Little Si is a family friendly and dog friendly hike great views from the summit. You can also easily add 1.5 miles via Boulder Garden Loop.
Little Si, neighbor to the bigger Mount Si is a decent hike for beginners and families with younger children. It is 4.7 miles round trip (including Boulder Garden Loop - 1.5 miles) gaining 1300ft in elevation - Discover Pass required. This trail is very popular, so if you want seclusion avoid this hike. On the weekends and sunny days parking can be an issue so give yourself extra time to find parking.
As you approach the trailhead do not be intimidated by its steep incline, the trail will level out by the 0.5 mile mark. Immediate switchbacks will welcome you but they too will diminish as you forge on. Be prepared for the trail to be dusty if it’s been a sunny dry week. If you want to add extra mileage to your hike you will have the chance to do so less than 0.5 miles in (the Boulder Garden Loop- 1.5 miles).
A little over 0.5 miles in you will finally approach the woodlands- though the once obvious trail will become difficult to follow due to so many people going off trail. The trail is marked every now and again by little signs or ribbon on the tree, look for these if you are unsure where the path is going. As you go through the woods you will pass massive rocks and rock climbers to your right.
On the final portion of the trail be prepared for more steep inclines. You will pass phenomenal views to your left near North Bend valley, less than 0.2 from the summit. This was less crowded and in my opinion a better view than the actual summit itself.
Once you get to the summit you can expect to have a lot of company and a beautiful view of the surrounding mountains and town below.
Things to keep in mind: