The 44th Annual Daniel Boone Pioneer Festival takes place in downtown Winchester on Labor Day Weekend, September 2 and 3, kicking off on Friday, Sept. 1, with an evening street dance—also downtown.

If you’ve attended past festivals, you already know how much fun the festival is with live music, handmade arts and crafts, a huge variety of festival foodie faves and lots of family fun . . . but there might be a few things you didn’t know. Read on!

1. It’s been around, and bounced around

The festival has been around since the first Susan B. Anthony coin was minted in the U.S. (representing the first time a woman appeared on a U.S. circulating coin) and the last iconic Volkswagen Beetle was manufactured in Germany.

Founded in 1978 by the Winchester Art Guild, the festival began as a way for local artisans to display and sell their handicrafts. In those early years, the festival was held on the steps of the Clark County Courthouse.

In the 1980s, as the number of attendees swelled, the festival was moved to College Park. Since both Mother Nature and world events seemed to conspire against it in that location—the former in the way of rain and mud, the latter in a global pandemic—the festival was moved again in 2019 . . . back to downtown where it has settled in very nicely along Main Street.

2. Festival admission is free

Yes, free. And it always has been.

3. 150+ tents mean a HUGE variety of arts, crafts, foods and fun

Booths, booths and more booths—lining downtown Winchester as far as the eye can see and filled with all sorts of goodies: pottery, ceramics, art, jewelry, body products (lotions, beard oils, soaps, more), bourbon barrel items, t-shirts, seasonal décor, gourd art, macrame, Shaker-style brooms and boxes, leather items, wood puzzles, painted rocks, heirloom children’s clothes, quilts, and other art and handicraft items; country ham sandwiches, steakbombs, blooming onions, pork rinds, hand-dipped corndogs, pulled pork cheese fries, famous crack chicken, fried Oreos, funnel cakes, ice cream, iced coffee, shaved ice, bubble tea and so. much. more. Find your favorite Winchester artists and vendors as well as those from all over Kentucky and from Ohio, Tennessee and Georgia, too.

4. New community gallery space opens during the festival

The Gallery Above, a free community space, presents the “Minds of Many,” a showing of more than 70 artists from the Winchester community. The multimedia event, held in the historic McEldowney Building at 5 Cleveland Avenue, will open its doors 10 a.m.-6 p.m. Saturday and Sunday during the festival, with the exhibition running through October 2023.

“Come celebrate the arts with us,” said Adam Kidd, co-director of the project goaled to make art accessible to the public. “The space will soon be accessible for artists to use and facilitate their own gallery shows.”

5. “Neon Hallelujah” artist headlines

Saturday evening’s headlining performer, county music star JD Shelburne, is excited to come to Winchester, the place Daniel Boone described, from atop Pilot Knob, as seeing “with pleasure the beautiful level of Kentucke.”

“Growing up in Kentucky and from playing on traveling sports teams across the Commonwealth to now touring full time—and getting to play hundreds of small towns across the Bluegrass— you can say I have seen my fair share of what makes Kentucky special and enriched in beauty,” said Shelburne.

Shelburne grew up about 75 miles west of Winchester, on a tobacco farm in Taylorsville, KY.

“A 120-acre family farm has been in my family for over 100 years, and one day it will be passed down to my brother and me,” said Shelburne. “Every inch of that land I grew up on runs through every single song I have ever recorded. I am proud of that and my heritage.”

6. 10:50 arrival . . . is that early, late? Nope! It’s right on time – here’s why

Winchester’s own 10:50 ARRIVAL trio is performing during Friday evening’s street dance, 7-9 p.m. Why 10:50? That is the time Gabriel, daughter of husband-and-wife harmonizers, David and Rebecca Jensen, arrived on scene, aka was born. Originally from Washington State, the family moved to Kentucky in 2020 to create beautiful music together.

“We enjoy playing music and singing together,” said David Jensen. “We have enjoyed Kentucky so far and have met so many nice people.”

Give a listen here, then plan to bust a move to 10:50 ARRIVAL’s tunes on Friday, Sept. 1.

