friday Event at Serpent Ridge Winery, are three of the Painted Ladies of Cape Cod. Maureen, Fran and Lynne will be displaying and offering for sale, their fine selection of watercolor paintings. Come meet the artists. They will be displaying, original paintings, framed and unframed and matted prints and giclees.

Serpent Ridge Vineyard

Cost:
0

When:
6:00 pm - 9:00pm

Where:
Serpent Ridge Vineyard
Get Directions


October 04

Live Music Saturday

Running Hare Vineyard

Featuring Gerry Swarbrick

Join us for wine tasting and live music by Gerry Swarbrick. Pack a picnic and bring your family and friends. A $5 cover includes a 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


October 04

Winestock Festival

Woodhall Wine Cellars

Hosted by Dove Valley Winery, Rising Sun, MD. Wine, food, music and fun! Tickets available at missiontix.com or call 410-658-8388

Woodhall Wine Cellars

Cost:
$10 in advance, $15 at the gate

When:
12-7

Where:
Woodhall Wine Cellars
Get Directions


October 04

CornroSt festival

Woodhall Wine Cellars

Corn roast festival

Woodhall Wine Cellars

Cost:
0

When:
1-6

Where:
Woodhall Wine Cellars
Get Directions


October 04

STOMP Festival '14

Sugarloaf Mountain Vineyard

Put Your Best Foot Forward!

Join us for our eighth annual Grape Stomp festival held on two consecutive weekends, October 4 & 5 and 11 & 12 from Noon - 6 pm each day. Featured throughout the festival is the popular and exciting Grape Stomp contest where you can test your skill and competitive juices in this ancient wine making tradition! Prizes will be awarded! And remember, it's not the size of your foot that matters... it's the power of your sole! • Tastings of all available vintages available for $10 • Tours of the fermentation and barrel rooms • Live Music - Oct 5 - MHB with Matthew Baron - Oct 6 - Ted Garber - Oct 11 - Shane Gamble - Oct 12 - Freddie Long Band • Food by JB Seafood Admission - Tickets will be available at gate. No advance ticket sales. 21 and older - $15 Under 21 and non-drinkers - $5 Admission includes entrance to the festival, a souvenir glass engraved by Jenny Muffler, choice of select glass of wine or sangria, tour, live music, and of course the opportunity to stomp the grapes! Bacchus Club members receive 2 free tickets. Tickets will be honored for any one of the four days of the event. Identification will be checked at the gate. Bring your chairs and blankets! This is a rain or shine event. We will have a jumbo tent to offer protection from rain/inclement weather. No refunds. This is a ticketed event. For these two weekends, the Tasting Room will be open for walk-in sales of closed bottles and cases only. SMV wines are the only alcohol permitted on the premises - including parking lots. Coolers will be checked.

Sugarloaf Mountain Vineyard

Cost:
$15 adults/$5 under 21

When:
12-5:30

Where:
Sugarloaf Mountain Vineyard
Get Directions


October 04

WINESTOCK Festival

Dove Valley Winery

CAN YOU DIG IT!!! Winestock Festival October 4th* 12-7pm Tickets can be purchased on line www.missiontix.com or 410-658-8388 Ticket includes: Wine tasting for all 4 Maryland Wineries in a keepsake wine glass. Get Groovy while enjoying music from three live bands..visit numerous on site artisans..and sipping award wines provided By your host Dove Valley Winery,Far Eastern Shore Winery,Cassinelli Winery, and Woodhall Wine Cellars.. Be adventurous ! Take a ride on a tethered Hot Air Balloon! Dove Valley's Summer Series of events are winding down, so don't miss out on this one! "Be there or be Square!" By law and insurance purposes, No outside beverages allowed on Dove valley premises.

