Fall Events on the North Shore
With summer coming to an end, we’ve put together a list of fun fall events happening on the North Shore. Don’t miss out on these family-friendly activities starting in September!
38th Annual Gloucester Schooner Festival: September 1st – 4th
“The Gloucester Schooner Festival is an event put on by Maritime Gloucester and has become a community wide celebration of the age of sail in Gloucester Harbor. Every year schooners from all over travel to Gloucester to race and to show off their beauty and grace both under sail and as a dock-side attraction.” – Maritime Gloucester

Photo: Trailsandsails.org
Sculpture at Maudslay: September 11th – October 2nd
Sculpture at Maudslay is an outdoor sculpture show at Maudslay State Park in Newburyport which features local artists from the North Shore. This year’s theme is Intersect.

Photo: Kate Donovan Photography
Porch Fest: September 26th & October 21st
Porch Fest is hosted by Byrony & Birch in Amesbury with live music, local food and beverages, small business pop-ups, and so much more!

Photo: Northshore Magazine
Topsfield Fair: September 30th – October 10th
Started by the Essex Agriculture Society in 1818, this fairground offers endless fun, activities, rides, games, music, and events – like The Great Pumpkin Weigh Off! Enjoy exhibitions like beekeeping, animal barns, and produce barns.
Russell Orchards (open seasonally)
Russell Orchards is a family owned and operated 120 acre fruit farm in Ipswich. Enjoy apple picking, hayrides, and pumpkin patches. Visit their barn market for seasonal produce, fresh cider donuts, and selection of house wines. And don’t forget to stop by the barnyard and say hello to their farm animals.
Appleton Farms
“Rolling grasslands, grazing livestock, stone walls, vegetable crops, and historic farm buildings comprise this 1,000-acre pastoral landscape, offering a rare glimpse into New England’s agricultural past. Start your visit at the white farmhouse affectionately called the “Old House,” and easily find your way to our many hiking and walking trails. Follow the paths to Sunset Hill, Wilson’s Field, Briar Hill, The Great Pasture, The Plains, and beyond.”

Mark Spooner Photography
Trails & Sails: September 16th – 25th
Enjoy 10 days of FREE events North of Boston. Be guided through unique landscapes on land and sea, explore historic properties, and take in cultural experiences of all kinds.
Looking to stay nearby all the excitement? Book at room at Briar Barn Inn and you will be centrally located to all the north shore has to offer!