Ref Connectivity - A 4 mile? rail link would make a significant difference to Guisborough, and to South Middlesbrough traffic - How much time is currently lost on the Marton Crawl, that people tell me is a big problem at peak times. The link would save millions each year in gained time.
Millbrook - Depends what you are all interested in and budget e.g outdoor high active, outdoor low active, history, scenary, food, music, sport, films.
Guisborough : Priory, Robert the Bruce family tomb @ St Nicholas Church, restaurant and interiors @ Guisborough Hall, small Museum, Tocketts Mill (Working water mill), lots of woodland walks through Forestry Commision land and old railway walkway, up to High Cliffe look out point, with very fine views. Great off road cyle tracks through the hills, New Gin refinery in Town Hall. There is a also an annual outdoor music concert in Priory grounds, Afternoon tea in style @ Pinchinthorpe Hall, Brickyard Bakery home made bread, sandwiches and cakes, book shop.
Redcar (4 miles) : Kirkleatham best set of Georgian buildings in the UK, interesting museum (Steel Stories, Gertrude Bell, Saxon Princess, local art), new Walled Garden, Brand new iconic cinema and cafe built over the beach, Sea Breeze one the best Fish and Chip shops in the UK. Race course events.
Great Ayton (4 miles) One of the prettiest villages in the UK for a riverside picnic, Captain Cook school house, walk to Roseberry Topping (marvellosu views, only UK location named after a Norse God), Sinclairs ice cream, Petchs pies. Drive up to Grizedale and walk up to Captain Cook monument, possibly over the start of the Moors to Commondale. Pub - Kings Head at Newton under Roseberry with decent carvery.
Iconic Pubs - Ship Inn @ Saltburn - old smugglers pub. Lion Inn @ Blakey Ridge both not far from G'Boro.
NYM centre at Danby is probably only 8 miles from Guisborough - nice cafe, location, small walks, and upmarket art gallery, there is also an infomative exhibition about the moors and some of its past industries.
Also a new totally renovated Ironstone Mining Museum @ Skinningrove. They say the beach at Skinningrove is one the top 10 in the UK, if you just want to chill on the beach/in the sea without crowds of people.
What you find is everything on the whole is very quiet compared with Whitby, so its fairly stress free to drive and park, but you need to check on opening times and events, as these are likely to be more restricted. Parking is often free or cheap.