15 Best Things to Do in Winchester, TN

Winchester, TN
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Winchester, Tennessee, is a small city along the cusp of Tims Ford Lake.

This place oozes old-school charm partnered with an abundance of beautiful nature surrounding its borders.

Since Tennessee has deep roots in the history of the American South, Winchester is also a historical hub.

You can find a few museums and historical sites there.

It’s also the home of several distilleries crafting world-famous Tennessee whiskey.

Are you ready to explore Winchester, Tennessee?

Here are the best things to do in the city:

Spend the Day at Tims Ford State Park

The waters of Tims Ford State Park
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Located along the Tims Ford Reservoir, the Tims Ford State Park is one of the most picturesque nature areas in Tennessee.

The park spans over 3,500 acres, with myriad activities and sights.

With its proximity to the water, the Tims Ford State Park is a favorite destination for fishing.

The park is a top bass fishing destination spot.

It is also a favorite recreational lake spot in the state, with other activities available such as boating and swimming.

You can rent kayaks and canoes nearby and explore the park waters.

Wooden footbridge at Tims Ford State Park
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There are also great recreational activities to do on-ground.

You can rent cabins along the wooded slopes of the lake, all equipped with cooking equipment, utensils, and linens for a good night’s sleep.

You can also bring in your campers to enjoy your stay in great Tennessee outdoors.

During the day, you can enjoy activities such as running, hiking, and biking, having a beautiful view of the reservoir while you go along the trails.

Tims Ford State Park is a beautiful destination in Winchester, filled with fresh air, clear waters, and stunning views.

A bicycle along Tims Ford State Park's paved trail
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Catch a Show at the Oldham Theater

The Oldham Theater opened in the 1950s.

Since then, it has become an institution in downtown Winchester.

Its exterior exudes old-school charm, with the vintage lights and displays greeting patrons as they walk in.

The inside, however, boasts state-of-the-art movie features as the establishment has undergone several renovations and improvements.

Book your tickets and catch a show in the theater’s two movie rooms.

Don’t forget to order a tub or two of fresh buttery popcorn to enjoy while you watch the show.

Admire the Beauty of Harvey’s Garden

Winchester local Harvey Templeton envisioned Harvey’s Garden as a beautiful green space within walking distance from downtown Winchester.

In 2003, his son and daughter-in-law helped realize Templeton’s entire vision.

Harvey’s Garden features beautiful flowers and shrubs of different varieties, all carefully landscaped with detail.

It is open to the public every day, and admission is free.

Take a stroll around the gardens and bask in relaxation as you take in the views at Harvey’s Garden.

Experience Old World Winchester at the Hundred Oaks Castle

Built in the 1800s, the Hundred Oaks Castle remains one of the country’s few standing castles.

Benjamin Decherd once owned the castle.

He was a planter who founded the City of Decherd.

Eventually, it changed ownership until the Bramlett Family bought the place in 1996.

They helmed its restoration.

Once you step inside the castle, you’ll feel like you’re taken back in time.

They have preserved the old-world look of the place from hundreds of years ago.

You can join guided tours if you want a detailed view of the different rooms of the castle, with some of the artifacts dating back to the building’s earliest days.

While you’re here, explore the beautiful sprawling gardens beside the castle.

Rosemary Verey of Barnsley Gardens designed the gardens here.

Mrs. Verey was a close personal friend of the Bramlett Family.

Kew Gardens featured this place in their book, with its foreword written by Prince Charles.

Go back in time and explore old Winchester on your visit to the Hundred Oaks Castle.

Dine like It’s the 50s at Holt’s Diner

Everything in Winchester makes you feel like you’ve stepped back in time, and Holt’s Diner is no exception.

Located along Dinah Shore Boulevard, Holt’s Diner provides patrons with American comfort food favorites served in the old diner style popular in the 50s.

Dig into their house specialties like the Broaster Chicken, a crispy and light chicken that locals have enjoyed for over 60 years.

Otherwise, try their handcrafted burgers, made with 100% certified beef.

Bring the whole crew and order the buckets and basket sizes of the Broaster Chicken.

Don’t forget to order sides to accompany your juicy chicken, such as French fries, potato wedges, or onion rings.

