Leave St. Louis around 7:00 AM for the roughly eight-hour drive to Dublin, following I-70 east through Illinois and Indiana. Plan fuel, coffee, and a proper meal stop rather than trying to do the trip in one stretch; Columbus is the final major service area before Dublin. Traffic is usually manageable, but allow extra time around Indianapolis and Columbus. After arriving, park and settle in at Aunt Pat’s before heading out again.
Spend the evening in Bridge Park, Dublin’s lively mixed-use district along the Scioto River. Start with an easy one-hour walk by the river, where the paved paths, modern apartment buildings, and public art give the area a pleasant after-dark atmosphere. Then have dinner at North Market Bridge Park, a food hall with several vendors, so everyone can choose something different; budget approximately $15–30 per person. Most vendors operate into the evening, but hours vary, so check the market’s listing before leaving Aunt Pat’s. The district has garages and street parking, though walking between the restaurant and riverfront is simpler than moving the car.
Finish with the Dublin Link, the illuminated pedestrian suspension bridge connecting the two sides of Bridge Park. Allow about 30 minutes to cross it, pause for river views, and take in the lights after dinner. It is an easy, low-key first evening after the long drive, and the surrounding district has benches and open spaces if you want to linger before returning to Aunt Pat’s.
Leave Dublin around 8:30 AM for the roughly three-hour drive east on I-70 to Triadelphia. After checking in at Comfort Inn & Suites, park at the hotel and allow a little time to settle in before continuing into Wheeling; the hotel is a convenient base, but the afternoon sights are several minutes away by car. Keep your afternoon flexible, since Oglebay Resort has winding roads and scenic pull-offs that are worth enjoying rather than rushing through.
Head to Oglebay Resort for about 1½ hours of lake scenery, wooded grounds, and an easy reset after the drive. The resort grounds are generally open to visitors during daylight, though individual attractions and facilities keep their own seasonal hours; check the resort’s October schedule before leaving the hotel. From there, drive a few minutes within the resort to Oglebay Good Zoo, allowing another 1½ hours for its compact collection of animals. Admission is typically in the mid-teens per adult, with reduced prices for children and seniors, but seasonal hours and ticket prices can change. Wear comfortable shoes—the zoo is hilly in places.
Drive into Wheeling’s Centre Market, the city’s historic market district, for an hour of browsing and dinner. The storefronts and restaurants are clustered close together, making this an easy, low-key stop after the zoo; budget roughly $15–30 per person, and check individual restaurant hours because some smaller businesses close earlier than expected. Finish with a short stroll on the Wheeling Heritage Trail, a mostly easy riverside path where 45 minutes is enough for a pleasant sunset walk without turning the evening into a hike. In October, bring a light jacket and use your phone’s flashlight after dusk; return to Triadelphia by car afterward, a drive of about 15 minutes depending on traffic.
Leave Triadelphia around 7:30 AM with coffee and breakfast to go; the drive to Shanksville takes roughly four hours via I-70, US-219, and I-76. Aim to reach the Flight 93 National Memorial in the late morning, when the grounds are usually quieter. Allow about two hours for the Memorial Plaza, Wall of Names, and overlook. The site is free, though the visitor center may have seasonal hours, so check the National Park Service schedule before leaving; wear comfortable shoes, as the memorial is spread across an open, often windy landscape.
Continue east toward the Lincoln Highway Experience near Latrobe, using it as a worthwhile roadside-history break rather than rushing straight to Gettysburg. Set aside about an hour for the exhibits and stories of early automobile travel along the historic highway. Check the museum’s opening days and hours in advance—fall schedules can be limited—and expect a modest admission fee. Afterward, grab a quick lunch in the Latrobe area or keep snacks in the car; you still have roughly 2½ hours of driving before reaching Gettysburg.
Arrive in Gettysburg in the late afternoon and go directly to the Gettysburg National Military Park Museum & Visitor Center. Spend about two hours with the museum’s displays, the Cyclorama, and the introductory film, which will make tomorrow’s battlefield touring much easier to follow. The center generally closes in the early evening and parking is straightforward, but leave enough time to get inside before the final admission period. From there, drive or walk into Gettysburg’s historic center—allow 10–15 minutes by car, or longer on foot—and settle in at Garryowen Irish Pub for dinner, where entrées typically run $20–35 per person. It is a relaxed choice after a long day, and the surrounding downtown blocks are pleasant for a short post-dinner stroll before checking into your hotel.
