September 1, 2026

The Best Fall Activities on the North Shore: Farms, Festivals, & Seasonal Fun

Looking for the best fall festivities on the North Shore of Massachusetts? You’re in the right place! With summer at an end, we've rounded up a list of fun autumn events happening this season. 

New England is known for its colorful foliage and the north of Boston has all the best activities to enjoy the outdoors. Whether it’s apple picking at charming local farms, exploring the iconic Topsfield Fair, raising a stein at Oktoberfest, or getting into the spooky spirit in Salem, there’s something for everyone!

Discover our curated list of the best things to do this fall below—and get ready to make the most of this beautiful time of year! Pick, sip, and explore fall on the North Shore!

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. 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 12th - October 25th (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 includes a pirate's ship, rope maze, jumping pillow, farm stand, and so much more!

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Cider Hill Farm: 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!       

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Oysterfest in The Port

September 26th (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.

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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:

  • Brewery Silvaticus (Amesbury) - September 12th
  • Notch Brewing Oktoberfest (Salem) - September 13th
  • BareWolf Brewing Oktoberfest (Amesbury) - September 19th
  • RiverWalk Brewing Oktoberfest (Newburyport) - September 19th
  • Alfalfa Farm Cellars Oktoberfest (Topsfield) - September 19th & 20th
  • True North Ales Oktoberfest (Ipswich) - September 26th

 

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 2nd - October 12th (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.

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Cape Ann Plein Air Festival

October 3rd - October 11th (Cape Ann)

Celebrate the birthplace of American Plein Air with local artists throughout Cape Ann. Enjoy live demo events, a welcome party, and a collectors’ preview where you can purchase artwork.

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41st Annual Essex Clam Fest and Arts & Crafts Festival

October 24th (essex)

Come for the Chowder Tasting Competition and stay for the arts and crafts vendors, live entertainment, and additional local eats!

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Renaissance Faire at Hammond Castle

November 7th & 8th (gloucester)

Step into a world of knights, artisans, performers, and merriment and spend the day immersed in Renaissance culture, history, fantasy, music, and adventure.

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