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!!

HAPPY HOLIDAYS from HAPPY JACK'S! ***

HAPPY HOLIDAYS from HAPPY JACK'S! ***

HAPPY JACK'S WINERY has Merchandise for all your Christmas shopping needs. Go to "Friends of Happy Jack's Winery" on FB for prices. Free delivery for purchases over $100 and Free Gift Wrap for purchases over $50!!!

HAPPY JACK'S WINERY has Merchandise for all your Christmas shopping needs. Go to "Friends of Happy Jack's Winery" on FB for prices. Free delivery for purchases over $100 and Free Gift Wrap for purchases over $50!!!

Happy International MERLOT Day

Thursday, Nov 7th, 2024

It’s absolutely THE most appropriate day to introduce Happy Jack’s newest flavor-MERLOT!!! Try it, we think you’ll love it.

And, if you hadn’t noticed…we’re pretty smitten with our kitten!! Guess what her name is?!?

Sip and Paint

w/Marleigh Made It

Fri, Dec 6th, 5:30-8pm CDT

Go to www.MarleighMadeIt.com to reserve your spot (Only 10 available)

We’re Fallin’ into Fall Ya’ll!!! It’s time for pumpkins and sweatshirts and some Happy Jack’s Wine by the fire!!

Be sure to ask about the Green Apple Mulled Wine, YUM!

Now that we have your attention: There are multiple places that you can enjoy some of Happy Jack’s Wine!!!

Steak and Stone Restaurant in Leitchfield (at the Alexander Hotel)

Nettie’s Restaurant (on Main Street in Hardinsburg)

The Bronze Star on SR 259…

are all now offering Happy Jack’s Wine for your sipping pleasure!!!

We are very excited to work with our local small businesses and hope you will visit these establishments to help support local ;)

Happy Jack’s Winery has Gift Certificates for your convenience…if you don’t know which wine she likes, let her choose her own! ;)

JUST AN FYI:

HAPPY JACK’S WILL BE OPEN THROUGHOUT THE WINTER… SAME DAYS, SAME HOURS!!!

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

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:

Nov 28-Thursday, CLOSED-MANY THANKSGIVING BLESSINGS-We will re-open regular hours Friday and Saturday!!

Dec 6-Friday, 5:30-8pm CDT-Paint and Sip with Marleigh of Marleigh Made It, Christmas themed (sign up details above)

Dec 7-Saturday, 10am-3pm CDT-Christmas at the Grounds Vendor Event hosted by Grateful Heart Events at the Breckinridge County Fairgrounds

Nov 21 through Dec 21-”Black Friday” Deals from HAPPY JACK’S WINERY. Go to “Friends of Happy Jack’s Winery” FB Event to see details and prices on Wine and HJW Merch!!

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! ***NOTE: WE WILL BE CLOSED THANKSGIVING DAY***

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!)