The first hints of autumn can often be bittersweet, as our last days of summer slip away and we start to re-focus on school, work and the winter ahead. But on Boston’s North Shore, September brings a slew of activities so fun and exciting that our light-hearted feelings of summer will linger all the way through the month. From schooner races to music festivals, here are some of the reasons that the North Shore stays hot, regardless of what the calendar says. Plan your September Cape Ann getaway today!
|The Annual Gloucester Schooner Festival
Labor Day Weekend (Aug 31 – September 3, 2023)
|Trails & Sails: 10 Days of Exploring Heritage in Essex County
September 15-24, 2023
September 16, 2023
Experience one of the best views on Cape Ann with a cold beer in your hand this September. Located next to the beach on the historic Stage Fort Park in Gloucester, sample hundreds of beers, ciders, and meads brewed by close to 40 Commonwealth breweries. Featuring Live Music, local food, vendors, non-alcoholic drinks, and more.
|Gloucester’s 400+ Events
Ongoing throughout 2023
Where to Stay
Atlantic Vacation Homes offers a wide variety of vacation rental homes across Cape Ann that would be perfect for your September Cape Ann getaway. Atlantic Vacation Homes’ wide selection of vacation rentals is fantastic, but the lower post-Labor Day rates are even better! To book your accommodations, simply view available rentals and enter your desired dates to get a quote. You can also call toll-free at (855) 853-9143 to speak with a Guest Experience Specialist.