10 Unforgettable Short Road Trips from Oshkosh, Wisconsin

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10 Easy Road Trips From Oshkosh, Wisconsin: Fun Things To Do Just Outside Winnebago County

If you live in Oshkosh, Wisconsin, or you’re visiting and have a car, you’re in a perfect spot for quick little adventures. Within an hour or so, you can reach rolling farm country, quiet lakes, quirky museums, and small towns that feel like a step back in time. The best part? These are all out-of-county road trips, so you’ll actually get a change of scenery from Winnebago County. We’ll head into nearby places like Fond du Lac County, Calumet County, Green Lake County, Outagamie County, Waupaca County, and Waushara County. Gas up, grab some snacks, and let’s hit the road.

1. Climb the Niagara Escarpment at High Cliff State Park (Calumet County)

Just about a 40–50 minute drive from Oshkosh, High Cliff State Park sits on the northeast shore of Lake Winnebago in Calumet County. It feels like a whole different world compared with the flat neighborhoods back in Oshkosh. You’ll find:
  • Beautiful hikes along the rocky limestone bluffs
  • A tower with sweeping views across Lake Winnebago
  • Old lime kiln ruins tucked into the woods
  • Picnic spots perfect for a quick lunch stop
On a clear day, you can see for miles. I remember standing up by the overlook one fall afternoon, watching sailboats dot the lake while the trees below glowed orange and red. It felt like being in a postcard. Road trip tip: Bring walking shoes. Even if you’re not a “hiker,” some of the shorter trails are very doable and totally worth it.

2. Sample Small-Town Charm in Chilton (Calumet County)

If you like friendly, low-key towns, set your GPS for Chilton in Calumet County. It’s an easy drive northeast of Oshkosh, and it makes a nice half-day trip when you want something slower paced. Things to do in and around Chilton:
  • Browse small local shops and cafés on the main streets
  • Visit nearby parks for a short walk or a riverside picnic
  • Plan around a festival or event – small-town Wisconsin takes these seriously
Chilton is one of those places where you can still find a classic diner breakfast, chat with locals over coffee, and actually hear yourself think. Sometimes, that’s all you need from a road trip. Road trip tip: Check local event calendars; county fairs and seasonal festivals can really bring the town to life.

3. Explore Lakeside Living in Fond du Lac (Fond du Lac County)

Head south from Oshkosh and follow the shoreline of Lake Winnebago down to Fond du Lac. It’s a bigger city, but it still has that friendly, Wisconsin feel. If you’re looking for things to do near Oshkosh but outside Winnebago County, Fond du Lac is an easy win. Popular stops include:
  • Lakeside Park – walking paths, playgrounds, and water views
  • Seasonal events and festivals by the lake
  • Local restaurants and ice cream shops for an easy date-night or family outing
On a summer afternoon, you can stroll by the shore, grab a burger, and watch the sun drop behind the lake. It’s simple, but that’s the charm. Road trip tip: If you like photography, go near golden hour; the light off the lake can be gorgeous.

4. Step Back in Time in Historic Ripon (Fond du Lac / Near Green Lake County)

A short drive west brings you to Ripon, a small city with a historic downtown and a college-town vibe. It’s close to the line between Fond du Lac and Green Lake Counties, and it’s packed with history. In and around Ripon, you can:
  • Walk the historic downtown streets and check out local shops
  • Enjoy coffee or lunch at a sidewalk café
  • Take a self-guided walk through older neighborhoods with charming homes
Ripon feels like the classic Midwest: tree-lined streets, brick buildings, and people who nod and say hello as you pass by. Road trip tip: Pair Ripon with a visit to Green Lake (see below) for a full day trip west of Oshkosh.

5. Relax at Wisconsin’s Deepest Natural Inland Lake: Green Lake (Green Lake County)

If you love water views but want something quieter than Lake Winnebago, drive to Green Lake in Green Lake County. This is one of the most peaceful road trips from Oshkosh and a favorite for couples’ getaways or low-key family days. Around Green Lake, you can:
  • Walk the lakefront and enjoy the views
  • Fish, boat, or paddle if you have gear or rentals
  • Browse small-town shops and grab lunch at a local spot
The lake has a calm, almost “up north” feel. I once spent an entire afternoon just sitting by the shore with a book, watching the light change on the water. Not a single minute felt wasted. Road trip tip: Bring layers; it can feel cooler by the water, even on warm days.

