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Jesters Winery & Cafe, Lebanon, KY

Jesters Winery & Cafe

4.5
4.5
138 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

May 2022
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7:00 PM


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

Menu

Main

  • Cheese Tray

    Pulled Pork or Pulled Chicken. Homemade Bacon, Onion, Orange Marmalade jam, Wine Infused, mild heat jalapeno pimento cheese, olive tapenade, local cheese, maple bacon glazed nuts and apple, balsamic glazed tomatoes

    • Full$16.00
    • Half$8.00
  • Caprese Style Flatbread$9.50

    Tomato, Basil, Mozzarella with a balsamic glaze and basil pesto base

    • BBQ Pulled Chicken or Pulled Pork Flatbread$9.50

      8 hour smoked bbq, mixed cheese blend, crispy onions, apple slaw

      • Soups$6.00

        Choice of homemade local tomato soup with balsamic glaze, or curry white chicken and white bean chili

        • Salad

          Seasonal Mixed Local Greens, Kale, Kolrabi, Dried Cherries, Apple Poppyseed Dressing, croutons, local tomatoes

          • Entrée$3.75
          • Side$7.50
        • Dessert$5.00

          Spiced apple pie cheese cake-ish, maple and rum syrup, crisp bacon

          • Turkey Sandwich$8.25

            Deli Sliced Turkey, mixed greens, tomato, homemade bacon jam

            • Turkey Wrap$8.50

              Broccoli salad, shaved brussel sprouts, kale, kolrabi, maple bacon dressing

              • Pulled Pork Wrap$8.50

                Pulled Pork, Homemade BBQ, mixed greens, potato salad, tomato

                • Pulled Chicken Wrap$8.50

                  Broccoli salad, crispy onions, mixed cheese, with homemade ranch and bbq sauce

                  • Jester Sub$9.00

                    Pulled pork or pulled chicken, pimento cheese, maple cayenne apple slaw (little heat)

                    • Jester Burger$9.75

                      50/50 pork/beef patty, brioche bun, pimento cheese, apple s

                      • Sides$2.50

                        Potato salad, Broccoli salad, c

                        Last updated: February 1, 2022

                        What 138 people are saying

                        Overall ratings and reviews

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

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

                        NoiseModerate

                        Sort by

                        Filters

                        1. SM

                          SamM

                          1 review

                          5.0

                          1 review

                          Dined 5 days ago

                          overall5food5service5ambience5

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

                        2. 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.

                        3. 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.

                        4. 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.

                        5. 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!!

                        6. 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!

                        7. B

                          Barbiblue

                          San Francisco

                          6 reviews

                          4.0

                          6 reviews

                          Dined on April 9, 2022

                          overall4food4service4ambience3

                          Limited menu. Served on paper plates with plastic utensils

                        8. 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

                        9. 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!

                        10. 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!

                        11. TS

                          TrinaS

                          Louisville

                          14 reviews

                          vip
                          5.0

                          14 reviews

                          Dined on December 17, 2021

                          overall5food5service5ambience5

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

                        12. CD

                          CDiggs

                          Richmond

                          10 reviews

                          3.0

                          10 reviews

                          Dined on December 10, 2021

                          overall3food3service4ambience3

                          A little chilly indoors but overall it was nice.

                        13. 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.

                        14. 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.

                        15. 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.

                        16. 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!

                        17. MD

                          MarioD

                          Chicago

                          25 reviews

                          4.0

                          25 reviews

                          Dined on November 13, 2021

                          overall4food5service5ambience3

                          Our group had a great time.

                        18. 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!

                        19. QB

                          QueenBea

                          Louisville

                          1 review

                          5.0

                          1 review

                          Dined on November 6, 2021

                          overall5food5service5ambience5

                          Beautiful scenery and great food and wine. Highley recommend

                        20. OT

                          OpenTable Diner

                          1 review

                          5.0

                          1 review

                          Dined on October 23, 2021

                          overall5food5service5ambience5

                          Great food, friendly people and amazing view

                        21. 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!