7. Festival walk is for the dogs

The 2023 “Walk with Friends” is a fundraising event to support/raise funds for the Clark County Animal Shelter. The walk, hosted by the George Rogers Clark cheerleading squad, will begin at 8 a.m. on Saturday, Sept. 2, at 303 Hickman Street (at Lincoln Street). A small portion of the proceeds may go to walk organizer, GRC Cheerleading, and to GRC Girls Golf.

The Clark County Animal Shelter strives to lower the number of unwanted and abandoned animals in our community. It also strives to adopt all of its animals and works very closely with rescue groups and other organizations to ensure our animals are placed in the best homes possible.

Built originally as a single-screen movie house in 1925, the Leeds Center for the Arts is today a restored and timeless treasure sharing the arts with the community through musical and drama performances, live music and occasional films and comedy.

The upcoming 2023/2024 season promises to be as exciting and entertaining as ever. It opens Aug. 11 with Matilda the Musical, which runs through Aug. 27, and is followed by Singin’ in the Rain JR (Nov. 10-19) and The 25th Annual Putnam County Spelling Bee (Feb. 23-March 3), closing with The Three Musketeers (May 3-12).

The Leeds’ fundraising event, the inaugural “Main Event,” will take place on Saturday, Sept. 23, and feature an evening of performance from favorite area actors and singers, as well as cameo appearances from Winchester celebrities and special deals with downtown restaurants. During the month leading up tothe event, Winchester’s Main Street will be transformed into a gallery of donated silent auction artwork with proceeds split between the theater and contributing artists.

On Tuesday, Aug. 22, a reception will be held at the Leeds beginning at 7 p.m. to unveil the biddable artwork. Following the reception, the artworks will hang in participating Winchester businesses from Wednesday, Aug. 23 through Saturday, Sept. 23.

Bo List, Leeds’ director of development and an award-winning educator, playwright and theatre director, shared insights about the theater, its upcoming season and the creative team’s dream productions.

Q: What is a little-known fact about the Leeds Center for the Arts that may surprise people?

A: We’re one year older than Ale-8-One (founded in 1926) and we’re figuring out howto celebrate our 100th anniversary. We are talking about it now—and we’ll be ready to go with a good party.

Q: Can you share a bit about the process of what goes into choosing productions?

A: It all starts with figuring out what productions we want. We look at what others are doing, what works and what doesn’t in Winchester, what our audience wants to see, and what they’d love to see if they knew it was out there.

Q: How many shows are selected each year?

We select four to five shows. We want children andfamilies to come together throughout the year and we want to give adults something to see, so our balance reflects the diversity of programming we try to present.

Q: How do you determine the order for the shows?

The season should open with a bang and this year, that’s Matilda. We’ll save our non-musical production for the spring—that’s when we want something fun and different, something with more grown-up appeal. That’s The Three Musketeers. Plus, one show for young performers only, and a less-familiar musical. We fill in the gaps in between with concerts and other events—anything we can do to bring people together.

Q: What is your favorite show?

A: A favorite show I love that I worked on and had the best effect on the audience is Parade.(Parade is the Tony Award-winning musical that tells the true story of Leo Frank’s wrongful arrest for the murder of a girl near Atlanta, GA, in 1913). I was part of the producing team for the Chicago premiere of that show. The audience was blown away.

Q: What are some dream productions the Leeds’ creative team would love to bring to the stage?

A: The musicals, Chicago, Hair and Cabaret, which all contain very mature content, and 42nd Street, which requires expert tap dancers. We’re not quite ready for these shows yet, but they feature prominently in our daydreams about what kind of work we’d like to share with our audience!

Q: Why is now a great time to support local arts organizations?

A: These organizations tend to suffer first when there’s a crisis, like the pandemic, and are the slowest to recover. The Leeds has been very fortunate. We were hit hard, but we have a loyal fan base and donors. I wish everyone knew that when they sign up to volunteer, make a donation or buy a ticket to the theater—these wonderful treasures that exist in their towns and cities—they’re making a very strong investment in the quality of life in their community. They’re not just sharing some time: They’re giving something important to everyone.

For information about or tickets to the Leeds Center for the Arts’ 2023/2034 productions, including the inaugural fundraising event, “Main Event,” visit www.leedscenter.org or call 859-749-2754.

