A hip downtown weekend in Ashland: choose your adventure! Within walking distance, enjoy world-class Shakespeare theater, restaurants, wineries, shopping, unique coffee shops and endless outdoor adventure with a stunning scenic backdrop! Art, culture, and downtown vibes - The Urban Gypsy Loft in Southern Oregon checks all the boxes for the best weekend getaway, girls trip or stay-cation. If outdoor adventure is your jam, you can enjoy the local hot springs, hiking, biking, skiing and boarding.