I'd say it's hit or miss, but widely everything is still as analog as ever.
From what I've heard and seen, some larger railroad support agencies have switched to NXDN (ie railroad police). Norfolk Southern Railroad Police switched from analog to NXDN some time around 2010, but lately, I haven't heard them on VHF (or anywhere else) at all in a long time, but it could just be my area.
Some short line operators with not a large quantity of radios or interchange have switched to digital, I recall reading an case study type article from Motorola about a short line somewhere down south moving to TRBO. Local to me, in Michigan, the Adrian and Blissfield and its other short line carriers under the same banner switched to NXDN a couple years ago.
In Detroit, following operating crew complaints about range of the narrow band radios (and generally the iCom radios that replaced Motorola models) Conrail has been slowly trying to roll out a yard repeater system using NXDN technology with an analog patch from an analog channel for non-digital radios to be able to know what's going on. Every major yard has a different repeater. I think this idea may be in place out east in Newark NJ, but I have no way of verifying that.
That's about the proliferation of digital modes in-use on the railroad that I know about.
As far as having radios that are capable of digital, pretty much every radio I've seen lately is digital capable- ranging from base stations, mobiles, and portables. Locomotive radios seem to vary, but slowly the Astro Spectra RR units and some of the older narrow-band capable GE 12R radios are being replaced by the JEMs and Ritron offerings. With 12.5Khz overall working well in analog (perhaps as a surprise to the theorists and nay-sayers), I believe that wide-spread use of NXDN for road trains, dispatching, etc is a ways away, if ever, going to happen. I think the FCC would have to force its hand to 6.25 Khz spacing before that would happen, and by then AMBE might already be phased out for something newer by then.