Dove Valley Winery

Cost:
10.00 advance,$15.00 at the Gate

When:
12-7pm

Where:
Dove Valley Winery
Get Directions


October 04

Winestock 2014 *(At Dove Valley Winery)*

Far Eastern Shore Winery

CAN YOU DIG IT!!! Winestock Festival October 4th* 12-7pm Tickets can be purchased on line www.missiontix.com or 410-658-8388 Ticket includes: Wine tasting for all 4 Maryland Wineries in a keepsake wine glass. Get Groovy while enjoying music from three live bands..visit numerous on site artisans..and sipping award wines provided By your host Dove Valley Winery,Far Eastern Shore Winery,Cassinelli Winery, and Woodhall Wine Cellars.. Be adventurous ! Take a ride on a tethered Hot Air Balloon! "Be there or be Square!" By law and insurance purposes, No outside beverages allowed on Dove valley premises.

Far Eastern Shore Winery

Cost:
$10 advance, $15 at the gate

When:
12-7

Where:
Far Eastern Shore Winery
Get Directions


October 04

Fall Melodies

Port of Leonardtown Winery

Join us for jazz on the patio with the dynamic Diane Daly. Bring your lawn chair & a picnic to stay & relax in the cool fall weather.

Port of Leonardtown Winery

Cost:
0

When:
4:00-7:00pm

Where:
Port of Leonardtown Winery
Get Directions


October 04

Live Music with the Negley Brothers

Red Heifer Winery

Saturday live music

Enjoy an evening of live music on the hillside overlooking the vineyard at Red Heifer Winery. Pack a picnic, bring a lawnchair, and enjoy the view, the music, and the wine. This event is 21+.

Red Heifer Winery

Cost:
free with wine purchase

When:
5-7

Where:
Red Heifer Winery
Get Directions


October 04

Millstone Apple Harvest Festival

Millstone Cellars

Cider, Apples, Harvest, Festival

Millstone's first annual Apple Harvest Festival! Featuring Specialty Cider, Cyser, & Mead Kegs Live Bluegrass Music Haint Blue, Manly Deeds and Dalton Dash Apple Picking/ Farm Games/ Orchard Tours Local Vendors & Food Trucks Tickets purchased here: https://www.eventbrite.com/e/millstone-apple-harvest-festival-tickets-12745031733

Millstone Cellars

Cost:
$20 ($5 - designated drivers/kids under 12 free)

When:
12-6PM

Where:
Millstone Cellars
Get Directions


October 05

STOMP Festival '14

Sugarloaf Mountain Vineyard

Put Your Best Foot Forward!

Join us for our eighth annual Grape Stomp festival held on two consecutive weekends, October 4 & 5 and 11 & 12 from Noon - 6 pm each day. Featured throughout the festival is the popular and exciting Grape Stomp contest where you can test your skill and competitive juices in this ancient wine making tradition! Prizes will be awarded! And remember, it's not the size of your foot that matters... it's the power of your sole! • Tastings of all available vintages available for $10 • Tours of the fermentation and barrel rooms • Live Music - Oct 5 - MHB with Matthew Baron - Oct 6 - Ted Garber - Oct 11 - Shane Gamble - Oct 12 - Freddie Long Band • Food by JB Seafood Admission - Tickets will be available at gate. No advance ticket sales. 21 and older - $15 Under 21 and non-drinkers - $5 Admission includes entrance to the festival, a souvenir glass engraved by Jenny Muffler, choice of select glass of wine or sangria, tour, live music, and of course the opportunity to stomp the grapes! Bacchus Club members receive 2 free tickets. Tickets will be honored for any one of the four days of the event. Identification will be checked at the gate. Bring your chairs and blankets! This is a rain or shine event. We will have a jumbo tent to offer protection from rain/inclement weather. No refunds. This is a ticketed event. For these two weekends, the Tasting Room will be open for walk-in sales of closed bottles and cases only. SMV wines are the only alcohol permitted on the premises - including parking lots. Coolers will be checked.

Sugarloaf Mountain Vineyard

Cost:
$15 adults/$5 under 21

When:
12-5:30

Where:
Sugarloaf Mountain Vineyard
Get Directions


October 05

Bacchus Club Pick Up Party

Sugarloaf Mountain Vineyard

Come pick up your new packages and taste a surprise from 2006!

