I just got back from a fantastic trip through Oregon and the California Redwoods. The rough rought was: Eugene (OR) - Oregon Country Fair, Ashland (OR), Redwood National Park (CA), Brookings (OR), Newport (OR), and Portland (OR).
While it's really hard to pick a favourite, my stay in Ashland was probably the winner: we stayed for 4 nights in a great bed & breakfast, got to unwind and relax on Monday (since there we had no plays that day), saw amazine Shakespeare productions later in the week, and had fun doing wine-tasting and eating out.
Obviously the main draw in Ashland is the Oregon Shakespeare Festival. We saw three shows: Tracy's Tiger, The Taming of the Shrew and Romeo and Juliet. The last two were in the open-air Elizabethan Theatre - a really stunning venue! (Watching the plays here reminded me of the open-air Shakespeare productions I saw when I was growing up in Cape Town - see these links if you're interested)
Be aware that it can rain in Ashland - even in summer. We were lucky and were far enough back to be under cover, but you'll want a rain shell, something warm, and maybe even a poncho or somethign for your legs in case of a thundersorm. Wednesday's performance of Romeo and Juliet was almost cancelled due to rain, but luckily was only delayed - we got to see the performers come out in rain-wear (mostly period-appropriate cloaks, except for the youngsters who were wearing modern school uniforms initially, and sported modern parkas).
In terms of accomodation, I can heartily recommend the B&B we stayed in: Ashland's Tudor House. The host, Raliegh, was very friendly and cooks incredible gourmet breakfasts. Our room was spacious and comfortable - the best bed of all the places we stayed! A communal lounge with a PC to use for email was a nice touch. The B&B is also within easy walking distance of central Ashland and the festival, but is set back from the main road, so it's nice and quiet.
Ashland had some nice surprises in terms of food - for such a small town (population of 20,000), there are tons of restaurants, and most are good. (100,000 visitors per year helps!)
Our favourites were Pasta Piatti (delicious salads, pasta and crusty, thin-base pizza) and Pangea (very veg*n-friendly, informal lunch and dinner spot featuring inventive wraps, soups and sandwiches).
The local Thai restaurant, Thai Pepper, was decent in terms of food, but great in terms of setting - it has an outside patio right on the creek, which is beautiful on a warm evening. Greenleaf also has creek-side seating (although we sat inside when we visitged). The food here is more like standard diner fare, but with a healthy twist and several veg*n options.
For "fine dining" we tried Monet, and enjoyed very good French food, although the style of food and restaurant decor felt a little dated - especially the very pink, grandparent-friendly interior. The food was traditional French fare (snails in garlic butter, roast duck, ris de veau, grilled fish) - the ris de veau reminded me a lot of my gran's cooking.
Raliegh's breakfasts at the Ashland's Tudor House B&B warrant their own accolades here: we had delicious eggs Benedict (with smoked salmon) one day with a really good light Hollandaise sauce, freshly-made walnut pancakes with maple syrup another, a baked pudding (calfoutis?) with fresh peaches on top another, and potato latkes with apple sauce and sour cream. As you can see, the food is not the normal toast-and-jam, or eggs-and-bacon type stuff...
In terms of wine, Ashland was also a great place to visit. The area is in Oregon's Rogue Valley wine region, and while it's not as high-profile as the regions to the north, there are several wineries to explore. We stuck to the ones closer to town, visiting Eden Vale and Weisinger's.
Both were really pretty and staffed with friendly, knowledgeable people, but if I had to pick a favourite, it would be Weisinger's: relaxed, unpretentious service, a nice lively vibe in their tasting room, a working beehive behind glass (with honey for sale), and good wines. I really liked the Weisinger's red blends (the Mescolare has some nebbiolo, and the Petite Pompadour is a Bordeaux-style blend with lots of cab franc). I wasn't a huge fan of their single-varietal reds, though... Their whites are not bad either - the Petite Blanc is a nice light white wine for summer picnics.
Eden Vale had a delicious white desert wine (a late harvest Viognier), but most of their reds were overpowered and alcoholic. (Probably great candidates for ageing, but I want some wine I can drink now!) My favourite red was the 2003 Syrah (it's won some awards), so I picked up a bottle to try again in the next year.
And finally, I have to mention the Rogue Creamery - makers of some of the best blue cheese in the world. They're a bot of a drive from Ashland (back up the I-5 towards Medford), and the cheesery is a bit underwhelming (no tours of the "cheese caves" where they age the blue cheeses, due to contamination worries. The creamery was also not making cheese due to technical problems). This is more of a tasting room and shop: We were able to taste several of their blue cheeses (including some I've not had before, like the Crater Lake Blue), and several cheeses from other producers in Oregon and California. They have a nice selection of imported food (lots of stuff from Ritrovo in Seattle!) and it's worth a visit if you like food, but I would have liked a more hands-on, "authentic" creamery visit.