The Lookout Trail like allof the trails in this area, can either be approached from the top, there is a sign marking the top of the trail through Shirley Heights Lookout to the right, or from the bottom just up the road from Freeman’s Bay, back up the road coming out of the Galleon Beach Resort. Difficulty is therefore dependent upon where you start from.
If hiking from the top it’s a nice easy trail, with at one point a few large rocks to climb over. Once you arrive down onto the road at the end of the trail, you can their either take the Jones Valley Trail or Carpenters Rock Trail. Alternatively, you can walk back up the road. If hiking by road turn right onto the road at the end of the trail and when you reach the main road at the top of the hill, take the right and keep going. There is a split in the road which to the left takes you up to Blockhouse, keep right to get back to Shirley Heights and the end of the trail. If you do this hike in the afternoon you can then enjoy sunset drinks at Shirley Heights Lookout.
If you hike from the bottom there is no warm up, so it can be fairly intense walking and hard on the heart straight off. That said, you get to the top really fast so it really depends on your preference. Personally, there is nothing like knowing on reaching the top, that it’s downhill all the way home. If you hike this way round you can take a refreshing swim in Freeman’s Bay.————