History, Whimsy & More: Check Out These Can’t-Miss Experiences in Mt. Sterling, Kentucky!

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Public art installations, historical sites, and a thriving downtown—welcome to Mt. Sterling, Kentucky. Considered the Gateway between the Bluegrass and the Mountains, this charming slice of small-town paradise is the perfect destination for a day of exploration or an overnight stay.

From family-friendly nights at the drive-in to local history and delicious dining, here’s why Mt. Sterling should be on your bucket list!

Shop ‘Til You Drop Downtown

A sunny day at Main Street Park in Mt. Sterling, Kentucky.

Strolling through Mt. Sterling’s historic downtown area feels like stepping back in time, with its red brick streets and century-old buildings, shops and trendy boutiques. Browse the shelves of Mooncat Book Co., sample unique scents at Lighthouse Candles, and then stop into The Hub Coffee for a caffeinated pick-me-up. Visiting in the fall? Check out the October Court Day Festival – this 230-year-old shopping extravaganza is Kentucky’s longest-running event, featuring antiques, collectibles, and handmade crafts.

Dig into Delicious Grub

A plate of pasta at Romero’s in Mt. Sterling, Kentucky.

You won’t go hungry during your visit to Mt. Sterling, thanks to a mouthwatering variety of dining options. Indulge in Italian fusion at the family-owned Romero’s (order the bruschetta with organic cherry tomatoes), grab a craft beer at Sterling MicroBrew, or enjoy a cone of soft-serve ice cream at Berryman’s Tastee Treat! For a juicy steak, Cattleman’s Roadhouse is a must-visit spot – don’t skip the rolls with cinnamon butter. And if you like things spicy, chow down on nachos, tacos and fajitas at Don Señor Mexican Bar & Grill.

Enjoy a Hole-in-One at Irish Hills Restaurant & Golf Club

An aerial view of Irish Hills in Mt. Sterling, Kentucky.

Practice your swing and enjoy Kentucky’s picturesque rolling hills at Irish Hills Golf Club’s 18-hole course. After you’ve teed off in style, enjoy comfort food with a view at the on-site restaurant. Fill up on fried green tomatoes, crispy onion rings, Kathy’s famous beer cheese or a mouthwatering Philly cheesesteak sandwich. Check out the rotating daily specials like Kathy’s delicious Kentucky Hot Browns or a juicy filet!

Judy Drive-In Theater

A night at the movies at Judy Drive-In Theater.

For a fun night out with the entire family, hop in the car and catch a movie under the stars at Judy Drive-In Theater, a Mt. Sterling landmark since 1952. This mom-and-pop drive-in features two giant screens, offering two movies for one ticket price! Only open on the weekends, this theater plays the latest box office hits, along with classic films like Jaws and Smokey and the Bandit. No need to pack snacks – the concession stand serves up delicious treats like burgers, chili dogs, and funnel cakes.

Journey to the Past at the Montgomery County History Museum

Montgomery County History Museum in Mount Sterling, Kentucky.

Discover Mt. Sterling’s history at the Montgomery County History Museum. Located next to the courthouse, this museum showcases exhibits from local Indigenous American tribes, historic presidential elections and insights into the century-old structures within Montgomery County. You’ll also find artifacts on display, like an 1822 Powder Horn. The museum is also the first stop on the Historic Downtown Walking Tour, where you’ll see historic sites and restored buildings, from the Ascension Episcopal Church to the restored Joseph Simpson Cabin.

Discover Arts & Culture at the Gateway Regional Arts Center

The colorful Umbrella Alley in Mt. Sterling, Kentucky.

While exploring downtown Mt. Sterling, it’s hard to miss the sunshine-yellow Gateway Regional Arts Center. Check out the Contemporary Kenyan Art Gallery, look through exhibits on rural arts and culture, and attend “meet the artist” gatherings. This arts center is also the first stop along the Mt. Sterling Art Trail – continue along the rest of the route to snap a few selfies at different downtown murals, including the Wings murals in Umbrella Alley, the Rainbow mural, and the “Greetings from Mt. Sterling” mural.

Explore, Splash & Play

A pavilion in Easy Walker Park.

Get outside and enjoy the fresh air at one of Mt. Sterling’s many parks. Play a game of pickleball at The Mound. At Botts Park, you can enjoy walking trails, a disc golf course and a playground for the kids. There’s even a beautiful butterfly garden. Don’t skip Easy Walker Park, where you can spend an afternoon fishing in the pond or kick the ball on the soccer fields. Need to cool off? Put on your swimsuit and hop in the brand-new MSMC Aquatic Center pool.

Indulge Your Sweet Tooth at the Ruth Hunt Candy Factory

Workers making Ruth Hunt Candy Factory’s famous bourbon balls.

There’s no better way to satisfy your sweet tooth than with a visit to the Ruth Hunt Candy Factory. For over 100 years, this candy company has been crafting sweet treats like caramel, toffee, and chocolate bars. Come for the free chocolate samples, and leave with tons of goodies like Blue Monday Candy Bars, Kentucky Pulled Cream Candy, and tons of knick-knacks from the extensive gift shop. You can’t leave without sampling the bourbon balls – these bonbons are infused with Kentucky bourbon and then covered with chocolate and pecans. Willy Wonka’s got nothing on this place!

Two Sisters Pumpkin Patch

Two Sisters Pumpkin Patch in Mount Sterling, Kentucky.

If you’re visiting in the fall, a trip to Two Sisters Pumpkin Patch should be at the top of your to-do list. Bring the whole family and spend an afternoon enjoying the hayrides, choosing your own pumpkins, and petting baby animals like miniature cows and calves. Craving something sweet? There’s no shortage of pumpkin-flavored baked goods at the concession stand – sample a fresh pumpkin roll and then wash it down with some homemade apple cider.

Take this guide on the go with Apple Maps on your iPhone!

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