Tom's Thumb and Tom's Thumb! We'll hike Tom's Thumb then go to Tom's Thumb for lunch. Tom's Thumb is the coolest hike and Tom's Thumb is the coolest deli/bbq/carwash/gas station.
Length: about 11-13 miles; we'll go out and back - I'm never quite clear the mileage, but it's a terrific hike (and who's counting?)
Elevation gain: about 1400 feet according to the MMP map
Time: about 5 hours of hiking, then lunch
Difficulty: yup! Lots of steep switchbacks
Dog friendly: yes, on leash, but be sure your dog is fit too. I wouldn't recommend it for most pooches I know.
Fitness level: You want to be fit for this one! It's long, with lots of upward slope and then very very steep in parts. No bouldering/climbing, just steep trail. This isn't a fitness hike exactly, but we tend to keep a good solid pace. You'll be happiest on this if you've hiked with me before and like my pace, or you've done lots of brisk hiking recently. I don't recommend this for beginners.
What to bring: WATER and lots of it; hat, sunscreen and lunch money. Our lunch place is:
http://www.tomsthumbfreshmarket.com/ Let me know if you're coming for lunch so I can reserve a table.