Plan the Perfect Romantic Weekend in Monroe County

Photo Credit: b3 Experience

When planning a romantic getaway, the first thing you often consider is a cozy, unique place to stay with nearby dining and entertainment. With so many retreats to consider, we have narrowed it down to some of our favorite unique spots. They might become your favorites too.

Rustic Driftless Cabin

The Outsider’s Rustic Retreat is a cabin outside Cashton with views of the hills and its own trout stream running through the property. Visitors have access to the upper loft of the barn on the property, which includes an honesty bar, a pool table, and darts. This location is for those who don’t mind a more rustic stay, so be sure to understand what amenities are and are not available. Visitors who stay comment on the beautiful surroundings and compare the retreat to “glamping”.

Cabin Retreat

For a more modern cabin stay near Cashton with incredible privacy and a beautiful view from the front porch, try Rocky Ridge Retreat. With lots of natural light, it is a unique stay with a ladder to the sleeping loft, Amish-made quality, and a vaulted knotty pine ceiling.

Historic Bank Stay

You can stay downtown in the village of Norwalk in a charming 1913 bank building. It is a great home base if your weekend includes exploring the Elroy-Sparta Bike Trail. For outdoor adventurers, hiking, kayaking, and, of course, bike riding are all nearby. The stay includes a massage chair, which can be awesome after a day of maybe paddling or pedaling too hard.

Cabins & Llamas

Justin Trails Resort offers cabins, cottages, B&B suites, and rustic tent camping. Set in a beautiful Driftless valley, there are llamas to feed treats, trails to wander, and bonfires to enjoy under the stars. Combined with an amazing country breakfast, your only job is to relax and enjoy.

Boutique Stay

A boutique stay above the cafe at b3 Experience in Sparta highlights art-inspired suites. It is a micro-hotel with four one-of-a-kind stays, featuring common areas including a pickleball court, a lounge with a pool table, and a creekside leisure area.

Lakefront Getaway

If a lake home with a private hot tub, large deck, and paddleboards and kayaks ready for use sounds perfect, then staying on the Lake Tomah Walking Trail might be a good choice. You won’t want to miss out on the early morning lake view while enjoying a peaceful, relaxing getaway.

Planning the Night Out

Whether you’re visiting in the warmth of summer or the coziness of winter, Monroe County offers plenty of ways to enjoy an evening together. During the summer months, outdoor concerts, community festivals, and block parties fill the calendar, creating the perfect setting to dance under the stars. When the temperatures cool, live music moves indoors to local venues, ensuring there’s always entertainment to enjoy.

For a laid-back date night, stop by one of Monroe County’s local breweries, where handcrafted small-batch beers and unique seasonal flavors showcase the area’s creative spirit. Pair your favorite brew with dinner at one of the county’s locally owned cafés, diners, or restaurants, where fresh ingredients and hometown hospitality are always on the menu. If you’re looking for a hidden gem, ask a local for their favorite spot or browse community reviews for inspiration.

Pro Tip for Couples: Time your visit to coincide with one of Monroe County’s signature events, such as the Warrens Cranberry Festival or Sparta’s popular summer concert series, for an unforgettable getaway filled with local flavor, live entertainment, and small-town charm. Be sure to check the event calendar before planning your trip.