How to family fun in Winchester

That family that plays together . . . well, you know the rest. Winchester has lots of ways for families to play, stay and spend the day together. Here are nine of them:

Paint together

Rainy day fun is hands-on fun at Created By You, Winchester’s professional ceramic studio. Choose a piece of pottery and spend a pleasant morning or afternoon painting your own designs—and creating family memories. Want to bring the good times home? Purchase your choice of Pottery-To-Go kits, complete with pottery, paint and brushes—everything needed for each family member to create a masterpiece.

Pitch together

A tent, that is. Family-friendly Red River Boat Dock and Campground offers tent sites, RV hookups and a few air-conditioned cabins for camping at the historic ferry crossing where the Red River meets the Kentucky River. Camping, fishing, hiking, live music, kayak rentals, cornhole tournaments, lots of food—there’s always something happening at this peaceful campground stretching out along Red River’s shoreline.

EVENT: On Saturday, July 8, Red River is planning its annual fireworks show. Bring a lawn chair and watch the sky light up while Renegade plays. Check Facebook page for updates.

Paddle together

Rent a canoe or kayak from Three Trees Canoe-Kayak Rental and RV Park for a day of exploring the ancient geologic formation, the Kentucky River Palisades. In the evening, settle in for the night at the RV Park, with full hook-ups, picnic tables and clean restrooms and showers. Three Trees is located just a mile from Fort Boonesborough State Park.

Climb together

Play at a park, but not just any park—one that comes alive with the sound of music, courtesy of a one-of-a-kind climbing musical instrument. The Dulcimer Climber pays tribute to the Appalachian string instrument created in the 1800s and Kentucky’s most renowned dulcimer-maker, Winchester’s own Homer Ledford. Ledford handcrafted more than 6,000 musical instruments (many of them dulcimers) during his lifetime. This unique feature anchors the fun at Legacy Grove, a 30-acre accessible park with adventure play area with swings, spinners, slides, fort and an Exploration Creek kids can splash in, plus nature trails, walking paths and more.

EVENT: The park’s Legacy Nights series, featuring family fun, food trucks and music by NVRMND with Sydney Norman (5:30-8 p.m.) takes place on Tuesday, July 11.

Hike together

Grab provisions for a day of hiking the Red in Winchester and then make the 35-minute drive to Red River Gorge. Gas, Ale-8, water, chicken and biscuits, assorted snacks—make one stop for everything at Winchester’s Clark’s Pump-n-Shop (famous for its Ale-8 “cave”)—and you can call ahead to place your food order.

Yikes! together

See an operating room from a century or so ago at the Bluegrass Heritage Museum. From 1927 to 1971, this building was the Guerrant Mission Clinic and Hospital and remained in use as a clinic until 1989 when the hospital closed. On the third floor, in the  Guerrant Clinic and Hospital Rooms exhibit, see an operating table, sterilizing machine, surgical tools and supplies and more from way back when. The gallery is among exhibits, including Homer Ledford’s workshop, a hotel’s barber shop, Civil War-era bullets, buckles and buttons and vintage phones – with one that goes back nearly 140 years. (How on earth does that fit into your pocket?)

Learn together

Although very little remains of the earthen fort at the Civil War Fort at Boonesboro, it is well worth a visit for the Insta-worthyviews. Follow the 1-mile loop trail for panoramic sweeps of the Kentucky River Valley. Then dial into a cell phone tour at 859-592-9166 and learn about this fort built and defended by Union Soldiers during the Civil War.

Eat together

Take a mid-week break and celebrate National Hot Dog Day on Wednesday, July 19 with a family picnic at a Winchester/Clark County park with shelters and playground, like Wiseman, Massie or Lykins park. P.S. July 19 is also National Daiquiri Day, so parents, steal away to DJ’s Steakhouse Bar & Grill or Hall’s on the River and order one of these frosty concoctions. (Need a picnic hamper? Poke around Winchester antique stores—Eve’s Uniques, the Old Red Barn Mall—for hamper, basket or bag to tote picnic supplies.)

Wow together

Head to the countryside for an overnight surrounded by acres and acres of rolling farm and pastureland beneath the open sky above. How many constellations can you find? The stars shine brighter in the country, making for ideal stargazing at these getaways: Franklin Ridge Farm sits on 150 country acres and features a guesthouse with front porch swings and outdoor firepit; Mt. Folly Farm’s Historic Log Cabin is perched in the midst of 1,000 acres where families can enjoy hiking, birding, and biking around the property; and the Basin Springs House, located in a private storybook setting at the Peacock Ranch.

