Choose one iconic mountain attraction — Rock City (scenic rock gardens & Lookout) or Ruby Falls (cave waterfall). Typical opening hours: Rock City ~9am–5pm; Ruby Falls ~9am–6pm — verify current hours & reserve tickets if possible.
Enter the Parkway at the southern approach (Cherokee area) and start the scenic drive northeast; speed is slower and travel is designed for scenery, not quick mileage.
Moderate, scenic driving with short hikes/overlooks along the way; Waterrock Knob has an overlook that’s a short walk from the parking area (check seasonal visitor hours).
Linville Falls offers excellent short hikes and overlooks; Grandfather Mountain has a nature park and the Mile High Swinging Bridge (check current opening hours & fees).
Moderate hikes and scenic viewpoints; the Peaks of Otter area is a classic Parkway highlight with lake and mountain views (visitor center hours often 9am–5pm).
Finish the Parkway near Shenandoah/Waynesboro; stop at overlooks you missed — visitor center hours may be limited so plan short stops earlier in the day.
Switch to interstate driving for more miles north; keep driving to no more than 5–6 hours today total — Harrisonburg is ~1 hour north of Waynesboro, Harrisburg ~3.5–4 hours further.
Scenic valleys give way to suburban interstate driving; total drive to Hartford is roughly 4.5–5.5 hours depending on exact start point and traffic — within your 6-hour daily cap.
Settle in Hartford or a nearby Connecticut town; use the late afternoon for a short walk or to visit a local attraction if desired (Wadsworth Atheneum hours typically 10am–5pm).
Options include a gentle town walk, visit to local parks, or drive into nearby historic Concord/Lowell (if interested) — adjust plans to your energy level after the trip.
Leisurely breakfast; use this day as a buffer for travel delays, an extra Parkway day you may want to extend, or local exploration of Boston/Central MA.