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Discover the best family-friendly activities and attractions in Winchester, TN

Looking for the most enjoyable things to do in Winchester, TN? Dig through this list and start planning your next fun and memorable day out with the entire family:

Bennett’s Pharmacy

Yes, the place is actually a pharmacy. But Winchester locals also know Bennett’s as the friendly neighborhood soda fountain, too. Stop by for filling sandwiches and creamy ice creams and milkshakes at this beloved Winchester institution that has been going strong for nearly six decades.

Downtown Winchester

Explore Winchester’s historic square – the spot where everything began for the Franklin County seat.

Right in the middle, you’ll find the picturesque courthouse – unmistakable with its Art Deco façade. All around the area, you’ll find so much more – from cozy neighborhood cafés and quaint gift shops, to fine dining restaurants and yoga studios. With so many options around, making the most of the experience is all up to you and your family’s whims and imagination.

Harvey’s Garden

You will find this local favorite just four blocks from downtown Winchester. And because admission is free, you’re free to stay and take a stroll this 34-acre garden sanctuary. Along the way, you and your family are sure to take in vibrant and rejuvenating sights and scents from the crepe myrtles, daffodils, pear tree blooms, and so much more.

This place is a testament to a family’s love for their home community, too. Winchester local Harvey Maxwell Templeton envisioned creating a lush, thriving garden that the entire community could enjoy at any time. When he passed away in 2003, his children inherited the vision and made it blossom into the beautiful public garden that it is today.

High on the Hog Festival

Winchester loves a good barbecue so much, the city has been dedicating week-long festivals for the mouth-watering smoked meat for more than 30 years now! The High on the Hog Festival is not just any food festival; it’s headlined by a world-class BBQ cook-off, so you can be sure that you’re getting nothing but the best grilled and smoked meats in town.

Hundred Oaks Castle

Built in 1830 for Benjamin Decherd – founder of the city of Decherd, TN – and completed in 1889, Hundred Oaks Castle is a stunning living relic of Winchester history. The picturesque mansion is certainly worth a visit for the many stories it proudly tells.

In 1860, the mansion was bought by Albert Marks, who served as governor of Tennessee in the late 1800s. It was his son Arthur, who decided to fashion a castle out of the original mansion after he fell in love with the distinct architecture he saw when he traveled to Scotland.

In the early 1900s until 1965, the structure was acquired and used a monastery by the Paulist missionaries. After that, the castle became the Franklin County Adult Activity Center. A massive fire nearly destroyed the building in 1990, but the property was acquired by the Bartlett family, who went to great lengths to restore it.

Plan ahead if you want to visit this remarkable destination as the castle is open only by appointment. Tours are available on a reservation-only basis.

Oldham Theatre

Care for a movie? The Oldham Theatre, located at 115 1st Avenue North East, will surely fit the bill.

But there’s more to this place than just a couple of hours well spent with blockbuster entertainment. You’ll also be embracing Winchester history. While its total count of two movie screens may seem modest, this theater has been part of the local community since 1950.

This place surely has stood the test of time and looks in great shape to last for much longer. Even its renovations have been deliberate about preserving its vintage look.

Tims Ford State Park

This one is a short drive away – about 10 miles, to be specific – but there’s no question that this place deserves a spot on this list.

Spanning 1,321 acres across, Tims Ford State Park provides the ideal complement to one of the most breathtaking lakes in the Volunteer State. Because of its location, the park offers an incredible range of activities that visitors of all ages can enjoy.

Bass fishing is one of the main draws of Tims Ford Lake, with several professional and local tournaments held throughout the year. Another exceptional way to appreciate the reservoir’s abundant natural resources is by bird-watching. The lush and thriving natural habitats around the area are populated by barred owls, pied-billed grebe, herons, and even bald eagles.

Eight public boat ramps provide access to the lake’s sparkling waters, while almost 30 miles of hiking and biking trails are available for anyone with a spirit for outdoor adventure.

Learn more about making the most out of owning a home in the Tims Ford Lake area. Contact us at Kay Caldwell Real Estate for the best real estate and lifestyle tips today. Call 931.434.0516 or BKRCaldwall(at)yahoo(dotted)com for more information.