Sugarloaf Mountain Vineyard

Cost:
Free to club members

When:
12-5:30

Where:
Sugarloaf Mountain Vineyard
Get Directions


October 05

Live Music Sunday

Running Hare Vineyard

Featuring California Bob

Join us for wine tasting and live music by California Bob. Pack a picnic and bring your family and friends. A $5 cover includes a 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 10

Wine Down Friday with Christian Lopez Band

Knob Hall Winery

Wine Down Fridays are family-friendly. Admission is $5 and your first glass of 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 11

Parrot Head Festival

Knob Hall Winery

This festival is family-friendly. Admission is $10 and your first glass of non-premium wine is only $3. Caterers will sell food at this event.

Attention parrot heads! Come listen to the music of Panama Jack and other Jimmy Buffett tribute bands.

Knob Hall Winery

Cost:
10

When:
2:00 pm

Where:
Knob Hall Winery
Get Directions


October 11

Fall Harvest Festival

Port of Leonardtown Winery

Celebrate all that is wonderful about Fall with the St Mary’s Craft Guild & Port of Leonardtown Winery. Craft Guild vendors, Chef Dan of Morris Point Catering, Forrest Hall Farm donuts, Barrel Infused Cigars, St. Mary’s Wine & Design, & more will be in the park. Enjoy live music from the OM Band performing from 1:00 – 4:00 pm followed by Groove Span from 4:00 pm – 7:00 pm. Bring your family & friends for this fantastic fall festival.

Port of Leonardtown Winery

Cost:
0

When:
11am-7pm

Where:
Port of Leonardtown Winery
Get Directions


October 11

Fiore Winery & Distillery Mason Dixon Moonshine Festival

Fiore Winery

Join us at the winery and distillery for our 1st ever Mason Dixon Moonshine Festival and try our latest moonshine flavors while enjoying some live bluegrass music.

Fiore Winery

Cost:
15

When:
12-6pm

Where:
Fiore Winery
Get Directions


October 11 - October 12

Harvest Daze

Galloping Goose Vineyards

In a daze that will amaze!

Grapes to Juice. Come stomp the grapes (big feet welcome). Taste the three stages of wine creation. Fall food are available in abundance. Original music performed by local artists.

Galloping Goose Vineyards

Cost:
TBD

When:
12-5pm (Grape stomping on Saturday only)

Where:
Galloping Goose Vineyards
Get Directions


October 11

Last Outside Second Saturday Music Event

Serpent Ridge Vineyard

Fall back with Music From Albarino

Don't miss our last outside musical event from Albarino, one of our regular, fantastic acoustic duos! Bring your friends, a snack to share and extra lawn chairs. Will have the propane heaters out to keep us toasty in addition to the wine!

Serpent Ridge Vineyard

Cost:
0

When:
5:30 - 8:30 pm

Where:
Serpent Ridge Vineyard
Get Directions


October 11

Live Music Saturday

Running Hare Vineyard

featuring Higher Standards

Join us for wine tasting and live music by Higher Standards. 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


October 11

STOMP Festival '14

Sugarloaf Mountain Vineyard

Put Your Best Foot Forward!

Join us for our eighth annual Grape Stomp festival held on two consecutive weekends, October 4 & 5 and 11 & 12 from Noon - 6 pm each day. Featured throughout the festival is the popular and exciting Grape Stomp contest where you can test your skill and competitive juices in this ancient wine making tradition! Prizes will be awarded! And remember, it's not the size of your foot that matters... it's the power of your sole! • Tastings of all available vintages available for $10 • Tours of the fermentation and barrel rooms • Live Music - Oct 5 - MHB with Matthew Baron - Oct 6 - Ted Garber - Oct 11 - Shane Gamble - Oct 12 - Freddie Long Band • Food by JB Seafood Admission - Tickets will be available at gate. No advance ticket sales. 21 and older - $15 Under 21 and non-drinkers - $5 Admission includes entrance to the festival, a souvenir glass engraved by Jenny Muffler, choice of select glass of wine or sangria, tour, live music, and of course the opportunity to stomp the grapes! Bacchus Club members receive 2 free tickets. Tickets will be honored for any one of the four days of the event. Identification will be checked at the gate. Bring your chairs and blankets! This is a rain or shine event. We will have a jumbo tent to offer protection from rain/inclement weather. No refunds. This is a ticketed event. For these two weekends, the Tasting Room will be open for walk-in sales of closed bottles and cases only. SMV wines are the only alcohol permitted on the premises - including parking lots. Coolers will be checked.

