Outdoor Activity

Join local history buff, Scott Jewell, on a walk around the town of Ipswich and learn about the fascinating history of its former bustling port. Once a hub of maritime trade and commerce, the fate of the port was intricately tied to the rise and fall of the town’s 18th century economy, and the fortunes (and misfortunes) of many of its residents. Part of Trails & Sails.

Fair in the Square is a time- honored tradition celebrating each other and showcasing our charming  town. Come shop local vendors and makers offering a wide variety of goods from local honey and bee related products to jewelry to facepainting to artists and more!

The Gloucester Schooner Festival is a  wonderful celebration of Gloucester's fishing and maritime history during labor day weekend. This year's festival, hosted by Maritime Gloucester, is Gloucester’s major marine event, with participating vessels coming from ports along the Eastern seaboard and beyond. There will be both large and small vessels—ranging from 19 feet to over 100 feet in length. You will see new boats and old boats, from newly built (Ardelle - launched 2011) to over 100 years old!

The Rockport Acoustic Music Festival is a day-long celebration of music at Millbrook Meadow in Rockport Massachusetts! Come relax and enjoy a beautiful setting, have a picnic, play with your kids and enjoy the music of local musicians and bands! This annual event is a fun time for all so don't miss it!