Jill Hamlin is the Executive Director of Tourism for Winchester-Clark County, Kentucky, where she leads innovative initiatives to promote the region’s unique culture and heritage. With a deep passion for the Appalachian region, Jill has dedicated her career to uplifting the arts, entertainment and tourism sectors.
We asked Jill about her plans for Winchester, what she loves about this community and how she plans to help more visitors discover its charms. Read about Jill’s plans, then learn about her background in “More About Jill” following this Q&A:
What made you pursue a job in travel and tourism?
I’ve always had a passion for sharing the rich stories of unique places, and Winchester has so much to offer, from the cultural events to the historic charm and incredible local businesses. Being able to promote all of this was a natural fit for me.
Tourism is more than just getting “people to visit”—it’s about creating experiences: memories that people of ALL ages, perspectives and abilities can take home with them. Those experiences are abundant here—whether it’s touring the Ale-8-One Factory, sipping coffee from The Hall Coffee and Social Club or exploring our heritage at the Bluegrass Heritage Museum.
What are some of the challenges you’re facing with tourism in Winchester and how will you solve them?
One challenge is ensuring that visitors explore all the incredible places Winchester has to offer, like the Beer Cheese Trail, which showcases our title as the Beer Cheese Capital of the World. Many visitors know about our world-renowned festivals, like the Daniel Boone Pioneer Festival and the Beer Cheese Festival so we’re working on promoting other experiences . . . events held at Legacy Grove Park, the Rock the Block live music events, and local eateries like Amy’s Asian Kitchen, Engine House Pizza and Pub, Loma’s at the Opera House, The Waterfront Grille, Halls on the River, The Hall Coffee and Social Club, Lucky Dog Café, Smoking’ Howards and Make a Mia Pizza; our distilleries, like Abettor Brewery and Regeneration Distillery; and our distinctive boutiques!
By creating more comprehensive marketing campaigns, working with our amazing locally owned and downtown businesses, improving digital outreach and offering guided experiences, we’ll help visitors discover all that Winchester has to offer.
What do you regard as the “best kept secret” in terms of tourist attractions in Winchester?
Shew! There are SO many! Just to start, there is the creative scene at Arts on Main, a vibrant nonprofit supporting local artists. The gallery and gift shop features everything from oil paintings to textile art, showcasing the incredible talent in our area. Visitors are often amazed at how much artistic variety we have here.
Another is our local shopping experience: Places like Mason on Main, Eklektic Alchemy and Court Street Gifts are filled with unique finds, from handcrafted items to curated home décor. These spots offer visitors a chance to take home a piece of Winchester’s charm, often surprising them with the creativity and craftsmanship in our community. Additionally, Fly Witches Bungee provides a fun, unexpected fitness experience that’s wildly popular among both locals and visitors.
Why should travelers visit Winchester?
Travelers should visit Winchester because it offers a unique mix of history, culture and modern experiences. Whether you’re exploring the Civil War Fort, taking in a fantastic show at the Leeds Center for the Arts, shopping in our fantastic downtown district, enjoying a locally brewed Ale-8-One, or tasting your way along the Beer Cheese Trail, Winchester is full of surprises. It’s the perfect destination for those who love small-town charm with a big heart—and our welcoming community ensures that visitors feel like they belong from the moment they arrive.
Do you remember the first time you visited Winchester? What was that experience like?
Absolutely. The first time I visited Winchester, I was struck by the blend of history and community spirit. I remember walking downtown, seeing the beautiful architecture and feeling how much pride the people here have in their town. The experience was like stepping back into a place where history is honored but the future is just as exciting. I knew right away that this was a place I could call home.
What inspires you about your work?
The PEOPLE!—and how tourism can bring people together. I love seeing visitors experience our culture, whether they’re exploring our local shops or attending events like the Rock the Block series. Knowing that my work helps highlight the spirit of Winchester and brings economic growth to the area keeps me passionate and motivated.
What makes you passionate about Winchester?
The sense of community and the rich, diverse experiences we offer. There’s so much to love, from the creative shops to our outdoor parks and historical landmarks. Winchester is a town that has embraced its history while continuing to grow and evolve, and I love being a part of that transformation. Sharing our unique events and promoting local treasures fuels my passion every day.
We’re introducing a new column in Winchester’s newsletter called Wade’s Tails that will share news from the perspective of a dog. Why was this important to you and what do you hope to share through this column?
This is a fun and engaging way to connect with both locals and visitors. Pets are an integral part of so many families here, and this column allows us to share Winchester news and events from a playful, lighthearted perspective. I hope it brings smiles to readers while also highlighting some of the pet-friendly activities and spaces in town, creating a sense of connection and community for all.
November’s Winchester newsletter also spotlights a new special coffee blend, created in partnership with local business, Creative Coffees Roastery and exclusively available through Winchester Tourism. Why is this significant and what does it mean for locals and visitors?
The introduction of the Winchester Wander Brew, with the slogan “Fuel your Journey, Savor the Adventure,” perfectly encapsulates what our Brews and Views campaign is all about. This coffee blend isn’t just a product—it’s an experience that represents the spirit of Winchester.
Whether you’re strolling through our historic downtown or embarking on the Beer Cheese Trail or the Traveling Trail—a nearly a mile-long trail situated within a large meadow of Kentucky bluegrass with shaded areas and benches where leashed and tagged dogs are welcome—Wander Brew is the perfect companion to fuel your adventure.
It’s significant because it highlights local craftsmanship through our collaboration with Creative Coffees Roastery, giving both locals and visitors a taste of Winchester’s creativity. We encourage everyone to stop by the Tourism office, grab a cup of Wander Brew and let it be the start of your journey as you savor all that Winchester has to offer—from the vibrant shopping scene to our lively events. There’s SO much more coming so make sure to stay tuned!
More about Jill
Jill Hamlin is the founder of the Appalachian Arts & Entertainment Awards (the APPYS), a program that celebrates established and emerging talent across the 13-state Appalachian region. The APPYS have garnered numerous accolades, including the Kentucky Travel Industry Association’s Bronze Traverse Award for Experience Development and the KCTCS Innovation Award for Diversity, Equity and Inclusion. Additionally, Kentucky Governor Andy Beshear signed a proclamation declaring March 18 as “Appalachian Arts & Entertainment Day” in recognition of Jill’s work with the APPYS.
Jill holds a master’s degree in social anthropology ethnomusicology from The Queen’s University Belfast located in Belfast in Northern Ireland and a B.A. in sociology with a minor in traditional music from Morehead State University. A passionate advocate for music and the arts role in addressing youth trauma, she has lectured on this subject as well as on the spiritual thumbprint of Appalachian music and taught college courses on cultural anthropology. Jill is a multi-instrumentalist, award-winning singer-songwriter, who has performed on local and international stages and other premier event spaces such as Nashville’s Bluebird Café.
She is a member of prestigious organizations such as the British Society of Ethnomusicologists, the Society of Ethnomusicology and the American Association for Access, Equity and Diversity. In her current role, Jill focuses on building strong community partnerships and is known for her leadership in developing tourism programs that highlight the distinct local culture.
Her efforts have earned her recognition as a Kentucky Colonel and a Commonwealth Ambassador. Beyond her work in tourism, Jill is also celebrated for her advocacy of the arts, supporting a range of programs designed to empower the youth, promote diversity and inclusion and foster a deeper connection to Appalachian heritage.