Summer 2025 in Monroe County, Wisconsin: Win a Trip & Celebrate the Season

Summer 2025 in Monroe County, Wisconsin: Win a Trip & Celebrate the Season

Win a trip to Monroe County while exploring its rich history, outdoor recreation, and unique events. 

Nestled in southwestern Wisconsin, Monroe County is home to vibrant small towns, nationally recognized attractions, and unforgettable events. Visitors can ride the legendary Elroy-Sparta State Trail, stroll through Amish country in Cashton, or celebrate big at the Budweiser Dairyland Super National Truck and Tractor Pull and Warrens Cranberry Festival. With friendly communities like Tomah, Sparta, Norwalk, and Warrens, there’s always something to explore—more than you know!

Here’s your summer event lineup for June through August 2025. Mark your calendars and make your travel plans today:

Summer Events
Budweiser Dairyland Super National Truck & Tractor Pull: June 26-28
Full Pull Stop & Shop Market: June 27-28
Sparta Farmer’s Market: June-October
Spring Street Social: Car, Truck, and Motorcycle Show: June 28
Creekside Concerts (ShockPocket): June 28
Tomah Farmer’s Market (Wednesdays & Saturdays: June-October
Americana Music in the Park (Wednesdays): June-August
Concerts in the Park (Wednesdays): June-August
Fort McCoy’s Commemorative Area (Fridays & Saturdays): June-August
Downtown Thursday Nights 2025 (Nathan Dean & The Damn Band): July 3
Tomah’s 4th of July Celebration: July 4
Downtown Thursday Nights 2025 (Brad Lee Schroeder): July 10
Creekside Concerts (Daddy’s Girls): July 11
Squirrelfest: July 12
Downtown Thursday Nights 2025 (Mallrats): July 17
All Holidays Weekend: July 17-19
Oakdale Fun Days: July 19
Creekside Concerts (Spies of Good Report): July 25
Monroe County Fair: July 23-27
Downtown Thursday Nights 2025 (Rumbleseat): July 31
“Little Shop of Horrors” Live Theatre (Tomah ACT): July 31-August 10
Tomah Crazy Daze: August 2
Downtown Thursday Nights 2025 (Hillbilly Rockstarz): August 7
Creekside Concerts (Village Vibes): August 8
Downtown Thursday Nights 2025 (Cherry Pie): August 14
2nd Annual Cannon Valley Bangarang: August 16
Creekside Concerts (Carlos Danger!): August 22

Whether you’re craving scenic adventure, small-town festivals, or quiet moments in nature, Monroe County has it all. Plan your trip at https://exploremonroecounty.org and discover the best places to stay, eat, shop, and explore.

Stay
From rustic retreats to cozy hotels, Monroe County has accommodations for every travel style. Explore top lodging near trailheads, cultural sites, and cranberry country.

Eat & Drink
Savor regional flavors with local diners, bakeries, supper clubs, and seasonal food trucks. Whether it’s fresh cheese curds, smoked meats, or Amish treats—you’ll leave satisfied.

Shopping
Browse antique shops, handcrafted Amish goods, art studios, and farmers markets. Monroe County’s local businesses make it easy to find unique souvenirs and gifts.