Enable JavaScript to run this app.
Skip to main content
OpenTable logo
  1. Home
  2. United States
  3. Central Kentucky
  4. Lexington
  5. Winchester

Best Historic Restaurants in Winchester

Price
Cuisine
Regions
Neighborhoods
Top Rated
Dining Options
Seating Options
Accessibility

18 restaurants available nearby

How are Featured results ranked

A photo of Merrick Inn restaurant
4.7
Exceptional(5363)
$$$$
• Contemporary Southern • Lexington
Booked 50 times today
Absolutely fantastic. Pricey but worth it. Steak was perfection. Wine list was great.
A photo of Frank and Dino's restaurant
4.8
Exceptional(2053)
$$$$
• Italian • Lexington
Booked 29 times today
Great food and service. One of our favorites in Lexington. Our server, Bella, was awesome!
A photo of Epping's on Eastside restaurant
4.7
Exceptional(2450)
$$$$
• Unspecified • Lexington
Booked 29 times today
We enjoyed our anniversary dinner at Eppings on Thursday evening. Our server Sam was great, he was attentive, happy and polite. The food was outstanding as always!Each time we have been Eppings we always enjoy the food, staff and the atmosphere! We have been to Coles before but I think Eppings is our favorite!❤️ Thank you !!
A photo of Carson's on Main restaurant
4.8
Exceptional(7271)
$$$$
• American • Lexington
Booked 128 times today
Great steaks and great value. Glad we took the suggestion at the hotel.
A photo of Dudley's on Short restaurant
4.8
Exceptional(2957)
$$$$
• American • Lexington
Booked 16 times today
Debbie and the crew at Dudley’s continue to impress!!!
A photo of Blue Heron Steakhouse restaurant
4.7
Exceptional(2422)
$$$$
• Steakhouse • Lexington
Booked 17 times today
Blue Heron is always a great dining experience! Great atmosphere and incredible food and service. Highly recommend!!
A photo of Coles 735 Main restaurant
4.8
Exceptional(3769)
$$$$
• American • Lexington
Booked 15 times today
Absolutely love this place! We have been multiple times and they have never disappointed. This time it was our 3 year anniversary. And they made it an amazing celebration!
A photo of Carson's Back Porch restaurant
4.8
Exceptional(310)
$$$$
• American • Lexington
Booked 82 times today
Food was amazing everything was unbelievably great, so was the cocktails and wine.highly recommend. The staff was so great friendly checked on us constantly throughout the our evening, the whole experience was the best anyone could ask for. From meeting Matt at the door the Host, to the manager Jayme, and our amazing server Carol. We’re going back next week for brunch Friday through Sunday, and definitely going back for dinner too. Outside seating too on nice days. This will be our go to restaurant at least 2-3 times a month.
A photo of Trackside Restaurant and Bourbon Bar restaurant
4.2
Awesome(142)
$$$$
• American • Paris
Booked 3 times today
Very nice. Enjoyed the quiet and restful atmosphere.
A photo of Holly Hill Inn restaurant
4.7
Exceptional(1466)
$$$$
• Farm-to-table • Midway
Booked 11 times today
WONDERFULL FOOD.VERY GOOD SERVICE.GREAT ENVIRONMENT.

See what locals rave about

From verified diners like you
From verified diners like you
  • Raymond
    Chicago / Illinois •13 reviews
    5.0
    Dined 3 days ago
    First time in Lexington! Was recommended to us by the team at ‘Dark Arts’ Distillery. What an amazing experience! Friendly & helpful staff, just a joy to talk to. Food was elevated and delicious. Can’t wait to come back!
    More info
    Dudley's on Short$$$$• American• Lexington
    •
    4.8
  • Jacqui
    Indiana •6 reviews
    5.0
    Dined 3 days ago
    Absolutely fantastic. Pricey but worth it. Steak was perfection. Wine list was great.
    More info
    Merrick Inn$$$$• Contemporary Southern• Lexington
    •
    4.7
  • Ted
    Key West / Florida Keys •10 reviews
    5.0
    Dined 5 days ago
    Great food and service. One of our favorites in Lexington. Our server, Bella, was awesome!
    More info
    Frank and Dino's$$$$• Italian• Lexington
    •
    4.8
  • PattyGold
    Central Kentucky •9 reviews
    5.0
    Dined 5 days ago
    We enjoyed our anniversary dinner at Eppings on Thursday evening. Our server Sam was great, he was attentive, happy and polite. The food was outstanding as always!Each time we have been Eppings we always enjoy the food, staff and the atmosphere! We have been to Coles before but I think Eppings is our favorite!❤️ Thank you !!
    More info
    Epping's on Eastside$$$$• Unspecified• Lexington
    •
    4.7
  • Vincent
    Central Kentucky •1 review
    5.0
    Dined 6 days ago
    Food was amazing everything was unbelievably great, so was the cocktails and wine.highly recommend. The staff was so great friendly checked on us constantly throughout the our evening, the whole experience was the best anyone could ask for. From meeting Matt at the door the Host, to the manager Jayme, and our amazing server Carol. We’re going back next week for brunch Friday through Sunday, and definitely going back for dinner too. Outside seating too on nice days. This will be our go to restaurant at least 2-3 times a month.
    More info
    Carson's Back Porch$$$$• American• Lexington
    •
    4.8
Discover
OpenTable
  • About Us
  • Blog
  • Careers
  • Press
More
Businesses
  • Restaurant Management Solutions
  • Restaurant Reservation Software
  • Restaurant Marketing Software
  • Restaurant Event Software
  • OpenTable For Restaurants
  • OpenTable For Restaurant Groups
  • OpenTable Pricing & Plans
Join us on
  • Privacy Policy
  • Terms of Use
  • Cookies and Interest-Based Ads
  • Accessibility Statement
  • Cookie Preferences
Copyright © 2026 OpenTable, Inc. 425 Market St Ste 1200, San Francisco CA 94105 - All rights reserved.
OpenTable is part of Booking Holdings, the world leader in online travel and related services.
Booking Logo
Priceline Logo
KAYAK Logo
Agoda Logo
OpenTable Logo