You can also order from their array of delicious sandwiches and daily plates that feature favorite Southern dishes.

Cap off your meal with a sweet treat such as their hand-scooped ice creams or delectable milkshakes.

You’ll leave Holt’s Diner hungry and happy.

Relax on the Waters of the Twin Creeks Marina

Are you looking for a relaxing place to stay during your visit to Winchester?

The Twin Creeks Marina is the perfect destination for you.

Situated right along Tims Ford Lake, the Twin Creeks Marina is a community that offers both locals and visitors a taste of tranquil lakeside living.

Book a stay at one of their waterfront cottages with a boat dock.

There’s nothing like waking up to a morning view and having your cup of coffee with a gorgeous water view.

For recreational activities, you can do all sorts of water activities, from boating, fishing, and other types of water sports.

The Twin Creeks Marina has even got your dining options covered, as they have a bar and grill on-site serving the freshest seafood dishes.

Spend your days enjoying great food and drink and beautiful views while you stay at the Twin Creeks Marina.

Enjoy a Meal Overlooking the Water at Hard Dock Café

Do you want a meal with a view?

You can experience this at the Hard Dock Café, located right on the Tims Ford Marina.

The café is famous for its burgers; people say they serve one of the best cheeseburgers in Winchester.

Don’t miss out and order one or two for yourself while you’re here.

They also have a great selection of pizzas and small bites fit for everyone.

They have a Breakfast Bar available on the weekends, serving up morning favorites like scrambled eggs, crispy bacon and sausages, French toast, and free-flowing coffee.

Discover Civil War History at the Old Jail Museum

Within walking distance of downtown Winchester is the Old Jail Museum, a small but exciting little destination in the city.

With Tennessee’s history running deep in the American South, the museum is an essential location for guests who want to know more about the city’s roots.

The building houses a collection of artifacts and memorabilia dating back to the Civil War and Pioneer eras.

It also houses some belongings of global celebrity Dinah Shore.

Before becoming a museum, the building was an old county jail from 1897 to 1972.

The Old Jail Museum is a nondescript little location but is worth a visit.

Grab a Cup of Joe at the Walnut Hill Coffee Company

There’s nothing like a good cup of coffee to get you started with your day as you prepare to explore Winchester.

Stop by the Walnut Hill Coffee Company for a quality cup partnered with great community vibes.

Sample one of their unique brews like the Coconut Caramel Macchiato.

You can also try the Fidgety Fox, a triple-shot of espresso with handcrafted vanilla syrup with ice and topped with half-and-half.

Of course, there are also the classics, such as a latte and americano.

There is also a fine selection of teas for those who prefer it over coffee.

Pair your drinks with something sweet from their pastry case or a warm sandwich from their food selection.

You’re fueled up for your day exploring the city after a visit to the Walnut Hill Coffee Company, located right in the heart of the city.

Explore the Winchester Parks and Recreation Campgrounds

What better way to enjoy a day out in Winchester than to do it in the great outdoors?

The Winchester Parks and Recreation Campground is another excellent location to see Tennessee’s beautiful surroundings.

Located on the cusp of Tims Ford Lake, the park covers a large expanse that is perfect for setting up lots of outdoor and water activities.

Pitch your tents and set up your campsites on the grounds.

For those with RVs, the grounds are fully equipped for you to hook up and set up camp.

The campgrounds are also adjacent to several more areas that make up Winchester Parks and Recreation.

These areas include the Winchester Dog Park, where you can walk and play with your furry friends.

You can also go to the City Park Disc Golf Course, and the Winchester Swimplex, the city’s public pool.

You definitely won’t run out of recreational activities to do at the Winchester Parks and Recreation Campgrounds.

Book a Stay at the Someday House

Do you want to have a little corner of Winchester all to yourself?

Book a stay at the Someday House, located on a private wooded lot tucked along the Tims Ford Lake.

The house features a covered porch, two large rear decks, and your private dock, making it perfect for a tranquil lakeside living experience.

Inside, the house has over three bedrooms, two bathrooms, and a fully-stocked kitchen.

You can whip up homemade meals for the family and enjoy them right in the comfort of the homey dining area.

Like most old-school homes, there’s also a front porch swing, which is great to relax on and take in the beautiful views of Tims Ford Lake.

