My husband and I are planning way ahead for retirement (hey, I'm a financial planner - can't help it), and looking at OR (as well as WA and CA) as a possibility.

We love where we live now, but not the 60"+ of snow we get each year.

We'd like to find something comparable in feel - we live on the coast right now, in a beautiful historic seaport, voted one of the best 100 art towns of America. There's always some sort of festival going on here, and we like that community feel. The population is about 18K (we like this size - not too big, not too small), with lots of good restaurants, a live theatre, waterfrong park where free concerts are held, great boutiquey shops, good library, other nice towns surrounding, very little crime, and beautiful architecture. An average home here (3BR/2BA) sells for @500K.

We don't want to move to a place that's great with nothing else around it, and want to stay withing driving distance of the coast. We also would like to be close to town so we could walk as we do now to the center of things. We definitely want a place with a vibrant "downtown". Being very close to a good hospital is also key, as my husband has had some heart problems.

We get about 40" of rain here a year, but I think we would be crazed with constant drizzle and no sun.

Of course we plan to visit the areas on our list, but to help in planning, we'd like to know if we are in the ballpark with any of our "picks":

Corvallis
Milwaukee
St. Helens
Ashland
Grants Pass

Any insight anyone can provide would be much appreciated.

Hi wanderer,
The way you describe your current town makes me wonder why you want to leave. It sounds delightful. However, to answer your question, of the places you listed, the only ones that I would recommend are Ashland and Corvallis.
First, let's dismiss the others. I'm sure there are those that love each of them, but they don't meet your criteria. Milwaukie is just a suburb of Portland, and hardly qualifies in itself as a cultural or scenic center. St. Helen's is on the Columbia River with questionable weather and little to offer in itself. Once you get past river rafting, the same can be said of Grants Pass.
So let's turn to Corvallis and Ashland.
Both are college towns with all they have to offer. Corvallis is closer to the ocean (maybe an hour away while Ashland is more like three hours), but has much more rain and dampness. Corvallis is also closer to a major city (Portland) than Ashland. It could be said that Ashland is an oasis in the middle of nothing, which you said you wanted to avoid, although Jacksonville is nearby with its Britt Festival, offering a variely of music programs. On the other hand, Ashland, especialy given its size of only 20,000 people, has an incredible amount of culture and art. Not only is it home to the Oregon Shakespeare Festival, but it has a lot of local theater, many art galleries, and music programs throughout the year. Gree band concerts are held weekly in the summer. It has its own hospital. It is surrounded by national forest lands that practically come to its doorsteps, plus has many parks. Good restaurants abound, as they undoubtedly do in Corvallis. I don't know the price of houses in Corvallis, but in Ashland a home like yours would run $400,000 to $600,000 depending on where in town it is located.
I think you should visit both towns to get a feel for what you prefer. Either would be a good choice, but for me Ashland won hands down. Good luck.

I'm fascinated at this town on the coast that gets 60 inches of snow a year. I've never heard of a place like that in the US -- usually there is little snow along the coast? Or have I just lived in Florida too long?

Anyway, I'm having a tough time picking any of those cities that sound like a decent trade off for where you live now.

Eugene is a possibility. Friends who live there say that it is only a couple of hours from the coast.

Yes, why *do* you want to move? The town you're in sounds lovely. Oh, the snow. Well, Oregon is a terrific place, but you also say, "we would be crazed with constant drizzle and no sun." In Oregon, we have a lot of overcast skies. It doesn't always rain--it just *looks* like it's going to. That said, Ashland sounds like it would suit you. Eugene is bigger, but far cozier than any suburb of Portland. Some of the locals in this metro area are getting really weary of the traffic. Any town in the Willamette Valley, the western half of Oregon, will be a nice day trip to the coast.

I agree with therenaissanceman that Corvallis and Ashland are probably your best bets. Ashland is located in the Rogue Valley which includes Jacksonville, Medford (the largest city), Central Point and several other smaller communities. Most of these communities are within 15-20 minutes of Ashland. The weather here is very nice. We do not get the rain like they do in the Willamette Valley or Portland. Winter can be cool but often we will have cool crisp days, with blue skies.

For the culture you want, Ashland would be great due to the things described by therenaissanceman. Medford (15 miles away) also has the Craterian Theater a performing arts theater with travelling Broadway productions, opera, symphonies, dance, etc.

You could definitely live near the center of things in Ashland, and there are many retirees who move to the Rogue Valley so we have excellent medical care at the hospital in Ashland as well as the two hospitals in Medford.

I would skip Milwaukee, Grants Pass and St, Helen's ffor the same reasons renaissanceman gave.

Thanks everyone. We struggle with a move, as we absolutely adore where we live. It is the smallest city in MA, called Newburyport. We are also @ 1/2 hr. from Boston.

But as we age, the weather wears on us. Sometimes the snow is from early Nov through March. Last winter we had many storms with over 3', and when you have morning meetings so have to get outside at 3am to shovel to be on the road at 6am, it is not fun. With wind chill, many days it was at 20 below.

We considered a second home, as we would love to just leave for the winter, but with a pet that is hard. Additionally, we would not be able to swing it financially.

Thanks for the insight. It's hard just reading about things.

One thing I forgot to mention.

We are skiers and would love to be within driving distance of a ski resort.

Right now we drive 4 hours to our place in VT, so that would be acceptable.

Is there skiing near either Ashland or Corvallis?

