The Itinerary
Nine Days, Stop by Stop
- 1
Wed, Aug 26, 2026
Oakland, NJ → St. Michaels, MD
A scenic first day from northern New Jersey to the Chesapeake Bay, with country-store, farm-market, and bakery detours through Pennsylvania and Maryland's Eastern Shore.
21
Stops
6h 36m
Drive
293
Miles
- 2
Thu, Aug 27, 2026
St. Michaels, MD → Williamsburg, VA
Down the DelMarVa peninsula with bakery, farm-market, and Liberty-statue detours, across the Chesapeake Bay Bridge-Tunnel, and into Colonial Williamsburg.
22
Stops
5h 42m
Drive
250
Miles
- 3
Fri, Aug 28, 2026
Williamsburg Local
Colonial Williamsburg day: pancakes, Governor's Palace, King's Arms Tavern, outlets, and a winery finish.
8
Stops
1h 32m
Drive
30
Miles
- 4
Sat, Aug 29, 2026
Williamsburg — Jamestown Day
Anheuser-Busch, Historic Jamestowne, Jamestown Settlement, and dinner at Captain George's.
8
Stops
1h 33m
Drive
33
Miles
- 5
Sun, Aug 30, 2026
Williamsburg → Waynesboro (Blue Ridge)
James River plantations, wineries, orchards, distillery, then onto the Blue Ridge Parkway to the Iris Inn.
26
Stops
6h 50m
Drive
252
Miles
- 6
Mon, Aug 31, 2026
Charlottesville Loop
Peach orchard, UVA (Poe Room), wineries, Monticello and Highland — back to the Iris Inn.
17
Stops
3h 41m
Drive
113
Miles
- 7
Tue, Sep 1, 2026
Waynesboro, VA → Ronks, PA
Shenandoah farm markets, Route 11 chips, Antietam, Gettysburg, and arrive at Hershey Farm Resort.
14
Stops
6h 19m
Drive
274
Miles
- 8
Wed, Sep 2, 2026
Ronks, PA — Amish Country & Hershey
Pretzels, smorgasbord, Hershey Chocolate World, Renaissance Faire estate, and creamery hopping.
20
Stops
3h 48m
Drive
114
Miles
- 9
Thu, Sep 3, 2026
Ronks, PA → Oakland, NJ (Home)
Bakeries, cidery, farm markets, and creameries all the way back home to Oakland.
19
Stops
4h 57m
Drive
174
Miles