The 2028 Great American Road Trip
Castle Rock → Kansas City → St. Louis → Kentucky → Nashville → Chattanooga → Alabama → Mississippi → Arkansas → Oklahoma → Kansas → Castle Rock
This is going to be a fun one! You’ll get a little of everything: presidential-era and military history, a national park underground, iconic American cities, Southern cooking, new states to explore, time with your brother, and two full days to investigate the Chattanooga area for your future glamping resort.
I’d keep the trip at 13 days and 12 nights, with three memorable hotel nights balanced against practical hotels with free parking. Since this is for summer 2028, the itinerary below is a planning blueprint; we can confirm opening hours, tours, restaurant details, and hotel rates closer to departure.
The day-by-day itinerary
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Day 1 — Castle Rock to Kansas City
About 8–9 hours driving · Night 1: Kansas City
Historic stop: National WWI Museum and Memorial. Give it a couple of hours at minimum; it’s a substantial museum, and the Liberty Memorial tower adds a panoramic view. Summer hours are currently listed as daily, 10 a.m.–5 p.m.
National WWI Museum and Memorial
Dinner: Joe’s Kansas City Bar-B-Que. Go for burnt ends if available, ribs, or the famous Z-Man sandwich.
Restaurant Menu
Hotel: Spark by Hilton Kansas City Plaza Streetcar, or another well-priced option with confirmed parking. Check whether a downtown hotel is worth its parking cost.
Day 2 — Kansas City to Evansville, via St. Louis
Roughly 6–7 hours driving, plus the stop · Night 2: Evansville
National park: Gateway Arch National Park. Visit the museum beneath the Arch, walk the grounds, and ride to the top if you want the signature experience. Add the historic Old Courthouse if time permits. Summer tram tickets can sell out, so advance reservations are recommended.
National Park Service
Food: Keep lunch casual near the Arch, then enjoy dinner in Evansville. One option is Samuel’s, a small downtown restaurant with sandwiches and steak frites. Important: it is currently 21+ only, so it won’t work if Evan is joining you.
Samuel’s
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Hotel: A practical downtown or highway hotel with free parking. This is a travel-heavy day, so I wouldn’t splurge here.
Day 3 — Evansville to Nashville, via Mammoth Cave
Allow most of the day for driving and the cave · Night 3: Nashville
National park: Mammoth Cave National Park. This is the main Kentucky experience: a guided cave tour through the world’s longest known cave system. I’d choose a moderate, accessible tour rather than an exhausting one, especially after the drive. Reserve ahead; summer is busy and tour tickets can sell out.
National Park Service
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Scenic bonus: If time allows, enjoy a short forest walk or overlook rather than trying to squeeze in a second major attraction.
Food: Try a country-cooking lunch near Cave City or park-area roads. A good Southern plate—fried chicken, biscuits, greens, and cornbread—is the goal. Verify the restaurant’s summer opening days before you set off.
Hotel: Your first night in Nashville. If you want to splurge at Union Station, this is a good night to start.
Day 4 — Nashville
Full city day · Night 4: Nashville
Morning history: Visit the Ryman Auditorium, the historic home of the Grand Ole Opry, and walk the downtown music district. If you want a deeper music-history experience, add the Country Music Hall of Fame.
Afternoon: Keep this mostly indoors. The Tennessee State Museum is a good option for Tennessee history without spending the hottest hours walking outside.
Dinner: Hattie B’s Hot Chicken for Nashville hot chicken, with heat levels ranging from no heat to very spicy. I’d start Evan at mild or medium unless he’s unusually confident about spice.
Hattie B’s Hot Chicken
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Hotel: If Union Station is your historic splurge, enjoy the building and its grand lobby tonight. If the parking-plus-room total is too steep, choose a practical hotel for both Nashville nights.
Day 5 — Nashville to Chattanooga
About 2–2.5 hours driving · Night 5: Chattanooga
On arrival: Explore the riverfront, walk across the Walnut Street Bridge, and get your bearings downtown.
