Having my aunt & uncle living in Ashikaga, I vistited there frequently growing up.
Ashikaga is a nice little city, quiet and laid back, not much going on, like a clean small town.
There is a slight accent in people's speech which I would not consider as a strong dialect.
I have seen some English speaking foreigners at a restaurant once and am sure there are more.
"Ashikaga-gakkou", Japan's oldest school, is in the middle of the city, that has a statue of 'Kou-shi(Confucius)', is a great place to visit.
Living cost is not as expensive as big cities, but expect the rooms to be small.
Enjoy your stay!