PYRTPlan Your Road Trips
Create TripMy TripsCommunityMerchandise
PYRTPlan Your Road Trips
Create TripMy TripsCommunityMerchandise
W
Destinations
Home›Destinations›Winchester
North AmericaUnited StatesKentucky

Winchester

Kentucky, United States · North America

About Winchester

Winchester sits on the route: 25 minutes from Mount Sterling, 53km from Red River Gorge.

Winchester is a town located in Kentucky, United States. With a population of 18,446, it is an important destination in North America.

On a road trip, Winchester sits in United States, where you drive on the right. It's in the America/New York time zone. Below you'll find where to stay, things to do nearby, and everything you need to add Winchester to your route.

About Winchester

The William Hickman House located at 31 West Hickman Street, is a brick house in Winchester, the county seat of Clark County, Kentucky. It was listed on the National Register of Historic Places in 1982. Its brick on the west facade is laid in Flemish bond; it is common bond elsewhere. Built by John Couchman in 1814,

Read more it was originally intended to be a tavern, but before he opened it, it was bought by local cabinet maker William Hickman. Six generations of Hickmans lived in the house, which remained a residence until it was bought by the Clark County Bank in 1982. In 1990 it was bought by Dykeman & Rosenthal, a law firm in Winchester.

Read more on Wikipedia

Where to Stay in Winchester

Compare prices across Booking.com, Airbnb, Expedia, and more. Select your dates to see availability.

Filter presets

Pick your must-haves once: provider links open pre-filtered. Each filter lists which sites it applies to.

Booking.comExpediaTripAdvisorHotels.comAgodaAirbnb

Compare before you book!

Prices can vary significantly between platforms. We recommend checking at least 2-3 sites to find the best deal for your stay in Winchester.

Explore the Area

Discover famous landmarks, scenic roads, and more near Winchester.

Loading map...
Open in Google Maps

Frequently Asked Questions

What are the best things to do in Winchester?

Winchester offers many attractions including tourist sites, museums, parks, and local restaurants. Explore famous landmarks, scenic roads, and natural wonders on our interactive map and plan your visit.

How do I plan a road trip to Winchester?

Plan your road trip to Winchester with Plan Your Road Trips! Add Winchester as a destination, and we'll help you find the best route and discover more amazing places along the way.

Where is Winchester located?

Winchester is located in Kentucky, United States, North America. The coordinates are 37.9901 latitude, -84.1796 longitude.

What is the population of Winchester?

Winchester has a population of approximately 18,446 people, making it a town in United States.

Plan a Road Trip

Add to your itinerary

Start planning your road trip with Winchester as a destination. Create a custom route and discover more amazing places along the way.

Start Road Trip

What's Nearby?

Discover destinations like Tinder

Swipe through stunning destinations near Winchester. Save your favourites and add them to your trip.

Explore now

Quick Information

Population
18,446
Continent
North America
Country
United States
Region
Kentucky
Timezone
America/New_York
Coordinates
37.9901, -84.1796

Emergency & Services

Essential numbers in United States

Police
911
Ambulance
911
Fire
911
Driving side
right

AAA roadside assistance: 1-800-222-4357. Right turn on red is legal in most states unless signed otherwise.

Full driving guide for United States

Tags

North AmericaUnited StatesKentuckyTown

Worth the detour from Winchester

1 notable place within an hour's drive.

natural wonder

Red River Gorge

A rugged canyon system in eastern Kentucky's Daniel Boone National Forest, renowned for its natural stone arches and world-class rock climbing.

53 km · about 60 min drive

Driving roads near Winchester

  • 71 kmKentucky Bourbon TrailA celebrated driving route through the bluegrass region connecting the state's premier bourbon distilleries, from Maker's Mark to Woodford Reserve.

Nearby Destinations

Other places to explore near Winchester.

Mount Sterling

🇺🇸 United States

22 km awayPop. 7,208

Paris

🇺🇸 United States

25 km awayPop. 9,870

Lexington-Fayette

🇺🇸 United States

25 km awayPop. 314,488

Camargo

🇺🇸 United States

26 km awayPop. 1,124

Lexington

🇺🇸 United States

26 km awayPop. 320,347

Clay City

🇺🇸 United States

27 km awayPop. 1,095

Mount Vernon

🇺🇸 United States

28 km awayPop. 2,583

Richmond

🇺🇸 United States

29 km awayPop. 33,533

Plan a trip around Winchester

North America road trip planner

Plan a Road Trip from Winchester

Create your perfect itinerary with our calendar-based planner. Add stops, discover attractions along the way, and share your trip with friends.

Start Planning
PYRT

The ultimate road trip planning platform. Discover 150,000+ destinations worldwide, plan scenic routes, and create unforgettable adventures.

Inspiration

  • Discover Trips
  • Travel Guides
  • Community

The Product

  • Calendar Planner
  • Integrations
  • How It Works
  • Collaboration Mode
  • Get the App
  • Merchandise: PYRT Supply Co.
  • Become a Creator
  • Trip Marketplace

Plan Your Trip

  • Road Trip Planner
  • Famous Routes
  • Planners by Country
  • Best Road Trip Planner App
  • Discover Road Trips
  • Events
  • Travel Guides
  • How It Works
  • My Trips
  • Community Groups

Company

  • Terms of Service
  • Privacy Policy
  • Support
  • Contact Us
  • Sign In
  • Create Account

© 2026 Plan Your Road Trips. All rights reserved.

•[email protected]
Data sources:GeoNames (CC BY 4.0)•Wikimedia Commons (CC BY-SA)•Mapbox•Photography: George Lawrence