A day trip to Winchester

A courthouse with a gold dome

Downtown Winchester’s courthouse | Photo by the LEXtoday team

As we near the end of the school year, our sights are set on summer and the vacations it will bring. To make planning a little easier for you, we’re sharing a curated day trip guide to Winchester.

Located just 18 miles east of Lexington, Clark County is the home of our famous soda Ale-8 + the birthplace of fan-favorite dip, beer cheese.

Pro tip: If you love taking the scenic route, we recommend heading straight out Winchester Road and taking Combs Ferry Road.

Image from iOS (42)

Beech Springs Farm Market | photo by the LEXtoday team

Stop No. 1 | Leisurely lunch at Beech Springs Farm Market, 4776 Old Boonesboro Rd. Like straight out of a movie, this roadside market features fresh produce, local jams and jellies, cheese plates, and pies. Sit for a spell in one of the rocking chairs or create your own fun with a game of cornhole.

A historic two story peach house surrounded by picnic tables

The Peach House at Harkness Edwards Vineyard | photo by the LEXtoday team

Stop No. 2 | Wine tasting at Harkness Edwards Vineyards, 5199 Combs Ferry Rd. The Peach House is picture-perfect for a day with friends or a picnic with the family. Walk-in wine tastings are welcome or check the events page for classes such as paint + sips or cake-decorating.
Stop No. 3 | Treasure hunting at the downtown shops, Main Street Downtown Winchester is a thrift + antique lovers dream. Dirty South Pottery is a local favorite featuring handmade mugs, bowls, and full place settings.

Image from iOS (45)

The Leeds Theatre in downtown Winchester | photo by the LEXtoday team

Stop No. 4 | Catch a show at the Leeds Center for the Arts, 37 N. Main St. Plan your visit around one of the historic theater’s upcoming performances, or just pose for a picture under the bright lights.

Stop No. 5 | Brews with buddies at Abettor Brewing Company, 128 N. Highland St. Head down the brick road of Depot Street to close out the day with some local craft beer or cider.

Pro tip: Download the Tour Winchester app for even more fun places to eat, stay + play.

More from LEXtoday
The James Beard finalist is bringing her Sri Lankan-inspired cooking to national television while celebrating 10 years of Tuk Tuk Snack Shop with limited Saturday pop-ups in Lexington.
We dive into horse-related place names around Lexington.
The Lexington Public Library offers free educational resources that citizens can utilize to learn new skills, advance their careers, or just continue to stay curious.
Make the most of good weather by taking your meals al fresco on one of Lexington’s many beautiful patios.
Put your money where your community is and help us create a guide to small businesses by submitting your favorite local spots and sharing this page with a friend.
Talk about a work walk of art.
Discover and document local species as part of a worldwide effort to track biodiversity this spring.
Directly north, east, south, and west of us, cities across the world await.
Bookmark this guide for a curated list of events taking place each month that we’re most looking forward to.
From breakfast to dinner — we’ve rounded up a day full of kid-friendly activities for the whole family to enjoy.