I'd say Bridge Pizza over Bullman's but I'm originally from Missoula so I may be biased. Both Blackfoot and 10 Mile have really cool breweries/atmosphere are in the downtown area (Bridge Pizza is right next to Blackfoot) so more walkable. Lewis and Clark makes great beer but are a little ways from downtown and parking can be a pain. They do serve food there although not sure how good it is. Toi's Thai on Last Chance Gulch is pretty good for MT Thai food. There is also a tour train that goes through the mansion district, etc for a pretty good history lesson about Helena. As stated the trail system is excellent. The Montana Historical Society just opened a new exhibit (Big Game, Big Stories: Montana's Hunting Heritage) that looks cool but I haven't had a chance to check it out. As for the Bob, I'd take the east side up from Helena through Augusta-Choteau-Browning to check out the Front range. Pretty country for sure.