Ascoli Piceno

Here are the books I used:
Le Marche: an insider's guide
Blue Guide The Marche & San Marino: 2nd edition
Umbria & the Marche Landscapes Series 2nd edition by Sunflower Books
The Marches: A Complete Guide to the Landscape and National Parks, and One Hundred Towns Including Urbino

I stayed in Ascoli Piceno a few nights, but we were mostly focused on hiking. If you enjoy hiking, there is a lovely walk at the town of Montefortino called Gole dell'Infernaccio.
We also enjoyed Senigallia (where we visited parks north of Pesaro and south of Ancona) and Sassoferrato. The driving along the coast is zippy; it is slower between hill towns--of which there are numerous attractive options.

You can always find plenty of info online.
Just Google REGION NAME or CITY NAME + TURISMO
In your case the region name is “Marche”.
Here are some hits, including official sites from the local Regional or City tourism agency
http://www.turismo.marche.it/
http://turismomarche.com/en/
http://visitascoli.it/en/

Will you have a car? We spent 10 days in Le Marche last fall and can recommend some of our favorite places that are easiest reached by car.

Becky...yes we will have a car. Would love any advice you may have. Thanks!

Not Becky, but where exactly are you staying? (the whole time, or are you changing bases at some point?, plus where do you arrive and depart?), how much driving do you prefer to do per day? what kind of things do you like to do?
The only place on the Adriatic in the vicinity of AP that sounded interesting to me was San Benedetto del Tronto and Grottammare, but I ran out of time to get to them. Further up the coast, I mentioned the most attractive coastal areas.

About 110 km north of Ascoli Piceno is a lovely natural reserve with an impressive Cistercian abbey started in 1142, Abbadia di Fiastra. Nearby in Urbisaglia, I recommend the Locanda le Logge. It’s a b&b, with a wonderful restaurant with both al la carte and set menus; recommended reservations. About 80 km northwest of Urbisaglia there’s a town, Sassoferrato that I highly recommend. There are lots of charming lodging options and we enjoyed eating at Le Rocca Ristorante Pizzaria. Inland Marche has many charming towns and villages and the scenery is spectacular.

Hi Valadelphia...we have no set plans. We have done most of the tourist sights so we are interested in just hanging out and enjoying the countryside. We do love the beach so at some point plan to be there for a few days. Three weeks prior we are doing Annecy France and Zermat, then a week in Cinque Terre and then a week around Lucignano for wine country then we are off to Ascoli Piceno and that area for three weeks since it will be all new to us we are looking for first hand advice. We have a car. We like everything! Just looking for some special out of the way places. Thanks for your interest in helping us!

Becky...thanks so much for your help. Will check them out! Getting excited!😎

It's all out of the way in le Marche--you'll love it.
The first and last book I listed provide a comprehensive overview. Get the Blue Guide if you like to go deep, and the Sunflower for scenic drives.

Valadelphia. Thanks for the info and guide books. Very helpful!