Mt. Sterling, Ky., in a Weekend


Emily McMackin

on January 4, 2013 at 3:57 am EST
Downtown Mt. Sterling, KY


Tucked between the foothills of the Appalachian Mountains and the Kentucky Bluegrass region, Mt. Sterling is steeped in rich history and friendly charm. From its tree-lined streets and renovated buildings where quaint shops reside to its Montgomery County outskirts that teem with working farms and natural wonders, discover the best things to do and see in Mt. Sterling, all within a weekend visit. 

Day 1
6 p.m.

Southern Style Dining at Terry & Kathy's on Main
Enjoy hearty helpings of Southern cuisine and mingle with locals at Terry & Kathy's on Main. Watch the sun set on the square, listen to occasional live music and choose from a long list of sandwiches, dinner specials and regional delicacies like the fried green tomato BLT. Linger as long as you like but save room for the restaurant's legendary cream pies!

8 p.m.
Movie at Judy Drive-In

Catch two feature films for the price of one at Judy Drive-In off of I-64. The 1950s-era drive-in, one of the oldest still operating in the country, is open April through October. Come early for a prime parking spot, bring chairs and blankets, and tune into your FM radio for the best sound. Stop by the concession stand for a funnel cake or a PIC coil to keep the bugs away. Drive-in closed? See a movie at Tenth Frame Cinema instead or go cosmic bowling at Sterling Lanes.

Day 2
9 a.m.
Historic Walking Tour of Downtown Mt. Sterling

Pick up a map from the Montgomery County Historical Museum and explore historic homes, hotels, churches and landmarks downtown. Don't miss the brick paving on Court and Broadway or the original iron vault at Farmer's Bank Building robbed by Confederate troops during the Civil War. Finish early? Check out regional artwork at the Gateway Arts Center or shop at antique and specialty stores on the square.

11 a.m.
Bourbon Balls at Ruth Hunt Candies
Tour Ruth Hunt Candies factory—maker of the official candy of Churchill Downs and the Kentucky Derby. Watch its cream candy bars, "Blue Mondays," being made and sample its famous bourbon balls.

Chili dogs at Berryman's Tastytreat

Stop for a quick bite at Berryman's Tastytreat on East Main—known for its chili dogs and hometown feel. Local sports memorabilia and pictures of townsfolk decorate the walls, and the menu offers everything from fast food fare to dipped ice-cream cones. Be sure to try a bottle of Ale-8-One—a ginger-flavored soft drink made in eastern Kentucky.  

1 p.m.
Apple Picking at Bramble Ridge Orchard

Stop by Bramble Ridge Orchard and pick your favorite apples from 13 varieties. Take a wagon ride to learn more about the farm, observe a beehive and take a turn at Kentucky's largest apple slingshot. Visit the Orchard Barn for jams, jellies, cider donuts, caramel apples, fried apple pies, and apple cider and slushies to take home.

3 p.m.
Hiking at Natural Bridge State Park

Enjoy an afternoon drive through the Kentucky's horse country to Natural Bridge State Park. Take the sky lift or hike over to the park's trademark 65-foot sandstone arch, explore the Red River Gorge and find more unique rock formations in the Daniel Boone National Forest. End the day by watching the sun set over the Appalachian foothills.

Day 3
7 a.m. 
Breakfast at Jerry's Restaurant

Before you hit the road, fuel up at Jerry's Restaurant on U.S. 60. Part of a Lexington-based chain that operated one of the earliest family-style roadside restaurants, Jerry's is the kind of place where waitresses remember your name, cups of coffee are bottomless, and meals come with fast, friendly service. For a local favorite, order the Husky Breakfast (two pancakes, two eggs and four bacon or sausage links).

Extra time? Check out:
Old Silo Golf Club, an 18-hole public course designed by Champions Tour player Graham Marsh and voted one of Kentucky's best by Golf Digest
Morgan Station, the site of the last organized Indian raid in Kentucky
Quilt Trail, a driving tour along the back roads of Montgomery County exploring historic barns on a trial marked by colorful square quilt patterns

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