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Jesters Winery & Cafe, Lebanon, KY

Jesters Winery & Cafe

4.8
4.8
163 Reviews
$30 and under
Winery
Two guys who used to do other things but decided creating award winning wines with new twists was a hell of a lot more fun.

Located between Makers Mark Distillery and Limestone Branch Distillery off of Route 49 in Marion County. We offer the most spectacular views whilst you enjoy our winning Dry, Sweet, or canned wines. Along with Wine Slushies and our newest product...Kentucky Kangria with some old faces being re-introduced.

Also, new apparel designs so you can wear our weirdness proudly.

Make a reservation

2 people

7:00 PM


Booked 1 time today

Additional information

  • Dining style

    Casual Dining

  • Cuisines

    Winery

  • Hours of operation

    Wed–Sat 11:00 am–5:00 pm

  • Phone number

    (859) 492-6528

  • Payment options

    AMEX, Discover, MasterCard, Visa

  • Dress code

    Business Casual

  • Catering

    please contact chris.horseshoebend@gmail.com for catering questions

  • Private party facilities

    Please contact chris.horseshoebend@gmail.com or greg@horseshoebend-ky.com for private party events

  • Neighborhood

    Lebanon

  • Cross street

    Route 49, Lebanon, Kentucky 40033

  • Parking details

    Private Lot

  • Additional

    Beer, Cafe, Entertainment, Indoor Fireplace, Outdoor Smoking Area, Patio/Outdoor Dining, Patio/Outdoor Dining, Takeout, View, Wheelchair Access, Wine

Popular dishes

What 163 people are saying

Overall ratings and reviews

Reviews can only be made by diners who have eaten at this restaurant

4.8
4.8 based on all time ratings
  • 4.8Food
  • 4.8Service
  • 4.7Ambience
  • 4.7Value

NoiseModerate

  1. SuellenD

    Tampa

    1 review

    5.0

    1 review

    Dined 7 days ago

    overall5food5service5ambience5
    Amazing views, fresh and delicious wines and food!

    Is this helpful?

  2. DerekD

    1 review

    5.0

    1 review

    Dined on May 25, 2023

    overall5food5service5ambience5
    Great food and service, ate on porch on a beautiful day 75 degrees, couldn’t have been better.

    Is this helpful?

  3. RobertV

    Raleigh

    3 reviews

    5.0

    3 reviews

    Dined on May 19, 2023

    overall5food5service5ambience5
    Flat breads were delicious. As others have said, make sure to try the broccoli salad. We liked some of the wines and not others, so recommend the flights to see what you like.

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  4. TimF

    1 review

    5.0

    1 review

    Dined on May 13, 2023

    overall5food5service5ambience5
    Relaxing atmosphere and fantastic food!! Great hospitality!

    Is this helpful?

  5. OpenTable Diner

    Louisville

    4 reviews

    5.0

    4 reviews

    Dined on April 28, 2023

    overall5food5service5ambience5
    Bourbon Tour group traveled from Minneapolis, MN and said it was the perfect spot, quiet and peaceful.

    Is this helpful?

  6. MermaidVA

    Richmond

    10 reviews

    vip
    5.0

    10 reviews

    Dined on April 25, 2023

    overall5food5service5ambience5
    Perfect lunch stop between distillery tours. Our meal was fresh and made to order. Sitting outside was peaceful and lovely, you can be in the sun or the shade. The view is beautiful! And the wine slushie was a refreshing treat!

    Is this helpful?

  7. FoodnWine

    Central Coast

    8 reviews

    5.0

    8 reviews

    Dined on April 21, 2023

    overall5food5service5ambience5
    Wine was great, but I was very impressed with the food. The snack box had the best black bean hummus, pimento cheese and olive tapenade I’ve ever tasted. Husband had the buffalo chicken sandwich which he said was the best he’s ever had and I had the Jesters Salad which was absolutely delicious. Made from scratch, quality ingredients and great service. We’ll definitely be back.

    Is this helpful?

  8. MatthewH

    Louisville

    3 reviews

    5.0

    3 reviews

    Dined on February 15, 2023

    overall5food5service5ambience5
    Perfect meal

    Is this helpful?

  9. StuartR

    Louisville

    1 review

    5.0

    1 review

    Dined on January 21, 2023

    overall5food5service5ambience5
    Food was outstanding, atmosphere perfect, owners super nice! Even my picky son ate every crumb of his food. We will be regulars now.

    Is this helpful?

  10. RBhappygma

    Louisville

    5 reviews

    4.0

    5 reviews

    Dined on January 13, 2023

    overall4food5service5ambience4
    Nice spot after Kentucky Cooperage tour. Personalized attention by owner as only diners. Good food and wine.

    Is this helpful?

  11. OpenTable Diner

    Louisville

    1 review

    5.0

    1 review

    Dined on January 7, 2023

    overall5food5service5ambience5
    Wonderful food and service! Great location with an awesome view. Beautiful outdoor dining area in warmer weather.

