Winchester, KY

clark seat · 40391

The Clark County seat, eighteen miles east of Lexington and the official home of Ale-8-One, the ginger-citrus soda locals treat as a personality trait. Downtown has done the slow, unflashy work of restoration: a working courthouse square, a few bars that take cocktails seriously, and the Leeds Center for the Arts hosting acts that punch above the zip code. The dating pool tilts toward Lexington commuters, UK alumni who wanted a yard, and the agricultural and manufacturing crowd that has always been here. It is less self-conscious than Versailles and less polished than Midway, which some people consider the entire point.

$36,522

median income

$938

median rent

The data

Winchester, KY by the numbers

Median individual income in Winchester, KY is about $36.5k.
● Verified · Census ACS 5-yr, 2019–2023
The median renter in Winchester, KY pays about $940 a month.
● Verified · Census ACS 5-yr, 2019–2023

On the ground

Local date spots

16 spots · tap a point, label, or class to filter

Class

Budget

Vibe

16 spots across Winchester, KY

Winchester, KY
Dining
Hall's On The River
Southern restaurant (US)$$$$★ 4.1 · 1,583
Outdoor seatingGood for groups
Find it
1225 Athens Boonesboro Rd, Winchester, KY 40391
Get there
Transit Drive Walk
Crowd read
4.1★ from 1,583 Google reviews
Split the bill
$$ · mid-range is our editorial bracket, not a real bill. Plug in what you expect to actually spend at Hall's On The River.
Estimate — adjust$
Your share$25
Their share$25
Even split — modern and uncomplicated.
Hours
Mon11:30 AM to 9 PM
Tue11:30 AM to 9 PM
Wed11:30 AM to 9 PM
Thu11:30 AM to 9 PM
Fri11:30 AM to 9 PM
Sat10 AM to 9 PM
Sun10 AM to 9 PM
Parking
Free parking lot
Dining
Outdoor seating · Onsite services · Takeout · Dine-in
Access
Wheelchair accessible entrance · Wheelchair accessible parking lot · Wheelchair accessible restroom
Crowd
Groups · Tourists
Contact
Call Site Maps
Winchester, KY
Dining
DJ's Steakhouse Bar and Grill
Steak house$$$$★ 4.3 · 752
Outdoor seatingGood for groups
Find it
836 Bypass Rd, Winchester, KY 40391
Get there
Transit Drive Walk
Crowd read
4.3★ from 752 Google reviews
Split the bill
$ · budget-friendly is our editorial bracket, not a real bill. Plug in what you expect to actually spend at DJ's Steakhouse Bar and Grill.
Estimate — adjust$
Your share$13
Their share$13
Even split — modern and uncomplicated.
Hours
Mon11 AM to 9 PM
Tue11 AM to 9 PM
Wed11 AM to 9 PM
Thu11 AM to 10 PM
Fri11 AM to 10 PM
Sat11 AM to 10 PM
Sun11 AM to 6 PM
Parking
Free parking lot
Dining
Outdoor seating · Delivery · Takeout · Dine-in
Access
Wheelchair accessible entrance · Wheelchair accessible parking lot · Wheelchair accessible restroom
Crowd
Family-friendly · Groups · Tourists
Pets
Dogs allowed outside
Contact
Call Site Maps
Winchester, KY
Drinks
Woody's Sports Bar & Grill
Bar & grill$$$$★ 4.3 · 739
Outdoor seatingGood for groups
Find it
923 Bypass Rd, Winchester, KY 40391
Get there
Transit Drive Walk
Crowd read
4.3★ from 739 Google reviews
Split the bill
$ · budget-friendly is our editorial bracket, not a real bill. Plug in what you expect to actually spend at Woody's Sports Bar & Grill.
Estimate — adjust$
Your share$13
Their share$13
Even split — modern and uncomplicated.
Hours
Mon10:30 AM to 12 AM
Tue10:30 AM to 12 AM
Wed10:30 AM to 12 AM
Thu10:30 AM to 12 AM
Fri10:30 AM to 1 AM
Sat10:30 AM to 1 AM
Sun12 to 10 PM
Parking
Free parking lot
Dining
Outdoor seating · Delivery · Takeout · Dine-in
Access
Wheelchair accessible entrance · Wheelchair accessible parking lot · Wheelchair accessible restroom