I suggest you take Milwaukee off your list and replace it with McMinnville. My in-laws live there and find it's just what they had wanted. FWIW, here are the other towns they lived in after retiring and why they left (be advised, my husband's parents moved around a LOT their entire lives):

Taos, NM: beautiful, small artists town. But too far from medical centers and it was too frustrating to get any repairmen or workers for anything.
Austin, TX: Lovely, lovely town. But just too hot in the summer.
Sequim, WA: Incredible climate, incredible scenery, not that expensive. But again, too far from medical centers (and also, they bought a property with too much land requiring too much upkeep).
Bellingham, WA: Pleasant, but kind of bland and the weather was much greyer than they wanted.
McMinnville: like a slow-learning Goldilocks, they finally pronounced this one just right. Nice community, easy drive from Portland or the coast, good medical care, not too expensive., etc.

Corvallis fits exactly what you describe!!! It's where my parents chose to retire (they had lived in both California and Connecticut). My sister & BIL live there as well. It is a very sweet town in a lovely area. I'd even think of it for myself, if I ever left the city (Seattle).

For skiing near Ashland there is Mt. Ashland. You could be up on the mountain skiing in about 30 minutes. It is a smaller skiing area not a big resort, but great for a quick day of skiing or great night skiing! Definitely a community feel.

Then there is Mt. Bachelor which is about 3 hours from Ashland. Much bigger ski area with more runs, lodges, etc. It is in Bend which is a wonderful place to vacation in winter or summer.

Corvallis is about 2 hours ( I think) from HooDoo Ski Area which is smaller, like Mt. Ashland but has recently had a lot of renovation including a brand new lodge. Corvallis is probably about 3 hours or so from Mt. Bachelor.

There is skiing only ten miles from Ashland on Mt. Ashland. It is not regarded as a great skiing site, but it seems to satisfy the locals. From Corvallis, the closest ski site would probably be Mt. Bachelor, near Bend. It is regarded as a finer ski site than Mt. Ashland, but is at least two to three hours away from Corvallis.

wanderer, I was almost sure you were describing Newburyport, particularly because of the arts comments, but that snow thing threw me. I was never aware that there was much snow at all there. Was that unusual last year, or do you really normally have that much snow?

Our daughter goes to school at SOU in Ashland. She spent the summer there last year (she's on an exchange in Australia now) and the heat really got to her (we live in NW Washington State). Although it is that famous "dry" heat, she still tired quickly of the 100+ days they often had in the summer.

For culture, you can't beat the Shakespeare Festival - it does draw hordes of visitors in the summer, significantly swelling the town's population. The university kids are mostly gone but that only takes about 5,000 out of the mix. For a small town like Ashland, the large Festival crowds sometimes feel overwhelming but they seem to handle it fairly well. Getting into restaurants pre-theatre is sometimes tricky!

Cost of living there is HIGH. Many college kids commute from Medford, Talent and the neighboring smaller towns. Doesn't sound like that is an issue for you though.

They are several hundred miles from larger cities such as Portland to the north and San Francisco to the south. That bothers my culturally-starved daughter at times (she is a theatre major) but driving to those cities, most of the year, isn't a problem. Sometimes the drive through the Siskiyous south is a problem and the southern Oregon passes to the north can be the same way. The road out to the coast via Grants Pass is a pretty one and drops you down into Crescent City - a few hours (?) from Ashland. The drive up to Crater Lake is gorgeous and about 2 hours from Ashland but not doable in the wintertime of course. Klamath Falls is to the east but that road can be dicey in the wintertime as well. Amtrak stops there with the Coast Starlight that can take you up to Seattle and down to LA.

I myself like Ashland quite a bit and will miss it when she graduates as we've really learned our way around and enjoy it quite a bit, but it is small and a little isolated and that isn't getting old for our daughter.

I do know that more and more retirees are discovering the place and building and buying there.

Sorry ... meant to say it IS getting old for her. Sheeesh.

ttt & good example of a travel thread...

Wow! Everyone has been really helpful.

Patrick - I asked DH this morning if I was off with the 60" snow thing, and he said No, that's a good winter. We have had many winters where we get 100"+. If not for that.... My husband says it we can't find something comparable we're staying put. Sonoma, CA is on our list, but we think we owe it to ourselves to look around, especially since we are not sure if our housing will keep pace with CA.

Corvallis and Ashland sound like possibilities. I should have mentioned we are interested in being near a bigger "city". I hadn't realize Ashland was so far from one.

Thanks again - great, very helpful comments. Just what I was looking for.

Of the places on your list, only in Ashland and Grants Pass would you not expect 40" of rain/drizzle and six+ months of gray skies. And of Ashland and Grants Pass, Ashland would be the clear choice. But it might be a little too cool for you in winter, and its funky, chicness might become tiresome. I honestly don't think there's a clear fit with your criteria in Oregon.

Would Port Townsend, WA work? How big is Mendocino, CA?

Port Townsend is great, but access to medical care is a problem on the OP. There is good general care, but you won't find a lot of top specialists there and the ones they do have are taking few new patients...they already have a full patient load.
Unfortunately, that is the Achilles heel for the OP as a retirement mecca. Another reason my in-laws like McMinnville so much...they have a good little medical center of their own and it's an easy drive to the big medical centers in Portland.
Housing is slightly cheaper there than in Corvallis and Eugene (actually a lot cheaper than Enear ugene's desirable university area and in the SW and SE hills) and there is definitely less traffic in McMinnville than in Eugene.

I will definitely check out McMinnville.

We would like a 4-season climate, or as close to it as we could get. If we had to exchange 6 months of snow for 6 months of rain/drizzle I'd rather to be honest have the rain. We get @ 42" of rain here but it is not constant gray and drizzle.

Yes, Port Townsend,WA is on the list. It seems very much like our home here, except perhaps much rainier weather. We are traveling in May to Mendocino, Nevada City and back again to Sonoma to spend some more time. I think Mendocino will be too remote and small for us, although looking forward to seeing it.