Top 15 Must-Do Activities in Winchester, KY

This city, situated east of Lexington, serves as the gateway to Eastern Kentucky’s Mountains and is also famed for delicacies such as beer cheese and the distinctive soft drink, Ale-8-One.

Downtown Winchester offers a captivating experience for history enthusiasts, with Main Street lined by an array of 19th-century storefronts.

This area boasts over 100 historic structures, vintage five-globed street lights, and a unique extended elevated sidewalk, features that are unparalleled in the Commonwealth.

While the city merits your exploration, the surrounding countryside also captivates, characterized by rolling green hills and rustic stone fences typical of the Bluegrass Region.

Located just south of Winchester is the site where Daniel Boone established Kentucky’s first Euro-American settlement, while the adjacent Lower Howard’s Creek Nature and Heritage Preserve safeguards an ecologically diverse river gorge.

1. Historic Downtown Winchester

Upon your arrival in downtown Winchester, the most rewarding undertaking is to simply begin exploring on foot, as there is a wealth of discoveries to be made.

It is advisable to obtain the Winchester Downtown Walking Tour guide, which offers valuable insights into the development of Main Street beginning in the late 18th century.

Often referred to locally as the “White Way,” Main Street derives its name from the five-globed lamp posts, originally installed in 1912, removed in the 1950s, and celebrated upon their reinstatement in 1983.

While most of the posts are replicas, two authentically original models exceeding 110 years in age still stand. Ascending the slope opposite the Clark County Courthouse (1855) reveals a stretch of Kentucky’s only elevated sidewalk, known as “High on Main,” showcasing distinctive character.

2. Bluegrass Heritage Museum

Situated just off Main Street, a grand Romanesque Revival building has been transformed into a museum dedicated to the heritage and culture of Central Kentucky’s Bluegrass Region.

This structure dates back to the late 19th century, having served as the Guerrant Clinic for a significant portion of its history until it was deserted in the 1980s.

The exhibits cover a broad spectrum of topics, including the 18th-century Native American meeting place Eskippakithiki, Daniel Boone, tobacco agriculture, the Civil War, the coal and lumber industries, Bluegrass music, and the esteemed local soft drink, Ale-8-One.

In addition to a room that showcases the historical Guerrant Clinic, this museum houses a variety of telephone artifacts from the former Pioneer Telephone Museum, which includes a switchboard, a phone booth, and a prototype “picture telephone.”

3. Leeds Center for the Arts

A cherished cultural asset in Winchester, the Leeds Center for the Arts began its life as a movie theater in 1925 and has since transformed into a performing arts venue.

Originally, the Leeds Theater was among the first cinemas in Winchester, notable for being one of the earliest buildings to feature air-conditioning.

After facing declining attendance, the theater closed in 1986, but it was acquired shortly thereafter by the Winchester Council for the Arts, restored to reflect its 1920s style and reopened as a multifunctional performance space.

Throughout the year, a rich array of musicals, dramas, live music, children’s entertainment, and community events are scheduled, along with regular classic film screenings.

4. Fort Boonesborough State Park

On April 1, 1775, the pioneer Daniel Boone and his team traversed the Kentucky River, founding the second European American settlement in Kentucky along its banks.

Within a few months, Fort Boonesborough expanded to include over 25 log cabins and four blockhouses. In September 1778, with Boone’s assistance, the fort successfully defended against an assault by British-allied Native Americans during the Revolutionary War, a historic event known as The Great Siege.

The fort fell into disuse by the 1820s and underwent an archaeological survey in the 1980s, which revealed significant structures including fortifications, Boone’s initial station, tobacco warehouses, and water springs.

Today, visitors to Fort Boonesborough State Park can experience a meticulously crafted replica, complete with period-appropriate furnishings, providing a vivid depiction of pioneer life in 18th-century Kentucky.

There is also a campground (167 sites) adjacent to the river, a beach, hiking trails, bike paths, and a boat launch.

5. Ale-8-One

Since 1926, Ale-8-One has been bottled in Winchester and is recognized as the sole soft drink invented in Kentucky that remains in production today.

Its creator, G. L. Wainscott, had prior experience in the carbonated beverage industry, establishing his facility on North Main Street in 1902 and launching Roxa-Kola in 1906 to compete with Coca-Cola.

This endeavor resulted in a lawsuit, which Wainscott ultimately won. However, in preparation for any eventualities, he sought a new flagship flavor, leading him to Northern Europe where he encountered ginger beer.

At the 1926 Clark County Fair, he debuted his innovative drink, Ale-8-One, a unique fusion of ginger and citrus flavors. Over a century later, Ale-8-One remains a family-owned operation, now in its fourth generation under the management of Wainscott’s great-great-nephew.

Visitors can explore the contemporary Winchester plant for tours, and the store offers a diverse collection of specialty items and Ale-8-One memorabilia.

6. Beer Cheese Festival

Winchester is recognized as the birthplace of another unique Kentucky delicacy, turning simple processed cheese into a delightful specialty.

Beer cheese is an appealing spread or dip made from processed cheese, complemented by beer, garlic, and a blend of spices including cayenne pepper and mustard powder, creating a delicious snack or appetizer.

The singular beer cheese festival globally takes over downtown Winchester for one day every June, attracting up to 20,000 attendees.

The heart of the festival is a beer cheese contest that allows the public to sample and vote for their preferred entries. Complementing this event, there is a variety of food and craft vendors, a beer garden, activities for children, and a live music stage located at the courthouse.

