Portland has some awesome restaurants, and a terrific walking old downtown. If you like craft brews, Gritty McDuffs has a restaurant, as does Sebago (the food and beer at Sebago is better, IMO).
Freeport is pretty close if you want to make a pilgrimage to the flagship LL Bean store, as well as having other outlet shopping as well. Very pedestrian friendly.
I'm sure others will chime in. I love Portland.
Oh - and for bike shops visit Bath Cycle - home of Bikeman.com.
SheFly