Crowd
Groups · Tourists
Contact
Call Site Maps
Winchester, KY
Drinks
Waterfront Grill and Gathering
Bar & grill$$$$★ 4.3 · 298
Outdoor seatingLGBTQ+ friendly
Find it
220 Athens Boonesboro Rd, Winchester, KY 40391
Get there
Transit Drive Walk
Crowd read
4.3★ from 298 Google reviews
Split the bill
$ · budget-friendly is our editorial bracket, not a real bill. Plug in what you expect to actually spend at Waterfront Grill and Gathering.
Estimate — adjust$
Your share$13
Their share$13
Even split — modern and uncomplicated.
Hours
MonClosed
TueClosed
Wed12 to 9 PM
Thu12 to 9 PM
Fri12 to 9 PM
Sat12 to 9 PM
Sun1 to 7 PM
Parking
Free parking lot
Dining
Outdoor seating · Takeout · Dine-in
Access
Wheelchair accessible entrance · Wheelchair accessible parking lot · Wheelchair accessible restroom
Crowd
Family-friendly · Groups · LGBTQ+ friendly
Pets
Dogs allowed
Contact
Call Site Maps
Winchester, KY
Dining
La Trattoria
Restaurant$$$$★ 4.5 · 262
Outdoor seatingGood for groups
Find it
30 N Main St, Winchester, KY 40391
Get there
Transit Drive Walk
Crowd read
4.5★ from 262 Google reviews
Split the bill
$ · budget-friendly is our editorial bracket, not a real bill. Plug in what you expect to actually spend at La Trattoria.
Estimate — adjust$
Your share$13
Their share$13
Even split — modern and uncomplicated.
Hours
MonClosed
TueClosed
Wed11 AM to 9 PM
Thu11 AM to 9 PM
Fri11 AM to 9 PM
Sat11 AM to 9 PM
Sun11 AM to 8 PM
Parking
Free parking lot
Dining
Outdoor seating · Delivery · Onsite services · Takeout · Dine-in
Access
Wheelchair accessible entrance · Wheelchair accessible parking lot · Wheelchair accessible restroom
Crowd
Family-friendly · Groups · Tourists
Pets
Dogs allowed outside
Contact
Call Site Maps
Winchester, KY
Dining
Tokyo Hibachi & Sushi
Japanese restaurant$$$$★ 4.5 · 262
Good for groupsWheelchair access
Find it
Winchester Plz, Winchester, KY 40391
Get there
Transit Drive Walk
Crowd read
4.5★ from 262 Google reviews
Split the bill
$ · budget-friendly is our editorial bracket, not a real bill. Plug in what you expect to actually spend at Tokyo Hibachi & Sushi.
Estimate — adjust$
Your share$13
Their share$13
Even split — modern and uncomplicated.
Hours
Mon11 AM to 9 PM
TueClosed
Wed11 AM to 9 PM
Thu11 AM to 9 PM
Fri11 AM to 9 PM
Sat12 to 9 PM
Sun12 to 9 PM
Parking
Free parking lot
Dining
Takeout · Dine-in
Access
Wheelchair accessible entrance · Wheelchair accessible parking lot · Wheelchair accessible restroom
Crowd
College students · Family-friendly · Groups
Contact
Call Site Maps
Winchester, KY
Dining
Loma's
Restaurant$$$$★ 4.3 · 258
Good for groupsWheelchair access
Find it
103 S Main St, Winchester, KY 40391
Get there
Transit Drive Walk
Crowd read
4.3★ from 258 Google reviews
Split the bill
$$ · mid-range is our editorial bracket, not a real bill. Plug in what you expect to actually spend at Loma's.
Estimate — adjust$
Your share$25
Their share$25
Even split — modern and uncomplicated.
Hours
MonClosed
TueClosed
Wed4:30 to 9 PM
Thu4:30 to 9 PM
Fri4:30 to 9:30 PM
Sat2 to 9:30 PM
SunClosed
Parking
Free parking lot
Dining
Curbside pickup · Onsite services · Takeout · Dine-in
Access
Wheelchair accessible entrance · Wheelchair accessible parking lot · Wheelchair accessible restroom
Crowd
Groups · Tourists
Contact
Call Site Maps
Winchester, KY
Dining
Smokin' Howards Sports Bar & Grill
American restaurant$$$$★ 4.5 · 255
Outdoor seatingGood for groups
Find it
20 N Main St, Winchester, KY 40391
Get there
Transit Drive Walk
Crowd read
4.5★ from 255 Google reviews
Split the bill
