Saturday & Sunday, July 13 & 14, 2024
Join the participating wineries of the Chesapeake Bay Wine Trail for the Trail’s newest event, “Pour Your Heart Out.” On this weekend, participating wineries will donate a portion of sales to benefit a charity of their choice.
We encourage you to check with participating wineries to learn more about their events, including hours and reservations policies.
Purchase one of our limited-edition 2024 Tasting Passes to save on wine tastings throughout the Trail.
(Please note: This event takes place at individual wineries throughout the Trail. Event hours may vary by winery.)
The following wineries are confirmed to be participating:
Caret Cellars
495 Meadow Landing Lane
Caret, VA 22436
540-413-6454
Visit website
Dates: Saturday, July 13 & Sunday, July 14
Description: Donations will be made to the Tappahannock Volunteer Fire Department and The Haven Shelter & Services. Donation amount will be based on percentage of sales or a flat rate, whichever is greater. On Sunday, July 14th, Caret will also sponsor a vendor craft fair from 1-4pm, and The Pull Up food truck will be onsite.
The Dog and Oyster Micro-Vineyard
Located at the Hope & Glory Inn
65 Tavern Rd
Irvington, VA 22480
804-438-6053
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Please note: Dog and Oyster will participate on Saturday, July 13th only.
Dates: Saturday, July 13 from 12-6pm
Description: 10% of sales will go to Friends of the Rappahannock.
General’s Ridge Vineyard
1618 Weldons Dr
Hague, VA 22469
804-472-3172
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Dates: Saturday, July 13 from 12-6pm & Sunday, July 14 from 12-7pm
Description: 10% of sales will be donated to the Westmoreland Animal Shelter. Feel free to bring (but not required) a donation of any of the following: food, laundry soap or cleaning supplies. On Saturday, the Healthy Harvest food truck will be onsite from 2-6pm, as well as live music by Carlos & the Castaways from 2-5pm. On Sunday, the El Padrino Taco Food Truck will be onsite, as well as live music by Brian & Sally from 1-3pm and Faron Hamblin from 4-7pm.
Good Luck Cellars
1025 Good Luck Rd
Kilmarnock, VA 22482
804-435-1416
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Dates: Friday, Saturday and Sunday, July 12 through July 14
Description: 10% of weekend sales will be donated to Smith Point Sea Rescue (all-volunteer organization that provides assistance to boats having difficulties in the mid-Chesapeake Bay Area). We’ll unofficially kick off the two-day event on Friday with live music by The Flattones from 5:30-7:30pm. Live music will be featured on Saturday by The Windbags and Sunday by City Farm Band, both from 1-4pm. Salty Bob’s Oyster & Seafood Co (food truck) will be onsite from 5-7pm on Friday and 12-4pm on Saturday and Sunday.
Ingleside Vineyards
5872 Leedstown Rd
Oak Grove, VA 22443
804-224-8687
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Dates: Saturday, July 13 & Sunday, July 14 from 12-6pm
Description: 10% of weekend wine sales will be donated to the St. Peter’s Episcopal Church Restoration and Rebuilding Fund. This historic local church experienced a devastating fire in December 2023 and plans are underway to rebuild and restore the church.
Jacey Vineyards
619 Train Lane
Wicomico Church, VA 22579
804-580-4053
Visit website
Please note: Jacey will participate on Saturday, July 13th only.
Dates: Saturday, July 13 from 12-5pm
Description: $5 from every bottle will be donated to the Chesapeake Bay Foundation.
Monroe Bay Winery
4786 James Monroe Highway
Colonial Beach, VA 22443
(804) 410-5628
Visit website
Dates: Saturday, July 13 & Sunday, July 14 from 12-5pm
Description: 10% of profits will be donated to the Colonial Beach Volunteer Fire Dept. In addition, squad members of the fire dept will receive $1 off their purchase.
Rivah Vineyards at the Grove
671 Kinsale Bridge Road
Kinsale, VA 22488
804-599-8552
Visit website
Dates: Saturday, July 13 & Sunday, July 14 from 12-6pm
Description: $2 from each bottle sold will be split between the Kinsale Museum and the Kinsale Volunteer Fire Dept. Customers will also receive 50% off their tastings when purchasing a bottle.
Learn More
– Like us on Facebook for updates
– View some sample itineraries and lodging options here
– Visit our Homepage for an interactive map of our Wine Trail
– View our Press Mentions