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  12. AncelB

    Cincinnati

    3 reviews

    5.0

    3 reviews

    Dined on November 11, 2022

    overall5food5service5ambience4
    Came for the wine. Stayed for food. Would come back just for the food!! But also the wine!! Steak tacos, Buffalo chicken ranch and bbq chicken flatbread was amazing!! Food was shockingly great!! If you like sweet, the blackberry concord wine is where it’s at for sure. Great experience. Will go back.

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  13. SueH

    Louisville

    1 review

    5.0

    1 review

    Dined on October 7, 2022

    overall5food5service5ambience5
    The food was delicious, the staff was accommodating and helpful. I love Jesters.

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  14. KathyK

    Indiana

    3 reviews

    3.0

    3 reviews

    Dined on October 7, 2022

    overall3food4service5ambience1
    Did not feel like a winery. Did not care for their wine’s. Food was okay. Service was great.

    Is this helpful?

  15. American

    Alabama

    1 review

    vip
    5.0

    1 review

    Dined on October 6, 2022

    overall5food5service5ambience4
    Jesters is an incredible stop for their delightful culinary selections, proximity to bourbon attractions including Makers Mark and Bardstown, and the special selection of wines. They are a hidden gem in the crown of bourbon country! Don’t miss it!

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  16. ChasityR

    Louisville

    4 reviews

    5.0

    4 reviews

    Dined on August 25, 2022

    overall5food5service5ambience5
    We really enjoyed our visit. The staff were very nice! Great food and drinks!

    Is this helpful?

  17. ReneeT

    Indiana

    3 reviews

    5.0

    3 reviews

    Dined on August 13, 2022

    overall5food5service5ambience5
    So close to Makers Mark - Had a GREAT lunch and they even had lunch specials. Good wine and Great Atmosphere. The owners are fantastic guys with a good sense of humor and they make it fun!

    Is this helpful?

  18. OpenTable Diner

    Louisville

    1 review

    5.0

    1 review

    Dined on July 29, 2022

    overall5food5service5ambience4
    Amazing experience! Delicious food, wonderful staff, and great wine!

    Is this helpful?

  19. OpenTable Diner

    Cincinnati

    3 reviews

    vip
    5.0

    3 reviews

    Dined on July 16, 2022

    overall5food5service5ambience5
    Great spot on our anniversary. Wine slushies and food were phenomenal and we went home with some great red wine. Look forward to our next visit at the end of Sept.

    Is this helpful?

  20. TrinaS

    Louisville

    15 reviews

    vip
    5.0

    15 reviews

    Dined on July 8, 2022

    overall5food5service5ambience5
    Love the food, ambiance and the service!

    Is this helpful?

  21. OpenTable Diner

    Atlanta Metro

    4 reviews

    vip
    1.0

    4 reviews

    Dined on June 25, 2022

    overall1food1service5ambience2
    Wines were all terrible.

    Is this helpful?

  22. DanielleT

    1 review

    4.0

    1 review

    Dined on June 18, 2022

    overall4food4service3ambience4
    Overall the experience was GREAT; from the food to the wine. The atmosphere was amazing! only complaint I have is we were newbies & lost at first; I feel like it needs more beginner guidance.

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  23. Marto

    1 review

    4.0

    1 review

    Dined on June 18, 2022

    overall4food5service5ambience5
    Wonderful people! Amazing food! We were visiting bourbon distilleries and stopped here for lunch. We sat outside and enjoyed the day and our lunch with some great wine slushies. We did the wine tasting—not great selections for our taste.

    Is this helpful?

  24. Crystal

    1 review

    4.0

    1 review

    Dined on June 16, 2022

    overall4food4service3ambience3
    The menu features unique choices. Definitely catered to finer palates. Would recommend the graze box appetizer. The pulled chicken was fantastic.

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  25. LeonardoH

    1 review

    4.0

    1 review

    Dined on June 3, 2022

    overall4food4service4ambience4
    Had our date for our 14th anniversary at their place... And we had a really nice time...got to do the wine testing and accompanied with some really cool dishes and topped it with some to go...it was around 6:30 - 7 when we got there and weather was perfect for the outside patio and the deck. Already recommended to some friends. Planning on coming back sometime this summer

    Is this helpful?

  26. SamM

    1 review

    5.0

    1 review

    Dined on May 14, 2022

    overall5food5service5ambience5
    Super fast service and the food was amazing! We will definitely be going back!

    Is this helpful?

  27. Lovetoeat

    Austin

    15 reviews

    vip
    4.0

    15 reviews

    Dined on April 30, 2022

    overall4food5service5ambience4
    Food and outside seating were great. Wine tasting was very reasonable with a huge variety to choose from.

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  28. CaroleP

    1 review

    5.0

    1 review

    Dined on April 30, 2022

    overall5food5service5ambience4
    We found Jester's while taking in the bourbon trail. The Staff was very accommodating and friendly. The food was great and so was the wine. We will certainly make this a visit on our next trip.

    Is this helpful?