Four years ago, June was officially designated “Great Outdoors Month.” Even further back, in the 1970s, June was named “National Camping Month.” It’s a busy month, June. Fortunately, Winchester has plenty of ways for you to get out and about and celebrate Mother Nature.

Here are nine ways to rock the Great Outdoors in Winchester:

• Travel back in time. At Three Trees Canoe – Kayak Rental and RV Park, paddle to a world as ancient as the beginning of Earth’s very earliest plants and arthropods. It is one that dates back to the Ordovician Period of about 450 million years ago when Earth’s first coral reefs emerged in the seas and North America at times lay almost entirely underwater: The Kentucky River Palisades. Three Trees offers canoe and kayak rentals, full hook-up RV sites with picnic tables and fire rings, onsite restrooms and showers, boat dock and river access.

• Hike a hidden gem: Inside the 400-acre Lower Howard’s Creek Nature & Heritage Preserve is the John Holder Trail, the only portion of the preserve open to the public. The 3-mile loop opens 9 a.m. to 1 p.m. Tuesdays and Thursdays, giving hikers the chance to enter this wonderland of rare plant and wildlife species, historic and archaeological features and second-growth forest in a twisting limestone gorge that is considered to be one of the region’s most scenic places. With the trailhead located next to Hall’s on the River, visitors can fuel up for their hike or relax afterward over fried catfish, smoked ribs and pan-seared crabcakes. (And for Beer Cheese trailblazers, Hall’s is a stop on the Winchester-Clark County Beer Cheese Trail.) Trail parking is available in the lot behind Hall’s.

• Family-friendly Red River Boat Dock and Campground offers tent sites, RV hookups and a few air-conditioned cabins, as well as bath houses, for campers staying at the historic Ferry crossing where the Red River meets the Kentucky River. Camping, fishing, hiking, live music, kayak rentals, cornhole tournaments, lots of food—there’s always something happening at this peaceful campground stretching out along Red River’s shoreline.

• Stay the course: Play 18 holes at one of Winchester’s two public golf courses: Cassell Creek Golf Course and Southwind Golf Course. The former features 6,714 yards of golf from the longest tees for a par of 72 on a course, which was designed by Danny McQueen and opened in 1961, with a rating of 70.0 and a slope rating of 116. Cassell golf course opened in 1961. The latter features 6265 yards of golf from the longest tees for a par of 71, a slope of 113 and a rating of 67.1. Opened in 1992, Southwind was designed by Kent Arnold.

• Treat yourself to an Insta-worthy view. Although very little remains of the earthen fort at the Civil War Fort at Boonesboro, it is well worth a visit for the views. Follow the 1-mile loop trail for panoramic sweeps of the Kentucky River Valley. Want more? Dial into a cell phone tour at 859-592-9166 and learn about this fort built and defended by Union Soldiers during the Civil War.

• Play at a park. But not just any park—one that comes alive with the sound of music, courtesy of a one-of-a-kind climbing musical instrument. The Dulcimer Climber pays tribute to the Appalachian string instrument created in the 1800s and Kentucky’s most renowned dulcimer-maker, Winchester’s own Homer Ledford. Ledford handcrafted more than 6,000 musical instruments—many of them dulcimers—during his lifetime. (Learn about Ledford’s life and times at Winchester’s Bluegrass Heritage Museum.) This unique feature anchors the fun at Legacy Grove, a 30-acre accessible park with adventure play area with swings, spinners, slides, fort and an Exploration Creek kids can splash in, plus nature trails, walking paths and more.

• Put your pedal to the metal. Ride the 28-mile River Route, a cycling experience for all levels, from the casual cyclist seeking a bit of a challenge to more experienced ones looking for a relaxing outing. Begin in downtown Winchester and follow the route south to the Kentucky River, riding along its banks before returning downtown. Download the map here.

