I currently live in Charlottesville, but am originally from CT and will be moving back relatively soon. What part of town do you live in? Towns in CT are basically the equivalent to the different ‘sides of town’ or neighborhoods here (Ivy, Downtown,Pantops, etc).

Madison, Guilford, Cheshire, Woodbridge, Orange/Milford, and Fairfield are all within 25/30 minutes of everything you mentioned. Milford is more commercial and not as quaint. All towns offer excellent public school systems, especially compared to Charlottesville/Albemarle. These places are essentially the equivalent to Ivy.

What I miss most about CT/New England is the ability to take weekend trips to all different types of destinations (mountains, ocean, cities). Being in central Virginia, I feel rather isolated and miss that freedom.