If you are crossing the border from Oregon to California on I-5 chances are you will probably see two exits for this little city, but since it is about three miles off of the freeway, chances are you probably haven't gone to the heart of this place. If you are a fan of Shakespeare you probably have heard about their annual festival. Here is an excerpt from their website, "Founded in 1935, the Tony Award-winning Oregon Shakespeare Festival (OSF) is among the oldest and largest professional non-profit theatres in the nation. Each year OSF presents an eight-and-a-half-month season of eleven plays in three theatres plus numerous ancillary activities, and undertakes an extensive theatre education program. Operating on a budget exceeding $26 million, OSF presents more than 780 performances annually with attendance of approximately 400,000."
If you are into Shakespeare or not Ashland is a beautiful town with tons of charm and it is one of my favorite places in Oregon!If you are looking for a place to lay your head there is the high priced luxury Ashland Springs Hotel located in the heart of Main Street this is a really beautiful hotel, but I found a couple of other choices, which I would suggest. The Peerless Hotel still close to Main Street shopping and the OSF, also about the same price range as the Ashland Springs Hotel, but its much smaller and located in Ashland's Historic Railroad and Gallery District. If this is out of your price range I would stay at the Columbia Hotel if you want to be on Main Street or my favorite The Palm, which is about a 5 minute drive (also very walkable) to Main Street. I stayed in a queen size room with a kitchenette. It was very affordable, very cute, and so comfortable. I felt like it was my own little apartment or like I was staying at a family member's house. This is a very rare and blessed experience when you travel as much as I do!
There are many shops and restaurants and cafes to enjoy on Main Street, for shopping I would suggest stopping into Fabric of Vision if you are at all into sewing or crafting. Nectar - Eco Boutique for cute clothes you can feel good about buying, and Paddington Station for unique gifts for you or for those on your Christmas list!
For places to eat Deep's Indian Cuisine, caught my eye as I drove past it earlier in the day. I thought it sounded good on a cold and rainy night. I heard it tends to be busy on the weekends, but went early on a Tuesday night and found it to be quite and cozy. I was surprised by how good the food was. I say this because I live in a small town and I know how international food in small towns can tend not translate well! Deep's went above and beyond my expectations. I had their Spinach Pakora for a starter, Chicken Vindaloo for my dinner entree, and Cheese Nan for a oh so satisfying side! After dinner I could have gone to Sikiyou Micro Pub, but I was craving something sweet. I walked back to Main Street and went to Mix Sweet Shop. They have lovely pastries and espresso to accompany. You should bring a date or a buddy to share one of their treats, because they tend to be on the large side, which is not a bad thing! I had a lemon bar (my favorite), but I was eyeing their cupcakes, which were very large and rich looking. I knew I didn't have room for it, but I will have to go back and try it next time!If you want to stay and eat in or are looking for a place to find lovely breakfast items or groceries. Stop by The Ashland Food Co-op for local and organic food items. Checkout their deli for a wide array of choices for breakfast or lunch. Their cheese section has a basket of all of the small remnant pieces from their speciality cheeses, which I love buying to try selections I haven't had before without the heavy price tag. They also sell cute "Green Bags", which in their case are brown bags with a yellow logo for 25 cents. I bought four! If you are on the Southeast side of town then visit Market of Choice, also has an amazing selection of organics, specialty items, and make sure you visit their wine department. If you need help picking a wine talk to William the store wine/coffee buyer who will gladly share his knowledge and expertise with you.
Ashland is also in it's off season right now, which means you cannot catch a play, but you can experience all of the other attractions Ashland has to offer saving some money too! OSF season begins again in February, which means prices will rise on hotel rooms around then. If you are traveling by Ashland drive a couple extra miles off of the freeway and have a visit!