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Jesters Winery & Cafe, Lebanon, KY

Jesters Winery & Cafe

4.3
4.3
148 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 3 times 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 148 people are saying

Overall ratings and reviews

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

4.3
4.3 based on recent ratings
  • 4.3Food
  • 4.5Service
  • 4.2Ambience
  • 4.2Value

NoiseModerate

Sort by

Filters

  1. CR

    ChasityR

    Louisville

    1 review

    5.0

    1 review

    Dined on August 25, 2022

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

    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!
  3. OT

    OpenTable Diner

    Louisville

    1 review

    5.0

    1 review

    Dined on July 29, 2022

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

    OpenTable Diner

    Cincinnati

    1 review

    5.0

    1 review

    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.
  5. TS

    TrinaS

    Louisville

    15 reviews

    vip
    5.0

    15 reviews

    Dined on July 8, 2022

    overall5food5service5ambience5
    Love the food, ambiance and the service!
  6. OT

    OpenTable Diner

    Atlanta

    1 review

    vip
    1.0

    1 review

    Dined on June 25, 2022

    overall1food1service5ambience2
    Wines were all terrible.
  7. DT

    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.
  8. M

    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.
  9. C

    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.
  10. LH

    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
  11. SM

    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!
  12. L

    Lovetoeat

    Austin

    13 reviews

    4.0

    13 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.
  13. CP

    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.
  14. CM

    CarolM

    Louisville

    3 reviews

    vip
    5.0

    3 reviews

    Dined on April 27, 2022

    overall5food5service5ambience5
    We absolutely love the food and atmosphere at Jesters.
  15. VD

    VeronicaD

    San Antonio

    2 reviews

    5.0

    2 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!!
  16. NR

    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!
  17. B

    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
  18. B

    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
  19. SW

    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!
  20. B

    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!
  21. TS

    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!
  22. CD

    CDiggs

    Richmond

    10 reviews

    3.0

    10 reviews

    Dined on December 10, 2021

    overall3food3service4ambience3
    A little chilly indoors but overall it was nice.
  23. BW

    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.
  24. KS

    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.
  25. BM

    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.
  26. JC

    JenC

    1 review

    5.0

    1 review

    Dined on November 19, 2021

    overall5food5service5ambience5
    Amazing food, the truffle mac and cheese and pimento cheese were awesome! Will be back for sure!
  27. MD

    MarioD

    Chicago

    25 reviews

    4.0

    25 reviews

    Dined on November 13, 2021

    overall4food5service5ambience3
    Our group had a great time.
  28. SD

    SDRII

    1 review

    5.0

    1 review

    Dined on November 6, 2021

    overall5food5service5ambience5
    What a wonderful meal and great service. We sat outside and enjoyed the scenerio and time to sit back and relax. Host was very attentive and we appreciated the laid back style! Great experience!
  29. QB

    QueenBea

    Louisville

    1 review

    5.0

    1 review

    Dined on November 6, 2021

    overall5food5service5ambience5
    Beautiful scenery and great food and wine. Highley recommend
  30. OT

    OpenTable Diner

    1 review

    5.0

    1 review

    Dined on October 23, 2021

    overall5food5service5ambience5
    Great food, friendly people and amazing view
  31. RE

    RENS

    1 review

    5.0

    1 review

    Dined on October 13, 2021

    overall5food5service5ambience5
    went in mid October for lunch /very quite area with patio and indoor seating /they had no problem that we had our dog outside /service was amazing/we tried the sampler flight of 7 wines pork tacos pimento burger and chicken wrap /the wrap was huge and had to take half home tacos were delicious with a kick of chipotle ranch & burger was good but hubby stated that coleslaw on it would be a good compliment/ the broccoli salad is not broccoli heads but more of a slaw type salad (as a heads up)/ potato salad had a great amount of cheddar (yum) and a ting of a smokey flavor but really good/ staff is super friendly and will accommodate/ will return again if ever back in the area!
  32. PB

    PadmineeB

    1 review

    5.0

    1 review

    Dined on October 2, 2021

    overall5food5service5ambience5
    The owners were so welcoming and they are family oriented. The food was absolutely amazing! I recommend the wine slushies for sure ♥️
  33. S

    Sirwinealot

    Louisville

    1 review

    5.0

    1 review

    Dined on September 18, 2021

    overall5food5service5ambience5
    Always a good time here ! Big Fan , love there food and there wine.
  34. LW

    LeanderWapshot

    Minneapolis

    3 reviews

    5.0

    3 reviews

    Dined on September 17, 2021

    overall5food5service5ambience5
    I love this place. A unique setting on a hill with a beautiful view. Best gourmet burgers around. Love the house pickles.
  35. TS

    TrinaS

    Louisville

    16 reviews

    vip
    5.0

    16 reviews

    Dined on September 10, 2021

    overall5food5service5ambience5
    Wonderful as always! The pork tacos were fabulous, the views beautiful, and the service is always great!
  36. RT

    RoseT

    1 review

    5.0

    1 review

    Dined on September 10, 2021

    overall5food5service5ambience5
    The owners were fantastic!!! I love this place they made us feel at home snd the service was fantastic, the food was amazing and the wine was fabulous.
  37. AE

    AmberE

    1 review

    5.0

    1 review

    Dined on September 10, 2021

    overall5food5service5ambience5
    Wonderful food and gorgeous scenery, we can’t wait to go back!
  38. TS

    TrinaS

    Louisville

    16 reviews

    vip
    5.0

    16 reviews

    Dined on September 4, 2021

    overall5food5service5ambience5
    Fabulous as always! Loved the Caprese Caesar salad special!💕
  39. m

    mojoe

    1 review

    5.0

    1 review

    Dined on August 26, 2021

    overall5food5service5ambience5
    Had a nice lunch here. Quite tasty food. Very good wine. The owners are super friendly. The surrounding area is pretty.
  40. EH

    ElaineH

    Louisville

    1 review

    5.0

    1 review

    Dined on August 26, 2021

    overall5food5service5ambience5
    Great dining experience. Very knowledgeable staff and quick food service

FAQs

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

Jesters Winery & Cafe is rated 4.3 stars by 148 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 3 times 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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