7. Winchester-Clark County Farmers’ Market

A small yet vibrant farmers’ market convenes on Saturday mornings during the summer months in Winchester, held in the parking lot at the base of the intriguing Sphar & Co. silos.

The assortment of vendors is dynamic throughout the season, but at the peak of summer, one can expect an abundance of fresh produce including green beans, tomatoes, cucumbers, peppers, and corn, all sourced locally.

Additionally, the market features free-range eggs, freshly roasted coffee, cheeses, wines, local honey, grass-fed non-GMO meats, teas, artisan bread, and organic soaps.

8. Dirty South Pottery

This pottery studio and retail establishment is located directly across Main Street from the Leeds Center for the Arts and is definitely worth a visit.

Operated by a husband and wife duo, Dirty South Pottery offers an extensive range of ceramics, with special emphasis on serving dishes, cake stands, and similar items.

All products available in the store are crafted, glazed, and fired on-site using an electric kiln. Customers can also observe talented artisans at work in the back of the store as they shape and create the pieces right before your eyes.

9. Beech Springs Farm Market

Situated along Boonesboro Rd just outside Winchester, this charming family-operated farm stand offers fresh fruits and vegetables.

Open from April through December, Beech Springs Farm Market provides a selection that varies with the seasons.

Anticipate finding asparagus, corn, cabbage, tomatoes, peppers, zucchini, and a range of other produce, as well as peaches and apples from the orchard planted behind the market in 2007.

In addition to fresh produce, the store features an enticing array of baked goods, local honey, homemade jams, jellies, and various other treats.

10. Lower Howard’s Creek Nature and Heritage Preserve

Located near Fort Boonesborough, this preserve encompasses the lower reaches of Lower Howard’s Creek, just upstream from its confluence with the Kentucky River. Here, the creek meanders through a deep gorge, flanked by towering cliffs draped in second-growth forest.

The valley bottoms provide a unique ecosystem featuring a stunning display of wildflowers in the spring.

This creek historically supported a stone milling industry during the 18th and 19th centuries, with lasting evidence present in five stone buildings registered on the National Register of Historic Places.

Recent acquisitions have expanded the preserve from 228 acres to 423 acres; however, it is advisable to verify opening hours before planning your visit, as they can be irregular.

11. Stone Fence Driving Tour

Among the picturesque scenes that characterize Kentucky’s Bluegrass Region are the charming limestone fences that define property boundaries.

The techniques employed in erecting these walls are believed to have been introduced to Kentucky by Scottish immigrants in the 18th century. At that time, the fences provided a means to protect crops from hungry livestock from neighboring farms.

Modern masons who construct these fences undergo extensive training, often completing up to four years of education and applying principles of algebra, geometry, and mechanical drawing in their craft.

You can access a downloadable map for the Stone Fence Driving Tour produced by the Winchester-Clark County Tourism Commission, which begins at Main Street and leads you on an unforgettable journey through the area’s backroads and down to the banks of the Kentucky River.

12. Harkness Edwards Vineyards

A family-owned vineyard, Harkness Edwards Vineyards opened its doors in 2006 at a picturesque location in the Kentucky River Valley.

As expected, the scenery is idyllic, featuring a tasting room within a cozy peach-colored farmhouse.

This establishment is set on a hilltop, offering views of verdant hills in the foreground, complemented by distant mountain vistas.

Guests are welcome for walk-in tastings, featuring selections such as Taste the Sun (Vidal Blanc) and Fling (semi-sweet Chardonnay), or can take part in experiences like the Tasting & Pairing Party for a deeper understanding of the winemaking process and flavor nuances.

13. Winchester Cemetery

This historic cemetery, established in 1854, is located mere minutes from downtown Winchester.

A reflective walk along the winding paths of Winchester Cemetery reveals much about the city’s residents, their lives, and their legacies.

The Winchester-Clark County Tourism Commission has produced a comprehensive brochure for a self-guided tour, including a map, detailed biographies of notable burials, and explanations of the various symbols found on 19th-century gravestones.

Notably, the guide points out an area believed to hold the unmarked graves of enslaved individuals and recounts the tragic Pastime Theater Tragedy of 1918, a wall collapse that remains etched in memory as the “worst disaster in Winchester’s history.”

14. Legacy Grove Park

Inaugurated in 2018, Legacy Grove Park represents a gift to the residents of Winchester from the Greater Clark Foundation.

This 30-acre space occupies the site of the former hospital in the western part of the city and features innovative landscaping, including the planting of over 200 trees arranged in a circular layout.

Legacy Grove Park is particularly enjoyable for children, featuring a custom-built dulcimer climber that pays homage to this iconic stringed instrument and the renowned Winchester-based dulcimer creator, Homer Ledford (1927-2006).

Spanning two acres, the children’s play area includes various amenities, and the park also boasts an ADA-accessible paved path along with designated dog parks for smaller and larger dogs.

15. Lykins Park

Located alongside Hoods Creek, Lykins Park is the largest public park in the city, nestled amidst the rolling hills to the northeast of Winchester.

This inviting community park features a concert stage that hosts a variety of outdoor events during the summer.

Significantly, the park serves as the venue for Winchester’s 4th of July fireworks display. Additionally, it offers opportunities for outdoor activities, including tennis courts, a basketball court, a ballfield complex, a popular skate park, a playground, and a walking trail.