Fine Dining at On the Green

Indulge in a delicious meal at On the Green, a charming restaurant located in the heart of downtown Oskaloosa. Enjoy a romantic dinner with your significant other in a cozy and elegant atmosphere. The menu features a variety of mouthwatering dishes made with locally-sourced ingredients. After dinner, take a leisurely stroll around the town square and enjoy the quaint shops and boutiques.

Alternative options: Stinocher Bar & Grill, Crouse Cafe

On-Demand Childcare in Your Neighborhood

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Catch a Movie at Penn Central Mall Cinema

Cozy up with your loved one and catch the latest blockbuster at Penn Central Mall Cinema. Enjoy popcorn and your favorite movie snacks while watching a movie on the big screen. Whether you’re into action, romance, or comedy, there’s something for everyone at this local cinema.

Alternative options: Oskaloosa True Value, Southgate Cinema

Paint and Sip at Brush and Barrel

Unleash your creative side at Brush and Barrel, where you can enjoy a fun and relaxing paint and sip session. Sip on your favorite beverage while following along with a local artist to create your very own masterpiece. It’s the perfect way to bond with your partner and create lasting memories together.

Alternative options: Wine & Design, Uptown Art

Stargazing at Edmundson Park

Escape the hustle and bustle of the city and head to Edmundson Park for a romantic evening of stargazing. Pack a blanket and some snacks, and find a cozy spot to lay back and admire the night sky with your significant other. It’s a simple yet perfect way to reconnect with nature and each other.

Alternative options: Lacey-Keosauqua State Park, Lake Keomah State Park

Live Music at the Oskaloosa City Bandstand

Enjoy a night of live music at the Oskaloosa City Bandstand, where you can listen to local bands and artists perform under the stars. Bring a picnic blanket and some wine, and relax while soaking in the music with your partner. It’s a memorable and romantic way to spend an evening together.

Alternative options: Stephen’s Auditorium, Honey Creek Resort

Bowling at Mahaska Bowl

Have a fun and competitive date night at Mahaska Bowl, where you can show off your bowling skills and enjoy some friendly competition with your significant other. Grab a pitcher of beer and some snacks, and spend the evening knocking down pins and making each other laugh.

Alternative options: Newton Lanes, Lazer Lanes

Coffee Date at Smokey Row Coffee Co.

Keep it simple with a cozy coffee date at Smokey Row Coffee Co., a popular local coffee shop in downtown Oskaloosa. Sip on a latte or a cappuccino, and enjoy some quality time with your partner in a relaxed and laid-back setting. It’s the perfect way to unwind and reconnect with each other.

Alternative options: Jitterz Coffee & Ice Cream, 3rd Street Coffee Co.

Take a Walk at Nelson Pioneer Farm

Explore the beautiful grounds of Nelson Pioneer Farm with your significant other and take a leisurely walk hand in hand. Discover the historic buildings, gardens, and nature trails while soaking in the peaceful and serene atmosphere. It’s a romantic and charming way to spend time together.

Alternative options: Lake Keomah State Park, Banner Lakes at Summerset State Park

Wine Tasting at Tassel Ridge Winery

Indulge in a wine tasting experience at Tassel Ridge Winery, where you can sample a variety of locally-produced wines in a picturesque setting. Learn about the different flavors and aromas of each wine while enjoying the company of your partner. It’s a sophisticated and unique date night idea for wine lovers.

Alternative options: Two Saints Winery, Nearwood Winery

Comedy Show at George Daily Auditorium

Laugh your way through a hilarious comedy show at George Daily Auditorium, where you can enjoy a night of stand-up comedy and improv performances with your loved one. Sit back, relax, and enjoy the show while sharing some good laughs and creating fun memories together.

Alternative options: Des Moines Funny Bone, Penguins Comedy Club

Whether you’re looking for a romantic dinner, a fun outdoor activity, or a relaxing evening, Oskaloosa has plenty to offer for parents in need of a night out away from the kids. With so many date night ideas to choose from, it’s easy to plan a memorable evening with your significant other. Don’t forget to use Wyndy to hire a qualified and reliable sitter so you can enjoy your date night without any worries.