Plan Your Romantic Getaway in Wisconsin

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With Valentine’s Day just around the corner, we’ve been on the hunt for romantic getaways to take all throughout Wisconsin. Many small towns across Wisconsin provide for cute little trips to take with a significant other, but we have three destinations that we are really loving for this Valentine’s Day season! Between Oshkosh, Columbus, and Ashland, you can find small town charm, romantic date nights, and wonderful stay at a Cobblestone Hotel. Let’s hop into why you need to plan your trip today!

Oshkosh

Photo Credit: Downtown Oshkosh // @downtownoshkosh via Instagram

Oshkosh definitely has a small town charm with a big city feel! And your romantic getaway can start right at the Cobblestone Hotel in Oshkosh. This beautiful hotel is conveniently located right in the heart of Winnebago County and is perfect for a weekend getaway. From their extravagant downtown with over 200 locally owned restaurants and bars to a fun shopping day at their local boutiques and retail stores, there’s definitely something fun for everyone on a romantic weekend in the event city!

Oshkosh is home to some of the best Valentine’s Day activities across the state. Not only do they have romantic date night things to do, but they also have fun for the whole family! One event that you’ll definitely want to book a getaway around is ‘The Wine Down – Amore Edition’ at the Gibson Social Club on February 14th. This themed extravaganza honors the holiday of love and offers a great night filled with a wine flight, charcuterie, live music, and an exclusive experience you can’t get anywhere else!

If you’re a foodie couple, Oshkosh offers up some delicious meal options during the romantic season. On February 11, 12, and 14 you can get a meal for two at TJ’s Highland Steakhouse and from February 12 – 14, you can get a delicious 4-course meal at Ground Round. If you’re not planning your trip around those dates, other foodie hot-spots that give a romantic atmosphere in Oshkosh are: Wendt’s on the Lake, Becket’s, and Gardina’s

Dive deeper into family-fun events, things for you and your valentine, and more in Visit Oshkosh’s Valentines Feature, ‘Valentine’s Day Fun for Everyone’, here!

Columbus

Photo Credit: Downtown Columbus // @breannaahmad via Instagram

Right when you arrive in Columbus, you will see why this small town is known for its sparkling charm. The downtown corridor provides a beautiful and romantic weekend getaway right in the heart of Central Wisconsin. First, plan your stay at the Boarders Inn & Suites right in Columbus and experience the convenience of being near everything that the small town has to offer! 

First things first, you’ll want to take a walking tour of the late-nineteenth-century Columbus architecture throughout the Downtown Historic District. In 1992, the district was placed on the National Registry and is known for the extraordinary buildings that cover the downtown area. The artistry that lies on the buildings are second to none and something you have to see with your own eyes! If you’re a big fan of quality craftsmanship, this will definitely check all the boxes off your romantic getaway list. Learn more about the Columbus Area Historical Society here. 

And if you’re a big fan of antiquing, you’ll find plenty of unique opportunities for that in Columbus. Just in their downtown area, you can find 5 antique shops along with Wisconsin’s largest antique mall. This serves as the perfect day spent with a significant other finding all of your favorite antique treasures!

Now romantic foodie locations look a bit different for everyone and in Columbus you can find a little bit of a different vibe to fill a quirky date night! Whether you’re wanting to visit a 50’s style drive-in or you’re wanting to get a taste of international food, you can find that and more in Columbus! Here are some of our top picks: Mullin’s Short Stop, Cercis Brewing Company, Yum Yum Thai Kitchen, and the James Street Pizza Company

Ashland

Photo Credit: Ashland, Wisconsin // @chadthetraveling_rn via Instagram

Right along the Chequamegon Bay lies Ashland, a delightful little town right in Wisconsin’s Northwoods. If outdoor fun is your style of a romantic getaway, then Ashland is the perfect playground for you this winter! From hundreds of miles of snowmobile trails, to finding the perfect ice-fishing hotspot on Chequamegon Bay, you can fulfill all of your outdoor adventure needs in Ashland.

One romantic date idea is to head to one of two locations in Ashland for a day or night on the ice! You can visit the East End Ice Rink or the Bay Area Civic Center for open skates throughout the month of February. Learn more about ice-skating in Ashland here.

After hitting the ice, you’ll want to warm up at a nice local restaurant. Ashland has many foodie hotspots, but we can’t talk about Ashland without mentioning the Deep Water Grille. This unique location has a mix of fine dining and pub fare with pints from the local brewery, South Shore Breweries, and their six microbrews on tap! Or if you’re more into the diner type feel as a romantic meal, Delta Diner is a wonderful and unique restaurant to nestle in for the night. Lastly, settle down after dinner with a stay at the Cobblestone Inn & Suites Main Street location in downtown Ashland. 

If you’re wanting to grab breakfast, brunch, or just a delicious cup of coffee the next morning, make a stop at the Black Cat Coffeehouse. This charming coffee shop has a delicious menu and gorgeous coffee drinks to get a kick-start to your day in town!

All-in-all, many small towns across Wisconsin offer romantic settings for this Valentine’s Day, but traveling to Oshkosh, Columbus, and Ashland, will have everything you’re looking for, no matter your flavor of romance. But don’t wait to put your Valentine’s Day weekend plans together at the last minute and plan your trip now with a stay at a Cobblestone Hotel! Let us know in the comments below where you end up booking for your small-town romantic getaway in Wisconsin!


Kortnee Hass: Social Media Coordinator for Discover Mediaworks. A Wisconsin ‘now & forever’ transplant with a soft spot for squeaky cheese curds, craft breweries, and all things Wisconsin tourism.

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