Follow the turning leaves to Winchester and fall fun

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.

One-stop fall-everything shop

That freshly dipped caramel apple? Pick up this and other delicious fall treats from Beech Springs Farm Market, where you can also stock up on pumpkins, gourds and more fall decorations, home accents and accessories, all beautifully arrayed outside and in.

This charming shop is all about local tastes and treats: jams, jellies, honey, salsas and sauces, beer cheese (a Winchester original) and Beech Springs’ famously delicious made-fresh-every-morning apple pies – made from apples picked mere steps away in the market’s own apple orchard.

Blueberry and peach pies, seasonal produce, mums and other flowering plants and more are also available. Beech Springs even whips up heat-and-eat meals like broccoli and cheddar soup to pick up and enjoy at home for a “no cooking, but plenty of good eatin’” kind of night.

Red, white and fruit

Celebrate the colors of fall with a bottle of wine from Hamon Haven Winery, where the Hamon family has been producing and perfecting their red, white and fruit wines for three decades.

In addition to dry reds including cabernet sauvignon, merlot and chamborcin, Hamon Haven has Marechael Foch, a hybrid French red wine grape variety, and Zinthiana, a cross between red grape varieties zinfandel and Norton. Each shows off a deep shade of red, making them perfect pours for wine and cheese pairings on crisp fall evenings.

Fall is a lovely time to visit the vineyard for a tour and tasting – just call for a tasting time. Cheese and charcuterie can be ordered ahead to enjoy along with the wine and view. 

Find fall in the country

Take a drive into the countryside to leaf peep and learn about some of Kentucky’s key Civil War sites.

The Clark County Civil War Driving Trail, part of Kentucky’s Civil War Heritage Trail, takes visitors to 16 historical sites, such as the Civil War Fort at Boonesboro, an earthen fort built by Union soldiers to defend the ford and ferry at Boonesboro, and the Guerrant Mission Clinic and Hospital, named for Confederate Army officer and physician Edward O. Guerrant and now home to the Bluegrass Heritage Museum.

Other sites featured on the tour include the Home of Mattie Wheeler, now Holly Rood, an events center; the Gen. John Hunt Morgan Kentucky Historical Marker at Court Street at the Clark County Courthouse, named for the Confederate general famous for his guerilla raid tactics; and the Winchester Cemetery, final resting place of many veterans of the Civil War, both Union and Confederate.

Download the map here. The Clark County sites are noted on page 8 with descriptions preceding them.

Explore like Daniel Boone

Daniel Boone knew this area to be the perfect jumping off point for exploring Red River Gorge, which he did in the late 1700s – after arriving and being swept away by the land (and its views) that is now Winchester.

With The Red, as this geologic wonder is nicknamed, just a quick 35-minute drive away in the Daniel Boone National Forest, a stay in Winchester offers the best of both worlds: shops, restaurants and accommodations in a small-town atmosphere and the rugged adventures of the Great Outdoors.

Favorite activities at Red River Gorge include hiking, climbing and being blown away by the incredible sandstone arches, rugged cliffs and other natural features (to say nothing of the views!) – probably what Daniel Boone himself experienced during his own explorations. Biking, zip lining and kayaking are also popular activities.

Off-the-grid getaway

Offering easy access to Red River Gorge is Mt. Folly Farm, a historic, eighteenth-century two-bedroom log cabin set on 1,200 acres of rolling pastureland. An official Kentucky landmark, this Winchester original is a working organic hemp farm where guests are free to hike, stroll, bike and go birding, help with planting the farm garden and feeding the goats.

The cabin offers pastural views all around, from the front lawn with it large oak trees to the goat holler to the greenhouse and farm gardens to the granary where farm owner Laura Freeman and her crew stone-mill corn and grain.

Inside are all the comforts of home: equipped kitchen, two full bathrooms, laundry and mudroom, a dining room stocked with dishes and pottery, family room with smart TV and a library stocked with books. Antique furnishings help tell the story of the cabin’s history.

Laura’s Mercantile at the Crooked House, a farm store stocked with Laura’s Hemp Chocolates, Homestead Alternatives Hemp Tincture, heritage grains from Mt. Folly and other regional specialties, books written by local authors and more, is operated on the honor box method. Guests can also rent a golf cart to tool around the property.The cabin, available for Thursday through Sunday rentals, may be booked through Airbnb.