40th Annual Gloucester Schooner Festival
August 28th - September 1 (Gloucester)
Kicking off Labor Day Weekend and the end of summer is the Gloucester Schooner Festival! Each year schooners from all over visit Gloucester Harbor for a weekend of sailing, chartering, and racing. See the ships set sail, visit them at the docks, or enjoy the downtown activities.
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Apple Picking at Russell Orchards
September - October (ipswich)
Enjoy apple picking, hayrides, and pumpkin patches at Russell Orchards. 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.
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Marini Farm Corn Maze
Every Saturday & Sunday from September 7th - October (Ipswich)
This family-friendly farm offers a 1-acre corn maze for younger kids AND an 7-acre corn maze for adults and older kids. The Maze Play Park area also includes a pirate's ship, rope maze, jumping pillow, farm stand, and so much more!
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Oysterfest in the Port
September 28th (Newburyport)
Oysterfest In The Port hosted by Newburyport FISH will bring together oyster farms and fish vendors from across New England to highlight delicious local seafood.
Photo: Newburyport Fish
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Halloween in Salem
October 1st - 31st (Salem)
Salem is home to many Halloween festivities and museums. Stroll through downtown and enjoy the shopping and decorations. Visit the Salem Witch Museum or The Peabody Essex Museum. Checkout Hunted Happenings for a full list of things to do during the month of October.
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Topsfield Fair
October 4th - October 14th (Topsfield)
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.
Photo: Northshore Magazine
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Cider Hill's Hard Cider Bar & Live Music
Every Weekend Through October (Amesbury)
Relax on the farm with free live music, hard cider bar, and farm snacks at the food truck. Checkout music schedule through the link below!
Photo: Cider Hill Farm
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Oktoberfest Celebrations
Many local breweries host an annual Oktoberfest party full of live music, steins of beer, festive food, and german attire, including the following:
- BareWolf Brewing Oktoberfest (Amesbury) - September 14th
- Notch Brewing Oktoberfest (Salem) - September 15th
- True North Ale Company Oktoberfest (Ipswich) - September 21st
- RiverWalk Brewing Oktoberfest (Newburyport) - September 21st
