Dreaming of Travel: Leiper's Fork, Tennessee

Published on September 24, 2020 - Updated on October 16, 2020

Quaint, family-friendly, and bursting with true southern hospitality, this tiny town deserves a special spot on your travel bucket list.

Free S’mores outside multiple small-town shops?  An honesty box for locally made honey?  A village façade that looks like a movie set or something that’s lost in time?  Sound like a dream?  It’s not: it is, in my opinion, the cutest small town in Tennessee: Leiper’s Fork.

Leiper's Fork Gallery.jpg

Leiper’s Fork makes for a great family day trip from Nashville or overnight from anywhere.  Only about a thirty-minute drive southwest from Nashville, it’s located on the Natchez Trace Parkway and is listed on the National Register of Historic Places as a historic district. 

While there are only about six hundred and fifty residents in the village, it boasts galleries and restaurants, and shopping that tells you that the visitors have caught on to its charms.  There are a number of inns and restaurants, antique stores, and art galleries along the tiny strip that comprise the business/commercial district.

Leiper's Fork Gallery 2.jpg

While it’s typically fun any day to head out to Leiper's Fork, there are a number of annual festivals and events for such a small town – music festivals, The Hillbilly Half Marathon & Little Billy 5K, and, of course, the annual "Almost Famous Leiper's Fork Christmas Parade" (the second Saturday in December).

Where to eat

The Country Boy is my favorite indoor spot to eat in Leiper's Fork. While it does not typically have outdoor dining options and it is normally the ideal choice if it's too hot, too cold, or raining, but currently in the era of COVID they now have outdoor seating available!  It's cute, friendly, and typically pretty fast getting your food.  

The inside is a low-key classic diner, and the menu is best for brunch or lunch.  Adults can choose from a range of delicious bites, including salads, sandwiches, and traditional brunch fare.  Young diners have a range of typical kid items - hamburgers, chicken strips, grilled cheese, etc.  It's located right on the main drag in Leiper's Fork, so grab a table well-situated to enjoy some fun people watching as you enjoy your meal.  

Puckett's Grocery Leiper's Fork.jpg

Right across from The Country Boy is the famous Puckett’s Grocery – it’s unpretentious, friendly, and always filled with locals and tourists.  The brisket is to DIE for and there are regular (and good!) musicians playing inside.  Outdoors there are picnic tables if it’s a nice day.

Where to shop

Leiper's Creek Gallery.jpg

Because it’s so small, you can pretty much hit up all the galleries, boutiques, and antique shops in an afternoon.  The shopowners are lovely to children and typically have a shop cat or dog and a piece of candy to give away.  However, my favorite things in winter are the S’ mores stations that sit outside multiple storefronts with a cute firepit and comfy seating.  What a win for both kids and adults!

If you're family is heading there for a laid-back, reenergizing escape, just don't forget to bring your masks!!

Where to stay

Sweeney Cottage was bought by the famed Holly Williams (daughter of Hank Jr. and granddaughter of Hank) and renovated to be honestly, quite dreamy.  What I love about it for families is that it’s right on the main drag of the action (in case little ones get tired) and has room to sleep six. It boasts a tiny but charming and efficient kitchen and cozy sleeping spaces. It also honors all COVID safety measures so it’s a convenient option for a safe little getaway.

What to do

Leiper's Running in the Field By the Barn.jpg

Driving around the country roads will leave you breathless as you spot lambs, horses, and cows.  Running through a local field is a great way to tire the kids out.  Puckett’s, as noted above, has a great schedule of live music. Timberland Park is a quick drive and boasts hiking trails and a butterfly garden.  And of course, if you’ve had enough eating and strolling through the galleries, the Spa at Leiper’s Fork might be a perfect place to refresh for tired mommas that can steal away for a spell.

Since you're already out that way, push a bit further on the Natchez Trace for an easy, kid-friendly hike to Jackson Falls before heading back home.

What’s your favorite road trip destination? Share your highlights on Instagram @gethappyly.

Explore more of our Dreaming of Travel series in another music lover’s paradise like Memphis, or find your happy place on Nantucket or Bear Lake: An Adventurer’s Oasis. If you’d prefer, Make Nature Your Focus in Harper’s Ferry, Plan Your Next Adventure in Savannah, Explore Grand Teton or Yellowstone, Dream about a Tubing Adventure in Salida, Colorado, or further fuel your wanderlust in the Dry Tortugas or at Mojave National Preserve. You can also explore the happyly app!

If you have a perfect getaway or a favorite landscape, please reach out to us at team@happyly.com and we'll be excited to cover it! 

Thoughtfully captured by:
Emily O'Grady
Emily O'Grady lives with her daughters Eloise (5) and Charlie (3.5), husband Mick, and their two senior dogs Porter and Francie, in Nashville. They’ve called Music City home for 7 years this September. After Emily and Mick met in New Zealand over 15 years ago, they’ve hiked and backpacked extensively across the globe for months at a time. In their new roles as parents, they’ve hit pause on their most extreme adventures for now, but they are consciously raising their daughters to love and appreciate nature, getting outside and exploring as much as they can in the hills of Tennessee and beyond. During the weekdays, you can find Emily leading teams across Asurion’s Product Development team, bringing the company’s service strategy to life across carrier clients. Before joining Asurion, Emily was an Engagement Manager for McKinsey & Company for 4 years, as well as held Analyst roles with Telephia (Nielsen) and Bank of America Global Corporate and Investment Bank. Emily holds a BBA in Finance, French and European Studies from Southern Methodist University and an MBA from Northwestern University, Kellogg School of Management.
More posts by Emily
Sharing tips that we hope will make your next Rocky Mountain National Park visit extra special
How to decide if an Au Pair is a good fit for you.
Emily O'Grady's favorite family traditions