Would you consider Norcia, in Umbria, 1.5 hours from Ascoli?

Oh eks, I've barely made it out of the Marche section, but I will certainly have a look! We really like to take our time and pore over a small area's nooks and crannies (also we are extremely lazy and don't get up early for work OR pleasure--that facilitates slow travel).

I'm recently back from a bit of time in Le Marche, but you've already received splendid info and advice; after a workshop in Ravenna, we went to San Marino, which my travel pal wanted to see, via train to Rimini and then by to SM. Then we hired a car/driver to take us to Urbino, which was lovely -- LMK if you need restaurant/lodging tips there. Finally, we went by car through the mountains (very windy road, but pretty views) to Arezzo and continued our trip.

I hope you have a wonderful trip there!

The area around Cagli sounds as though it would suit you. There is excellent hiking around Fonte Avellana, a 12th century hermitage, now a monastery. The town of Frontone has several restaurants; we've mostly eaten at the Taverna della Rocca, in the upper town, which has good hearty food. It gets a bit overwhelmed on Sundays, and the quality sometimes takes a hit. There are great views of the countryside from the upper town, and there's also a castle there. All of these places are an easy drive from Cagli. In the other direction, Cagli is near the beautiful Gola di Furlo and several pretty little towns. It's not far from Urbino, either.

Rural Le Marche has few towns big enough to support a hotel. Most rural lodging is in agriturismi or "country houses", not in towns.

Corinaldo has several good restaurants, and a hotel. However, it's quite near Senigallia, and since you plan to stay in Senigallia, you may want a town a bit farther away. There are some nice rural roads for walking, but you'd have to get farther from the coast for real hiking.

Loretello is a very tiny town, with a small castle and one restaurant. We haven't eaten at the restaurant in over five years, but it was pretty good then.