There are a lot of Kentucky towns that have amazing holiday festivals and definitely know how to do Christmas right. Grand Rivers, Louisville, Lexington, and Newport, to name just a few, are all pretty spectacular and have plenty to do to get into the holiday spirit. However, one town in Kentucky goes all out and celebrates for almost two straight months. That town is Ashland, and it transforms itself into a winter wonderland every year and is arguably the best winter town in Kentucky.

Ashland is the largest city in Boyd County, and is on the Kentucky-West Virginia border. Even just walking the streets in downtown Ashland during the Christmas season can be magical. This winter wonderland town in Kentucky knows how to celebrate the holidays and there are several events throughout November and December.

Facebook/Winter Wonderland of Lights Festival-Ashland, Kentucky

Every year, their Winter Wonderland of Lights Festival transforms Ashland into a magical Christmas town. In 2019, the Opening Night ceremony takes place November 18th and the parade will be held on November 26th. You can see all of the details here.

Facebook/Winter Wonderland of Lights Festival-Ashland, Kentucky

The parade has a different holiday-related theme every year, and 2019’s theme is “Candy Cane Christmas.” Get excited for all of the floats and parade participants to go all out with this charming and festive theme.

Facebook/Winter Wonderland of Lights Festival-Ashland, Kentucky

The drive-thru light display at Central Park in Ashland is also a must-see part of the town and should top your list of places to visit in winter in Kentucky.

Facebook/Winter Wonderland of Lights Festival-Ashland, Kentucky

On Sunday through Thursday from dusk until 10pm, and until 11pm on Friday and Saturday, you can drive around and admire the incredibly intricate light displays.

Facebook/Winter Wonderland of Lights Festival-Ashland, Kentucky

The Christmas lights in Ashland truly are some of the best in the state.

Facebook/Winter Wonderland of Lights Festival-Ashland, Kentucky

Volunteers work hard to make sure the displays are top notch.

Facebook/Winter Wonderland of Lights Festival-Ashland, Kentucky

You’ll also find “Christmas Cards to the Community” among the lights.

Facebook/Winter Wonderland of Lights Festival-Ashland, Kentucky

Another awesome Christmas event in Ashland is the Festival of Trees and Trains at the Paramount Arts Center. As yet another enchanting part of this town, you can visit the festival from November 22nd through December 1st.

Facebook/Festival of Trees and Trains-Paramount

The Festival of Trees and Trains is a fundraiser put on by the Paramount Women’s Association to raise money for the Education Department of the Paramount Arts Center.

Facebook/Festival of Trees and Trains-Paramount

This family-friendly event features cocoa with Santa, holiday music, amazing toy train displays, and more than 200 trees decorated by community members and groups.

Facebook/Festival of Trees and Trains-Paramount

It’s fairly obvious that Ashland is in the running as the best winter town in Kentucky. If you’re looking for places to visit in winter in Kentucky, add this magical town and all of its festivities to your list. And if Ashland is too far of a drive, check out our list of enchanting Christmas towns to find one closer to you.

Facebook/Winter Wonderland of Lights Festival-Ashland, Kentucky

Facebook/Festival of Trees and Trains-Paramount

For more information on the Winter Wonderland of Lights Festival in Ashland, follow along on Facebook here.

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Address: Ashland, KY, USA

The OIYS Visitor Center

Best Winter Town In Kentucky October 11, 2019 Andrea Limke What other places are the most festive towns in Kentucky? As the holidays approach, Kentucky has many towns that transform into winter wonderlands. Of course it’s always more festive when there is snow on the ground, but no matter what the weather is like, these are the best places to visit in winter in Kentucky. If you are looking for another best winter town in Kentucky, you can always try the bigger cities such as Louisville and its huge tree, Newport and its ice skating rink, or Lexington and its charm and light displays. Also check out 12 other Christmas towns in Kentucky that are always festive, featured in our previous article here. What are the best things to do for Christmas in Kentucky? There is no shortage of festive things to do for Christmas in Kentucky. Check out a local light display, have breakfast with Santa, take a ride on the Polar Express, or even drive through an underground light show at the Louisville Mega Cavern. This is just the beginning of the festive fun you can have in Kentucky during the holidays. Check out a variety of our Christmas articles featuring places in Kentucky here. What kinds of activities can I do in winter in Kentucky? Many of the things to do in winter in Kentucky revolve around the holidays, but there are other options once the festivities are over. Go horse back riding in the snow, take a hike, or consider a visit to an ice skating rink.

The OIYS Visitor Center

Best Winter Town In Kentucky

October 11, 2019

Andrea Limke

What other places are the most festive towns in Kentucky? As the holidays approach, Kentucky has many towns that transform into winter wonderlands. Of course it’s always more festive when there is snow on the ground, but no matter what the weather is like, these are the best places to visit in winter in Kentucky. If you are looking for another best winter town in Kentucky, you can always try the bigger cities such as Louisville and its huge tree, Newport and its ice skating rink, or Lexington and its charm and light displays. Also check out 12 other Christmas towns in Kentucky that are always festive, featured in our previous article here. What are the best things to do for Christmas in Kentucky? There is no shortage of festive things to do for Christmas in Kentucky. Check out a local light display, have breakfast with Santa, take a ride on the Polar Express, or even drive through an underground light show at the Louisville Mega Cavern. This is just the beginning of the festive fun you can have in Kentucky during the holidays. Check out a variety of our Christmas articles featuring places in Kentucky here. What kinds of activities can I do in winter in Kentucky? Many of the things to do in winter in Kentucky revolve around the holidays, but there are other options once the festivities are over. Go horse back riding in the snow, take a hike, or consider a visit to an ice skating rink.

The OIYS Visitor Center

The OIYS Visitor Center

As the holidays approach, Kentucky has many towns that transform into winter wonderlands. Of course it’s always more festive when there is snow on the ground, but no matter what the weather is like, these are the best places to visit in winter in Kentucky. If you are looking for another best winter town in Kentucky, you can always try the bigger cities such as Louisville and its huge tree, Newport and its ice skating rink, or Lexington and its charm and light displays. Also check out 12 other Christmas towns in Kentucky that are always festive, featured in our previous article here.

What are the best things to do for Christmas in Kentucky?

There is no shortage of festive things to do for Christmas in Kentucky. Check out a local light display, have breakfast with Santa, take a ride on the Polar Express, or even drive through an underground light show at the Louisville Mega Cavern. This is just the beginning of the festive fun you can have in Kentucky during the holidays. Check out a variety of our Christmas articles featuring places in Kentucky here.

What kinds of activities can I do in winter in Kentucky?

Many of the things to do in winter in Kentucky revolve around the holidays, but there are other options once the festivities are over. Go horse back riding in the snow, take a hike, or consider a visit to an ice skating rink.