In September, the air turns fresh and crisp, leaves begin to transform. Come, take a trip with Capt. Bill and Sons Whale Watch, aboard Miss Cape Ann. Gloucester’s attractions are plentiful and varied, a great tourist destination for a good reason.

• Friday, August 31 to Monday, September 3 – Gloucester Schooner Festival – The Mayor’s Race for 100′ schooners, races for other classes, parade of sail, deck tours, public sails, lighted boat parade, fireworks, and other maritime activities.

• Friday, September 7 to Sunday, September 9 – Herrmann’s Royal Lipizzan Stallions of Austria, Cogswell’s Grant, Essex – The Herrmann family, breeders and trainers of the famed Lipizzan horse for over three hundred years, demonstrate the highest levels of horsemanship in three shows. The stallions of the Herrmann line are among the last horses capable of executing the “Airs Above the Ground” maneuvers. These dramatic leaps and plunges were developed as aggressive battle maneuvers in the sixteenth century, and are now among the most beautiful displays of equine grace and strength.

• Friday, September 15 – Downtown Gloucester Block Party – Main Street from Pleasant Street to Washington Street. 6:00pm. to 11:00pm. Come one, come all! Free downtown block party! Get ready to dance and party.

• Friday, September 21 to Sunday, September 23 and Friday, September 28 to Sunday, September 30 – Trails & Sails: Two Weekends of Walks & Water Essex County – Go Hike! Go Bike! Go Paddle! Go Sail! Go experience the natural beauty, cultural resources and American heritage found in the Essex National Heritage Area.

• Saturday, September 29 – Coastal Farming Walking Tours – Walk through the fields and down to the marsh, learn about the rich history of the families that lived and farmed at Cogswell’s Grant, Essex, and how coastal farming has evolved over nearly four centuries.

• Saturday, September 29 and Sunday, September 30 – Gran Prix of Gloucester – Known nationally as “the New England Nationals”, the Gran Prix of Gloucester unfolds at one of the most beautiful race venues in the country: the wind-swept oceanside Stage Fort Park on beautiful Cape Ann. Two days of international cyclocross races where competitors from all over the US, Canada and Europe converge to race on the most beautiful race course in North America.