Ravenswood Park, a Trustees of Reservations property, has about 10 miles of carriage roads and trails that allow for easy to moderate hiking. The carriage roads are great for trips with the stroller, while the hiking trails lead to an overlook of Gloucester's Harbor. The park also offers a ton of wildflowers, most off the beaten path. Small swamps along the carriage roads house frogs, birds and sometimes ducks for families and kids to check out. The Ledge Hill trail is a favorite of ours (might want to bring a child carrier for this trail). It's a 2-mile loop, easy enough to hike for families with kids ages 2 and up and it brings you to the overlook of Gloucester's Harbor and the ocean. Along the way, you'll see small waterfalls, streams, huge boulders and a ton of different ferns and flowers. Ideal for families with dogs, as they can be off leash. You can also bring your mountain bikes. A must: bug spray! Trails are very shady and keep you pretty cool during your trip. At the entrance of the park you'll see the building for the Cape Ann Discovery Center, which has a ton of activities for kids as well on set dates. A board outside the building will tell you what's next on their agenda.

Gloucester downtown has a lot of small shops, a playground at Stage Fort Park, and the Marine Museum, where kids can check out ocean animals, such as sea stars (they can even hold them along with crabs and other animals).

The Pilot House in Gloucester on Rt. 127 has great food at a great price.