10 Things to Do in Winchester That You Shouldn't Miss

August 2, 2017 Veronika Gaddis

Winchester is a home rule-class 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.
Restaurants in Winchester

1. Red River Gorge Geological Area

3451 Skybridge Rd, Winchester, KY 40380-7136 +1 606-663-8100
Excellent
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4.5 based on 255 reviews

Red River Gorge Geological Area

Reviewed By Gabe10101 - Lexington, Kentucky

Hiking and Camping. That's the name of the game at Red River Gorge. Oh yeah, and rock climbing. And maybe canoeing, rappelling, birdwatching? What makes "The Gorge" special are the myriad rock formations situated among mountains and streams in a dense forest. These formations include spectacular rock bridges, sheer cliffs, rock shelters, waterfalls, balanced rocks, monoliths, chimneys, a few caves, and so much more. The gorge has perhaps the densest collection of natural bridges in the world. Many are accessible by established trails and many more require determined hikes through wilderness. There is so much to see. Hikes from a few steps to dozens of miles are available. You could spend 30 days here and still not experience everything the Gorge has to offer!

Each season changes the Gorge into another destination worthy of repeat visits! Spring brings flowers and rains that swell creeks and waterfalls. Summer brings dense foliage and nice weather. Fall brings amazing colors. Winter brings frozen streams and waterfalls and the opportunity for snow hikes. Dress appropriately!

If you decide to visit (and you should!) here are a few tips:
- Visit any day, but check weather ahead of time. Roads are narrow and curvy. They become outright dangerous when icy.
- If you have only an hour when passing through, drive the loop consisting of routes 77, 715 and a little bit of 15 on either end. Stop at Ange Windows for a brief hike. You can't see much of the rock formations from the road, but the drive is still beautiful. DO NOT attempt this drive in an RV or large vehicle!
- Nada tunnel is an old railroad tunnel that is now part of the road. It is wide enough for only one car and about 300 feet long. Use common sense when traversing the tunnel. Turn on your lights and don't enter if another car is coming toward you. Be prepared to reverse out of the tunnel. If you can drive in reverse, have someone else drive.
- Fuel and food are available at the Slade exit from the Mountain Parkway. That's the North entrance into the Gorge.
- Parking is extremely limited in the Gorge. Many people park along the road in short pull-offs. Get there early or you may not find parking, especially on weekends.
- Plan ahead. Read trail sites for maps and recommendations. Some trails are not marked. Getting lost is common. Fortunately, if you have a good sense of direction, bushwhacking back to your car is a common activity in the Gorge!
- Some trails require stream crossings, so be prepared to get wet or muddy after rains.
- Definitely bring a GPS. Also bring water and snacks even if you plan a short hike. Bring binoculars, and especially a flashlight to peer into caves and help you get out if you are lost past dark.
- Speaking of dark, start early especially in the winter. Getting lost in the dark is no fun.
- Rock Bridge, near the South (Beattyville) entrance is a great place to start exploring the Gorge.
- Vehicle and Camping permits ($5) are necessary for overnight camping, but not for day hikes.
- Wildlife is scarce. Snakes are present, but stay away from trails. I don't think anyone has ever been bitten by a snake in the Gorge.
- Winter hiking is spectacular. Streams and waterfalls freeze if the temperature is sub-freezing for several days. Copperas Falls is a highlight in any season, but winter is especially spectacular. Check out the photos. But if the temperature is near freezing, mud will make your visit unpleasant and perhaps dangerous.

2. Daniel Boone National Forest

Winchester, KY 40376 +1 859-745-3100
Excellent
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4.5 based on 74 reviews

Daniel Boone National Forest

Boat, fish, hike and hunt to your heart's content in this scenic national forest.

Reviewed By Ann M - McMinnville, Tennessee

I visited in the winter. I would love to return in the other seasons and experience all this National Forest has to offer. Lots of things to do and see. Could use a few more trail markers.

3. Bluegrass Heritage Museum

217 S Main St, Winchester, KY 40391-2455 +1 859-745-1358
Excellent
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5 based on 21 reviews

Bluegrass Heritage Museum

Reviewed By Vicki G - Winchester, Kentucky

The museum is housed in an old hospital and has a variety of antique items on display. The surgical instruments from the early 1900's and other medical equipment fill the rooms. There is also a small gift shop where you can get relevant souvenirs. I really enjoyed my time there.

4. Lower Howard's Creek Nature and Heritage Preserve

1945 Athens Boonesboro Rd, Winchester, KY 40391-9287 +1 859-744-4888
Excellent
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5 based on 9 reviews

Lower Howard's Creek Nature and Heritage Preserve

Reviewed By Gabe10101 - Lexington, Kentucky

Wow, what an amazing place Lower Howard's Creek Nature and Heritage Preserve turned out to be. Check out the pictures! We were a little skeptical since many nature trail in central Kentucky, while nice for a locals, aren't worth the drive for anyone more than an hour away. This one is the best of the bunch! Details and suggestions:

