Maryland Wineries Association

Wine Flight at Celebration Cellars Winery - Frederick - 12 PM to 6 PM
2025-12-20 12:00 - 18:00, 2025-12-13 12:00 - 18:00, 2025-12-06 12:00 - 18:00, 2025-11-29 12:00 - 18:00, 2025-11-22 12:00 - 18:00, 2025-11-15 12:00 - 18:00 (America/New_York) | MD
Wine Flight at our Intimate Venue 12 PM to 6 PM
Includes a Flight of 5 Wines between 12:00 PM and 6:00 PM. You can bring your own food, sit at one of the indoor or outdoor tables and enjoy the view while you dine and sip. Limited Seating – up to 26 indoors and 30 outdoors (depending on weather) keeping it semi-private for you! $20.00

Santa's Panic Pop-Up!
2025-12-20 11:00 - 15:00 | Layton’s Chance Vineyard & Winery, 4225 New Bridge Rd, Vienna, MD, 21869, United States
Still checking names off your Christmas list? Don’t panic—we’ve got the perfect last-minute gift solutions all in one festive stop!
Join us at Layton’s Chance for our Santa’s Panic Pop-Up, featuring THREE incredible vendors ready to help you finish your holiday shopping in style.
🎀 Charmed by Chloe ✨ Permanent jewelry that lasts beyond the season ✨ A full charm bar for DIY bracelets & necklaces ✨ Jewelry grab bags and more beautifully giftable pieces!
🍫 The Market at Church Creek The beloved local chocolatier is back with gorgeous holiday chocolates, sweets, and treats—perfect stocking stuffers or host gifts!
🖋️ Bulldog Creations MD Offering on-the-spot engraving & personalized gifts! Customize wallets, journals, ornaments, leather items, and more. Because last-minute doesn’t have to mean impersonal! 😉
But that’s not all…
🎁 Layton’s Chance 𝐄𝐗𝐂𝐋𝐔𝐒𝐈𝐕𝐄 𝐎𝐍𝐄-𝐃𝐀𝐘 𝐃𝐄𝐀𝐋𝐒!
🍷 𝐏𝐫𝐞-𝐰𝐫𝐚𝐩𝐩𝐞𝐝 “𝐃𝐮𝐨” 𝐖𝐢𝐧𝐞 𝐏𝐚𝐜𝐤𝐚𝐠𝐞𝐬 – 𝐝𝐢𝐬𝐜𝐨𝐮𝐧𝐭𝐞𝐝!! — Farm Red & Farm White — Joe’s Cool Red & Joe’s Cool White We also have prepackaged mulled wine gift sets, make at home slushie kits & more! Save on these ready-to-gift sets!
👕𝐀𝐥𝐥 𝐋𝐚𝐲𝐭𝐨𝐧’𝐬 𝐂𝐡𝐚𝐧𝐜𝐞 𝐀𝐩𝐩𝐚𝐫𝐞𝐥 𝐃𝐢𝐬𝐜𝐨𝐮𝐧𝐭𝐞𝐝! Come shop small, shop local, and shop merry. Whether you need a heartfelt keepsake, something sweet, a personalized treasure, or a festive wine bundle… We’ve got your last-minute gifting covered!
📍 𝐋𝐚𝐲𝐭𝐨𝐧’𝐬 𝐂𝐡𝐚𝐧𝐜𝐞 𝐕𝐢𝐧𝐞𝐲𝐚𝐫𝐝 & 𝐖𝐢𝐧𝐞𝐫𝐲 🗓 𝐒𝐚𝐭𝐮𝐫𝐝𝐚𝐲, 𝐃𝐞𝐜 𝟐𝟎 • 𝟏𝟏𝐚𝐦–𝟑𝐩𝐦
We can’t wait to help you wrap up your holiday shopping! 🎁✨

Live Music Fridays
2025-12-19 18:00 - 20:30, 2025-12-12 18:00 - 20:30, 2025-12-05 18:00 - 20:30, 2025-11-28 18:00 - 20:30, 2025-11-21 18:00 - 20:30 | MD
Enjoy live music every Friday at Windridge!

