Fine Dining at The Cottonwood Supper Club

For a romantic date night, head to The Cottonwood Supper Club for a delicious meal in a cozy atmosphere. Enjoy dishes like steak and seafood while sipping on cocktails or wine. The intimate setting and attentive service make this restaurant a top choice for couples looking to enjoy a special evening together.

Alternative options: The Whistle Stop Restaurant, Hank’s Dairy Bar

On-Demand Childcare in Your Neighborhood

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Movie Night at The Fennimore Plaza Theatre

Catch the latest blockbuster or an indie film at The Fennimore Plaza Theatre. Sit back, relax, and enjoy a movie together in this historic theater. Share a tub of popcorn and a box of candy for the ultimate movie night experience.

Alternative options: Hill Theatre, AMC Dine-In

Wine Tasting at Weggy Winery

Indulge in a wine tasting experience at Weggy Winery, where you can sample a variety of locally made wines. Take a leisurely stroll through the vineyards and enjoy the picturesque surroundings while sipping on your favorite wines with your significant other.

Alternative options: Whispering Bluffs Winery, Spurgeon Vineyards & Winery

Couples Spa Day at Tranquil Moments Massage & Spa

Relax and unwind with your partner at Tranquil Moments Massage & Spa. Treat yourselves to a couples massage or facial for a pampering experience that will leave you both feeling rejuvenated and refreshed.

Alternative options: Essential Massage & Spa, Renew Aesthetic Clinic

Game Night at The American Legion

Get competitive with your partner at The American Legion, where you can enjoy a night of pool, darts, and other games. Grab a drink at the bar and challenge each other to a friendly game to spice up your date night.

Alternative options: 2 Rivers Gaming, Fennimore Lanes

Stroll Through Whispering Bluffs Winery

Explore the beautiful grounds of Whispering Bluffs Winery with your loved one. Take a leisurely walk through the vineyards and enjoy the scenic views while savoring a glass of wine. Don’t forget to pick up a bottle to enjoy at home!

Alternative options: Weggy Winery, Spurgeon Vineyards & Winery

Live Music at The Cotton Exchange

Dance the night away with your partner at The Cotton Exchange, where you can enjoy live music performances by local artists. Sip on a cocktail and hit the dance floor for a night of fun and entertainment.

Alternative options: Stash’s Bar & Grill, Toby’s Bar & Grill

Cooking Class at Tri-County Catering

Learn a new skill together by taking a cooking class at Tri-County Catering. Bond with your partner as you prepare a delicious meal under the guidance of experienced chefs. Enjoy the fruits of your labor together at the end of the class.

Alternative options: Driftless Market, Sweet N Saucy

Outdoor Picnic at Swan Lake Park

Pack a picnic basket and head to Swan Lake Park for a romantic outdoor meal with your significant other. Enjoy the serene surroundings of the park as you indulge in a delicious spread of sandwiches, fruits, and cheeses. Don’t forget a blanket to sit on!

Alternative options: Merchant Park, Depot Park

Karaoke Night at Stash’s Bar & Grill

Let loose and have a blast at Stash’s Bar & Grill with a fun-filled karaoke night. Sing your hearts out to your favorite songs and cheer each other on as you take the stage for a memorable date night experience.

Alternative options: The Cotton Exchange, Toby’s Bar & Grill

As a parent, it’s important to take time for yourselves and enjoy a date night with your partner. Wyndy makes it easy to find a trusted and reliable babysitter so you can have peace of mind while you’re out on the town. Book a sitter through Wyndy and make the most of your date night in Fennimore!