Jamestown was relatively isolated by land at this point. The previous attempt to explore the surrounding areas in 1644 had ended in uprisings from the Powahatan. Jamestown had spread across the James River by then and plantations like the one where Bacon's Rebellion later occurred were being set up. However, riding North it would be over 170 miles until you found the next settlement in Maryland, perhaps St. Mary's City or Providence (Annapolis). This stretch might take you 2-4 days by horse with roads or good paths, but there weren't any built yet. And with rivers to cross like the Rappahannock, there might be times you would have to go far out of your way to find a crossing point.

Continuing on from Maryland there would be Dutch trading posts in modern day Bristol, PA and Gloucester City, NJ. However, the British just took over the Dutch possessions in that area in 1664. I can't say I know how that might have affected those posts. New Amsterdam (New York) was established, although it too was taken over by the British in 1664. Though I do know there were only minimal uprisings over this. The next stops might be the New Haven colony and Saybrook before reaching Plymouth.

Overall, it's going to be about 600 miles between the two. This doesn't account for going out of your way to cross water, avoid bad areas, or seek out settlements. Many of the areas you'd traverse wouldn't have been well explored, if at all, so maps would be rough at best. You'd have to carry a good deal of food, water, and supplies just to make the first leg of the trip. And hope your horse never steps something wrong and gets hurt. It'll take a few weeks and a lot of luck to make it. I can honestly say I don't personally think it would be possible, at the least it would be very improbable.

The Iroqouis and Susquehannocks were at war at this point in the Maryland/PA area so that might be a bit dangerous.