Corteau Vineyards Finally Friday
2025-12-19 15:00 - 20:00, 2025-12-12 15:00 - 20:00, 2025-12-05 15:00 - 20:00, 2025-11-28 15:00 - 20:00, 2025-11-21 15:00 - 20:00 | Corteau Vineyards, 38713 Golden Beach Rd, Mechanicsvilel, MD, 20659

Sunday sunshine and a wine flight - Frederick - 12pm to 5pm
2025-12-14 12:00 - 17:00, 2025-12-07 12:00 - 17:00, 2025-11-30 12:00 - 17:00, 2025-11-23 12:00 - 17:00, 2025-11-16 12:00 - 17:00 | MD
Enjoy the fresh air in one of many outdoor spaces, bring your food and we will pour the wine. We are open on Sundays from 12pm to 5pm, and we have an upper and lower deck with spectacular views of the valley, as well as an outdoor fire pit, a screened in private room, and of course indoor seating in case the weather does not cooperate. Your tasting includes 5 wines of your choosing.

Live Music! Joe Esham 1:00-4:00
2025-11-30 13:00 - 16:00 | Chesapeake Manor Vineyard, 2015 Love Point Road, Stevensville, MD, 21666, United States
Head out to Chesapeake Manor Vineyard to sip wine & welcome Joe Esham. Joe is a musician specializing in Americana, Reggae, and Funky Blues performed on Slide Guitar.

Lighting of the Vineyard
2025-11-30 04:00 - 18:00 | Crow Vineyard & Winery, 12441 Vansant Corner Rd., Kennedyville, MD, 21645, United States
Join us this holiday season for the lighting of the vineyard. Ticket includes a glass of featured wine. Bonfires will be set up to keep you warm on the patio or enjoy the views from inside the Haybarn Tasting Room. Additional food and wine will be available for purchase. (Dress for the weather.)

Live Music! Michael K 1:00-4:00
2025-11-23 13:00 - 16:00 | Chesapeake Manor Vineyard, 2015 Love Point Road, Stevensville, MD, 21666, United States
Michael K (Pretty Big Deal Band) joins Chesapeake Manor Vineyard on Sunday, November 23rd. Local Wine & music such as pop, rock, funk and originals.

Live Music! Justin Singleton 1:30-4:30
2025-11-22 13:30 - 16:30 | Chesapeake Manor Vineyard, 2015 Love Point Road, Stevensville, MD, 21666, United States
Justin Singleton, local to Kent County, Maryland will join Chesapeake Manor Vineyard on November 8th. With several hundred public performances – Justin continues to spread his sound and music.

Seven Course Dinner Pairing w/ Chef Robbie Jester
2025-11-21 18:00 - 21:00 | Crow Vineyard & Winery, 12441 Vansant Corner Rd., Kennedyville, MD, 21645, United States
Join us for an unforgettable culinary experience on Maryland’s Eastern Shore, where acclaimed Chef Robbie Jester presents an exclusive chef’s table dinner crafted and plated right before your eyes.
As each of the seven courses come to life, Chef Jester shares his inspiring journey from television appearances on shows like Beat Bobby Flay to building his culinary legacy in our region. Each dish is thoughtfully paired with rare selections from Crow Vineyard & Winery’s private library, newly released vintages, and a special insider’s preview of our winemaker’s preparations for the 2025 wines. Limited seating available – reserve your place at the table for this one-of-a-kind evening of storytelling, craftsmanship, and flavor.

Live Music! Daphne Eckman 3:00-6:00
2025-11-21 15:00 - 18:00 | Chesapeake Manor Vineyard, 2015 Love Point Road, Stevensville, MD, 21666, United States
Welcome singer-songwriter, Daphne Eckman, to Chesapeake Manor Vineyard on Friday, November 21st!

Live Music! Jayce Gallagher 1:30-4
2025-11-16 13:30 - 16:30 | Chesapeake Manor Vineyard, 2015 Love Point Road, Stevensville, MD, 21666, United States
Singer/acoustic guitar player, Jayce Gallagher will be joining Chesapeake Manor Vineyard on Sunday, November 16th.

Live Music! Guava Jelly Duo 1:00-4:00
2025-11-15 13:00 - 16:00 | Chesapeake Manor Vineyard, 2015 Love Point Road, Stevensville, MD, 21666, United States
Guava Jelly is an acoustic trio based in Annapolis playing a great mix of reggae, pop, rock and country. Please welcome them at Chesapeake Manor Vineyard!
