Our Family-Friendly Roadtrip from Pennsylvania to Wyoming (7 days)

This summer, we packed up our 7-year-old, Oliver, and his new puppy, Fox, in our Jeep Grand Cherokee, and set out from the Philly suburbs to the Grand Tetons in Jackson, Wyoming. We kept our itinerary flexible, always mindful of our son's unique needs and challenges as a child with autism.

It took 7 days to reach our destination, while stopping along the way to create a memorable journey for our family. See all of our stops and recommendations, including a few we weren't able to make time for, as well as a few we'd recommend skipping if this is your first time making the drive.

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Overview:

• Day One: Philadelphia, PA to Columbus, OH (~7.5 hours)

• Day Two: Columbus, OH to Normal, IL (~6 hours)

• Day Three: Normal, IL to Sioux Falls, SD (~8.5 hours)

• Day Four: Sioux Falls, SD to Wall, SD (~4 hours)

• Day Five: Wall, SD to Keystone, SD (~1.5 hours)

• Day Six: Keystone, SD to Casper, WY  (~3.5 hours)

• Day Seven: Casper, WY to Jackson, WY  (~4.5 hours)

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DAY ONE: Philadelphia, PA to Columbus, OH (~7.5 hours)

For Day One, our top priority was to make good time. We knew Oliver and Fox would be their least restless on the first day in the car, and planned to take full advantage by limiting us to essential stops only. So while there were tons of places to stretch legs around Lancaster, Harrisburg, and Pittsburgh, we opted to keep moving as long as the kiddos were cooperating. Ultimately it was one of our longest days, but front loading the trip with longer days meant we'd be able to take our time later.

Day 1: Pit Stop #1 – The Pretzel Hut, Newmanstown, PA

When I see an opportunity to let Oliver pet a goat, I take it. This free petting zoo, playground and ice cream parlor was the perfect way to let him tire himself out before settling in for a long drive.

Honorable Mention:

Pickle Nickel, Dillsburg, PA

Hickory Hearth Highlands, McDonald, PA

Ohiopyle Falls, Ohiopyle, PA (adds drive time)

Fallingwater, Mill Run, PA (adds drive time, $$$)

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DAY TWO: Columbus, OH to Normal, IL (~6 hours)

For Day 2, we planned ahead for a comfortable 6-hour ride, with the Children's Museum of Indianapolis high on our list of must-see places (it's rated one of the best in the country). Our overnight stop in Normal, IL was a logistical choice, allowing us to split the day into two easy 3-hour legs before stopping.

Day 2: Pit Stop #1 – Hilliard Station Baking Co., Hilliard, OH

A big thanks to TikTok for alerting me to this picturesque bakery on Hilliard's historic main street. We stopped by early for coffee and fresh cinnamon buns. The area was lovely - with more time (and less rain), we likely would have strolled past a few shops and enjoyed the outdoor fountain for a bit. Definitely take your time here before getting on the road!

Day 2: Pit Stop #2 – The Children's Museum of Indianapolis, Indianapolis, IN

As cool as expected! Oliver spent about 2 hours here with Dad, but easily could have filled a half a day. Meanwhile, Fox and I grabbed some coffee down the street, and stretched our legs in a nearby park.

Honorable Mention:

Hocking Hills State Park, Logan, OH (adds drive time)

Dollar Book Swap, Dayton, OH

Uranus Fudge Factory, Richmond, IN

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DAY THREE: Normal, IL to Sioux Falls, SD  (~8.5 hours)

This ride was a doozy, but one more long day would allow for smooth sailing on our remaining days. We played it by ear, with plenty of opportunities to stop in Des Moines, Omaha, or Sioux City if we reached our limit in the car. Armed with buckets of coffee, and thanks to an incredible summer sunest to keep us motivated, we were able to make it all the way to Sioux Falls in one shot (but if we were to do this again, we would definitely stop sooner).

Day 3: Pit Stop #1 – Orange Cup Side Hustle, Gailsburg, IL

An absolute 10/10. Plan your coffee break or lunch stop here. Family-owned, incredible menu, impeccable vibe, and super dog-friendly. We'll be stopping here again.

