Downtown Winchester is a treat for amateur historians, and Main Street passes through a canyon of 19th-century storefronts.
There are more than 100 historic buildings here, as well as vintage five-globed street lamps and a long stretch of elevated sidewalk, not found anywhere else in the Commonwealth.
While the city deserves your attention, so does the countryside, with the rolling green hills and rustic stone fences typical of the Bluegrass Region.
Not far south of Winchester is where Daniel Boone founded Kentucky’s first Euro-American settlement, while the nearby Lower Howard’s Creek Nature and Heritage Preserve protects an ecologically rich river gorge.
1. Historic Downtown Winchester
The first thing to do once you arrive in downtown Winchester is simply start walking, as there’s so much to uncover.
Make sure to download the Winchester Downtown Walking Tour, which is a fantastic companion, giving background on Main Street’s development, starting at the end of the 18th century.
Main Street is still commonly known to locals as the “White Way”, which comes from the five-globed lamp posts, first installed in 1912, removed in the 1950s, and reinstated to great fanfare in 1983.
Most are replicas, but two of the lamp posts are originals, more than 110 years old. Up the slope, opposite the Clark County Courthouse (1855), is a stretch of the only elevated sidewalk in Kentucky, known as “High on Main” and full of character.
2. Bluegrass Heritage Museum
Just off Main Street, a grand Romanesque Revival building has been turned into a museum for the heritage and culture of Central Kentucky’s Bluegrass Region.
This building goes back to the end of the 19th century and housed the Guerrant Clinic for much of its history until it was abandoned in the 1980s.
Exhibits deal with a wide array of topics, like the 18th-century Native American meeting place Eskippakithiki, Daniel Boone, tobacco farming, the Civil War, the coal and lumber industries, Bluegrass music and the prized local soft drink, Ale-8-one.
As well as a room for the old Guerrant Clinic, this museum also has a host of telephone artifacts from the former Pioneer Telephone Museum, including a switchboard, a phone booth and a prototype “picture telephone”.
3. Leeds Center for the Arts
An enduring cultural treasure for Winchester, the Leeds Center of the Arts is a movie house from 1925 reborn as a performing arts stage.
The original Leeds Theater was one of the first movie theaters in Winchester, and also one of the earliest buildings in the city to have air-conditioning.
Due to declining attendance the theater closed in 1986, but was soon purchased by the Winchester Council for the Arts, returned to its 1920s appearance and reopened as a versatile performance venue.
Year round there’s a feast of musicals, dramas, live music, children’s entertainment and community events, as well as regular classic movie screenings.
4. Fort Boonesborough State Park
On April 1, 1775, the pioneer Daniel Boone and his men crossed the Kentucky River, founding Kentucky’s second European-American settlement on the bank.
Within months, Fort Boonesborough had grown to more than 25 log cabins and four blockhouses. In September 1778, the fort, with Boone’s help, withstood an attack by British-allied Native Americans in the Revolutionary War, remembered as The Great Siege.
The fort was abandoned by the 1820s and an archeological survey was made in the 1980s, identifying elements like the fortification, Boone’s initial station, tobacco warehouses and water springs.
What you’ll encounter today at Fort Boonesborough State Park is a faithful reproduction, complete with period furnishings to paint the clearest picture of the life of Pioneers in 18th-century Kentucky.
There’s also a campground (167 sites) by the river, a beach, hiking trail, bike trails and a boat launch.
Bottled in Winchester since 1926, Ale-8-One is the only soft drink to be invented in Kentucky and still be made today.
The founder, G. L. Wainscott had been in the carbonated beverage game for some time, establishing his plant on North Main Street in 1902 and launching Roxa-Kola, a Coca-Cola rival, in 1906.
As you can imagine, this led to a lawsuit, which Wainscott eventually won. But to prepare for all eventualities he went on a hunt for a new flagship flavor, leading him to Northern Europe where he came across ginger beer.
At the Clark County Fair in 1926, he launched his new drink, Ale-8-One, a ginger and citrus blend. A century later, Ale-8-One is still a family operation, now in its fourth generation and run by Wainscott’s great-great-nephew.
You can visit the modern Winchester plant for a tour, and there’s a trove of specialty items and Ale-8-One memorabilia at the store.
6. Beer Cheese Festival
Winchester is the birthplace of another Kentucky-specific delicacy, turning humble processed cheese into something exciting.
Beer cheese is a tasty spread/dip with processed cheese as a base, combined with beer, garlic and a blend of spices including cayenne pepper and mustard powder to become a delicious snack or appetizer.
The only beer cheese festival on the planet takes over downtown Winchester for one day every June bringing as many as 20,000 people.
The soul of the festival is a beer cheese competition, allowing the public to sample and vote for their favorite. As an accompaniment there’s a roster of food and craft vendors, a beer garden, children’s activities and a live music stage at the courthouse.
7. Winchester-Clark County Farmers’ Market
There’s a small but lively farmers’ market on Saturday mornings during the summer months in Winchester. This takes place in the parking lot at the foot of the curious Sphar & Co. silos.