Historic stop: The Chattanooga Choo Choo terminal complex reflects the city’s railroad heritage. The city also highlights Ross’s Landing and the National Medal of Honor Heritage Center among its major history sites.
Historic Sites & Heritage Attractions
Food: Bea’s Restaurant is a classic family-style Southern meal option. For barbecue with a view, consider Sugar’s Ribs.
Hotel: The Read House is the historic splurge to consider here. If you choose it, I’d stay one night, then move to a practical hotel with free parking for the next two.
Day 6 — Chattanooga’s Civil War history and scenic overlooks
Full day · Night 6: Chattanooga
National military park: Spend the morning at Chickamauga and Chattanooga National Military Park. Explore the battlefield, monuments, and visitor-center exhibits. The park preserves the story of major Civil War campaigns around Chattanooga. Check the current fee and visitor-center schedule closer to your trip.
National Park Service
Afternoon: Visit Lookout Mountain for views and one chosen attraction, such as Point Park or Rock City. Don’t try to do every attraction in the heat.
Food: Make this your barbecue night. Sugar’s Ribs is the scenic choice; another local barbecue restaurant can be the backup if the wait is long.
Glamping scouting: On the drive back, pay attention to the transition from city to rural land: road grades, wooded slopes, views, noise, and how long it takes to reach groceries and hospitals.
Day 7 — Chattanooga area scouting day
Full day · Night 7: Chattanooga
This day is especially valuable for your glamping-resort idea. Rather than trying to tour too many attractions, use the morning and early afternoon to explore several potential corridors around Chattanooga.
Look at:
- Land shape: usable level areas, drainage, flood exposure, and steep slopes.
- Access: road quality, emergency-vehicle access, distance from the interstate, and winter maintenance.
- Utilities: water, septic feasibility, electricity, broadband, and cell coverage.
- Regulations: zoning, campground/RV rules, short-term lodging requirements, and environmental restrictions.
- Demand: proximity to hiking, river activities, scenic overlooks, and Chattanooga’s attractions.
Optional stop: Tennessee Valley Railroad Museum if you want a little more local history.
Food: Keep lunch casual, then choose a place you missed earlier. This is a good day to ask locals about the area rather than spend the whole evening driving to another attraction.
Day 8 — Chattanooga to Huntsville, Alabama
About 2–2.5 hours driving · Night 8: Huntsville
Major attraction: U.S. Space & Rocket Center. This is a strong first Alabama stop and a good fit for the family. Set aside several hours for rockets, spaceflight history, and exhibits.
Historic bonus: If you have energy, visit the Huntsville Historic District or the downtown area after the museum.
Food: Blue Oak BBQ is worth considering for smoked brisket, pork, chicken, or smoked wings.
Huntsville.org
Hotel: Choose a practical hotel with free parking. One night isn’t enough to justify a downtown parking surcharge.
Day 9 — Huntsville to Tupelo, Mississippi
About 2.5–3 hours driving, plus stops · Night 9: Tupelo
Scenic national parkway: Explore a portion of the Natchez Trace Parkway. The Parkway Visitor Center just north of Tupelo has exhibits, maps, and ranger information; it is currently listed as open daily from 9 a.m. to 4:30 p.m.
National Park Service
Historic stop: Elvis Presley Birthplace is the obvious Tupelo landmark. If music history interests your family, this is a worthwhile stop.
Food: Seek out fried catfish or Southern meat-and-three cooking. Mississippi’s food traditions vary by region, so I’d choose a well-reviewed local spot in Tupelo rather than detour far south for Delta specialties.
Hotel: Hotel Tupelo. It gives you a bit of boutique character while keeping parking simple.
Day 10 — Tupelo to Little Rock, Arkansas
About 5–6 hours driving · Night 10: Little Rock
Historic site: Little Rock Central High School National Historic Site. The site
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Food: Wright’s Barbecue for slow-smoked meats and brisket. The Little Rock location currently lists hours Monday–Saturday, 10:30 a.m. until 9 p.m. or until food runs out, so a late lunch is safer than arriving at closing time.