Day 3: Pit Stop #2 – Iowa 80 - The World's Largest Truck Stop, Walcott, IA

Kitchy and fun! It's a tourist trap and crowded. But it's worth the stop on the long drive. Tons of souvenir shopping and food options. Ideal for a kid who just needs a break.

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DAY FOUR: Sioux Falls, SD to Wall, SD (~4 hours)

If I'm being honest, Day 4 is when the trip truly began. Up until then, we were fully en route, prioritizing drive time over comfort or scenery. Once we hit South Dakota, we were finally able to take our time and start taking everything in.

Day 4: Pit Stop #1 – Falls Park, Sioux Falls, SD

Wake up early, grab some coffee (or chocolate milk) and donuts, and head over to Falls Park at sunrise to enjoy the view. It's quiet with very few visitors, so you'll be able to take some great family photos and explore each overlook. Pro-tip: Go on the weekend to catch the Fall's Park Farmer's Market - good coffee, local vendors and live music.

Day 4: Pit Stop #2 – The Corn Palace, Indianapolis, IN

My kind of roadside attraction - a palace dedicated to corn. We grabbed lunch across the street and then took a stroll through this delightfully air-conditioned work of art. Entry is free, they allow dogs on leash, and you can breeze through quickly, or spend time in the eccentric gift shop. Not much further down the interstate is Dignity of Earth and Sky, a 50-foot art installation that's as striking from a distance as it is beneath her feet. She stands atop the Missouri River, making this rest stop and overlook an essential scenic stop.

Hotel: Badlands Frontier Cabins, Wall, SD

There are plenty of places to stay in Wall, but Badlands Frontier Cabins was the obvious choice for their cozy cabins and outdoor areas. Wall Drug is open late, and is an essential stop in town, as is the main street full of adorable shops - there's a lot of history here, and the town fully caters to its tourist stop status.

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DAY FIVE: Wall, SD to Keystone, SD (~1.5 hours)

The ultimate "choose your own adventure." There is so much to see around Rapid City and the Black Hills, we really didn't know where to begin. There is something for every interest, and you won't be able to see all of it in one day. In hindsight, 2 full days in this area would have been ideal, but we were still able to cover SO much ground in just a day, squeezing in a few unexpected stops, and adjusting our overnight plans to avoid feeling rushed.

We started the day off with breakfast at Wakin' Bacon's food truck, and took photos in front of the enormous Jackalope carving across the street at Dahl's Chainsaw Art. A

Day 5: Stop #1 – Badlands Ranch Store, Philip, SD

This unexpected little gem was not originally on our list of stops, but we had to pull over when Oliver saw the Giant Prarie Dog statue out front. Stop by the store for a bag of peanuts and spend a little time feeding the hundreds of prarie dogs that live right by the roadside here. A very charming little stop.

Day 5: Stop #2 – Badlands National Park, South Dakota

We were not prepared for how incredible this landscape would be. We took photos at the first overlook and explored some of the more accesible areas where boardwalks allowed for easier navigating. Because dogs are not allowed much further than the paved areas, we kept our time here brief, and enjoyed the scenic drive as we made our way to Rapid City for an inevitable oil change. (Note: Only head to Rapid City if you have specific stops planned there - otherwise, you can head straight to Keystone from the Badlands.) See more photos from our time here - the landscape was incredible.

Day 5: Stop #3 – Mount Rushmore, Keystone, SD

After a quick oil change and coffee refill in Rapid City, we made our way south through the Black Hills toward Mt. Rushmore. For me, this was entirely obligatory (are you really on a cross-country family road trip if you don't stop at Mt. Rushmore?), and despite my low expectations, I was looking forward to Oliver getting to see this infamous monument. What I was not prepared for were all of the charming roadside attractions along the way. Once at the monument site, it truly is impressive to look at, and the visitor center offers plenty to make the time worthwhile, however brief.

In hindsight, I wish we had prioritized the Crazy Horse Memorial first, but I'm glad we had this quintessential experience together as a family. Before you make the drive, be sure to explore all of the other attractions in the area, as they overly cater to families and tourists - there's something for everyone and lots to do, including exploring the historic town of Keystone (see Honorable Mentions below).

