If you're after some serious shopping pleasure, then York is, by far, the place to head. There are 3 shopping parks on the outskirts of town; McArthur Glen Designer Outlet (on A64 south of York), Monks Cross and Clifton Moor (both on the north side of York ring road).
It is the city centre however, which wins the shopping experience hands down. Dump the car at the A19 park and ride and bus yourself into the centre. ALong with usual suspects of branded shops, you'll find a wealth of independent shops, boutiques and specialist outlets. The narrow cobbled streets make for a very unique shopping atmosphere and tired feet will either take you to Betty's teamroom or one of the many cafes and pubs that adorn the centre.
If the sun is out, head for the museum gardens with an ice cream for a little respite, or take a river cruise on York Boat and sip a cool glass of white wine while watching the world pass slowly by . . . .
Helmsley has some wonderful boutique food shops, while it's bookshops and galleries at Stokesley. Thirsk, Pickering and Malton are more traditional market towns but are great for stocking up and getting those all important pressies for the family.