Yes. Amtrak is on the Northeastern Regional Service that has regular trains between Boston and Richmond, VA and beyond. There is Vermonter service to Springfield, MA, Essex Junction (Burlington), VT and St. Albans, VT. There is Atlantic Coast service to Raleigh, Charleston, Savannah and Florida. There is Crescent service to Atlanta and New Orleans. There is Carolinian service to Raleigh and Charlotte. There is Cardinal service to Cincinnati, Indianapolis and Chicago. And there is Capitol Limited service to Pittsburgh, Cleveland and Chicago.
The closest Amtrak station to Winchester is Martinsburg, WV. The Capitol Limited runs between Washington DC and Martinsburg.
Yes. Baltimore and New Carrolton, MD are served by Amtrak's Northeast Corridor Line to Washington, DC. You can change in Washington DC for Amtrak's Capitol Limited, which serves Cumberland. MD, or ride the MARC commuter rail system, or Metro to the Maryland Suburbs.
Amtrak
Yes. DC's Amtrak station, Union Station, has a lot of parking available.
You can take Amtrak from NY to Baltimore Penn or Washington DC and there are Greyhound buses from each of these to Ocean City MD
Amtrak is not a good option since you will have to go up to Washington, DC and then catch another train to come back down to New Orleans.
2.5 days
You will have to take Amtrak to either New Carollton, MD or Washington, DC.
Harpers Ferry, WV. From there you can go east to Washington DC or west to Pittsburgh or Chicago.
Bus to Richmond Amtrak Station; then Amtrak to Washington Union Station OR SOuthwest Airlines Norfolk to BWI Airport;p then either Amtrak, MARC Commuter Train or Van service to DC
No. The nearest stations are in Washington, DC and New Carollton, MD.
Some, like the Acela Express do, but most others don't. Most of the ones that do are on the east coast. I live on the East Coast and I take Amtrak from New Jersey to the South. From New Jersey to Washington, DC Amtrak runs on electricity. In DC, Amtrak switches over to diesel to continue South.