Jesters Winery & Cafe

Name: Jesters Winery & Cafe
Address: 25 Arthur Mattingly Road, Lebanon, KY, United States, 40033
Telephone: (859) 492-6528
Price range: $30 and under
Rating: 4.8

4.8

156 Reviews

$30 and under

Winery

Top Tags:

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

Party Size

2 people

DateTime

Apr 1, 2023

7:00 PM

Order delivery or takeout

Takeout

(859) 492-6528

Additional information

Dining style
Casual Dining
Cuisines
Winery
Hours of operation
Wed–Sat 11:00 am–5:00 pm
Phone number
(859) 492-6528
Website
http://www.jesterswinery.com/
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

Location
25 Arthur Mattingly Road, Lebanon, KY 40033
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

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

What 156 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

Noise • Moderate

Sort by

Filters

MH
MatthewH
Louisville
2 reviews
5.0
2 reviews
Dined on February 15, 2023
overall5food5service5ambience5
Perfect meal
SR
StuartR
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.
RB
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.
OT
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.
AB
AncelB
Cincinnati
2 reviews
5.0
2 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.
SH
SueH
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.
KK
KathyK
Indiana
1 review
3.0
1 review
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.
A
American
1 review
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!
CR
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!
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!
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!
OT
OpenTable Diner
Cincinnati
2 reviews
5.0
2 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.
TS
TrinaS
Louisville
15 reviews
vip
5.0
15 reviews
Dined on July 8, 2022
overall5food5service5ambience5
Love the food, ambiance and the service!
OT
OpenTable Diner
Atlanta Metro
4 reviews
vip
1.0
4 reviews
Dined on June 25, 2022
overall1food1service5ambience2
Wines were all terrible.
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.
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.
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.
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
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!
L
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.
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.
CM
CarolM
Louisville
4 reviews
vip
5.0
4 reviews
Dined on April 27, 2022
overall5food5service5ambience5
We absolutely love the food and atmosphere at Jesters.
VD
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!!
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!
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
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
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!
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!
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!
CD
CDiggs
Richmond
10 reviews
3.0
10 reviews
Dined on December 10, 2021
overall3food3service4ambience3
A little chilly indoors but overall it was nice.
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.
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.
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.
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!
MD
MarioD
Chicago
25 reviews
4.0
25 reviews
Dined on November 13, 2021
overall4food5service5ambience3
Our group had a great time.
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!
QB
QueenBea
Louisville
1 review
5.0
1 review
Dined on November 6, 2021
overall5food5service5ambience5
Beautiful scenery and great food and wine. Highley recommend
OT
OpenTable Diner
1 review
5.0
1 review
Dined on October 23, 2021
overall5food5service5ambience5
Great food, friendly people and amazing view
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!
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 ♥️

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 156 OpenTable diners.

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

Make a reservation

Party Size

2 people

DateTime

Apr 1, 2023

7:00 PM

Order delivery or takeout

Takeout

(859) 492-6528

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

Website
http://www.jesterswinery.com/
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

Jesters Winery & Cafe

Make a reservation

Order delivery or takeout

Takeout

Additional information

Popular dishes

Jester Burger

Salad

Cheese Tray

Menu

Main

Cheese Tray

Caprese Style Flatbread$9.50

BBQ Pulled Chicken or Pulled Pork Flatbread$9.50

Soups$6.00

Salad

Dessert$5.00

Turkey Sandwich$8.25

Turkey Wrap$8.50

Pulled Pork Wrap$8.50

Pulled Chicken Wrap$8.50

Jester Sub$9.00

Jester Burger$9.75

Sides$2.50

What 156 people are saying

Overall ratings and reviews

Sort by

Filters

FAQs

Does Jesters Winery & Cafe offer delivery through OpenTable or takeout?

How is Jesters Winery & Cafe restaurant rated?

Is Jesters Winery & Cafe currently accepting reservations?

Make a reservation

Order delivery or takeout

Takeout

Additional information