Hotel: Under Canvas Mount Rushmore, Keystone, SD

THIS! I cannot emphasize enough how special the campground at Under Canvas Mount Rushmore truly was. The atmosphere was safe and cozy. Tons of food options and live music at the main tent, and smores kits provided each night to roast by the campfires around the grounds. Not to mention a clear view of Mt. Rushmore from their main sitting area. Despite the severe summer thunderstorm that rolled through in the middle of the night, this was one of the Top 3 highlights of our entire trip. See more photos and read more about our time at this magical campground.

Honorable Mention:

South Dakota Air and Space Museum, Rapid City, SD

Museum of Geology, Rapid City, SD

Reptile Gardens, Rapid City, SD

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DAYS SIX: Keystone, SD to Casper, WY (~3.5 hours)

After 5 days on the road, we continued to take our time, splitting up the final 8 hours of driving across two final days. When in doubt, we opted for the scenic route, and lingered for a while at stops where we could spread out and relax.

Day 6: Custer State Park, South Dakota

Do not skip this incredible park. The scenic drive is worth the extra time. Take the Wildlife Loop through the park for a better chance of seeing bison herds and wild donkeys. Plan for a beach day at the lake, and definitely make a stop at one of the park's nature centers - they're kid friendly, full of wildlife info, have nicer bathrooms and gift shops, and make for a scenic rest while you make your way through the park.

Honorable Mention:

Crazy Horse Memorial, Crazy Horse, SD

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DAYS SEVEN: Casper, WY to Jackson, WY (~4.5 hours)

Our final day on the road was definitely the longest stretch. The drive from Casper to Jackson is only about four and a half hours, but the road feels endless — long, flat, and wide open. Some parts are stunningly scenic, while others seem to stretch on forever without much change.

Be sure to plan your stops carefully: gas stations, businesses, and even cell service can be few and far between. That said, it was a beautiful way to wrap up the 7-day drive, with a few memorable scenic and historic stops along the way. We could’ve taken a more direct route, but chose to detour slightly for the more scenic drive into Jackson from the south — and it was absolutely worth it.

We kicked off the day with protein coffee and waffles at Copper Cup Coffee Co.—the perfect start before hitting the road. We didn’t spend much time in Casper, but this historic city has a fun mix of old charm and new gems. With more time, we definitely would’ve wandered through downtown. The planetarium here is actually a designated dark sky viewing site, and many of the historic centers offer free admission—plenty of reasons to plan a longer visit next time!

Day 7: Stop #1 – Independence Rock, Alcova, WY

One of our first Oregon Trail stops! There isn’t a ton to see here, but the history alone makes it worth the visit. Standing at this iconic landmark, it’s easy to imagine the countless pioneers who paused here on their long journey west. You can still see the names they carved into the rock all those years ago—a tangible link to the past. For us, it was a quick stop for photos (and a bathroom break), but we were so glad we took the time to experience it in person.

Day 7: Stop #2 – Fremont Lake, Pinedale, WY

The perfect ending to a long journey out west! We stopped at Fremont Lake for a picnic lunch by the beach and a refreshing dip in the cool water on a hot day. The lake is beautiful—surrounded by mountains, with an excellent campground and plenty of options for swimming, kayaking, or just relaxing by the shore. It’s family-friendly (though there are a few restrictions on dog access) and only a short drive from Jackson, making it the ideal final stop before the scenic ride into town.

The southern route into Jackson offers some of the most stunning scenery in Wyoming. Rolling hills transition into expansive valleys, leading to the dramatic rise of the Teton Mountains along the horizon. It’s a drive known for its panoramic views and peaceful stretches that invite you to slow down and enjoy the landscape. Taking this route added a bit of extra time to the trip, but the reward of arriving in Jackson surrounded by such iconic scenery made it well worth it.

Takeaway: There are countless ways to plan a road trip out West, with an incredible variety of scenic routes, historic landmarks, and iconic stops to explore along the way. It’s impossible to see everything in one trip, but that’s part of the adventure—there’s always something new to discover on the return drive. This route became one of the most memorable parts of our journey, and we look forward to revisiting many of these destinations in different seasons to experience how the landscape and atmosphere transform throughout the year.

Have you done this route before? Share your favorite stops—we’d love to check them out on our next adventure!