Events Calendar - Visit Winchester Kentucky

Board Game Night at Abettor Brewing @ Abettor Brewing Company Depot Street

Tickets

Sep 27 @ 5:22 pm – 6:22 pm

Time to play! Come to Abettor Brewing for Board Game Night. Play one of their games or bring your own.

$8 beer flights & Rotating food trucks 5-9pm

Abettor is open 3pm – 9pm

Sep

29

Fri

Harvest Moon Party – Harkness Edwards Vineyards @ Harkness Edwards Vineyards

Tickets

Sep 29 @ 5:00 pm – 8:00 pm

Join us at the vineyard to celebrate the Harvest Moon! We will have a special barrel tasting at the Peach house, along with $5 glasses of Wine, Sangria and a speciality fall drink. Free to attend.

Joining us will be live music from Lauren Mink and Dale Adams, Cookies and Cream dessert truck, permanent jewelry by The Spark Collection Lex (appointment link available soon), Tarot card readings, and cooking classes with Sassy Ashley.

This is our last Golden Hour of the year! We are ending an AMAZING season with our Harvest Moon Party.

A Harvest Moon Party is a festive event that celebrates the arrival of the Harvest Moon, which is the full moon that occurs closest to the autumnal equinox. This moon is known for its unique characteristics, including its bright and luminous appearance, which historically allowed farmers to extend their working hours in the fields during the fall harvest. We will be celebrating our grape harvest under the Harvest Moon, which will first appear on the evening of Friday, September 29th.

Sep

30

Sat

Opening Day & Vendor Market – Gourd Times Pumpkin Patch @ Gourd Times Pumpkin Patch

Tickets

Sep 30 @ 11:00 am

Join us for the grand opening of our pumpkin patch’s first season!

We are hosting a Vendor Market on the same day, filled with unique treats, treasures, décor & fun!

Grasstoberfest @ The Parklette

Tickets

Sep 30 @ 2:00 pm

YOU ASKED FOR IT SO WE’RE DOING IT!

A special thanks to West Sixth Brewing & Winchester First for helping make the 2nd Annual Grasstoberfest Music Festival happen. Start stretching those dancing legs!

Rumke Mountain Boys

Reedy River String Band

Tom and Matt Fassas

Highland Tiger

The First Annual BBQ Cook Off

Kids Activities

Beer Garden

Grasstoberfest Music Festival @ The Parklette

Tickets

Sep 30 @ 2:00 pm – 11:00 pm

Fall / Halloween Market – Beech Springs Farm Market @ Beech Springs Farm Market

Tickets

Sep 30 @ 5:00 pm

Festivities start at 5:00. Admission at the gate is $5 for adults and $3 for kids 12 and under. ALL PROCEEDS go to the Stride Program. This allows them to continue to help amazing individuals with developmental and intellectual disabilities.

Vendors will be set up selling fall and Halloween themed items.
List of vendors include:
Charming Crafts
Creations by AM
Chelsea’s Chocolates
Busic Creations
Rockbridge Farmstead
Freckle & Bee
The Black Barrel Market Co
La Patisserie de Lindsay
Back Forty Soco
Sarabee Designs & Fiber Farm
Southern Songbird Farm
Creative Coffees Roastery
Bell on Wheels – come hungry
Yadi Win Hapycorner Barr

Vendors are all dressing up for Halloween, and you get to vote on which one is your favorite. The vendor who wins will get a special award. Also, vendors are passing out candy to your little ones, so make sure to bring a treat bucket.

What else will be happening?????
We will have a haunted walking trail from 7:30-9:00. It will be a short section of our walking trail decked out in Halloween decor and maybe a hidden jump scare or two. It will be up to the parents to decide whether the child is old enough to participate.
We will also have a movie going on our outdoor movie screen. We will be showing the 1995 Casper starting at 8:00 P.M. Bring your blanket and chairs if you want to stay for the movie.

Still working on a few other details, which we will announce at a later time.

Oct

4

Wed

Board Game Night at Abettor Brewing @ Abettor Brewing Company Depot Street

Tickets

Oct 4 @ 5:22 pm – 6:22 pm

Time to play! Come to Abettor Brewing for Board Game Night. Play one of their games or bring your own.

$8 beer flights & Rotating food trucks 5-9pm

Abettor is open 3pm – 9pm

Oct

7

Sat

Winchester Walks Ghost Tour @ Downtown Winchester

Tickets

Oct 7 @ 7:00 pm – 8:30 pm

Winchester Walks Ghost Tour

Join us for an eerie adventure on foot through the Historic Downtown Winchester! Get ready to be spooked as we explore the haunted tales and chilling legends of this ghostly Blue Grass city. Our knowledgeable guide will tell chilling stories that will send shivers down your spine. Whether you’re a skeptic or a believer, this in-person event promises a thrilling night of spooky fun to kick off your Halloween Season!

This is a walking tour that lasts 1.5 hours, and is approximately 2 miles long. The tour takes place after dark and although there are street lights present, flashlights will be provided. Some areas of the tour have uneven sidewalks, our guide and attendants will provide ample warning.

Frequently asked questions

What happens if it rains?

This tour will take place rain or shine, take note of the forecast and dress appropriately. In the case of an extreme weather event an alternate date will be provided.

Where should I park?

There is ample street parking available, additionally after 5:00pm the Winchester City Hall Employee parking lot, off of S Maple between the Speedway and City hall, is open to the public.

How long is the walk?

The Tour is approximately an hour and a half and covers approximately two miles.

Will the tour take us inside any of the haunted locations?

No, this is a walking tour and will take place entirely on public sidewalks. We will not be going inside any private homes or businesses. We also ask that all participants be respectful of our Winchester neighbors during the tour and adhere to the rules of conduct as explained by our Guide.

Is this tour for children?

The tour is geared for adults, it does involve spooky stories and murderous tales.

Oct

10

Tue

Legacy Nights Summer Concert Series – Legacy Park @ Legacy Grove

Tickets

Oct 10 @ 5:00 pm – 8:00 pm

FREE COMMUNITY EVENTS!!!

MUSIC!
Featuring local and regional musicians!

MAY 9 – MOJOTHUNDER
JUNE 13 – LAID BACK COUNTRY PICKER
JULY 11 – NVRMND
AUG 8 – OX-EYED DAISIES
SEPT 12 – DRIFTWOOD GYPSY
OCT 10 – THE ALLMAN BUTTER BAND

Two performances each night!

FOOD!
Food trucks from Winchester and the Bluegrass! Enjoy dinner, desserts, and drinks!

VENDORS!
Visit local craft vendors, sponsors, and non-profit organization booths during the event!

FAMILY ACTIVITIES!
Fun for kids and families!

Oct

11

Wed

Board Game Night at Abettor Brewing @ Abettor Brewing Company Depot Street

Tickets

Oct 11 @ 5:22 pm – 6:22 pm

Time to play! Come to Abettor Brewing for Board Game Night. Play one of their games or bring your own.