Three Fall Weekend Road Trips To The Place Where Kentucky Started

Harrodsburg, Kentucky Octoberfest | I-75 Exit Guide

I-75 Road trippers will find plenty of local color for fall weekends in Harrodsburg, Kentucky, home of the first permanent settlement west of the Allegheny Mountains, with a trio of special weekend events featuring headlining musicians, a variety of craft beers and frights that could have come from a Hollywood special effects crew. See details about these events as well as all fall festivals and fun at

All That Jazz

Bringing his high-energy show to the Fort Harrod Jazz Festival, scheduled this year for Sept. 20-22, is Adrian Crutchfield. Known for his neo-soul sound, Crutchfield’s jazz creds date back to his childhood when he was given his first sax by Kenny G. He is the last sax player to have performed with Prince and was featured on many of the revered musician’s final masterpieces, including the 2017 Grammy-nominated album, Hit-N-Run Phase 2 – the last to be released during Prince’s lifetime. Crutchfield has also performed with such legendary luminaries as Bette Midler, Lionel Richie, hip hop sensation Young Jeezy and R&B icon Anthony Hamilton.

Held at Old Fort Harrod State Park, this annual three-day, free-admission festival also features a non-stop lineup of regional and national ensembles performing their music; the foods that go best with jazz – barbecue, brisket, burgers and wings, plus sweet treats and craft and domestic beer; and casual seating on the lawn of the park. On Sept. 21, some of the region’s finest artists and craftspeople will join the fun at the fort, showing their original handmade arts and crafts during the Kentucky Artisans Expo. Bring lawn chair or blanket and settle in for one hot jazz weekend.

Pair with overnight accommodations at The Inn at Shaker Village at Pleasant Hill, whose recently reopened 1820 Meeting House presents its own music program, that of beautiful Shaker music performed at 11 a.m. daily. The music as well as tours of the Village are part of the daily adventures offered at Shaker Village and are included for the length of a stay. Fall is the perfect time to add a Dixie Belle cruise excursion to the geologically ancient Kentucky Palisades and dinner at Trustees’ Table for seasonal Kentucky fare.

Roll Out the Barrels

Central Kentucky’s largest Oktoberfest celebration gets underway in downtown Harrodsburg the weekend of Oct. 11-13, with a live music lineup featuring the soul, rhythm and funk of Bootsie & Funkability; the high-energy beach-themed show of Conch Republic; the Southern rock of No Fences; and the folk and pop hits by Mike Archer; as well as lots of bluegrass, rock, country and more performed by local and regional musicians.

Get a jump on holiday shopping at the artisan craft booths. Nosh on delicious German and specialty foods and raise a stein or three of local, regional and craft beer. Let the kids loose in the children’s play area and set your own inner child free with nonstop games of cornhole, giant Jenga, Connect Four, dominos and more.

The free-admission, family-friendly festival is perfectly accompanied by a stay at Bright Leaf Golf Resort with its lighted nine-hole, Par 3 golf course for nighttime play and famous Friday Night Seafood Buffet.

A Haunting We Will Go

Every October, the ghoulish masterminds behind one of Kentucky’s scariest Halloween-time experiences – the Haunted Frontier– dare thrill seekers to step through the East Gate at Old Fort Harrod State Park and enter the smoky darkness to pick their way through a horror landscape at the fort, surrounding woods and the oldest (and possibly creepiest) cemetery in the state.

Waiting for these brave (or foolhardy) souls? A really good scare – on the scale of something straight out of a Rob Zombie movie. Think “House of 1000 Corpses,” “Halloween,” “The Lords of Salem.” Each year, Haunted Frontier is changed up, with new themes introduced and old themes presented with new and hair-raising twists. Everything (from tour lengths to paths through the fort and woods) is altered to keep the experience new.

“With the September premiere of supernatural horror film, ‘It Chapter 2,’ Pennywise might
make his return visit to the fort,” hints Haunted Frontier “Scare Master” Laura Goode.

Dates for the 2019 Haunted Frontier are Oct. 25, 26, 30 and 31. It is not recommended for children under 10 or the weak-hearted. Tickets: $7/adults; $4/ages under 12.

After setting your spine to tingling and pulse to racing, calm your nerves with a bourbon flight and overnight at the historic Beaumont Inn, marking its 100th anniversary in 2019. Bourbon flights take place in the inn’s cozy Old Owl Tavern and feature three or four pours from a choice of more than 50 fine bourbons, including Pappy Van Winkle, George T. Stagg and Old Forrester Signature.

More Fall Fun, Fests and Frights

Other fall Harrodsburg fun includes Shaker Village at Pleasant Hill’s HarvestFest, Sept. 28-29, and Trick-or-Treat, Oct. 25-26, with hayrides, kids’ crafts and bonfires; Fort Harrod Beef Festival, Oct. 3-5; Devine’s Corn Maze & Pumpkin Farm for activities including Zip Line Racers and Paintball Cornstalk wars and Field of Horror event, Nov. 1-2. Visit to plan your fall road trip to Harrodsburg.

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