Live Music by Shawn Owen
2025-10-25 13:30 - 16:30 (America/New_York) | Chesapeake Manor Vineyard, 2015 Love Point Road, Stevensville, MD, 21666, United States
Professional snowboarder turned songwriter, Shawn Owen performs 300+ shows per year as a solo performer and fronting the Shawn Owen Band, sharing the stage with national acts such as The Wailers, Slightly Stoopid, G. Love and the Special Sauce, Dropkick Murphys, Passafire, Michael Franti and Spearhead, Donovan Frankenreiter, Larry Keel, Dirty Heads, The Aggrolites, Iration and many more, bringing their distinctive reggae/jam/ska/party vibe throughout the east coast from upstate New York to southern Florida and all in between. Their debut full length LP “Make Money” was released June 2015.

2025 Car Cruises
2025-10-25 16:00 - 20:00 | Harford Vineyard & Winery, 1311 West Jarrettsville Rd., Forest Hill, MD, 21050, United States
Come meet up at Harford Vineyard and relax with fellow car lovers! Enjoy great local wines, amazing cars, and beautiful scenery.
4th Saturday of the month | April – September 4:00 – 8:00 PM
October 2:00 – 6:00 PM
Food by Fire on-site
No outside food | No outside alcohol by law!
All updates regarding weather will be made on Facebook the day of event.

Upcoming Car Cruise Dates:

April 26, 2025

4:00 PM – 8:00 PM
Hosted by Harford County Mopars
Rain Date: April 27th, 12:00 PM – 4:00 PM

May 24, 2025

4:00 PM – 8:00 PM
Hosted by Save the Hobby
Rain Date: May 25th, 12:00 PM – 4:00 PM

June 28, 2025

4:00 PM – 8:00 PM
Hosted by Passion 4 Pavement
Rain Date: June 29th, 12:00 PM – 4:00 PM

July 26, 2025

4:00 PM – 8:00 PM
Hosted by Harford Mustangs & Our Friends
Rain Date: July 27th, 12:00 PM – 4:00 PM

August 23, 2025

4:00 PM – 8:00 PM
Hosted by AACA
Rain Date: August 24th, 12:00 PM – 4:00 PM

September 27, 2025

4:00 PM – 8:00 PM
Hosted by AACA / Save the Hobby
Rain Date: September 28th, 12:00 PM – 4:00 PM

October 25, 2025

2:00 PM – 6:00 PM
Hosted by Corvette & Van Clubs (Trunk or Treat)
Rain Date: October 26th, 12:00 PM – 4:00 PM

Harvest Celebration Dinner w/ Robbie Jester
2025-10-25 18:00 - 21:00 | Crow Vineyard & Winery, 12441 Vansant Corner Rd., Kennedyville, MD, 21645, United States
An annual tradition to host a celebration of the grape harvest with a family style dinner, paired with Crow wines. The evening ends with a peek into the winery and a presentation with the winemaker to see the process of winemaking.

Sunday sunshine and a wine flight - Frederick - 12pm to 5pm
2025-10-26 12:00 - 17:00, 2025-11-02 12:00 - 17:00, 2025-11-09 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 by Michael Kocher
2025-10-26 13:30 - 16:30 | Chesapeake Manor Vineyard, 2015 Love Point Road, Stevensville, MD, 21666, United States
Michael hails from Pennsylvania but has made the Annapolis area his home now for close to two decades. A songwriter with a penchant for hooky, heartfelt songs and love for all things music. Pop/Rock/Funk.

Corteau Vineyards Finally Friday
2025-10-31 15:00 - 20:00, 2025-11-07 15:00 - 20:00, 2025-11-14 15:00 - 20:00, 2025-11-21 15:00 - 20:00 | Corteau Vineyards, 38713 Golden Beach Rd, Mechanicsvilel, MD, 20659

Live Music by Jude Strawley
2025-10-31 16:00 - 19:00 | Chesapeake Manor Vineyard, 2015 Love Point Road, Stevensville, MD, 21666, United States
Live music by Jude Strawley, an alternative acoustic music artist.

Live Music Fridays
2025-10-31 18:00 - 20:30, 2025-11-07 18:00 - 20:30, 2025-11-14 18:00 - 20:30, 2025-11-21 18:00 - 20:30 | MD
Enjoy live music every Friday at Windridge!

Wine Flight at Celebration Cellars Winery - Frederick - 12 PM to 6 PM
2025-11-01 12:00 - 18:00, 2025-11-08 12:00 - 18:00, 2025-11-15 12:00 - 18:00 | 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

Live Music by PJ & Neal
2025-11-01 16:00 - 19:00 | Chesapeake Manor Vineyard, 2015 Love Point Road, Stevensville, MD, 21666, United States
Live music with everyone’s favorite duo, PJ & Neal. No cover!

Live Music! Anna Burgess 1:30-4:30
2025-11-02 08:00 - 17:00 | Chesapeake Manor Vineyard, 2015 Love Point Road, Stevensville, MD, 21666, United States
Sip local wine & enjoy live music by singer songwriter, Anna Burgess.

Spaghetti & Meatball Cooking Class w/ Robbie Jester
2025-11-02 16:00 - 18:00 | Crow Vineyard & Winery, 12441 Vansant Corner Rd., Kennedyville, MD, 21645, United States
A good day for making spaghetti and meat balls, with Chef Robbie Jester. Enjoy his cooking demonstration while putting together a family favorite, using local ingredients, his special blend of herbs and spices, and Crow beef sausage. Included in the cost is a salad and dessert and your choice of a glass of Crow wine. Additional wine can be purchased by the glass or bottle.

Live Music! Justin Singleton 1:30-4:30
2025-11-08 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.

Live Music! Michael Waskey 1:00-4:00
2025-11-09 13:00 - 16:00 | Chesapeake Manor Vineyard, 2015 Love Point Road, Stevensville, MD, 21666, United States
Michael Waskey is a first-rate performing songwriter and storyteller who delivers familiar yet never derivative music filled with vivid colors, broad textures and purposeful imagery. A multi-instrumentalist maestro, Michael’s guitar prowess stands out. From heartfelt country melodies to spirited indie anthems, his performances traverse genres. His constant pursuit of perfection drives him to refine his craft, delivering an unmatched musical experience.

Live Music! Chris Sacks Solo 4:00-7:00
2025-11-14 16:00 - 19:00 | Chesapeake Manor Vineyard, 2015 Love Point Road, Stevensville, MD, 21666, United States
Chris Sacks, the creator of Chris Sacks Band is a full-time Maryland based singer/songwriter.

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!

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! 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!

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.
