Great choice for selecting Ashland as your gateway to Amtrak and the Northeast.
The station is really quite charming and a perfect way to begin a train trip... It was built by the Richmond, Fredericksburg and Potomac Railroad in 1923 and they sought out Duncan Lee, a well regarded architect of that day, to design the station. It is an amazing building and a Virginia Historical Landmark. Duncan Lee had also designed some of the grand homes on Monument Avenue in Richmond.
I think about 40 to 50 trains pass there every day, maybe even more, so it is a wonderful location for train watching. Amtrak alone will send 20 per day and I think 10 of those trains stop there.
In the mornings CSX usually has Amtrak on the outside track (2nd track from the platform/station), the northbound track. If you notice, there is a narrow, wooden pedestrian/passenger crossing just in front of the station to allow walking across the two tracks - without having to step over the rails and the ballast.
When the northbound train approaches from the south, you have to be alert and attentive. If the approaching train is on the outside track (normal), you really need to be in place on the proper side - the opposite side of the station. However, I once caught the 8:13 AM and it was on the inside track (the southbound track), so we all had to hurry and cross back over before the engine pulled into the station. It is a bit tricky. I guess if you are on the wrong side they would probably wait for you to walk around the train to the proper side - but no guarantee of that. Plus - they seem to always be in a hurry to stay on schedule.
If you are in business class - and they are short handed with conductors, then you will have to board with all of the other passengers at the coach door - and walk the train north to BC. That is if there is only one conductor. They should have two.
BTW - there is a nice Cracker Barrel restaurant in Ashland with a fireplace. If you have time, grab a big breakfast there before catching the train. That's if you get there really early. There is also a good coffee shop just down from the station, on the corner of Railroad Ave and Route 54. And the Henry Clay Inn is directly behind or should I say, right next to the station on Railroad Ave. It is very nice and I think that they serve breakfast there. The Inn is really close so consider staying there - if you need lodging the night before you leave. The front porch of the Inn has these really nice rocking chairs and you are very close to the tracks - great view from the Inn.
You can park for free on the street in Ashland. There are even some spaces on the street that Ashland has designated for "Amtrak Passengers only". Ashland is very Amtrak friendly and the town has fought hard to keep that Amtrak stop (not that Amtrak wanted to drop it), but there were some recent discussions regarding high speed rail and improvements, and one option eliminated Ashland. That is no longer on the table - so Ashland will keep their Amtrak stop...The town really seems to love the trains - even though Amtrak blocks the main thoroughfare when the trains make their stops in Ashland. All the more reason to be ready and board the train quickly - from the proper side.