For recreation, you can take advantage of its closeness to the water and do a bit of boating or paddling.

The Someday House is also close to the Twin Peaks Marina.

Book your tranquil and relaxing stay at the Someday House today.

Explore Downtown Winchester

A walk along Downtown Winchester makes you feel like you’re back in the 1900s.

Most of the buildings preserve the iconic architecture of the decade.

The Franklin County Courthouse is the piece-de-resistance of the old downtown buildings, built in the Art Deco style.

Walk through the different shops along the boulevard, selling everything from clothes to antiques and homeware items.

You can also grab a bite to eat from the various restaurants sprawled all over, offering a variety of Southern favorites and other types of dishes.

The Oldham Theater is also within walking distance of the downtown area.

Downtown Winchester also makes for the perfect postcard souvenir to commemorate your stay, exuding the old-world look and charm the city is known for.

Other Things to Do Nearby

Get Your Favorite Whiskey from the Jack Daniels Distillery

Exterior of Jack Daniels Distillery
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Jack Daniels is a proudly Tennessee product made in Lynchburg, Tennessee, 30 minutes from Winchester.

Jasper Newton Daniel, more commonly known as Mr. Jack, made this world-famous whiskey.

He introduced the Old No. 7, his signature charcoal-mellowed Tennessee whiskey.

See how the distillery crafts this worldwide favorite at the Jack Daniels Distiller.

Learn the secrets of what made the drink a household name for over 150 years.

Alcohol samples in Jack Daniels Distillery
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Visitors can join guided tours of the distillery, seeing every step of the process.

Watch them collect the limestone and water, roast the charcoal for mellowing, sending ingredients to fermentation and bottling to get the spirit.

After the tour, you can enjoy homemade Southern food at Miss Mary Bobo’s Restaurant, just like Mr. Jack did a century ago.

Don’t forget to take home a bottle or two of Jack Daniels.

Nothing beats a fresh brew right from the source.

Don’t miss a visit to the Jack Daniels Distillery.

Experience for yourself how an American icon comes to life.

Old fireplace at Jack Daniels Distillery
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See the Natural Architectural Marvel of the Walls of Jericho

Waterfall at Walls of Jericho
Fredlyfish4, CC BY-SA 4.0, via Wikimedia Commons

Located South of the city, and almost half-hour drive to the Tennessee-Alabama border, are the Walls of Jericho.

You can find it in Belvidere, Tennessee, 22 minutes from Winchester.

It is a natural architectural marvel, with the “walls” themselves being a natural stone amphitheater with various water features such as waterfalls and pools.

The hike up to see the main site is quite strenuous, with the seven-mile walk taking on rocky terrain and gushing waters.

The waters of Walls of Jericho
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The general area covers over 25,000 acres that cross Jackson County in Alabama and Franklin County in Tennessee.

It’s no easy feat to travel to and from the Walls of Jericho, so allot yourself over six hours to get through the hike.

However, the sight of this natural beauty is definitely worth the effort.

Take a Sip of Tradition at Prichard’s Distillery

Exterior of Prichard’s Distillery
Brian Stansberry, CC BY 3.0, via Wikimedia Commons

Located in neighboring Kelso, Tennessee is Prichard’s Distillery, considered one of the state's first “legal” distilleries.

This place is 27 minutes from Winchester.

Established in 1997, the distillery hand-crafts its spirits in traditional copper pots.

This process is similar to how the early settlers in America did it over 200 years ago.

The tours and tastings Prichard’s offers are free to the public.

There’s no need for you to book an appointment either.

Just come by, and they would be happy to accommodate!

The owners believe in providing a warm and hospitable experience for their visitors.

After all, their grandad and founder Phil Prichard did the same thing in the early days.

See how Prichard’s brews their line-up of liquors, from rums, whiskies, vodkas, liqueurs, and moonshine.

Don’t forget to take home a bottle or two of your favorite flavors.

Final Thoughts

Winchester, Tennessee, is an exciting destination, offering endless bounds of nature, rich history, and warm Southern hospitality.

There’s no other destination that could offer the vast array of activities that the city has.

Experience the hustle and bustle of downtown to the tranquil confines of your lakeside cottage.

What are you waiting for?

Book your visit to Winchester today!