©

Winchester trip planner

Create a fully customized
day-by-day itinerary for free

Itinerary Planner
+ Add destination
2 adults
Adults
- +
Teens
- +
Kids
- +
Close

Winchester

Trip Planner USA  /  Kentucky  /  Winchester
Winchester is a city in and the county seat of Clark County, Kentucky, United States. The population was 18,368 at the 2010 census. It is part of the Lexington-Fayette, KY Metropolitan Statistical Area.HistoryIt was named after Winchester, Virginia.GeographyWinchester is located northwest of the center of Clark County, east of Lexington and west of Mt. Sterling. Kentucky Route 1958 (Bypass Road) is an outer loop around the town. Kentucky Route 627 (Boonesborough Road) leads towards Richmond, to the south. U.S. Route 60 (Winchester-Lexington Road/Lexington Avenue) runs through downtown Winchester. Interstate 64 passes through the northern part of the city, with access from exits 94 and 96. The Mountain Parkway turns off I-64 just northeast of Winchester and leads east to Salyersville.According to the United States Census Bureau, Winchester has a total area of 20.4km2, of which 20.3km2 is land and 0.1km2, or 0.67%, is water.
Plan your trip to Winchester and other United States destinations using our handy United States driving holiday planner.
Source
Create a full itinerary — for free!

Plan your trip to Winchester

  • Get a personalized plan

    A complete day-by-day itinerary
    based on your preferences
  • Customize it

    Refine your plan. We'll find the
    best routes and schedules
  • Book it

    Choose from the best hotels
    and activities. Up to 50% off
  • Manage it

    Everything in one place.
    Everyone on the same page.

Where to stay in Winchester

Browse hotels, guesthouses, and unique homes and book your stay on the world's leading accommodation sites.
Live like a local, find unique places to stay
Millions of travel reviews on TripAdvisor

Recently planned trips to Winchester

4 days in Winchester BY A USER FROM UNITED STATES November, relaxing, historic sites, slow & easy, popular PREFERENCES: November, relaxing, historic sites ATTRACTION STYLE: Popular PACE: Slow & easy 1 day in Winchester BY A USER FROM UNITED STATES November, teens, popular PREFERENCES: November, teens ATTRACTION STYLE: Popular PACE: Medium 1 day in Winchester BY A USER FROM UNITED STATES January, popular PREFERENCES: January ATTRACTION STYLE: Popular PACE: Medium 11 days in Winchester BY A USER FROM UNITED STATES November, historic sites, wildlife, slow & easy, popular PREFERENCES: November, historic sites, wildlife ATTRACTION STYLE: Popular PACE: Slow & easy 4 days in Winchester BY A USER FROM UNITED STATES October, teens, popular PREFERENCES: October, teens ATTRACTION STYLE: Popular PACE: Medium 5 days in Campton & Winchester BY A USER FROM UNITED STATES October, outdoors, relaxing, historic sites, wildlife, slow & easy, hidden gems PREFERENCES: October, outdoors, relaxing, historic sites, wildlife ATTRACTION STYLE: Hidden gems PACE: Slow & easy 1 day in Winchester BY A USER FROM UNITED STATES December, popular PREFERENCES: December ATTRACTION STYLE: Popular PACE: Medium 4 days in Kentucky BY A USER FROM UNITED STATES October, popular PREFERENCES: October ATTRACTION STYLE: Popular PACE: Medium 2 days in Winchester BY A USER FROM UNITED STATES October, relaxing, beaches, popular PREFERENCES: October, relaxing, beaches ATTRACTION STYLE: Popular PACE: Medium 5 days in Kentucky BY A USER FROM UNITED STATES November, outdoors, relaxing, beaches, wildlife, hidden gems PREFERENCES: November, outdoors, relaxing, beaches, wildlife ATTRACTION STYLE: Hidden gems PACE: Medium 3 days in Winchester BY A USER FROM UNITED STATES October, outdoors, relaxing, romantic, wildlife, popular PREFERENCES: October, outdoors, relaxing, romantic, wildlife ATTRACTION STYLE: Popular PACE: Medium 8 days in Winchester & Hot Springs BY A USER FROM UNITED STATES September, culture, relaxing, historic sites, slow & easy, hidden gems PREFERENCES: September, culture, relaxing, historic sites ATTRACTION STYLE: Hidden gems PACE: Slow & easy
View more plans