Leave Gettysburg around 8:00 AM and follow US-30 east toward Lancaster; allow roughly 2½ hours, with morning traffic possible near Lancaster. Park in a downtown garage—Prince Street Garage is convenient—and walk to Lancaster Central Market on North Market Street. The market is open Tuesday, Friday, and Saturday mornings, generally until early afternoon, so verify the October 12 schedule before setting out. Give yourselves about an hour to browse the stalls and have breakfast or an early lunch: expect roughly $10–25 per person for coffee, baked goods, sandwiches, or Pennsylvania Dutch specialties. Bring small bills and reusable bags, and remember that many vendors are cash-oriented.
From downtown, drive about 15 minutes east to the Amish Farm and House near the US-30 corridor. Allow around 1½ hours for the house tour and exhibits, which offer useful context on Amish traditions and daily life; admission is typically in the $15–25 range, and tour times can be seasonal, so reserve or check the October schedule in advance. Continue roughly 10 minutes to Kitchen Kettle Village in Intercourse, where a relaxed 1½-hour wander suits the afternoon better than trying to shop every store. Browse the small craft and food shops, pick up a jar of preserves or a whoopie pie, and be courteous around nearby working farms—this is a residential, agricultural community rather than a theme park.
Leave Kitchen Kettle Village around 4:00 PM for Philadelphia or Valley Forge, taking US-30 west and then I-76. The drive is usually about 1½ hours, but weekday traffic can make the final approach considerably slower, especially around King of Prussia. Your Fairfield Inn & Suites by Marriott is the practical evening base; check in, unload, and avoid adding another major attraction tonight. If you still have energy, take a short walk near the hotel and keep dinner simple—after Lancaster’s full day, an early night will make tomorrow’s Philadelphia sightseeing much more enjoyable.
Start early at Valley Forge National Historical Park, ideally around 8:30 AM, before the walking trails become busy. Allow about 2½ hours for the encampment sites, reconstructed huts, Muhlenberg Brigade area, and a section of the park’s scenic trails. The park grounds are open from sunrise to sunset, and admission is free; the visitor center typically opens later in the morning, so check the National Park Service schedule before leaving. Drive between the spread-out sites rather than attempting to walk the entire park, and wear comfortable shoes—the terrain is gentle but distances add up.
From Valley Forge, allow roughly 30–40 minutes by car to Reading Terminal Market in Center City, depending on traffic. Parking is easiest in a nearby garage rather than searching for street parking, and the market is generally open daily until early evening. Give yourself an hour to browse the aisles and choose lunch from the vendors—plan on about $15–30 per person. This is a good place to keep the meal casual and flexible; seating fills quickly around noon, so look for an open table before collecting food.
Continue to Old City, about a 15-minute drive from the market, or use a rideshare if you prefer not to move the car. Reserve or confirm timed admission for Independence Hall in advance; the tour takes about an hour and entry is controlled, so arrive 15–20 minutes early. Afterward, walk a few minutes along Chestnut Street to the Liberty Bell Center, which is free and usually takes about 45 minutes, including the exhibits and the classic view across to Independence Hall. Leave Philadelphia around 4:30 PM for Hershey, following I-76 west and PA-743; expect about two hours, plus possible turnpike tolls and evening traffic, before checking in at SpringHill Suites.
Start at Hershey’s Chocolate World when it opens—typically around 9:00 AM, though hours vary by date. The free Chocolate Tour takes about 15 minutes, but allow roughly 1½ hours for the ride, shops, and optional paid experiences. Parking is generally free, and it is easiest to leave the car there while visiting the other Hershey attractions. The sweet shop is tempting, but save room for lunch; the café and quick-service options are convenient if you need something before continuing.
Walk or make the short drive into downtown Hershey for The Hershey Story Museum, where exhibits explain Milton Hershey’s company town and legacy. Allow about 1½ hours. Admission is usually in the roughly $15–20 adult range, with separate pricing for the chocolate-lab activity if you choose it. From here, Hershey Gardens is about a 10-minute drive; spend around 1½ hours among the seasonal plantings and the Butterfly Atrium. Check the atrium schedule before arriving, since timed entry or seasonal hours can apply.
