Places in Winchester
Antiques, Main Street & more in Winchester
1,277 places in Winchester: 142 places to eat and drink, 137 shops, 65 things to do and 12 places to stay. Local spots first, with directions to every one.
All places
1,277
66 per 1,000 residents
Eat & drink
142
7.4 per 1,000 residents
Shops
137
26 gifts · 14 antiques · 5 books
Things to do
65
18 outdoors · 10 arts · 12 landmarks
Places to stay
12
0.6 per 1,000 residents
What kind of places does Winchester have?
Read from every listing. The page puts what stands out first.
The map
Where Winchester gathers
263 of Winchester’s 1,277 places sit within a five-minute walk of S Main St. A second center gathers around Bypass Rd.
263places in a five-minute walk of S Main St21% of Winchester’s places
138around Bypass Rd11% of Winchester’s places
★ What stands out · Shops
See all →137 shops
26 gifts & boutiques, 16 home & hardware, 14 antiques & vintage. Local spots first.
Eat & drink
See all →142 places to eat & drink
100 restaurants, 26 cafés & treats, 10 bars & breweries. Local spots first.
See all 100 restaurants →
Puerta Grande- Winchester
Bar and grill restaurant · 120 April Way
Woody's Sports Bar & Grill
Bar and grill restaurant · 923 Bypass Rd
Things to do
See all →65 things to do
25 fitness & sports, 18 parks & outdoors, 12 history & landmarks. Local spots first.
Sheltowee Trace National Recreation Trail
Active life · 1700 Bypass Rd
Fifth Element Brazilian Jiu Jitsu
Martial arts club · 16 N Main St
Man-O-War Apartments
Landmark and historical building · 707 W Lexington Ave
Oliver School Apartments
Landmark and historical building · 30 Oliver St
Winchester Hills Apartments
Landmark and historical building · 200 Hubbard Rd
Hillcrest Manor Apartments
Landmark and historical building · 260 Oxford Dr
Createdbyyou Ceramic-Studio
Arts and entertainment · 36 N Highland St
Leeds Center For The Arts
Theaters and performance venues · 37 S Main St
Places to stay
See all →12 places to stay
12 hotels & inns. Local spots first.
Everyday
See all →768 errands & services
Groceries, gas, the barber, the vet, the bank.
Health care 174First Care Urgent Care · Dr. Ronald B. Snowden · Winchester ChiropracticOffices & pros 110White, McCann & Stewart · Kentucky Custom Screen Printing · Infiltrator Water Technologies - Winchester, KYAuto & gas 98NAPA Auto Parts · Speedway · SpeedwayBanks & insurance 83Williams Agency Inc · Kentucky Farm Bureau Insurance · TruistHome services 80Contech Construction Products Inc. · Keith P. Clark and Son Funeral Home · Haggard Septic SolutionsHair & beauty 54Luxe Med Spa · SmartStyle · Ultimate Massage and Wellness SpaGroceries & convenience 26Full Circle Market · Hickman Street Grocery · South Main GroceryPets 11A Diamond In the Ruff · Aristocatic Maine Coons · Boonesboro Animal ClinicOther services 132Kentucky Orthopaedics & Spine · Rowland Arts Center · Winchester Municipal Utilities
Community
See all →153 schools, churches & public places
Where Winchester learns, worships and gets things done.
Places of worship 57First Baptist Church · Grace Bible Academy · First Church of GodSchools & childcare 37Calvary Christian School · Clark County Public Schools · Conkwright Elementary SchoolTown & public services 32Clark County Public Library · Clark County Circuit Court Clerk · Clark County Health DepartmentCommunity groups 27Goodwill Kentucky · Winchester Country Club · Clark County Community Services
Talk & tips
Favorites, openings and closings from Winchester neighbors.
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Is Golden Corral the best place to eat in Winchester?
Your answer becomes a post in Town Square.
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Some place details from Overture Maps (CDLA-Permissive-2.0), checked against the Census town line. Places added by neighbors go live once a second neighbor confirms them. Spot a mistake? Open the place and tap Edit mode.
How we sort and count
Each list puts neighbor favorites first (ratings and photos), then the most complete listings (a website, a phone number, a note), with local, independent spots ahead of national chains. Categories come from each place’s map category, so a café filed under “Shops” still shows up with the cafés. “A five-minute walk” is a quarter mile from the busiest spot on the map. Per-1,000 figures use the Census population.