Two of the best places to walk on Nantucket with kids are Squam Swamp and the Gardner Property. When I am not too busy in the summer renting baby equipment we try to make it to these two spots at least weekly.
Squam Swamp is always quiet and there are roots bursting forth from the earth making magical patters and there are many fun bridges to cross. I think there are 54 place markers so you always know where you are, though if you have walkers under the age of three I would suggest turning back before the number 20. The most fun day I can imagine on Nantucket would be to pack a lunch and head out about 10 AM. Drive out to Squam Swamp by way of Polpis Road to the Wauwinet Road. Near the end of the Wauwinet Road you will see a 30MPH sign and almost immediately after a parking lot on the right. Park and walk to your hearts content. If you are walking with kids under three I would suggest some sort of Ergo baby carrier you can wear on your back so you can be sure of your footing. This is not really a walk to do with a stroller and even though the jogging strollers I rent are great, they are not up to the task of a forest march. If you feel the need to stroll then check out the Gardner property.
The Gardner property can be found after Sandole’s fish market at 167 Hummock Pond Road. After you pass the market (which you should be sure to visit on your way back into town – they are unbelievable) look for the parking lot on your right. Park and walk. One of my favorite places on Nantucket to take my kids, no matter the weather, is the cool hidden bridge. For starters it isn’t really hidden, just follow the path and stay to the left when you get to the clearing. TAKE YOUR CAMERA. The bridge is a perfect setting to capture an image for your family holiday card. This walk is good for all ages and is stroller accessible. Call me at the office if you get stuck!