$ · budget-friendly is our editorial bracket, not a real bill. Plug in what you expect to actually spend at Smokin' Howards Sports Bar & Grill.
Estimate — adjust$
Your share$13
Their share$13
Even split — modern and uncomplicated.
Hours
MonClosed
Tue11 AM to 8 PM
Wed11 AM to 8 PM
Thu11 AM to 8 PM
Fri11 AM to 8 PM
Sat11 AM to 8 PM
SunClosed
Parking
Free parking lot
Dining
Outdoor seating · Onsite services · Takeout · Dine-in
Access
Wheelchair accessible entrance · Wheelchair accessible parking lot · Wheelchair accessible restroom
Crowd
Groups · Tourists
Pets
Dogs allowed outside
Contact
Site Maps
Winchester, KY
Dining
The Urban Stack & Co
Hamburger restaurant$$$$★ 4.3 · 252
Wheelchair access
Find it
1600 Bypass Rd, Winchester, KY 40391
Get there
Transit Drive Walk
Crowd read
4.3★ from 252 Google reviews
Split the bill
$ · budget-friendly is our editorial bracket, not a real bill. Plug in what you expect to actually spend at The Urban Stack & Co.
Estimate — adjust$
Your share$13
Their share$13
Even split — modern and uncomplicated.
Hours
Mon11 AM to 9 PM
Tue11 AM to 9 PM
Wed11 AM to 9 PM
Thu11 AM to 9 PM
Fri11 AM to 9 PM
Sat11 AM to 9 PM
Sun11 AM to 9 PM
Parking
Free parking lot
Dining
Curbside pickup · No-contact delivery · Delivery · Onsite services · Takeout
Access
Wheelchair accessible entrance · Wheelchair accessible parking lot · Wheelchair accessible seating
Crowd
Family-friendly · Tourists
Contact
Call Site Maps
Winchester, KY
Dining
The Bodega "Home of The Sloppy Dogs"
Restaurant$$$$★ 5 · 173
Outdoor seatingWheelchair access
Find it
515B W Lexington Ave, Winchester, KY 40391
Get there
Transit Drive Walk
Crowd read
5★ from 173 Google reviews
Split the bill
$ · budget-friendly is our editorial bracket, not a real bill. Plug in what you expect to actually spend at The Bodega "Home of The Sloppy Dogs".
Estimate — adjust$
Your share$13
Their share$13
Even split — modern and uncomplicated.
Hours
Mon11 AM to 6 PM
Tue11 AM to 6 PM
Wed11 AM to 6 PM
Thu11 AM to 6 PM
Fri11 AM to 6 PM
SatClosed
SunClosed
Parking
Free parking lot
Dining
Outdoor seating · Curbside pickup · Onsite services · Takeout · Dine-in
Access
Wheelchair accessible parking lot
Crowd
Tourists
Pets
Dogs allowed outside
Contact
Call Maps
Winchester, KY
Dining
Maka Mia on Main
Pizza restaurant$$$$★ 4.6 · 171
Outdoor seatingWheelchair access
Find it
44 S Main St, Winchester, KY 40391
Get there
Transit Drive Walk
Crowd read
4.6★ from 171 Google reviews
Split the bill
$ · budget-friendly is our editorial bracket, not a real bill. Plug in what you expect to actually spend at Maka Mia on Main.
Estimate — adjust$
Your share$13
Their share$13
Even split — modern and uncomplicated.
Hours
Mon11 AM to 8 PM
Tue11 AM to 8 PM
Wed11 AM to 8 PM
Thu11 AM to 8 PM
Fri11 AM to 8 PM
Sat11 AM to 8 PM
SunClosed
Parking
Free parking lot
Dining
Outdoor seating · Delivery · Onsite services · Takeout · Dine-in
Access
Wheelchair accessible entrance · Wheelchair accessible parking lot · Wheelchair accessible seating
Crowd
Family-friendly · Tourists
Contact
Call Site Maps
Winchester, KY
Drinks
Abettor Brewing Company
Brewery★ 4.6 · 160
LGBTQ+ friendlyWheelchair access
Find it
128 N Highland St, Winchester, KY 40391
Get there
Transit Drive Walk
Crowd read
4.6★ from 160 Google reviews
Split the bill
Price tier unlisted — plug in what you expect to spend at Abettor Brewing Company.
Estimate — adjust$
Your share$25
Their share$25
Even split — modern and uncomplicated.
Hours
Mon3 to 9 PM
Tue3 to 9 PM
Wed3 to 10 PM
Thu3 to 10 PM
Fri3 to 11 PM
Sat3 to 11 PM
Sun3 to 8 PM
