Goodrich Castle - splendid views over the Wye Valley and beyond from the top level of the keep. Plenty of others in the Marches area
http://www.castlewales.com/wales_se.html
Malvern Hills
Glasshouse, as mentioned above: park in one of the pubs (promising to return for lunch) and walk to the top of May Hill (located just off the A40 half way between Ross & Gloucester).
Forest of Dean -
http://www.visitforestofdean.co.uk/ lots to do, especially if you like outdoor sports. Follow the links for cycling, hire a bike from Pedalabikeaway, do the 10km ride, then get lunch or dinner at The Woodman, Parkend
http://www.woodman-parkend.co.uk/
Fancy food: Bell at Skenfrith as mentioned above or try to get a reservation at the Michelin starred restaurant at Whitebrook
http://www.crownatwhitebrook.co.uk/home.html
Markets:
http://www.monmouthshire.gov.uk/Monmouth/English/Leisure_and_Visitors/Markets/ - I like the farmers' markets where you can sample the produce
Ross itself, dining: Obilash Indian restaurant was good last time I ate there. Pheasant Bistro has a fab wine list. Avoid the pubs at the lower end of Broad St and Brookend St. Crown & Sceptre is the best real ale pub and does decent food, gets very busy with trendy young types at weekends. At the weekend, the pubs over the bridge at Wilton are more relaxed. My favourite is the White Lion
http://www.wyenot.com/whitelion01.htm
Go to the Prospect, just off the main churchyard, for fine views of the River Wye. Not much in the town to entertain you on a wet day: do you really want to visit a button museum?
Thrill seeking: lots of outdoor activities available. Hot air ballooning; kayaking; paintball; quad biking and various stuff to do with psycho quadrupeds aka horses. Travel a bit further into Mid Wales and there are rally schools and various off road biking things.
For little kids there are many open farms. My niece likes this one near Hereford
http://www.courtfarmleisure.co.uk/shop_pyo.htm which has animals, pyo fruit & a play area.
Older kids might like the Big Pit museum at Blaenavon.
Bored now. If you have any specific requirements then ask and I'll try to help.
) to Ross for a long break - last time we went to Tintern, Symonds Yat, Chepstow, Hereford and a few other places.
but to be honest I don't think he actually knows anywhere ( he used to be a house husband 
)