The selection and lineup of vendors changes during the season, but at the height of summer you can expect to find garden-fresh produce like green beans, tomatoes, cucumbers, peppers and corn, all harvested locally.
Also available are free range eggs, fresh roasted coffee, cheeses, wines, honey from local hives, grass-fed non-GMO meats, teas, fresh bread and organic soaps.
8. Dirty South Pottery
This combined pottery studio and store is across Main Street from the Leeds Center for the Arts, and merits a stop.
Run by a husband and wife team, Dirty South Pottery produces a wide variety of ceramics, in particular serving dishes, cake stands and other serving-based items.
Everything sold in the store is handled, glazed and fired on-site using an electric kiln. While you shop you can also visit the back of the store, where talented artists work the wheel and create the store’s pieces before your eyes.
9. Beech Springs Farm Market
Heading out of Winchester on the Boonesboro Rd there’s a cute family-owned farm stand selling fresh fruits and vegetables.
The Beech Springs Farm Market is open April through December, and the selection changes with the season.
Think asparagus, corn, cabbage, tomatoes, peppers, zucchini and much more, as well as peaches and apples from the orchard planted behind the market back in 2007.
As well as all this great produce the store has a tempting selection of baked goods, local honey, homemade jams, jellies and other treats.
10. Lower Howard’s Creek Nature and Heritage Preserve
Close to Fort Boonesborough, this preserve is on the lower reaches of Lower Howard’s Creek, just before its mouth on the Kentucky River. Here the creek twists through a deep gorge with lofty cliffs covered with second growth forest.
Down on the valley bottoms there’s a unique ecosystem and a marvelous display of wildflowers in spring.
The creek powered a stone-milling industry in the 18th and 19th centuries, evidence for which survives at five stone buildings on the National Register of Historic Places.
Recent land purchases have increased the preserve’s area from 228 acres to 423 acres, but it’s worth checking opening times before you visit as these can be irregular.
11. Stone Fence Driving Tour
Among the sights encapsulating Kentucky’s Bluegrass Region are the quaint limestone fences marking the boundary of properties.
The skills used to construct these walls are thought to have been brought to Kentucky by Scottish immigrants in the 18th century, At that time the fences helped prevent ravenous livestock from crossing into neighboring properties to graze.
The masons who continue to build the fences have come through as much as four years of education and employ algebra, geometry and mechanical drawing in their work.
You can download a map for the Stone Fence Driving Tour, produced by the Winchester-Clark County Tourism Commission. Setting off from Main Street this will take you on a memorable journey along the area’s backroads down to the banks of the Kentucky River.
12. Harkness Edwards Vineyards
Another endearing family operation, Harkness Edwards Vineyards opened at a farm in the Kentucky River Valley in 2006.
As you would hope, the setting is nothing short of idyllic, with a tasting room in a cozy peach-painted farmhouse.
This is posted on a hilltop with green hills in the foreground and distant mountain views behind.
You can come by for a walk-in visit to taste selections such as Taste the Sun (Vidal Blanc) and Fling (semi-sweet Chardonnay), or book an experience like the Tasting & Pairing Party, for more insight into the winemaking process and flavor profiles.
13. Winchester Cemetery
This historic cemetery, established in 1854, is just a matter of minutes from downtown Winchester.
Taking a reflective stroll along Winchester Cemetery’s winding paths you’ll find out a lot about the city’s inhabitants, how they lived and how they are remembered.
The Winchester-Clark County Tourism Commission has published an in-depth brochure for a self-guided tour. This has a map, extensive biographies of noteworthy burials and even a key to the various symbols that appear on 19th-century funerary monuments.
On a painful note, the guide indicates an open space, thought to hold the unmarked graves of enslaved people, and also recounts the Pastime Theater Tragedy of 1918, caused by a wall collapse and still remembered as the “worst disaster in Winchester’s history”.
14. Legacy Grove Park
Unveiled as recently as 2018, Legacy Grove Park was a gift to the people of Winchester by the Greater Clark Foundation.
The 30-acre space is on the site of the former hospital in the west of the city, and features creative landscaping, with more than 200 trees planted in a circular pattern.
Legacy Grove Park is a joy for children in particular, with a custom-built dulcimer climber, as a tribute to this iconic stringed instrument and the famous Winchester-based dulcimer maker, Homer Ledford (1927-2006).
The children’s play area is on two whole acres, while other features include an ADA-accessible paved path and dog parks for smaller and larger dogs.
15. Lykins Park
This attractive community park is on the banks of Hoods Creek, out in the rolling hills northeast of Winchester.
Lykins Park is the largest public park in the city, and has a concert stage that hosts a succession of outdoor events in the summer.
Most notably, the park is the venue for Winchester’s fireworks on 4th of July. At other times this is a place to come and be active, with tennis courts, a basketball court, ballfield complex, a popular skate park, a playground and a walking trail.