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!!

Jam Session

Saturday, April 19 4-7pm CST

Do you play an instrument, like to sing along to good music, enjoy hanging out by the fire?

Join us at Happy Jack’s Winery…and please leave your fears at the door (no judging here, just fun)!!!

Music with Michael Keys

Saturday, April 26th, 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!!

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:

Blueberry Green Apple

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

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 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!!

  • Fresh Fruit Wines

  • Enjoy the view

  • Meet the owners

  • 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:

April 17-Thursday, 4pm-7pm CST Wine Tasting at Nettie’s Restaurant on Main Street in Hardinsburg

April 19-Saturday, 4pm-7pm CST Happy Jack’s Winery Jam Session ( see above for details )

April 20-HAPPY EASTER TO ALL OUR PEEPS!!!

April 26-Saturday, 7am-12pm EST, HJW at Hardin County Farmer’s Market, Elizabethtown

April 26-Saturday, 5pm-8pm CST Music with Michael Keys ( see above for details )

May 3-Saturday-Happy Derby Day-Come on out and watch the Races at Happy Jack’s Winery!!

May 3-Saturday-7am-12pm EST, HJW at Hardin County Farmer’s Market, Elizabethtown

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!)