Sugarloaf Mountain Vineyard

Cost:
$15 adults/$5 under 21

When:
12-5:30

Where:
Sugarloaf Mountain Vineyard
Get Directions


October 11 - October 12

Explorer's Weekend

Distillery Lane Ciderworks

Featuring special lecturers, orchard tours, apple picking, original local musicians, and food vendors- fun for the whole family

Distillery Lane Ciderworks

Cost:
5

When:
Saturday 10-5; Sunday 12-5

Where:
Distillery Lane Ciderworks
Get Directions


October 11

Harvest Dinner with Chef Robbie Jester

Crow Vineyard and Winery

Harvest Dinner with Chef Robbie Jester As the 2014 harvest wraps up at Crow Vineyard, learn about this year’s harvest & wine making from the Crow Vineyard Team and the plans for our 2014 wines. Chef will prepare a 5 course meal to celebrate our harvest.

Crow Vineyard and Winery

Cost:
$60 single or $55 wine club member

When:
5pm

Where:
Crow Vineyard and Winery
Get Directions


October 11

Italian Festival

Charis Winery

CASA of Allegany County is proud to bring back the Italian Festival. Mark your calendars for Saturday, October 11th, 2014 from 12-6pm! Downtown Cumberland, MD.

Charis Winery

Cost:
0

When:
12 till 6pm

Where:
Charis Winery
Get Directions


October 11

Live Music with Jon Ingels

Red Heifer Winery

Saturday live music

Enjoy an evening of live music on the hillside overlooking the vineyard at Red Heifer Winery. Pack a picnic, bring a lawnchair, and enjoy the view, the music, and the wine. This event is 21+.

Red Heifer Winery

Cost:
free with wine purchase

When:
5-7

Where:
Red Heifer Winery
Get Directions


October 12

STOMP Festival '14

Sugarloaf Mountain Vineyard

Put Your Best Foot Forward!

Join us for our eighth annual Grape Stomp festival held on two consecutive weekends, October 4 & 5 and 11 & 12 from Noon - 6 pm each day. Featured throughout the festival is the popular and exciting Grape Stomp contest where you can test your skill and competitive juices in this ancient wine making tradition! Prizes will be awarded! And remember, it's not the size of your foot that matters... it's the power of your sole! • Tastings of all available vintages available for $10 • Tours of the fermentation and barrel rooms • Live Music - Oct 5 - MHB with Matthew Baron - Oct 6 - Ted Garber - Oct 11 - Shane Gamble - Oct 12 - Freddie Long Band • Food by JB Seafood Admission - Tickets will be available at gate. No advance ticket sales. 21 and older - $15 Under 21 and non-drinkers - $5 Admission includes entrance to the festival, a souvenir glass engraved by Jenny Muffler, choice of select glass of wine or sangria, tour, live music, and of course the opportunity to stomp the grapes! Bacchus Club members receive 2 free tickets. Tickets will be honored for any one of the four days of the event. Identification will be checked at the gate. Bring your chairs and blankets! This is a rain or shine event. We will have a jumbo tent to offer protection from rain/inclement weather. No refunds. This is a ticketed event. For these two weekends, the Tasting Room will be open for walk-in sales of closed bottles and cases only. SMV wines are the only alcohol permitted on the premises - including parking lots. Coolers will be checked.

Sugarloaf Mountain Vineyard

Cost:
$15 adults/$5 under 21

When:
12-5:30

Where:
Sugarloaf Mountain Vineyard
Get Directions


October 12

Live Music Sunday

Running Hare Vineyard

Featuring Groove Span

Join us for wine tasting and live music by Groove Span. 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 12

Paint & Wet your Palette "Glass of Red Wine"

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 13

Open House

Knob Hall Winery

Enjoy special discounts on purchases of bottles and/or cases of wine!