- The entrance is in the parking lot of "Hall's on the River" restaurant. There is a large sign and maps are available at the trailhead. If you're not sure where to park, ask inside the restaurant. Be courteous to this business and it's patrons so we don't have conflicts that limit parking and access. Why not have a meal at Hall's after your hike?
- The complete trail is about 1.5 miles each way. There is a road at the far end, but no parking. You could arrange to have someone pick you up at the end if you don't want to walk back.
- The trails are dirt with some improvements, but they will be muddy after rain. Elevation changes are mild, but steep in a few places.
- Trails are not handicap accessible.
- Speaking of rain, check ahead after heavy rain because the trails could become flooded. Don't cross fast-flowing streams!
- You can walk through the creek most of the time so consider shoes that can get wet.
- Most of the trail is shaded by vegetation. Sunscreen shouldn't be necessary.
- The trail passes ruins of several homes and buildings. Really neat, but some are enclosed in chain link fencing, which prevents good pictures, but is necessary to prevent vandalism, I suppose.
- The waterfalls are officially "Off Limits". Hopefully the preserve will be expanded some day because they are truly wonderful to view along the first small tributary to the right about a quarter mile from the trailhead.
- The water and shade makes for a cool hike on a hot day. Enjoy!
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5. Winchester Peddlers Mall

110 Shoppers Village Plz, Winchester, KY 40391-1030 +1 859-737-2700
Excellent
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4 based on 19 reviews

Winchester Peddlers Mall

Peddlers Mall stores are located throughout Kentucky, and well known within the Antique & Collectible community. In 2013 we expanded to Ohio opening our first store in Lebanon, a northern suburb of Cincinnati. Peddlers Mall will open additional stores as we expand our footprint throughout the Ohio region in 2014-2015.

Reviewed By informer1955 - ky

Large flea mall lots of everything been there many times from antiques to new junk worst thing is the old smell it's the same in all these placesThanks for the review! We have definitely smelled some oldies but goodies ;)) hope you come back to visit us again soon.

6. Clark County Public Library

370 S Burns Ave, Winchester, KY 40391-1876 +1 859-744-5661
Excellent
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4.5 based on 3 reviews

Clark County Public Library

Reviewed By Dodd D - Winchester, Kentucky

I just love this place. It adds such value to the community. The staff is always so friendly and helpful. So appreciative of the wide selection. I just checked out a book on ancient Egyptian short stories. How cool is that? I doubt that if I had gone to a bookstore I would have come away with a similar title. Best thing is that it was free and they have extended the checkout time to allow busy readers more time to read their selections. If they don't have the book that you are looking for then they will attempt to locate it on interlibrary loan or just purchase it for yours and others use at the library.

7. Historic Downtown Winchester

Winchester, KY 40391
Excellent
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4 based on 8 reviews

Historic Downtown Winchester

Historic Winchester was placed on the National Register of Historic Places in 1981. The business district looks much as it did over a hundred years ago with the five globe lampposts and elevated sidewalk. Downtown is filled with quaint shops, wonderful restaurants and charming character. Enjoy a tour at your own pace. Stop by 2 Sotu Maple for a brochure with a map.

Reviewed By Vicki G - Winchester, Kentucky

Historic Downtown Winchester is a vibrant and active place. The people of the town come together for festivals, family events and specialized shows of antique cars, along with parades. There are many different events that cater to visitors walking and visiting the shops along Main Street. With wine tastings and holiday open houses and decorations.
There is something going on so often. Some nights there are family movie nights, and family style dancing.

There are some amazing antique shops, art galleries, restaurants and specialty shops. It is nice to walk the lovely shops. The evenings are usually cooler and comfortable to stroll in.

8. Clark Mansion aka Holly Rood

28 Beckner St, Winchester, KY 40391-1810
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4.5 based on 2 reviews

Built in 1814 by James Clark, 13th Governor of Kentucky, the house follows the simple lines of Federal style architecture. Tours by appointment.

Reviewed By Brad W - Winchester, Kentucky

Holly Rood is a required trip for local school kids. The home is pretty, and steeped in history, but definitely doesn't make for a long visit. Not worth a trip specifically for this attraction, but worth killing an hour if you're in the area.

9. Leeds Center for the Arts

37 N Main St, Winchester, KY 40391-2605 +1 859-744-6437
Excellent
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4.5 based on 2 reviews

Built in 1925 and refurbished in the mid-1980’s, the theater offers cultural and community events including plays, musicals, concerts, classes, seminars and children’s programming.

Reviewed By LindaKay1959 - Louisville, Kentucky

Leeds is a grand historic theater. Growing up Terry spent a lot of time in Winchester at his grandmothers house which was just down the street from the Theater. So to see the theater restored to its original state was such a thrill for him.
The theater was very clean, refreshments were very affordable- bottle of water, bottle of Ale 8 (drink Winchester is known for) and popcorn totaled $3.00
Winchester is a charming country town, located close to Lexington. It is always an enjoyable place to visit as everyone is very cordial.

10. Scenes from the Kentucky River Mural

1240 Ford Road, Winchester, KY 40391 +1 859-744-0556
Excellent
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4.5 based on 2 reviews

Scenes from the Kentucky River Mural

Among the many reasons to visit the Civil War fort at Boonesboro is the impressive mural adjacent to the parking lot. The mural’s 12 colorful panels illustrate significant eras and events in the history of the area, including the era of Native Americans, Clark County’s first church, and commerce and industry through the centuries.

Reviewed By Carey I

My boys and I go here often. This is a short hike uphill and at the top there is a beautiful view and a canon. Along the way there our signs that tells about the history of the trail. The rock wall along the way is beautiful also. I wouldn't recommend going into the bathrooms at the top of the hill if they are unlocked, because there are wasp nests everywhere.

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