6. Spend a Laid-Back Day in Waupaca and the Chain O’ Lakes (Waupaca County)

Head northwest to Waupaca in Waupaca County for a classic Wisconsin lake country escape. You’ll find the famous Chain O’ Lakes, a group of clear, spring-fed lakes connected by channels. Things to enjoy near Waupaca:
  • Boat tours or rentals on the Chain O’ Lakes (in season)
  • Kayaking or canoeing on calm water
  • Relaxing at lakeside bars or cafés with outdoor seating
The area has that “cabin weekend” vibe, even if you’re only there for the day. It’s perfect when you want to feel like you’ve really gotten away from Oshkosh without driving hours north. Road trip tip: Weekdays are usually quieter on the water; weekends can get busy in summer.

7. Find Quiet Forests and Clear Lakes in Waushara County

If you’re craving pine trees, rolling hills, and quiet backroads, point your car toward Waushara County. Towns like Wautoma and nearby lake areas offer a slower, woodsy escape. What to do:
  • Take a scenic drive on winding rural roads
  • Stop at roadside farm stands for local produce in season
  • Enjoy lake access points and small county parks for picnicking or fishing
Waushara County feels more “up north” than its distance would suggest. It’s an easy way to get that Northwoods feeling without the long drive. Road trip tip: Pack a picnic and explore one or two lakes; the small, lesser-known ones are often the most peaceful.

8. Explore Appleton’s Urban Energy (Outagamie County)

Just north of Oshkosh, on the Fox River, you’ll find Appleton in Outagamie County. If you’re craving a more urban road trip with shops, restaurants, and culture, this is a great pick. Around downtown Appleton, you can:
  • Walk along College Avenue and browse shops and boutiques
  • Try a new restaurant, bar, or café – there’s a lot of variety
  • Catch a show or live music when events line up with your visit
Appleton makes a good “rainy day” destination from Oshkosh too. When the weather isn’t great for hiking or lakes, you can still have a fun, full day here. Road trip tip: Parking garages downtown are convenient; you can park once and walk everywhere.

9. Get a Taste of Small-City Life in Kaukauna & Little Chute (Outagamie County)

If you’d like something a bit quieter than Appleton but still want river views and local flavor, check out nearby Kaukauna or Little Chute in Outagamie County. These Fox River communities offer:
  • Riverfront parks and walking paths
  • Local bakeries and pubs with a neighborhood feel
  • Scenic spots to stretch your legs and snap a few photos
This is a “slow road trip” idea: drive up, wander, grab a coffee or a bite, enjoy the views, and head back to Oshkosh feeling refreshed. Road trip tip: Combine this stop with Appleton in one loop if you want a full day along the Fox River.

10. Enjoy Country Roads and Hidden Gems in Rural Calumet & Fond du Lac Counties

Sometimes the best road trips from Oshkosh are the ones where you don’t plan too much. East and south of Oshkosh, the backroads of Calumet County and Fond du Lac County are full of rolling fields, quiet churches, and little surprises. Try this:
  • Pick a small town you’ve never heard of and drive there
  • Stop at any roadside stand, local bar, or tiny café that catches your eye
  • Take photos of barns, silos, and old farmhouses along the way
I once ended up at a tiny town festival completely by accident on a drive like this. There was homemade pie, a local band, and kids running around with face paint. It wasn’t on any “must-see” list, but it felt like real Wisconsin. Road trip tip: Keep some cash on hand; small-town spots and farm stands don’t always take cards.

Planning Your Oshkosh Road Trips: Quick Tips

To make your short road trips from Oshkosh smoother:
  • Check drive times: Most places listed are within about 30–75 minutes.
  • Watch the weather: Lakes and bluffs are best on clear days; towns and cities are great backups for rainy days.
  • Pack basics: Water, snacks, a light jacket, and comfy shoes go a long way.
  • Stay flexible: Some of the best finds come from taking a random turn or following a sign.

Share Your Favorite Road Trips From Oshkosh

Have you taken any fun day trips from Oshkosh into Calumet, Fond du Lac, Green Lake, Outagamie, Waupaca, or Waushara Counties? Did you discover a great café, trail, or lakeside spot? Tell us about it! Drop your stories, tips, and hidden gems in the comments so other travelers can try them too. And if you found this guide helpful, please share it with friends or family who are looking for easy weekend ideas near Oshkosh, Wisconsin. The next great little adventure might be just a 45-minute drive away.
Location: Georgetown, IN, USA

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