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!!

  • It all begins with an idea. Maybe you want to launch a business. Maybe you want to turn a hobby into something more.

  • It all begins with an idea. Maybe you want to launch a business. Maybe you want to turn a hobby into something more.

  • It all begins with an idea. Maybe you want to launch a business. Maybe you want to turn a hobby into something more.

Spring has Sprung, come see us and enjoy the sites, smells and TASTES at Happy Jack’s Winery!!!

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

Now that we have your attention: Look locally for other places that you can enjoy some of Happy Jack’s Wine!!!

Nettie’s Restaurant on Main Street in Hardinsburg and the newly opening bar The Bronze Star on SR 259 will now offer 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 ;)

Elizabethtown

Wine Festival

Happy Jack’s Winery is so pumped to be invited to this Festival!! Looking forward to mixing and mingling with some awesome peers!!

Never fear, though, Happy Jack will be at the Winery for those that want to enjoy a quiet bottle of wine overlooking Rough River

Don Thomason Music

Come sit with us and enjoy music while sipping some of Happy Jack’s finest on Saturday, May 25th, 4-7pm CST

Don Thomason hails from south of Nashville and is returning to Happy Jack’s Winery to share his take on many Americana, Rock and Rockabilly songs…always a good time!!!

If you happen to be over in Leitchfield enjoying the free concerts on East Main Market, stop by Happy Jack’s!!

We’ll be set up on June 22, July 27, and Aug 24!!

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

Well, Jack and I have survived our first TAX season as new business owners!!! Come on out to the Winery and enjoy a glass of wine… (with us, we could sure use one)!! ;) We look forward to meeting with those that would like to visit the winery, and will be out and about for your purchasing and tasting pleasures as well!!

As we get our first glimpses at beautiful weather, we are beginning to plan for some fun and exciting wine-tasting adventures for the Spring and Summer! Painting, fur babies, yoga, vintage cars, food, and live music to name a few…

Follow us on FB: “Friends of Happy Jack’s Winery” and here on the website for upcoming events!!

  • Fresh Fruit Wines

  • Enjoy the view

  • Meet the owners

  • Award Winning Wines

Make It

Here are few pics of all the fun stuff going on at 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:

2024

April 27-Saturday, 7am-12pm EST-Hardin County Farmer’s Market

April 27-Saturday, 4pm-7pm CST-Derby Themed Paint and Sip with Marleigh Made It and

May 4-Saturday, DERBY DAY!!! Wear a Derby Hat to the Winery and get 10% off your first glass of wine!!

May 4-Saturday, 8am-12pm EST-Meade County Farmer’s Market-OPENING DAY!!

May 11-Saturday, 12pm-9pm EST-Elizabethtown Wine Festival, see above info. (PS-the Winery will be open as well!!)

May 18-Saturday, 8am-12pm EST-Meade County Farmer’s Market

May 25-Saturday. 8am-12pm EST-Meade County Farmer’s Martket

May 25-Saturday, 4pm-7pm CST-Don Thomason Music (see above info)

June 1-Saturday, Happy Jack’s 1st Annual Cruise In, with Vintage Cars, Food Trucks, Vendors, Music and of course, WINE!!! See above info.

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!)