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Oregon Snowmobiling Questions

My adult son is moving to the state of Oregon. Portland, Oregon to be exact. I would like to visit him in the future and take him snowmobiling so I have a few questions.

What is the typical snowmobiling season in the state of Oregon near Portland?
What are the best times within that season to visit and rent snowmobiles?

Any suggested places to rent snowmobiles, cabin packages, etc for 3 to 4 people for a one day excursion. If rental locations are near Portland there would not be a need to get a cabin but would want a FULL day out on the trails. Initially looking for a one day outing but a FULL day with 50 to 100 miles if possible. Would prefer a nice experience with great sight seeing over just logging miles but not afraid of doing some miles to get to a few great locations. Could make it two days depending on costs but that would probably be too expensive. Son going to law school so there is a budget!

We want to stay within a couple of hours from Portland and stay in USA. Nothing against Canada, just too far from Portland for this possible adventure on a short visit.

Riders will be flatlanders (no mountain experience) ranging in experience down to one or two times out experience (my son). So we would not be interested in conquering mountains or sidehilling. My son has been living in Southern California and I live in Michigan. I am an experienced trail rider, my 23 year old son is an "aggressive novice", other riders will be experienced trail riders. We will be interested in groomed trail systems but not guided tours if the trails are reasonably marked and mapped. As stated l am a fairly experienced snowmobiler, good map reader with GPS unit etc.

Any suggestions or comments. Just trying to make plans for next season.
 
You will end up having to drive a few hours from portland for good sledding. We normally are riding by thanksgiving and not done until mid june where I am in Oregon(central).

Check out;
Elk Lake Resort near Bend, Oregon roughly 150 miles from Portland, they have everything you are looking for.

There are many other resorts that will fit your needs also, I'm sure people will end up chiming in.
 
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You can rent sleds and cabins at Crescent Lake which is off highway 58. I believe you can rent sleds and a room or cabin at Diamond Lake Resort. Otherwise, for day trips, you can ride in the Mt. Hood area which is off highway 26 east of Portland on rented sleds. The Santiam Pass area on highway 20 would be a nice place for "flat-land" riders as the terrain is open enough to play, groomed, trails are marked and there are shelters as well (I'm in this club). This area also has some hills to climb, or short destination rides as well. I believe there is a guy that rents sleds out of Molalla, so you could pick (or have delivered) and then ride somewhat locally.

When you get closer, drop another line on here and someone within your intended area to ride should be able to chime in and give you some more help.

Random pictures from the Santiam Pass area, first one is me with my 2 daughters, second is east side of Three Fingered Jack, last is of Three Sisters.

You can also ride into Crater Lake from Diamond on rental sleds. If the weather is clear, you will have a hard time finding a better view. http://travel.usatoday.com/destinat...e-Oregons-Crater-Lake/56242578/1?csp=34travel
 
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