Leave Hershey around 3:00 PM for the drive to Pittsburgh, using I-76 and the Pennsylvania Turnpike. Allow 3½–4 hours, plus a brief service-plaza stop; tolls can add roughly $25–40, so an E-ZPass is helpful, though Pennsylvania also supports toll-by-plate billing. After checking in at the Hampton Inn Pittsburgh-Monroeville, give yourself time to settle in before heading into Oakland—expect roughly 20–30 minutes by car depending on traffic and parking. Have dinner at The Porch at Schenley, a relaxed spot beside Schenley Plaza with a casual menu usually running about $20–35 per person. Evening parking can be easier in a nearby garage than on the street; if you are tired after the long drive, make dinner the final stop and return to Monroeville rather than adding another attraction.
Start around 9:00 AM in Oakland at Phipps Conservatory and Botanical Gardens, allowing about two hours for the glasshouse rooms, seasonal displays, and outdoor gardens. Check the October opening time and current exhibit schedule before leaving; admission is typically around $21–23 for adults, and advance tickets are sensible on a busy fall day. The on-site parking garage is convenient, but spaces can fill quickly—arrive early or use a nearby metered space. From Phipps, it is an easy five-minute walk across Schenley Drive to the Carnegie Museum of Natural History. Spend roughly two hours with the dinosaur halls, mineral collection, and Powdermill Nature Reserve displays; combined museum admission with the adjacent art museum is generally in the $25–30 range, with hours commonly beginning at 10:00 AM.
Walk a few blocks to Pamela’s Diner on Forbes Avenue for a relaxed Pittsburgh breakfast or lunch—its hotcakes, omelets, and crispy-edged home fries are especially popular. Expect about $10–20 per person, and bring a little patience because the small dining room can have a line around midday. After lunch, drive or take a short rideshare to the Strip District, where you can spend the afternoon wandering along Smallman Street and Penn Avenue. Browse Pennsylvania Macaroni Company, The Strip District Terminal, and the neighborhood’s spice, coffee, cheese, and international-food shops; most stores keep daytime hours, often roughly 10:00 AM–5:00 or 6:00 PM. Street parking is competitive, so a paid lot or garage is usually worth the few dollars.
Leave the Strip District around 4:00 PM for Station Square on the South Shore, allowing extra time for traffic and parking. Ride the Duquesne Incline up Mount Washington for the classic view over downtown, the Three Rivers, and the Point; round-trip tickets are generally about $6–7, and the ride plus lookout takes around an hour. The incline can be busy near sunset, so check the day’s operating hours and leave enough buffer for the return drive. Around 5:30 PM, begin the drive from Pittsburgh to Dublin via I-70—roughly three hours and about $25–45 in fuel. Use Google Maps or Waze for construction and traffic updates, park at Aunt Pat’s, and plan a simple late dinner or takeout after arriving around 8:30 PM.
Leave Dublin around 8:00 AM for the roughly eight-hour drive back to St. Louis on westbound I-70. Top off the tank before leaving town and expect a straightforward highway day with several useful service plazas in Ohio and Indiana; rotating drivers and stopping every two hours will make the final leg much easier. Keep the schedule flexible for traffic around Columbus, Indianapolis, and St. Louis, and budget approximately $70–110 for fuel.
Before settling into the long western stretch, make a coffee and light-meal stop along the Columbus Coffee Trail—choose a café with easy parking near your route rather than detouring into downtown. Allow about 45 minutes and roughly $10–20 per person. This is a good final local breakfast, so grab something portable for the car as well.
Break up the drive with an optional visit to the National Road Zane Grey Museum in Zanesville, a convenient stop near I-70. Allow around 45 minutes for the exhibits on the historic National Road, transportation, and local author Zane Grey; check the museum’s seasonal hours before departing, as October schedules can be limited. Parking is generally simple, and this works best as a brief stretch-and-history stop rather than a full sightseeing visit.
Continue west on I-70, planning one more fuel and restroom stop in Indiana before reaching the St. Louis area. If traffic is moving normally, arrival should be in the late afternoon; add extra time for the approach through St. Louis County. Once home, unload first and leave any trip unpacking for tomorrow—the road trip is complete, and a relaxed dinner close to home will be a better finish than adding another outing.