YES! You absolutely can. Back pre-pandemic I used the Wageworks website to purchase PHL-NY monthly passes for commuting. INTERESTINGLY, if you use the Wageworks website then you could get a discount from the $1620 that it was for a monthly pass, down to about $1400 and change. And then, you could use your $270 tax free transit benefit a month and apply it towards that.

Right before the pandemic I obtained the Wageworks card, actually because HR kept asking me to for some reason, and figured I'd only use it twice a year - once my $270 added up after multiple months to the $1400 needed to buy a monthly pass. Not to get into it, but the very slow / hand process that Amtrak used to process Wagework monthly passes was getting very hard to deal with. But, with the pandemic, I wasn't commuting, the monthly pass got cut to $900 a month and now I don't need to commute in as often.

SO, to answer your question, Yes, I can buy a roundtrip on the Wageworks card for a 1 day trip, but yes, you do as other people have pointed out, need to be commuting for work, since that is what the tax free benefit of the wageworks card is for.

Hope that helps!