Knob Hall Winery

Cost:
0

When:
2:00 pm

Where:
Knob Hall Winery
Get Directions


October 16

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 17

Date Night in the Vineyard

Running Hare Vineyard

Featuring John Luskey

Looking for a great way to end your work week? Come to the vineyard, the best place to start your weekend in Calvert County! Live music by local musician John Luskey starts at 7PM. Pack a picnic and bring your family, friends and co-workers. A $5 cover charge includes a wine tasting. The Tasting Room will be open noon - 11PM.

Running Hare Vineyard

Cost:
5

When:
7:00 PM - 11:00 PM

Where:
Running Hare Vineyard
Get Directions


October 17

Vinyl & Vino - Create Your OWN Wine Glass + Wine Tasting

Serpent Ridge Vineyard

Wine glass decorating and tasting!

Whether you are artistic or not, YOU can create your very own personalized wine glass with vinyl creations! Glassy Gurlz will provide everything you need for the event! Choose from polka dots, monograms, quotes and more to decorate your glass! We will offer tastings of of popular wines during the event (included in the event price)! Bring along a friend or two and your favorite snack/appetizer to enjoy while working on your master piece! Sign up at: Vinyl & Vino - Create Your OWN Wine Glass + Wine Tasting at https://www.eventbrite.com/e/vinyl-vino-create-your-own-wine-glass-wine-tasting-tickets-11997405563

Serpent Ridge Vineyard

Cost:
30.00

When:
7pm - 9pm

Where:
Serpent Ridge Vineyard
Get Directions


October 17

Wine Down Friday with Joshua Morningstar

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 18

Fall Melodies

Port of Leonardtown Winery

Richard Wagner returns to perform live on the patio. Gather your friends for some fall fun on our patio with Richard’s music & our great wines.

Port of Leonardtown Winery

Cost:
0

When:
4:00-7:00pm

Where:
Port of Leonardtown Winery
Get Directions


October 18 - October 19

Autumn Reggae Festival

Linganore Winecellars

Wine, Music, & Art festival. details coming soon! Tickets on sale July 21.

Linganore Winecellars

Cost:
0

When:
11am-6pm

Where:
Linganore Winecellars
Get Directions


October 18

3rd Annual Harvest Day (w/ Andy Belt & Friends)

DeJon Vineyard

3rd Annual Harvest Day. Food, live music, hayrides, pumpkins, scarecrows, crafts, and more! Great fun for the whole family. Andy Belt & Friends blends Country, new grass and Americana overtones, with traditional folk rock, allowing for a wide range of stylistic exploration. More details and info coming soon. By law, no outside alcohol permitted. No pets allowed.

DeJon Vineyard

Cost:
TBD

When:
12:30-4:30PM

Where:
DeJon Vineyard
Get Directions


October 18

Live Music Saturday and Benefit Day

Running Hare Vineyard

Featuring Fran Scuderi

Join us for a benefit day to support Linda Canfield, a member of the Running Hare Vineyard family. Live music featuring Fran Scuderi begins at noon. Pack a picnic and bring your family and friends to support a worthy cause. A $5 cover includes a wine tasting. The Tasting Room will be open from noon - 6:00 PM.

Running Hare Vineyard

Cost:
5

When:
Noon - 4:00 PM

Where:
Running Hare Vineyard
Get Directions


October 18

HOWL-O-WINE

Sugarloaf Mountain Vineyard

Details to come...

Sugarloaf Mountain Vineyard

Cost:
0

When:
12-5:30

Where:
Sugarloaf Mountain Vineyard
Get Directions


October 18

Live Music with Brad Munn

Red Heifer Winery

Saturday live music

Enjoy an evening of live music on the hillside overlooking the vineyard at Red Heifer Winery. Pack a picnic, bring a lawnchair, and enjoy the view, the music, and the wine. This event is 21+.

Red Heifer Winery

Cost:
free with wine purchase

When:
5-7

Where:
Red Heifer Winery
Get Directions


October 19

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:
4:00 - 6:00 pm

Where:
Serpent Ridge Vineyard
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

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

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

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

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

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 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

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 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

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

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 - 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

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 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 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 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 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

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 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 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 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 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