Wisconsin’s heartland packs a lot of personality into a small stretch of map. The area features scenic state parks, small-town wineries, and the kind of oddball roadside attractions that make backseat passengers actually look up. The 70-mile drive from Madison to Oxford passes most of the good ones. You can knock it out in a day, or stretch it into a slow, all-weekend detour (honestly, we’d recommend the second option).
The route follows I-39 north out of Madison, with easy off-the-highway hops into Middleton, DeForest, Prairie du Sac, Baraboo, and Portage before you roll into Oxford. Pack the cooler with your favorite snacks, queue up a hot playlist, and consider this your guide to everything worth pulling off the highway for on your journey.
Madison to Oxford, Wisconsin
- Total stops – 5
- Must-see destinations – 2
- Quirky roadside gems – 3
- End point – Oxford, WI
Must-See – Prairie du Sac
Wollersheim Winery & Distillery
7876 WI-188, Prairie du Sac
🍷
This is Wisconsin’s oldest winery, founded in 1840 and a National Historic Site. It offers cellar tours, an on-site distillery, and bluff-top picnics overlooking the Wisconsin River.
Must-See – Baraboo
Devil’s Lake State Park
S5975 Park Rd, Baraboo
⛰️
With 500-foot quartzite bluffs, a glacial 360-acre lake, and 29 miles of trails, this site serves as Wisconsin’s most-visited state park and truly lives up to the hype. Hike, swim, paddle, or climb.
Quirky Roadside Attraction – Middleton
National Mustard Museum
7477 Hubbard Ave, Middleton
🌭
Offering 6,000+ mustards from every U.S. state and 70+ countries, plus a tasting bar to sample options before you buy, this is a great addition to your road trip. Free admission, weirdly fascinating, and minutes off I-39.
Roadside Attraction – DeForest
Sissy the Cow at Ehlenbach’s Cheese Chalet
4879 County Rd V, DeForest
🐄
This 19-foot, two-ton Holstein has been watching over DeForest since 1969. Snap the family photo, then grab cheese curds and summer sausage to fuel the rest of the drive.
Roadside Attraction – North Freedom
Dr. Evermor’s Forevertron
S7703 US-12, North Freedom
🤖
Check out the world’s largest scrap-metal sculpture – a 320-ton Victorian space machine built from salvaged industrial parts and a NASA decontamination chamber. Free, surreal, and gloriously weird.
Plot Your Stops Along the Way
Wine Lovers: Wollersheim Winery & Distillery
Roughly 30 miles north of Madison, this winery is Wisconsin’s oldest, making it a worthy first stop. Wollersheim has been around since 1840, and it’s a National Historic Site for good reason
pours award-winning reds and whites (the Prairie Fumé is a solid first pick if you’ve never been), and the on-site distillery turns out brandy, bourbon, and gin. Meanwhile, the hillside grounds overlook the Wisconsin River, and the picnic spots up top are honestly some of the best in the state. Pack a sandwich and slow down for an hour – you won’t regret it.
Outdoor Enthusiasts: Devil’s Lake State Park
Wisconsin’s most-visited state park earns the crowds. Devil’s Lake hits you with 500-foot quartzite bluffs the second you drive in, plus a 360-acre glacial lake and 29 miles of trails along the East and West Bluffs.
Climbers come for the 1,600+ established routes, but the casual hiker has plenty too – the path to Balanced Rock and Devil’s Doorway is short and pays off with the kind of view that ends up on a fridge for the next decade. If it’s warm out, bring swimsuits. Both beaches rent kayaks and stand-up paddleboards, and a quick swim after a hike is one of those small Wisconsin pleasures that’s hard to beat.
Mustard Lovers: National Mustard Museum
Yes, the National Mustard Museum is exactly what it sounds like, and yes, it’s better than you’d expect. A short detour west of downtown Madison, the place houses more than 6,000 mustards from every U.S. state and 70+ countries.
The collection was curated over decades by one famously obsessed founder. The tasting bar is the real draw: dozens of varieties to sample, from classic Dijons to wasabi, blueberry, and even chocolate. Admission is free, the gift shop is unlike any other in the country, and the whole stop takes about half an hour – a good early-trip stretch break before you hop back on I-39.
Cheese Heads and Photo Ops: Sissy the Cow
Just off I-39 in DeForest, a 19-foot, two-ton Holstein named Sissy has been keeping watch outside Ehlenbach’s Cheese Chalet since 1969. She’s named after the shop’s first owner – Lucille “Sis” Ehlenbach – and she’s free to visit whenever, day or night. Once you’ve got the family photo, head inside the chalet for cheese curds, summer sausage, and Wisconsin-made gifts that will keep the cooler stocked the rest of the way north.
Art and Oddity Hunters: Dr. Evermor's Forevertron
The Forevertron isn’t easy to describe, which is part of the appeal. Officially the world’s largest scrap-metal sculpture, it’s a 320-ton Victorian-era contraption built by sculptor Tom Every out of salvaged industrial parts – yes, including a decontamination chamber from the Apollo program.
Tucked off US-12 near North Freedom, the surrounding sculpture park is free to wander and is packed with whimsical bird-band figures, oversized insects, and other strange creatures that look like they wandered out of a Jules Verne novel. It’s seasonal, so check the hours before you make the drive. If it’s open and you’re anywhere nearby, go – it might be the strangest hour you spend on the whole trip, in the best way.
Additional Stops Worth the Detour
Here are three more spots worth squeezing into the itinerary:
- 🎪 Circus World Museum (Baraboo) – Built on the original Ringling Bros. winter headquarters, this 64-acre museum holds the largest collection of authentic wood-carved circus parade wagons in the world (over 260 of them). Seven original Ringling structures are open for tours, and live big-top performances run all summer long.
- 🎿 Cascade Mountain (Portage) – Just 30 minutes south of Oxford, Cascade is a year-round playground. Winter brings 47 ski runs and a terrain park; warm months unlock zip lines, mountain biking, and summer tubing, plus a chairlift scenic ride if you’d rather just take in the view.
- 🍇 Fawn Creek Winery (Wyocena) – Fifteen minutes from Oxford, Fawn Creek leans hard into fruit-forward favorites like Razz Prairie, Granny’s Gold, and Just Peachy. Sample 12–15 wines plus two slushies for $10, share a Big Buck’n Pretzel, and hang out on the 36-acre property with disc golf, cornhole, and weekend live music.
End Your Trip at Emrick Lake Campground & Resort
After a day of bluffs, mustards, and giant cows, Emrick Lake is the easy place to land. Tucked into the lakes and woods of Oxford, the resort has a full slate of amenities for travelers who want more than a place to park the RV. There are campsites, rustic and deluxe cabins, and seasonal rentals to pick from.
Plus, we offer pools and waterslides, a 9-hole golf course, a restaurant and bar, frisbee golf, a gel blaster arena, a jumping pillow, dog parks, hiking trails, pickleball, and a petting zoo. Guests keep coming back season after season, and once you’ve spent a weekend here it’s pretty obvious why.
Book Your Getaway at Emrick Lake
Planning a weekend escape or settling in for a longer stay? Our team can help match you with the right campsite, cabin, or rental! Got questions about seasonal sites or any of the amenities? Reach out today – we’d love to have you in Oxford.
