I lived in Ashland for three years and every day marveled at the incredible beauty. Generously green and lush, this is a highly walkable town with an almost picture perfect community. For it's small population of about 20,000 residents, it offers abundant community events (the place loves its parades), art, restaurants and theater. It is home to the Shakesphere Festival, so popular that it runs about 8 months out of the year and attracts visitors from across the globe. Lithia Park, which extends nearly a mile from the town center, is absolutely magical.
The people consist mainly of retirees, undergraduates and more "healers" than you can shake a rain stick at. Many people from California's Bay Area cashed in and retired to Ashland, driving up housing costs. A 3 bedroom house near downtown now is in the $500K range. Pride of ownership is high and this shows in the beautifully landscaped yards and well kept properties.
This is a highly liberal town and most folks are very environmentally conscientious. There's something incredibly sweet, quirky and lovely about this community.
Sadly, there is a dearth of working professionals in their 30s and 40s. This is not a great place for singles or for jobs. But is a place to make friends and be part of a peaceful and gorgeous community. It is overcast and rains quite a lot from October through April. Snow is minimal. Summers are absolute bliss.