10 Valentine’s Weekend Date Ideas

Looking for something to do this Valentine's Day?

10 Valentine’s Weekend Date Ideas
Valentine's Day Ideas

It's the sweetest time of year! Plan a memorable Valentine's adventure for your love this year.

You don’t have to look far for a vibrant community that offers unique indoor and outdoor activities for everyone. To help make it easier, we put together this list of 10 local Valentine's date and family-fun ideas, many of which you’ll want to revisit again and again. 

1 - Join the Winchester 5th Annual Chocolate Walk

The Downtown Winchester Program is holding its fifth annual Chocolate Walk on Saturday, February 12th, from 10:00 am to 2:00 pm. Visit the shops, get free sweet treats, and listen to romantic music while you stroll around downtown Winchester. Tickets are only $10, with pre-purchase recommended.

2 - Spring for a fancy coffee drink.

Specialty latte with foam art

Valentine’s dates don’t have to be extravagant or expensive but find a way to make them special. Maybe it’s a leisurely breakfast for two at Sunrise (The Breakfast Place), or splurging on a specialty coffee drink at one of the local coffee shops. Try the Salted Caramel Turtle Frap at Java Hut or go for a fruit smoothie at the Walnut Hill Coffee Company truck. Don’t want to get hit by Cupid’s arrow? It sounds like an Ugly Break Up from Holy Grail Coffee Co might be just what you need.

3 - Visit the University of the South in Sewanee.

Coffee drinks and fresh baked goods in hand, why not head out just 20 minutes away and visit the University of the South campus in Sewanee? Founded in 1857, the University of the South is a beautiful private Episcopal liberal arts college. Not only are the campus and grounds exceptional, but it’s also home to All Saints Chapel, a breathtaking chapel with dozens of stained glass panels that rival many European cathedrals. 

Sewanee also features 60 miles of hiking trails and the very popular Memorial Cross, situated atop the Cumberland Plateau overlooking a magnificent bluff - a sight to behold any time of the year. 

4 - Take a lakeside hike closer to home.

If beautiful scenery sounds romantic, you don’t have to go further than Tims Ford Lake, one of Tennessee’s most picturesque lakes. Spend the day exploring the 1,300 acres of state park or stroll along the lakeside walking trails at Twin Creeks, checking out the construction progress on our new waterside cottages while you’re at it.  Go in the late afternoon, and you’ll be treated to one of the best sunsets on the lake.

5 - Buy a last-minute gift in Downtown Winchester.

Winchester, TN on Tims Ford Lake

If you haven’t been downtown in a while, a lot has changed. You’ll find several new, eclectic shops and restaurants. Stop in one you've never visited before. You never know what treasures await.

6 - Go bowling with your family. 

Bowling is an ideal date or family-fun activity. Visit nearby Tullahoma Lanes to enjoy laid back food and fun with the people you love. If you want to mix things up, try downloading printable games to play while bowling, like Bowling Bingo or Funky Bowl. You’ll have a blast. 

7 - Enjoy a wine or spirit tasting.

Spirit tasting room

If you’re a wine, beer, or spirit lover, there are many nearby attractions to visit. Try a wine tasting at Beans Creek Winery or make a day of going to Lynchburg and checking out the Lynchburg Winery, the Jack Daniels Distillery, and historic downtown Lynchburg. Beer fans will enjoy a visit to a local craft brewery such as Ole Shed Brewing Company in Tullahoma, where, during nice weather, you can even take your (leashed) dog on the patio. After all, isn’t your dog your true love anyway?  

8 - Dress up and dine out.  

If you’re looking for an opportunity to dress up and experience fine dining,  Emil’s Bistro and Lounge in Tullahoma boasts excellent food and craft cocktails. Their menu offers unique dishes of both classic French and traditional Southern cuisine for you to enjoy.

9 - Visit the drive-in.

If you’re tired of watching Netflix from your sofa, pack up the rest of the Valentine’s candy and head out to the drive-in. You can stay toasty in your car while still enjoying a movie on the big screen at this unique out-of-home experience at Montana Drive-In, which is open year-round.


10 - Book a weekend getaway.

Give your love something to look forward to by booking a weekend getaway at the lake. Twin Creeks Marina and Resort offers a variety of affordable lake rental options, including lake house rentals, waterside cottages, luxury lake houses, and RV park sites

Each rental property comes equipped with the essentials to make your stay comfortable, including decked-out kitchens, four to six bedrooms, plenty of bathrooms, easy access to the lake and boat rentals, internet, cable, an outdoor grill, cozy patios, and some of the best views at Tims Ford Lake. Many also feature a fire places indoors, private docks, covered porches, and outdoor fire pits close by.   

No matter how you prefer to celebrate Valentine’s Day, you’ll find many great local experiences to share - or to enjoy solo. What are some of your favorite local businesses or attractions? Share them with us in the comments or on Facebook

*This post was first published in 2021 and updated in 2022.