A Little Bit About Us
We are Jack and Tee Pleasant. Our Small Farm Winery started out as a hobby. After many evenings dreaming, Jack’s gift of piddling and a lot of “research”…here we are!! Our plan is to grow old together doing something that we love, together.
We turned our weekend getaway for 9 years at Rough River Lake into our home in July of 2021. We are both originally from Louisville and have decided to retire from our years of service as a police officer (Jack) and nurse (Tee). We would like instead to serve YOU~some delicious wine in a serene and peaceful country setting.
Our focus is small batch wines so that we can satisfy all different types of wine drinkers, from the novice to those that consider themselves pros!!
We have come across a lot of you wondering when and where to get some Happy Jack’s wine. We have lots of opportunities for any and all to come visit, taste and purchase what we have been working so hard to offer to you. Check out the event schedule below for where you can find Happy Jack’s Wine while we are out and about, or give us a call…we’ll come to you!! We look forward to meeting and seeing each of you!! CHEERS!!
As a (Very) Small Batch, Small Farm Winery, Happy Jack’s Winery will do it’s best to keep your favorites available. Since everyone’s tastes are different, we ask that you be patient with us. Happy Jack is a busy, busy, busy guy…and is doing his best to turn out some incredible flavors sure to please everyone!!
Current Available Flavors at Happy Jack’s Winery:
Green Apple Pearish The Moment
Pink Moscato You Make Me Randy Red
Strawberry Sue Really Reisling
Well, That’s Just Peachy Liebfraumilch
Cherry Hideaway Chardonnay
Pineapple Pearadise Rough & Red
Dam Concord Merlot
Christmas Cranberry Black & Blue
Raspberry Dragonfruit Breck Blackberry
Come join Happy Jack’sWinery at the
BG Wine Fest
Held at the Historical Railpark and Train Museum in Bowling Green, KY…Saturday, July 12 from 11am-6pm CDT
Click on the link to purchase tickets
Happy Jack’s Wine will be at Hardin County Farmer’s Market most Saturdays and some Wenesdays throughout this summer, check dates and times below!!
Happy Jack’s Winery is proud to be a part of the 2025 Twin Lakes National Fiddle Festival in Leitchfield, KY. Held all day, Saturday, July 19, in the Courthouse Square…Happy Jack’s will be there 4:00pm CDT-close. Bring a chair, bring a friend!!!
National Fiddler Contest
Antique Car Show
Rides, Vendors and Food Trucks
Adult Beverages (including Happy Jack’s Wine)
Free Concert after the contest featuring The GRASCALS!!!
Come visit Happy Jack’s Winery at Breck Co Fairgrounds
Music with Michael Keys
Saturday, Aug 2nd, 5-8pm CST
Michael, who is originally from Chicago, now resides in Leitchfield, Ky. He has been entertaining crowds with Rock N Roll, Pop, and occassionally some Hip Hop and Rap for over 15 years. But his favorite genre is Country. His short time in Nashville allowed him to grow and eventually open up for acts such as Sam Hunt, Elvie Shane, Shinedown and Smash Mouth. Michael, at one point, has been named Nashville’s Bluebird Cafe’s Golden Pick Artist!
Happy Jack’s is excited to bring Michael to the Winery!! He is looking forward to hearing from YOU!!! One of Michael’s favorite things to do is to play requests of any genre, ensuring to get everyone dancing and singing along. Come on out!! Bring a chair, Bring a friend!!
Happy Jack’s Winery is available for private parties/events. Consider having us at your home for an intimate get together; or possibly at a larger venue for an engagement party or the company Holiday Party, to serve your personally selected variety of wines.
Contact us on “Friends of Happy Jack’s Winery” on FB or give us a call at 1-270-617-0206
For Upcoming Events follow us on FB: “Friends of Happy Jack’s Winery” and see below for dates/times as well!!
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Fresh Fruit Wines
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Enjoy the view
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Meet the owners
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Award Winning Wines
Here are few pics of all the fun stuff going on with Happy Jack’s!
What we offer:
Wine Tastings on Site
Wine Tastings Offsite (pls call to schedule)
Local Farmer’s Markets
Paint and Sips (pls call to schedule)
Small Venue availability for Bridal Showers, Birthday Parties, Anniversary Celebrations (pls call to schedule)
Private and Public Events onsite and offsite
Upcoming Schedule:
June 21-Saturday-7am-12pm EST, HJW at Hardin County Farmer’s Market, Elizabethtown, KY
June 22-Sunday-2-6pm CDT, Wine Tasting at Big Mouth’s Restaurant, 14033 Falls of Rough Rd, Falls of Rough, KY
June 26-Thursday, 6-8pm CDT-Wine and Clay with Art by Ava St Clair, sign up at www.artbyavastclair.com or call Ava at 1-270-617-3321
July 4-Thunder Over The Mill (Brown’s Hideaway Fireworks at the Barn), festivities start at the barn around 6pm CDT. Fun for the whole family!!
July 5-Saturday-7am-12pm EST, HJW at Hardin County Farmer’s Market, Elizabethtown, KY
July 9-Wednesday-Fundraiser Event for Rough River Theater Project, sponsored by Breck United-more details to follow
July 12-Saturday-11am-6pm CDT-Happy Jack’s Winery will be at the BG Wine Fest at The Historic Railpark and Train Museum, Bowling Green, KY, (see above for details)
July 19- Saturday-begins at 9am CDT-Downtown Leitchfield, KY-The Twin Lakes National Fiddler Championship (see above for details)
July 26-Saturday-10am-3pm CDT-3rd Annual Summer at the Grounds Vendor Show, at Breckinridge Co Fairgrounds
Aug 1-Friday-all day at the Winery 12-7pm-Sip and Snip Fundraiser to benefit Breckinridge Co Animal Friends, silent auction and baby kittens!!!
How to find us:
Located in Breckinridge County between Hardinsburg and McDaniels, KY. Put our address in your GPS. Once you find Morton Brown Lane off SR 1740, look for our sign, and follow the directional signs. It’s a beautiful drive…enjoy!!
Located in beautiful Breckinridge County, Happy Jack’s Winery sits right on the edge of Rough River Lake. The address is 1580 Morton Brown Lane located in Brown’s Hideaway. Watch for the signs!
Hours of Operation:
Tuesday-Wednesday: by appt only
Thursdays: 1pm-7pm CST
Friday-Saturday: 12pm-7pm CST
Sundays-Mondays Closed
( These times are subject to change…
so keep an eye on the website,
e-mail or call us!)