Parking
Free parking lot
Access
Wheelchair accessible entrance · Wheelchair accessible parking lot · Wheelchair accessible restroom
Crowd
LGBTQ+ friendly · Transgender safespace
Contact
Call Site Maps
Winchester, KY
Dining
Regeneration Distilling Co.
Distillery★ 4.3 · 151
LGBTQ+ friendlyWheelchair access
Find it
31 E Broadway St, Winchester, KY 40391
Get there
Transit Drive Walk
Crowd read
4.3★ from 151 Google reviews
Split the bill
Price tier unlisted — plug in what you expect to spend at Regeneration Distilling Co..
Estimate — adjust$
Your share$25
Their share$25
Even split — modern and uncomplicated.
Hours
MonClosed
TueClosed
Wed11 AM to 3 PM
Thu11 AM to 3 PM
Fri11 AM to 3 PM
Sat11 AM to 3 PM
SunClosed
Access
Wheelchair accessible entrance · Wheelchair accessible parking lot · Wheelchair accessible restroom
Crowd
LGBTQ+ friendly
Contact
Call Site Maps
Winchester, KY
Drinks
Broadway Liquor and Bar
Bar★ 4.3 · 112
Wheelchair access
Find it
137 E Broadway St, Winchester, KY 40391
Get there
Transit Drive Walk
Crowd read
4.3★ from 112 Google reviews
Split the bill
Price tier unlisted — plug in what you expect to spend at Broadway Liquor and Bar.
Estimate — adjust$
Your share$25
Their share$25
Even split — modern and uncomplicated.
Hours
Mon11 AM to 11 PM
Tue11 AM to 11 PM
Wed11 AM to 11 PM
Thu11 AM to 11 PM
Fri11 AM to 1 AM
Sat11 AM to 1 AM
Sun1 to 8 PM
Parking
Free parking lot
Dining
Drive-through · Onsite services
Access
Wheelchair accessible entrance · Wheelchair accessible parking lot
Contact
Call Maps
Winchester, KY
Cafés
The Hall on Main Coffee & Cafe
Coffee shop$$$$★ 4.8 · 108
LGBTQ+ friendlyGood for groups
Find it
17 S Main St, Winchester, KY 40391
Get there
Transit Drive Walk
Crowd read
4.8★ from 108 Google reviews
Split the bill
$ · budget-friendly is our editorial bracket, not a real bill. Plug in what you expect to actually spend at The Hall on Main Coffee & Cafe.
Estimate — adjust$
Your share$13
Their share$13
Even split — modern and uncomplicated.
Hours
Mon7 AM to 3 PM
Tue7 AM to 3 PM
Wed7 AM to 3 PM
Thu7 AM to 3 PM
Fri7 AM to 3 PM
Sat8 AM to 3 PM
SunClosed
Parking
Free parking lot
Dining
Curbside pickup · Onsite services · Takeout · Dine-in
Access
Wheelchair accessible entrance · Wheelchair accessible parking lot · Wheelchair accessible restroom
Crowd
Family-friendly · Groups · LGBTQ+ friendly
Pets
Dogs allowed outside
Contact
Call Site Maps
Winchester, KY
Drinks
Harkness Edwards Vineyards
Winery★ 4.8 · 62
Wheelchair access
Find it
5199 Combs Ferry Rd, Winchester, KY 40391
Get there
Transit Drive Walk
Crowd read
4.8★ from 62 Google reviews
Split the bill
Price tier unlisted — plug in what you expect to spend at Harkness Edwards Vineyards.
Estimate — adjust$
Your share$25
Their share$25
Even split — modern and uncomplicated.
Hours
MonClosed
TueClosed
Wed12 to 6 PM
Thu12 to 6 PM
Fri12 to 8 PM
Sat12 to 6 PM
Sun1 to 6 PM
Dining
Onsite services
Access
Wheelchair accessible entrance · Wheelchair accessible parking lot
Pets
Dogs allowed inside
Contact
Call Site Maps

Winchester, KY

Winchester, KY by the numbers

Local date spots

Hall's On The River

DJ's Steakhouse Bar and Grill

Woody's Sports Bar & Grill

Waterfront Grill and Gathering

La Trattoria

Tokyo Hibachi & Sushi

Loma's

Smokin' Howards Sports Bar & Grill

The Urban Stack & Co

The Bodega "Home of The Sloppy Dogs"

Maka Mia on Main

Abettor Brewing Company

Regeneration Distilling Co.

Broadway Liquor and Bar

The Hall on Main Coffee & Cafe

Harkness Edwards Vineyards

Reach Winchester, KY singles right where they plan dates.