Personally, I'd leave out Bewdley because it's not particularly convenient, nor is it actually that good for ale. My recommended itinerary:
Start in Kiddy: the King and Castle. Tremendous ale pub based at the station itself. Does Bathams.
Get on the train - you can buy good beer on the train - I recommend the Bewdley Ales (I have never found these actually IN Bewdley before!!). Sir Keith Park is a good beer.
Get off at Highley - maybe visit the engine house whilst you're there? For lunch, go to the riverside because The Ship Inn not only does amazing beer, but the food is top notch.
Back on the train - get another bottled ale on board and go to the end of the line at Bridgnorth.
When alighting, you HAVE to go to the Railwaymans Arms as it's a real ale mecca.
After there, go into Bridgnorth town. Plenty of excellent pubs which do good food which I'm sure you'll locate. Worth a look around.
If you get a freedom of the line ticket, you can go on however many trains you like for the day so it's well worth it. What time of year are you looking to do this? Bear in mind that the timetable changes when it's high season, and if there are special events on, it WILL be very busy. It's also closed during January and half of February.
If you absolutely must do Bewdley, you may find it's not convenient with train times as the station is the wrong side of the river. But go to the Little Pack Horse and have a cow pie. But in all seriousness, I'd leave Bewdley out and go Kiddy - Highley - Bridgnorth.
Arley and Hampton Loade are no good if you want a decent pint.