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Having lived in both Bozeman and Bend- there are many common things about them.
Outdoor activities are great-- Bend probably has more diversity of activities. Both have lots of hiking but more lakes in Bend that are accessible. Bend has high desert area and coastal areas nearby.
Hospital and medical in bend area larger with more specialities. More stores.
Lots more golf. Both have lots of biking-- Bend more with better access for bikes in town and nearby.
Bozeman has more of a small town feel because of population in and around it. Both have good restaurants- Bend has more due to size of town and surroundings.
Both are sunny-- Bend not as cold during winter but find the nights and mornings colder in the summers. Bozeman has larger college. Close to Yellowstone area- which is spectacular for wildlife viewing.
Both towns seem safe- you'll find crime anywhere if you look hard enough. Would say Bozeman has slight edge in that department for safety.
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