Patricia's Guidebook
Food scene
This is a locally owned and operated favorite. It is minutes away from the BNB. They serve pub food, offer a full bar, and live music on occasion. In warmer weather you will love sitting on the back deck for your meal. Our favorites there are the cheese burger, onion rings, steak quesadilla, grilled chicken sandwich, and asparagus. They have a great club salad and beer cheese tray as well. If you haven’t had beer cheese, and like both beer and cheese, it is delicious. It was actually invited just up the road at Hall’s on the River. Hall’s is another local favorite. It is worth a visit, but is currently closed for renovations.
7 locals raden deze aan
Waterfront Restaurant and Lounge
220 Athens Boonesboro RdThis is a locally owned and operated favorite. It is minutes away from the BNB. They serve pub food, offer a full bar, and live music on occasion. In warmer weather you will love sitting on the back deck for your meal. Our favorites there are the cheese burger, onion rings, steak quesadilla, grilled chicken sandwich, and asparagus. They have a great club salad and beer cheese tray as well. If you haven’t had beer cheese, and like both beer and cheese, it is delicious. It was actually invited just up the road at Hall’s on the River. Hall’s is another local favorite. It is worth a visit, but is currently closed for renovations.
They offer a diverse menu and a finer dining experience. They have a full bar and desserts. I recommend the dessert.
7 locals raden deze aan
Loma's
103 South Main StreetThey offer a diverse menu and a finer dining experience. They have a full bar and desserts. I recommend the dessert.
This is a great lunch or dinner choice. We love the panini’s and pizza. The atmosphere is fun and festive. They are always decorated for the upcoming holiday, with matching cocktails. They also have live music on occasion.
8 locals raden deze aan
Engine House Pizza Pub
9 W Lexington AveThis is a great lunch or dinner choice. We love the panini’s and pizza. The atmosphere is fun and festive. They are always decorated for the upcoming holiday, with matching cocktails. They also have live music on occasion.
Farm to table menu, need I say more? Family owned and operated. Outside dining and music are a must in the summer and fall.
6 locals raden deze aan
Wildcat Willy's Distillery and Restaurant
31 E Broadway StFarm to table menu, need I say more? Family owned and operated. Outside dining and music are a must in the summer and fall.
This comfort food keeps you coming back. Our favorite side is the macaroni and cheese. They have daily specials that are a sure bet. Ask about the homemade pie for dessert. They also have a full service bar.
Smokin' Howards Sports Bar & Grill
20 North Main StreetThis comfort food keeps you coming back. Our favorite side is the macaroni and cheese. They have daily specials that are a sure bet. Ask about the homemade pie for dessert. They also have a full service bar.
This is a great restaurant. There is live music often. We recommend the brisket grilled cheese. There is a huge sand area and you are looking at the river.The view is great.
13 locals raden deze aan
Proud Mary BBQ
9079 Old Richmond RdThis is a great restaurant. There is live music often. We recommend the brisket grilled cheese. There is a huge sand area and you are looking at the river.The view is great.
This gives you an authentic old fashioned diner experience. The food is not good expensive and the service is great. We recommend the Winchester Special if you are going for breakfast. There is also a shopping and auction area at the front of the restaurant. We have found some pretty unique things here.
Broadway Cafe
26 East Broadway StreetThis gives you an authentic old fashioned diner experience. The food is not good expensive and the service is great. We recommend the Winchester Special if you are going for breakfast. There is also a shopping and auction area at the front of the restaurant. We have found some pretty unique things here.
Winery
Harkness offers tastings, cheese boards and more. During the warmer seasons they often host local food trucks, Yoga classes, and musicians. You can check their Facebook page for updates on hours and events. I seriously recommend a visit.
8 locals raden deze aan
Harkness Edwards Vineyards
5199 Combs Ferry RdHarkness offers tastings, cheese boards and more. During the warmer seasons they often host local food trucks, Yoga classes, and musicians. You can check their Facebook page for updates on hours and events. I seriously recommend a visit.
Yoga Studio
The om Place
815 Quisenberry LaneThey offer a variety of classes in a serene studio. All the teachers are glorious.
Brewery
There are so many options on tap. They have a trivia night, margarita flight night, food truck access, and live music from time to time. There are two locations in Winchester. Checkout their Facebook page to learn more.
6 locals raden deze aan
Abettor Brewing Company
128 N Highland StThere are so many options on tap. They have a trivia night, margarita flight night, food truck access, and live music from time to time. There are two locations in Winchester. Checkout their Facebook page to learn more.
Shopping
Art, antiques, bow ties, gifts, and more! Mason handcrafts the bow ties and I’ve never seen a finer or more fabulous selection.
Mason on Main
70 South Main StreetArt, antiques, bow ties, gifts, and more! Mason handcrafts the bow ties and I’ve never seen a finer or more fabulous selection.
Sometimes I don’t know where to shop for clothes. The answer is always Betsy’s. Great dressing rooms and options in every color. YOLO-Buy it at Betsy’s.
Betsey's Boutique Shop
18 North Main StreetSometimes I don’t know where to shop for clothes. The answer is always Betsy’s. Great dressing rooms and options in every color. YOLO-Buy it at Betsy’s.
Sugar Belle's Boutique
21 S Main StFun and on trend. Sweet selections from casual to dressy.
Dirty South Pottery
38 North Main StreetShop, Experience, Learn - You won’t leave empty handed.
Local, Kentucky Proud foods. One of our favorite stops for delicious produce, farm raised beef, and cheeses. Go for lunch on Saturday from 11-2. Try the fried pies!
Beech Spring Farm Market
4776 Old Boonesboro RoadLocal, Kentucky Proud foods. One of our favorite stops for delicious produce, farm raised beef, and cheeses. Go for lunch on Saturday from 11-2. Try the fried pies!
Arts
This theater has been part of our community for ages. I sometimes refer to this town as little Broadway because of our community theater’s success. This is one of two theater production groups. The other is Winchester Player’s. You can find them on Facebook. Their venue changes but they always deliver quality productions.
Leeds Center For The Arts
37 N Main StThis theater has been part of our community for ages. I sometimes refer to this town as little Broadway because of our community theater’s success. This is one of two theater production groups. The other is Winchester Player’s. You can find them on Facebook. Their venue changes but they always deliver quality productions.
This is a great spot for getting in touch with your creative side. I visit seasonally with my kids. It’s never a disappointment. I leave feeling connected to my children and at peace with myself.
Created By You, LLC
36 North Highland StreetThis is a great spot for getting in touch with your creative side. I visit seasonally with my kids. It’s never a disappointment. I leave feeling connected to my children and at peace with myself.
Coffee
The Daily Grind
225 Redwing Dr
Creative Coffees Roastery
2000 Fortune Drive