• Winchester is lucky enough to have two family-owned wineries producing not only artisanal wine, but hosting tours and tastings and other events. At Hamon Haven, tasting room hours are flexible Monday through Saturday so call ahead for tasting times. And if you’d like a charcuterie, let the winery know in advance of your visit; they’ll prepare one for your party to enjoy while sipping. (Additional cost.) Harkness Edwards Vineyards is open Wednesday through Sunday and is the site of several summertime events, including Golden Hour: 5-8 p.m. Fridays through Sept. 29; Sangria Sundays, 3-6 p.m. through Sept. 24, with bottomless sangria (bring lawn chairs and picnic blankets); and live music Fridays and Sundays featuring local and regional musicians. See “Events” for dates and details.

• Star gaze the night sky. Head to the countryside for an overnight surrounded by acres and acres of rolling farm and pastureland beneath the open star-studded sky. Winchester has several perfect getaways for stargazing and enjoying the outdoors: stately Franklin Ridge Farm sits on 150 country acres and features a four-bedroom guesthouse with game rooms, front porch swings and outdoor firepit; Mt. Folly Farm’s two-bedroom Historic Log Cabin is perched in the midst of 1,000 acres where visitors can enjoy hiking, birding and biking around the property; and the three-bedroom Basin Springs House, whose music room features a Yamaha mini grand player piano, sits on five acres on the grounds of Peacock Ranch.

Follow the trials and tribulations of aspiring writer Jo March and her sisters, Meg, Amy and Beth, when the Leeds Center for the Arts brings Little Women: The Broadway Musical to Winchester on May 5-7 and 12-14.

Based on Louisa May Alcott’s beloved coming-of-age story published in the late 1860s, the musical answers all the burning questions (pun intended) . . . Will headstrong Jo sell her stories? Will impetuous Amy set them ablaze first? Find showtimes and purchase tickets here.

Continue reading Spring events in the vineyard, at the booths and on the boards

A day to salute steak. A day to seize for cheese. (Actually, many days.) There is a National Beer Day and a National Superhero Day. Have you embraced an antique lately? Not to worry; there is a national day earmarked just for that.

Read on to see how you can bring a local vibe to these national day celebrations.

Continue reading Celebrate ‘National Days’ locally

In March of 2022, we presented some fun and quirky facts about Winchester—truly an original among Kentucky towns with its early Daniel Boone ties, elevated downtown sidewalk, hemp history, geology quirks and Ale-8-One—the only soft drink invented in Kentucky still in existence. Here are more strange and unusual things to see, do and know about in the town that gifted the world with beer cheese:

Continue reading Did You Know?

Forty-five years ago, in 1978, a group of local artists got together and formed the Winchester Art Guild. Through the decades, the Guild has attracted a diverse and dynamic group of artists working in all mediums: painting, woodworking and fine furniture making, textile art, needle arts, photography, soap and candle making, stained glass, jewelry, pottery and more. Members’ work may be seen and purchased at the Arts on Main Gallery in downtown Winchester. 

Continue reading Artistic expressions

Many photographers, professional and hobbyists alike, put their cameras into hibernation when winter arrives, but it can be an exciting time for seeing a different side of familiar and favorite landscapes and creating dramatic images. Especially in Winchester. 

Continue reading Capture Winchester in winter with these photography tips

Legend holds that during the third century, a Greek bishop named St. Nicholas helped three poor daughters with their dowries by tossing bags filled with gold coins through a window into their home. As luck would have it, the bags landed in stockings the girls had hung by the chimney to dry.

And thus began the tradition of the Christmas stocking.

Inflation has most likely killed all hope of Santa stuffing those stockings with bags of gold this year; however, Winchester shops and restaurants have lots of ideas that will make you look every bit as swish as Santa.

Continue reading Elevate your Santa game with these local stocking stuffers

Make your list and check it twice for some fantastic, festive holiday events taking place in Winchester – everything from open house merriment to farmers market fun.

“Put us on your list of holiday must-dos,” said Bailey Milheiser, manager of Beech Springs Farmers Market.

“Our Christmas Market is a great way to meet all kinds of local artists and crafters all in one place,” she said. “We think it gets everyone in the holiday spirit – and that it’s a great way to shop Small Business Saturday!”

Continue reading Have a holly-jolly Christmas with Winchester’s holiday events

Crunch, crackle, cackle – these are the sounds of fall . . . biting into a freshly dipped caramel apple, kicking fallen leaves into the air, watching a spooky movie from the TV in your cabin getaway in the hills of central Kentucky.

Continue reading Follow the turning leaves to Winchester and fall fun