Summer is the perfect time to shake up your routine and plan a memorable date night. Whether you’re into outdoor adventures, local eats, or laid-back evenings with live music, the La Crosse area offers plenty of fun ways to connect. We’ve paired up some favorite local spots and experiences to help you make the most of warm nights and weekends. From riverside strolls to rooftop cocktails, your next great summer date night is right around the corner!
Elmaro Winery & Winghaven Pizza Farm | Trempealeau area
Start your evening with wood-fired pizza served in a scenic outdoor setting at Winghaven Pizza Farm — bring a blanket or snag a picnic table under the trees. Once you’re full and relaxed, head just a few minutes down the road to Elmaro Vineyard for a wine flight and vineyard views that feel straight out of Napa. Both spots offer a peaceful, countryside vibe that’s perfect for an unplugged summer date.
Riverside Park Walk + Pearl Ice Cream Parlor | Downtown La Crosse
Grab a scoop (or two 😉) at The Pearl (the cappuccino Oreo flavor is a must-try!) and enjoy your treat while wandering through Riverside Park. Watch the boats drift by, explore the flower gardens, or catch a sunset at the riverfront bandshell. It’s a simple, classic date night that feels like summer nostalgia in the best way.
Hike at Hixon Forest + Outdoor Drinks at Alpine Inn | La Crosse
Kick off your evening with a hike through Hixon Forest, where shaded trails lead to panoramic views from the bluffs. Then head to Alpine Inn, a favorite local hangout perched on the ridge, for drinks and hearty eats on their outdoor deck. It’s a perfect mix of active and relaxed — with bluff views the whole way through.
La Crosse Loggers Game + Pre-Game Dinner at Moxie’s | Northside La Crosse
Start your date with burgers and beers on the patio at Moxie’s, where you can dine right next to the Black River. Then catch a La Crosse Loggers game at Copeland Park — an affordable, spirited night out with stadium snacks, summer energy, and the occasional fireworks show. It’s a fun, low-key combo perfect for baseball fans or anyone who loves a lively summer atmosphere.
Thursday Night Concerts at the Park + Food Truck Picnic | Riverside Park
If your week could use a refreshing reset, Thursday night Moon Tunes in Riverside Park is the perfect combo of music, community, and sunshine. Bring lawn chairs or a picnic blanket, grab dinner from rotating food trucks, and enjoy free live music right on the Mississippi River. It’s casual, fun, and one of La Crosse’s best summer traditions. For an added bonus while you’re there, make sure to stop in for a drink at The Hatchery!
Driftless Axe & Arcade + Taproom Drinks at Turtle Stack Brewery or 608 Brewing Company | Downtown La Crosse
Unleash your competitive side with an hour of axe throwing or hitting up the arcade games at Driftless Axe, where the laid-back vibe and helpful staff make it approachable for first-timers. Afterward, head to Turtle Stack Brewery or 608 Brewing to swap scorecards over a craft beer flight or seasonal pint. It’s a playful, energizing night out — perfect for couples who love a little friendly challenge.
Charmant Rooftop Terrace + Art Gallery Hop | Downtown La Crosse
Enjoy wood-fired pizzas and cocktails on the rooftop at The Charmant Hotel, with cozy seating and views of downtown and the Mississippi. Before or after dinner, stroll through downtown and pop into local art galleries like Pump House Regional Arts Center or River City Gallery to take in regional art and exhibits. It’s a sophisticated, relaxed date with just the right amount of inspiration.
No matter which pairing you choose, the best part of any summer date night is who you’re sharing it with — but a great view, good food, and a little local charm certainly don’t hurt!