  29. CarolM

    Louisville

    4 reviews

    vip
    5.0

    4 reviews

    Dined on April 27, 2022

    overall5food5service5ambience5
    We absolutely love the food and atmosphere at Jesters.

    Is this helpful?

  30. VeronicaD

    San Antonio

    4 reviews

    5.0

    4 reviews

    Dined on April 16, 2022

    overall5food5service5ambience5
    My husband and I had date night at Jesters Winery & Cafe and we ordered the Jester Burgers. They were delicious. I never had pimento cheese on a burger but oh my goodness, it was so good!!

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  31. NancyR

    1 review

    5.0

    1 review

    Dined on April 13, 2022

    overall5food5service5ambience5
    A nice place to get off the bourbon trail to relax, have a glass of wine and some tasty food. The staff are all very friendly and accommodating. We would highly recommend the lobster roll and broccoli salad!

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  32. Barbiblue

    San Francisco

    9 reviews

    vip
    4.0

    9 reviews

    Dined on April 9, 2022

    overall4food4service4ambience3
    Limited menu. Served on paper plates with plastic utensils

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  33. Bobw

    Louisville

    2 reviews

    vip
    5.0

    2 reviews

    Dined on March 24, 2022

    overall5food5service4ambience3
    I can rely on Jester's catering to my groups when I'm late, early or forgot to book a reservation. Love these folks

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  34. SharonW

    Louisville

    1 review

    5.0

    1 review

    Dined on March 4, 2022

    overall5food5service5ambience5
    The food was so fresh and expertly seasoned; best burger ever! Pickles and pimento cheese were very good! Beautiful setting and fun atmosphere; highly recommend!

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  35. Bobw

    Louisville

    2 reviews

    vip
    4.0

    2 reviews

    Dined on February 10, 2022

    overall4food4service4ambience4
    I was concerned when my tour guest told me he was on a plant-based diet, but the great folks at Jester's winery came to the rescue with Arugula salad, broccoli salad and some fun wines to accommodate. Thanks a bunch!

    Is this helpful?

  36. TrinaS

    Louisville

    16 reviews

    vip
    5.0

    16 reviews

    Dined on December 17, 2021

    overall5food5service5ambience5
    Food was fabulous as always, love the atmosphere and great service!

    Is this helpful?

  37. CDiggs

    Richmond

    10 reviews

    3.0

    10 reviews

    Dined on December 10, 2021

    overall3food3service4ambience3
    A little chilly indoors but overall it was nice.

    Is this helpful?

  38. BillW

    Louisville

    2 reviews

    3.0

    2 reviews

    Dined on December 4, 2021

    overall3food4service5ambience3
    While I'm sure we went at the "off" time of year, the food was great, but for what we paid for it, I would have expected to at least eaten off of a plate instead of a to go box.

    Is this helpful?

  39. KurtS

    1 review

    5.0

    1 review

    Dined on November 27, 2021

    overall5food5service5ambience5
    We got a little carried away for our lunch date but this place had some of the best potato salad and pork that we have had in a long time. Loved the pickles and begged for a jar. The bourbon bubbly was great too. Highly recommended.

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  40. BrandonM

    1 review

    5.0

    1 review

    Dined on November 20, 2021

    overall5food5service5ambience5
    Jesters is the best restaurant in the county in my opinion. They use local ingredients and the food is handcrafted. This is not something that you can experience anywhere else in a 30 mile radius. The prices are very reasonable. The wine cans are delicious. I love the owners sarcasm, and their menu even states that they are "The best at being humble." This place is a hidden gem. I highly recommend that you stop here if you are ever in the area. You WILL NOT be disappointed.

    Is this helpful?

FAQs

Jesters Winery & Cafe offers takeout which you can order by calling the restaurant at (859) 492-6528.

Jesters Winery & Cafe is rated 4.8 stars by 163 OpenTable diners.

Yes, you can generally book this restaurant by choosing the date, time and party size on OpenTable.

Make a reservation

2 people

7:00 PM


Booked 1 time today
Google Map for Jesters Winery & Cafe

25 Arthur Mattingly Road, Lebanon, KY 40033

Additional information

  • Cross street

    Route 49, Lebanon, Kentucky 40033

  • Neighborhood

    Lebanon

  • Hours of operation

    Wed–Sat 11:00 am–5:00 pm

  • Cuisines

    Winery

  • Dining style

    Casual Dining

  • Dress code

    Business Casual

  • Parking details

    Private Lot

  • Payment options

    AMEX, Discover, MasterCard, Visa

  • Additional

    Beer, Cafe, Entertainment, Indoor Fireplace, Outdoor Smoking Area, Patio/Outdoor Dining, Patio/Outdoor Dining, Takeout, View, Wheelchair Access, Wine

  • Phone number

    (859) 492-6528

  • Catering

    please contact chris.horseshoebend@gmail.com for catering questions

  • Private party facilities

    Please contact chris.horseshoebend@gmail.com or greg@horseshoebend-ky.com for private party events

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