Wright’s Barbecue in AR
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Hotel: The Capital Hotel is the third historic splurge candidate. It is beautiful, but with $35 valet parking, compare the total against a practical hotel before committing.
Official Website
Day 11 — Little Rock to Owasso, Oklahoma
About 4–4.5 hours driving · Night 11: Owasso
Main event: Family time with your brother. I wouldn’t overstuff this day with tourist stops.
Optional stop: If the timing works, take a short leg-stretch at a historic town square or Route 66-related stop around Tulsa. But the priority is arriving with enough time to visit and have a relaxed meal together.
Food: Let your brother recommend a local favorite. That’s often the best meal of the trip, and he may know a place you wouldn’t find on a typical tourist list.
Hotel: Holiday Inn Express & Suites Tulsa Northeast–Owasso, or another practical option with free parking.
Day 12 — Owasso to Dodge City, Kansas
About 4.5–5.5 hours driving · Night 12: Dodge City
Old West history: Visit Boot Hill Museum. It interprets Dodge City’s cattle-town past, with historic-style Front Street, exhibits, and seasonal reenactments. In summer, the museum currently operates daily, with live gunfights and a dinner/show option on selected dates.
National Park Service
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Food: The museum’s Beatty & Kelley Restaurant and Ice Cream Parlor offers hearty, old-fashioned American food in a Wild West setting. That’s a fun fit for the final overnight.
Boot Hill Museum
Hotel: Hampton Inn & Suites Dodge City or another straightforward hotel with free parking and breakfast.
Day 13 — Dodge City to Castle Rock
About 5–6 hours driving, depending on traffic and stops
Head home without adding another major attraction. If you’d like one last roadside stop, choose it spontaneously based on energy and weather. After nearly two weeks of driving, arriving home at a reasonable hour is the win.
The food hit list
These are the meals I’d try hardest to fit in — the ones that give you a taste of the region rather than just another convenient dinner.
Kansas City: Joe’s Kansas City Bar-B-Que
Burnt ends, ribs, or the Z-Man sandwich.
Restaurant Menu
Kentucky: Country cooking near Mammoth Cave
Fried chicken, biscuits, cornbread, and vegetables. Make this your classic Southern lunch.
Nashville: Hattie B’s Hot Chicken
Hot chicken with pimento mac and cheese or greens.
Hattie B’s Hot Chicken
Chattanooga: Sugar’s Ribs
A barbecue dinner with a scenic view.
Huntsville: Blue Oak BBQ
Smoked meats and wings.
Huntsville.org
Mississippi: Local fried catfish
A great regional meal to seek out around Tupelo.
Little Rock: Wright’s Barbecue
Slow-smoked barbecue and brisket.
Wright’s Barbecue in AR
Dodge City: Beatty & Kelley Restaurant
Homestyle food and ice cream inside the Boot Hill Museum complex.
Boot Hill Museum
National parks and major history stops at a glance
| Place | Why it earns a stop |
|---|---|
| National WWI Museum and Memorial | A major American history museum |
| Gateway Arch National Park | Iconic monument, museum, and Old Courthouse |
| Mammoth Cave National Park | A guided underground adventure |
| Chickamauga and Chattanooga National Military Park | Civil War battlefields and monuments |
| Natchez Trace Parkway | Scenic drive through a historic travel corridor |
| Little Rock Central High School National Historic Site | A powerful Civil Rights history experience |
| Boot Hill Museum | Dodge City’s Old West and cattle-town history |
A few things I would protect in the schedule
- Book Mammoth Cave first. Tour schedules vary, and summer tours can sell out.
National Park Service
- Keep both full Chattanooga days. One for the major sights and one for serious glamping-area exploration.
- Don’t overload the driving days. The Arch and Mammoth Cave are worthwhile stops, but they make those days longer than a simple point-to-point drive.
- Keep a weather buffer. July heat, thunderstorms, and occasional severe weather can disrupt outdoor plans.
- Confirm hotel parking costs before booking. For the historic hotels, compare the full total against a practical hotel with free parking.