                        22. 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 ♥️

                        23. 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.

                        24. 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.

                        25. TS

                          TrinaS

                          Louisville

                          15 reviews

                          vip
                          5.0

                          15 reviews

                          Dined on September 10, 2021

                          overall5food5service5ambience5

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

                        26. 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.

                        27. 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!

                        28. TS

                          TrinaS

                          Louisville

                          15 reviews

                          vip
                          5.0

                          15 reviews

                          Dined on September 4, 2021

                          overall5food5service5ambience5

                          Fabulous as always! Loved the Caprese Caesar salad special!💕

                        29. 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.

                        30. 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

                        31. S

                          Susie

                          Louisville

                          1 review

                          5.0

                          1 review

                          Dined on August 20, 2021

                          overall5food5service5ambience5

                          This was an unexpected wonderful find in the country. The setting was beautiful, the food outstanding and the host was inviting to first time visitors.

                        32. JH

                          JenniferH

                          Louisville

                          1 review

                          4.0

                          1 review

                          Dined on August 14, 2021

                          overall4food5service5ambience3

                          Great food! Very friendly staff! We enjoyed the outdoor area a lot!

                        33. G

                          Geojag

                          1 review

                          5.0

                          1 review

                          Dined on August 12, 2021

                          overall5food5service5ambience5

                          Jester's winery is worth checking out. The staff members are great the wine tastings are great and the cheese platters are phenomenal. If you haven't done a wine tasting at Jesters you're missing out.

                        34. QB

                          QueenBea

                          Louisville

                          2 reviews

                          5.0

                          2 reviews

                          Dined on August 7, 2021

                          overall5food5service5ambience5

                          The greek wrap was amazing, as always! Two people in our party had the burgers which was also delicious.

                        35. MA

                          MitziA

                          1 review

                          4.0

                          1 review

                          Dined on July 27, 2021

                          overall4food4service4ambience4

                          After scanning others food selections on my way in there are other items I want to try on the menu so I’ll be back. The chicken flatbread did not disappoint.

                        36. TS

                          TrinaS

                          Louisville

                          15 reviews

                          vip
                          5.0

                          15 reviews

                          Dined on July 23, 2021

                          overall5food5service5ambience5

                          Great food, fabulous service and the best views!

                        37. AB

                          AngelaB

                          Louisville

                          1 review

                          5.0

                          1 review

                          Dined on July 16, 2021

                          overall5food5service5ambience5

                          Great food, great service! Treated like family. Had a great time with friends.

                        38. OT

                          OpenTable Diner

                          1 review

                          5.0

                          1 review

                          Dined on July 13, 2021

                          overall5food5service5ambience5

                          Great food, great service and great outdoor views. Highly recommend!!

                        39. MM

                          MollyM

                          Denver

                          1 review

                          5.0

                          1 review

                          Dined on July 10, 2021

                          overall5food5service5ambience5

                          Awesome winery and cafe! We stopped for lunch, but we still ending up leaving with wine. Most of the wines are canned and the bourbon barrel bubbly is really refreshing, which was perfect for a summer afternoon. My fiance raved about the burger and I really liked the pulled chicken sandwich. Whether you are looking for lunch while visiting local distilleries or need a wine break in bourbon country, I would recommend stopping here!

                        40. OT

                          OpenTable Diner

                          Louisville

                          1 review

                          5.0

                          1 review

                          Dined on June 29, 2021

                          overall5food5service5ambience5

                          Bruce and Jackie were amazing! They were on point with checking in with us, accommodating our taste and suggesting amazing food and drink combinations. Easy to talk to staff and really beautiful scenery. We will definitely be back in the near future!

                        FAQs

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

                        Jesters Winery & Cafe is rated 4.5 stars by 138 OpenTable diners.

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

                        Make a reservation

                        2 people

                        May 2022
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                        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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