Wilmore Fall Festival: Small Town Charm

Crisp Fall Air + Shopping = Happy Saturday

After weeks of nearly 90° days, it’s lovely to feel some crisp Fall air in the Bluegrass— a perfect day for a fall festival!

Momma and I are big fans of shopping small, so we went to Wilmore to check out what their fall festival had to offer. Wilmore is a small town just south of Lexington, with a lot to offer.

As soon as we turned onto Main Street, we saw people filling the street. Tents filled both sides of the street and people spilled in and out of the local shops.

The local shops are some of the cutest you can find, and just my style!

The Olive Branch

My friend, Erika Miller, owns The Olive Branch- a boutique that works with 20+ Kentucky makers & artisans. From adorable throw pillows to calligraphy prints, inspirational tees and so much more.

Hey Y'all Pillow

One of my favorite finds at Erika’s shop, this adorable “Hey Y’all” pillow! It looks perfect in our living room. Right after Momma & I walked in, I saw it and knew it would have to come home with me.

Drinklings Coffee Roastery shares a space with The Olive Branch. It’s such a cute & charming coffee shop. And, if you’re like me and love the smell of coffee, then you definitely want to check them out.

Sweet Erika & her hubby bought the space and renovated it all…and let me tell you, it’s gorgeous!

Scoops on Main

My new favorite addition, Scoops On Main! It’s an adorable ice cream cart serving homemade ice cream by the scoop. During the fall festival, Momma & I tried their cookies & cream ice cream. It was delicious!

The Olive Branch is open Monday-Saturday 10 AM-5 PM. Drinklings Coffee Roastery is open 7:30 AM-5 PM.

Wilmore Fall Festival

Who doesn’t love fresh flowers? Joy Lee, owner of Floral Joy has teamed up with Erika at The Olive Branch to offer beautiful flowers.

Floral Joy

Pumpkin succulent

Joy’s flowers are gorgeous! The first time I met her, she had a flower cart set up outside The Olive Branch during Wilmore’s Night Market.

In full disclosure y’all, I am not a very good plant momma, but I’m a work in progress.

During the fall festival, Joy had the cutest pumpkin succulents! I couldn’t resist. She gave me tips to keep my little plant alive, and believe me y’all, I’m trying! After pumpkin season passes, Joy said the succulent will continue to thrive.

Joy & Erika often team up to offer floral arranging classes at The Olive Branch. I can’t wait to try one!

Next door is another adorable boutique, Shades of Bluegrass.

Shades of Bluegrass

Shades of Bluegrass is an adorable boutique featuring local goods by local artisans. Their slogan- for the love of Kentucky.

The first time I walked into their shop, I loved all of their locally made items. From personalized barrel heads, to cute door hangers, handmade jewelry & much more.

The owner is so sweet! She makes all of her customers feel welcome.

We had a great time at the Wilmore Fall Festival! It was so quaint & full of fun!

If you’re ever in the area, I absolutely suggest checking out Wilmore’s small town charm!